--- title: "How a $20K Pilot Became a $30M Deal" episode: 124 podcast: "The LeanScale Podcast" publisher: "LeanScale" guest: "Tim Yandel" guest_title: "Chief Revenue Officer, Imubit" date_published: 2026-09-23 date_modified: 2026-09-28 duration: 01:15:36 word_count: 14164 topics: ["enterprise-sales", "forecasting", "revenue-operations", "sales-leadership", "ai-in-gtm"] canonical_url: https://www.leanscale.team/knowledge/podcast/tim-yandel-imubit-20k-pilot-30m-deal/ source: "LeanScale Knowledge Hub — https://www.leanscale.team/knowledge" license: "Free to quote and cite with attribution to The LeanScale Podcast." --- # How a $20K Pilot Became a $30M Deal _Tim Yandel on the personal consequence hiding behind every compelling event, why fear of messing up kills more enterprise deals than competitors, forecasting when every deal slips, and why the best RevOps metric in an enterprise motion has nothing to do with the buyer_ **Episode 124 · The LeanScale Podcast** Tim Yandel, Chief Revenue Officer, Imubit · Hosted by Anthony Enrico Published September 23, 2026 · Updated September 28, 2026 · 01:15:36 Canonical: https://www.leanscale.team/knowledge/podcast/tim-yandel-imubit-20k-pilot-30m-deal/ **Topics:** Enterprise & Public-Sector Sales · Forecasting · Revenue Operations · Sales Leadership · AI in GTM ## Executive summary Tim Yandel is Chief Revenue Officer at Imubit, which sells closed-loop AI process optimization to refineries and chemical plants at half a million to over a million dollars a year in license alone. He started as a technical recruiter in Chicago, ran global sales at Sama in computer vision and data labeling, and was CRO at Regrow. Along the way he closed a $29.4 million contract that began as a $20,000 pilot with a German global manufacturer. He rounds it up to $30 million, he admits, because it sounds better. His first lesson came from recruiting. A candidate is a perishable asset: the longer you wait, the more likely they take another job, so every deal comes with a deadline built in. "When you're selling software, there is no critical event that's naturally aging." You have to find it inside the person you're selling to. In the $29.4M deal the pilot looked like a science project until it reached someone who cared about being a first mover, and who saw the project as a way to get promoted inside a global organization. That personal motivation drove the deal. The ROI came afterwards to back it up. The opposite force is what Tim calls FOMU, fear of messing up. He says 85% of enterprise deals are lost to no decision, not to competitors, and at a century-old brick-and-mortar company, attention can be a risk rather than a reward. That changes the seller's job. It is diagnosis, not prescription: show the buyer you've done this many times and take the fear out of the decision. Pushing more urgency or more ROI on a scared buyer just adds pressure, and the deal stalls. He sees the same pattern in enterprise sales teams. High-velocity "revenue athletes" learn fast because months end and deals die on their own. Enterprise "chess players" have eight-to-eighteen-month cycles, so a proposal that misses Friday goes out Tuesday and the team gets comfortable. Anthony Enrico puts numbers on the cost: cut a 12-month cycle to nine and the extra deals can move a fundraise from 80% growth to 2x. Much of the conversation is about forecasting and RevOps. Tim assumes every enterprise deal will slip at least a quarter. No deal goes into best case or most likely without a credible critical event, and if that event can move by quarters, it isn't one. He asks buyers "have you approved a deal this size before?" as a conversation rather than a yes-or-no question. He treats the forecast as the executive team's shared call, not "the Tim show". He calls RevOps his secret weapon. His head of RevOps built a Slack deal desk that replaced two-hour weekly meetings, and started tracking how fast legal requests are answered, because the end buyer is not the only thing RevOps can measure. The episode closes on AI and focus. Imubit runs an internal app store where employees publish the agents they build. One pairs a listener agent with a scrutinizer agent so Slack updates stay quiet enough that the team doesn't switch them off. Tim ties it back to his time as a server at TGI Fridays, when a thick menu was cut to one page: people don't want more options, they want to make the right decision. That applies to a demo, a follow-up email and an AI setup. His advice is to dive as deep as you can, but not so deep that you forget the job you're supposed to be doing. ## Key takeaways 1. **Software never hands you a critical event — you have to find it in the person** — In recruiting, the candidate is a perishable asset: the longer you take, the more likely they take another job, so every deal carries a natural deadline. Tim's point is that software has nothing equivalent. There is no critical event that's naturally aging, so the seller's job is to find one inside the person they're talking to — and then keep surfacing every conversation around it. _Why it matters:_ Treat finding the critical event as the actual work of enterprise sales, not a qualification checkbox. If you haven't located what makes this date matter to this person, you haven't found the deal yet. _For:_ Sales Leaders, Revenue Executives, Founders 2. **The critical event that moves a deal is personal, and the ROI comes second** — The $29.4M deal began as a $20K pilot to prove computer vision and data labeling worked. It stayed a science project until it reached the right person with the right message — first mover or fast follower? — and became a personal achievement: how that buyer would get promoted inside a global organization. That personal motivation was the emotional driver; the ROI was built afterwards to back it up. _Why it matters:_ Personal motivation is what every decision is made out of, whether software, services or recruiting. Find the champion at the right level whose own outcome depends on the project; at the wrong level the same work does nothing. _For:_ Sales Leaders, Revenue Executives 3. **Deals die to FOMU, not competitors** — Tim cites that 85% of enterprise deals are lost to no decision rather than to a competitor, and names the cause: it isn't fear of missing out, it's fear of messing up. At a fast-growing tech company, attention is a reward; at a brick-and-mortar business that has been around for a hundred years, it can be the opposite. Sometimes the motivation is promotion; sometimes it's the risk of being replaced by an outsider who does innovate. _Why it matters:_ Discovery has to uncover which way the personal stakes cut for this buyer and this culture. A pitch built on excitement can land as risk to someone whose safest move is to do nothing. _For:_ Sales Leaders, Revenue Executives 4. **Diagnosis, not prescription — more urgency and more ROI backfire** — When the buyer's problem is fear, pushing urgency pushes more fear onto someone who already doesn't want to decide, and the critical moment becomes an insurmountable one. What takes fear out of a deal is signalling that you've done this many times: every other customer before them worried about the same data wrangling or imperfection. Anthony adds that very few things signal competence more than speed — a same-day proposal or an NDA turned around immediately. _Why it matters:_ Get into advisor mode, where it's about the buyer rather than you, and get to the emotional reason the deal makes sense. Then move fast on every small ask, because speed is itself proof you know how this goes. _For:_ Sales Leaders, Revenue Executives 5. **Revenue athletes versus chess players — and why enterprise teams get lax** — High-velocity sellers get many at-bats, learn from every interaction, and don't take losses personally. Enterprise sellers are strategic but lack natural urgency: with an eight-to-eighteen-month cycle, a proposal that misses Friday goes next week and nobody worries. Tim argues that speed is coming to the enterprise whether you like it or not, especially when selling AI. _Why it matters:_ Don't accept "it's strategic sales" as an excuse to whiteboard and wait. Measure the internal clock — time to NDA, time through deal desk — and the threading: single- versus multi-threaded, the right level, and whether eight-plus people are engaged, which he says sharply raises the odds of moving from stage three to stage four. _For:_ Sales Leaders, RevOps Leaders, Revenue Executives 6. **Close-lost the deal that says "a couple more quarters"** — Enterprise teams Tim has taken over reported 18-to-24-month cycles only because they lacked the rigor to close deals out when they should be closed. If a buyer likes what you're selling but needs a couple more quarters, try to talk them out of waiting — and if you can't, close-lost it and run a retro on what would have made them not want to wait. _Why it matters:_ Closing lost creates the learning moments a slow cycle otherwise denies you, and keeps the pipeline honest. A fake pipeline, in his words, is an empty pillow to sleep on. _For:_ Sales Leaders, RevOps Leaders 7. **Land small on purpose and architect the expansion** — Even the $29.4M deal was, by Tim's count, an expand deal if you treat the pilot as the land. The days of closing $30 million land deals are few and far between. Instead of asking for a $500K pilot or first-year deal and waiting 18 months, close a $20K pilot in 90 days that is set up from the start for expansion into a $5 million deal. Anthony notes the bigger deal converts at a much higher rate once the value is proven. _Why it matters:_ Treat deal structure as a design variable. Break up your own sales process, try things, and see what works for the buyer you're selling to — the expansion flywheel matters more than the size of the first signature. _For:_ Sales Leaders, Revenue Executives, Founders 8. **Stage three is where deals stall — go slow to go fast** — Whatever the sale, the pipeline bunches up at stage three, the technical deep-dive. Teams rush through discovery to get there, then hand the buyer everything at once and lose control of the deal. Tim's alternative is to spend longer in discovery, find the pain point and critical event early, and earn the right to each new stakeholder — trading access level for level. _Why it matters:_ Brief your own technical people on what to say: if the product has 20 worthwhile things, say no more than three. Undervalue your time early and the buyer will too, and you end up the person who schedules meetings rather than the one driving the deal. _For:_ Sales Leaders, Revenue Executives 9. **Build the mutual close plan backwards from the critical event** — Once both sides want to keep going, tie the critical event to a date — not etched in blood — and work backwards through legal and every other step to a go-live. Tim will even say out loud that the date will most likely slip, but ask both sides to hold themselves accountable to it. Alongside it, turn the org chart into a power chart: who has influence and authority, who is the business champion, who has influence without authority. _Why it matters:_ The plan shows you've done this before and that you, not the buyer's 15-vendor evaluation process, are shaping how the purchase happens. A new rep who hasn't done a deal like this should borrow a colleague's story and run the same play. _For:_ Sales Leaders, Revenue Executives 10. **Forecast as if every enterprise deal will slip** — Tim assumes at least a quarter of slippage and, when forecasting to a board, that a deal which hasn't slipped yet will. Inherited CRM data rarely helps: close-lost rigor may have been absent, so historical cycle times can't be trusted. He uses conversation intelligence to read the buyer's and champion's actual language, and watches for both happy-ears reps and pessimists who only forecast deals that are practically signed. _Why it matters:_ No deal enters best case or most likely without a credible compelling critical event. If the event can move by weeks, it still counts; if it can move by quarters, it isn't a critical event, because there is no consequence of no action. _For:_ RevOps Leaders, Sales Leaders, Revenue Executives 11. **Ask whether they've approved a deal this size — without asking it directly** — Anthony raises the qualifying question Tim uses: has the buyer personally gotten a deal this size approved before? Tim's warning is that a yes-or-no question is the dangerous question. Instead: I'm sure you've closed deals like this before — what was the last process of similar magnitude, any learnings? If nothing comes to mind, it's their first one, and that's fine. _Why it matters:_ Once a deal passes $100K it gets scrutinized, and at millions there's a committee. The answer tells you whether to build the business justification with the buyer; framed well, it puts them at your level rather than exposing them. _For:_ Sales Leaders, Revenue Executives 12. **Enterprise selling is more internal than external** — Tim says the enterprise seller has more internal selling to do than external. No one gets a gold star for closing a big deal alone; if a board member hears nobody else was involved, it raises concern. The buyer is buying the company, not just the product, so he deliberately brings in executives matched to the buyer's people — for example, having his head of product follow up after a roadmap workshop while a deal sits in legal. _Why it matters:_ The same collaborative stance applies to the forecast: present it as the executive team's forecast and invite them to poke holes, instead of defending it as your own. Anthony has watched isolated CROs get destroyed and collaborative ones pull product, finance and the CEO into winning. _For:_ Revenue Executives, Sales Leaders, Founders 13. **RevOps is the force multiplier — and it can measure the seller's own organization** — Tim calls RevOps his secret weapon, partly because he hates doing it himself. Treat them as data wranglers and that's what you get. His head of RevOps replaced two-hour weekly deal desk meetings with a Slack flow that routes commercial, product and services questions to the right approver and ends with the CEO, and proposed measuring response time on legal requests — trending it from three days to two. _Why it matters:_ The end buyer isn't the only thing RevOps can measure. Internal SLAs turn your own organization into revenue athletes and make the customer's buying experience predictable. Tim adds that a 1% improvement per stage per quarter across a seven-stage process compounds into significant impact over a year. _For:_ RevOps Leaders, Revenue Executives, Sales Leaders 14. **Data without story is nothing to grab onto — so set measurement gates** — Story without data isn't relevant; data without story gives nobody anything to hold. If 40 to 60% of losses go to no decision, you need theories about why and how to fix it, and a way to know quickly whether a fix works. When Tim ran marketing, 10–15 short content pieces a week were judged first on site traffic (up) and only then on leads (not up), which pointed at content quality and calls to action. _Why it matters:_ Agree in advance what you'll measure and when you expect to see it — two weeks, a month, 60 days for extending discovery from one call to two or three. Don't accept the first data story, and don't fall in love with your own fix. _For:_ RevOps Leaders, Revenue Executives, Marketing Leaders 15. **Less is more — for buyers, and for your AI stack** — At TGI Fridays, Tim watched a menu that used to be a thick book get cut to two sides: drinks and food, around five items each. Research showed too many options stress people out. As much as we want more information, we don't actually want more information — we want to make the right decision. Send one thing to review, not twelve; demo three features, not twenty. _Why it matters:_ The same curation applies to AI. Anthony describes pulling back from 18 open sessions to a handful of supercharged daily processes; Tim's rule is dive as deep as you can, but not so deep that you forget the job you're supposed to be doing. _For:_ Sales Leaders, Revenue Executives, Founders ## Frameworks ### The Personal Critical Event (02:22) **Definition:** In software there is no critical event that ages on its own, as a candidate on the job market does in recruiting. The seller must find one inside the buyer — ideally a personal stake, such as a promotion or the risk of being replaced — and keep every conversation anchored to it. Tim learned it by contrast with recruiting, where the perishable asset creates urgency for free. In the $29.4M deal, the pilot only turned into a program when it reached a buyer for whom being a first mover was a personal achievement inside a global organization. ROI is built afterwards to back up the emotional driver, not the other way round. ### FOMU: Fear of Messing Up (05:39) **Definition:** The reason most enterprise deals are lost to no decision rather than to a competitor: the buyer isn't afraid of missing out, they're afraid of messing up. Tim cites 85% of enterprise deals being lost to no decision. How the fear shows up depends on culture — at a fast-growing tech company attention is a reward, at a century-old brick-and-mortar business it can be a liability. The counter is to remove fear by showing you've done this many times, not to add pressure. ### Revenue Athletes vs. Chess Players (07:41) **Definition:** High-velocity sellers are revenue athletes: many at-bats, fast learning, losses that don't sting. Enterprise sellers are chess players: strategic, but without natural urgency, so they drift. Recruiting and high-velocity SaaS force urgency because months end and deals die. With an eight-to-eighteen-month cycle, the enterprise team gets lax. Tim's answer is to borrow the athlete's discipline — measure time to NDA, deal-desk turnaround, single- versus multi-threading — and later, via RevOps, to build revenue athletes inside your own organization. ### Diagnosis, Not Prescription (16:38) **Definition:** Take fear out of an enterprise deal by acting as an advisor who has seen this situation many times, rather than prescribing urgency or piling on ROI. Pushing urgency onto a buyer who is afraid of messing up turns the critical moment into an insurmountable one. Signalling experience — every customer before you worried about the same data wrangling — lowers the fear. It's not about more urgency or more ROI; it's about getting to the emotional reason the deal makes sense. ### Stage Three: Say Three Things, Not Twenty (18:20) **Definition:** The pipeline bunches up at the technical deep-dive stage because sellers rush discovery and then hand the buyer everything. Slow down early, earn each stakeholder, and ration information stage by stage. Tim architects access like a chess match: he'll bring in a new person on his side when the buyer brings in someone at a matching level. Before his technical team engages, he tells them what to say — if there are 20 worthwhile things, say no more than three — because once everything has been shown, control passes to the buyer. ### Mutual Close Plan and Power Chart (24:11) **Definition:** Tie the critical event to a date, work backwards through legal and every step to go-live, and turn the buyer's org chart into a power chart of influence and authority. Tim openly tells buyers the date will most likely slip but asks both sides to hold to it. Mapping who has influence and authority, who is the business champion and who has influence without authority — ideally with a colleague — lets him bring matching reference stories and anticipate the legal team's pain before it arrives. ### The Critical-Event Forecast Gate (30:30) **Definition:** No deal enters best case or most likely without a credible compelling critical event. If the event can move by weeks, it counts; if it can move by quarters, it isn't a critical event. Tim assumes enterprise deals slip at least a quarter, discounts deals that haven't slipped yet (for example to a 50% close probability), and distrusts inherited historical cycle data where close-lost rigor was weak. Whatever the methodology — SPICED, MEDDPICC — the critical event must be there, with a real consequence of no action. ### Our Forecast, Not the CRO Show (37:26) **Definition:** Present the enterprise forecast to the executive team as a shared call, asking for their read on each deal, rather than defending it as the CRO's own. Tim has found more success asking colleagues who have been on calls how they would forecast a deal. Doing it collaboratively keeps him from getting defensive when people poke holes. The forecast reflects what sellers reported; there's no reason to take pride of ownership in it. ### The Slack Deal Desk and Internal SLAs (45:23) **Definition:** RevOps as a systems-thinking force multiplier: replace long deal-desk meetings with a Slack approval flow, and measure the seller's own organization — such as legal request response time — not just the buyer. Imubit's deal desk routes commercial, product and services questions to the right approvers before the CEO, with a yes-or-no ping instead of a two-hour weekly meeting and no CPQ. Its head of RevOps proposed trending legal SLA response times, from three days to two, which Tim frames as building revenue athletes inside the company. ### Data Plus Story, With Measurement Gates (52:29) **Definition:** Data without a story gives people nothing to grab onto, and a story without data isn't relevant. Pair them, form several hypotheses, pick the one with the shortest learning cycle, and agree up front on the metric and the time horizon. Tim's example: if 40 to 60% of losses go to no decision, you need theories on why and a quick way to test fixes rather than waiting six months for closed-won. His content experiment was gated first on traffic, then on lead volume. He warns against accepting the first data story or falling in love with your own solution. ### Listener and Scrutinizer Agents (01:03:31) **Definition:** An agent workflow that pairs a listener agent, which proposes updates from recorded calls and messages, with a scrutinizing agent that rejects weak items before anything reaches a human. An Imubit employee built it to replace a collaboration tool, drawing on Otter recordings of internal and external calls and Slack as the company's internal channel. Tim picked it because most bots he builds get switched off for annoying his sales team; the scrutinizer keeps the output quiet enough to keep. ### The TGI Fridays Menu: Less Is More (01:08:15) **Definition:** Curate choices down to a few. Buyers don't want more information; they want to make the right decision. Tim watched TGI Fridays cut a thick menu to two sides with around five items per course, backed by research that too many options stress people out. Applied to sales: send one thing to review instead of twelve, demo three relevant features instead of twenty. Anthony extends it to AI — be intentional and curate, rather than spinning in circles. ## Quotes _Speakers inferred from an undiarized transcript — verify before attributing._ > "When you're selling software, there is no critical event that's naturally aging. So you got to find it within the person you're talking to." > > — Tim Yandel, The LeanScale Podcast Ep. 124 (02:22) > "It was a personal kind of motivation that ended up being like the emotional tenet of driving that deal forward. And then you just back it up with ROI after that." > > — Tim Yandel, The LeanScale Podcast Ep. 124 (04:18) > "In enterprise, 85% of deals don't get closed lost to competitors. They get lost to no decision." > > — Tim Yandel, The LeanScale Podcast Ep. 124 (05:22) > "It's not FOMO, which I'm sure you've heard. It's FOMU, which is fear of messing up." > > — Tim Yandel, The LeanScale Podcast Ep. 124 (05:39) > "If the pipeline is fake, then that's an empty pillow to sleep on." > > — Tim Yandel, The LeanScale Podcast Ep. 124 (15:05) > "I still think very few things signal competence more than speed." > > — Anthony Enrico, The LeanScale Podcast Ep. 124 (15:49) > "It's not about more urgency, it's not about more ROI, that stuff can backfire a lot if you don't get to the emotional driver." > > — Tim Yandel, The LeanScale Podcast Ep. 124 (17:37) > "I don't care what sale you're in, but it's always stage three. It doesn't matter, it's where the pipeline bundles up." > > — Tim Yandel, The LeanScale Podcast Ep. 124 (18:20) > "If you have 20 things in your product that are worthwhile, just say no more than three." > > — Tim Yandel, The LeanScale Podcast Ep. 124 (20:20) > "And when you undervalue your time in the deal, then so will the person you're talking to." > > — Tim Yandel, The LeanScale Podcast Ep. 124 (23:18) > "But if the critical event can move quarters, it's not a critical event. And there's no consequence of no action." > > — Tim Yandel, The LeanScale Podcast Ep. 124 (30:43) > "Yes or no question is the dangerous question." > > — Tim Yandel, The LeanScale Podcast Ep. 124 (32:09) > "It's not the Tim show. It's not the CRO show saying this is my forecast." > > — Tim Yandel, The LeanScale Podcast Ep. 124 (37:26) > "You have more internal selling to do than external selling." > > — Tim Yandel, The LeanScale Podcast Ep. 124 (40:50) > "RevOps has always been my secret weapon, partly because I hate doing RevOps myself." > > — Tim Yandel, The LeanScale Podcast Ep. 124 (44:19) > "The end buyer isn't the only mechanism for measuring RevOps." > > — Tim Yandel, The LeanScale Podcast Ep. 124 (47:03) > "If you're on a $20 million plan and assume you have enough pipeline to feed it, if you can increase your conversion rate by five points, that could mean another $5 million into your overall year." > > — Anthony Enrico, The LeanScale Podcast Ep. 124 (51:27) > "If you have the story with no data, then there's no story that's relevant. If you have the data without the story, then you don't have anything that people kind of grab onto." > > — Tim Yandel, The LeanScale Podcast Ep. 124 (52:29) > "As much as we want more information, we don't actually want more information. We just want to make the right decision." > > — Tim Yandel, The LeanScale Podcast Ep. 124 (01:09:14) > "Dive as deep as you can, but not so deep that you forget what the job you're supposed to be doing." > > — Tim Yandel, The LeanScale Podcast Ep. 124 (01:12:11) ## Practical advice by role ### Sales Leaders - Make finding the buyer's personal critical event — promotion, first-mover status, or the risk of being replaced — the explicit goal of discovery. - When a buyer is stalling out of fear, stop adding urgency or ROI; show them you've run this exact deal before. - Turn around NDAs and proposals same-day or next-day; speed signals competence even when it doesn't move the close date. - Spend longer in discovery and ration information: brief your technical team to say no more than three things. - Build a mutual close plan backwards from the critical event, and say out loud that the date will probably slip. - Map the buyer's org chart into a power chart with a colleague before deciding who to bring in next. - Ask about prior approvals of a deal this size as an open question, never as a yes-or-no. - Close-lost the deal that needs "a couple more quarters," and run a retro on why. ### RevOps Leaders - Track single- versus multi-threading and the number of engaged buyer contacts; Tim sees eight-plus as a strong signal for moving past stage three. - Measure internal cycle times — NDA turnaround, deal-desk approval, legal response — and trend them month over month. - Replace long weekly deal-desk meetings with an approval flow in Slack that routes each part of a deal to its owner. - Don't trust inherited cycle-time data until you know whether close-lost discipline existed. - For every change, agree the metric, the gate, and the time horizon before you start; pick the hypothesis with the shortest learning cycle. - Aim for small stage-by-stage improvements; 1% per stage per quarter compounds. ### Revenue Executives - Forecast as if every enterprise deal slips at least a quarter, and discount deals that haven't slipped yet. - Require a credible compelling critical event before any deal enters best case or most likely. - Bring a story with the data to the board — cohorts, slippage-adjusted probabilities, and the reasoning behind them. - Present the forecast as the executive team's call and invite challenge rather than defending it. - Deliberately involve executives matched to the buyer's people; a big deal closed by one person should worry you. ### Founders - Structure first deals as small, fast pilots designed from day one to expand, instead of waiting 18 months on a large land. - Treat sales-cycle compression as an enterprise-value lever: closing in December rather than March can change the growth rate you fundraise on. - Give RevOps a strategic seat; treated as data wranglers, that's all you'll get. - Create an internal place for employees to publish the agents and skills they build so others can reuse them. ### Marketing Leaders - Gate content experiments step by step — traffic first, then lead volume — so each result tells you what to change next. - When traffic rises but leads don't, look at content quality and the call to action before abandoning the channel. - Send one piece of follow-up material, not twelve; curation gets read. ## AI takeaways **Thesis:** Tim sells AI and uses it heavily internally, but his message is about curation: AI works when it supports a few important jobs, and fails when it multiplies noise, open sessions and work nobody asked for. - **** — - **** — - **** — - **** — - **** — - **** — **Agent & automation ideas** - A listener agent over call recordings and Slack that drafts task and status updates, paired with a scrutinizer agent that rejects low-value items before anything posts. - A Slack deal-desk agent that routes each part of a deal to its approver and returns a yes-or-no request with only the context that approver needs. - A forecast-review agent that reads call transcripts for buyer and champion language and flags deals with no credible critical event or a critical event that can move by quarters. - An internal-SLA tracker that measures response times on legal and deal-desk requests and reports the monthly trend. ## Operations takeaways ### Revenue operations - **.** - **.** - **.** - **.** - **.** - **.** ### Pipeline & marketing ops - **.** - **.** - **.** - **.** - **.** ## Metrics mentioned | Value | Metric | Context | | --- | --- | --- | | $29.4M | Largest deal closed | A contract with a German global manufacturer that started as a $20K pilot; Tim rounds it to $30 million. | | $20K | Starting pilot | The small pilot to prove the computer vision and data labeling technology worked, which surfaced the bigger problem. | | 85% | Enterprise deals lost to no decision | Tim's figure for enterprise deals that are lost to indecision rather than to a competitor. | | 40–60% | Losses due to no decision | Tim's example of a data point that needs a story and a fix, not just a slide. | | 8–18 months | Enterprise sales cycle | The cycle length that lets enterprise teams get comfortable; Tim has taken over teams reporting 18–24 months because they never closed deals out. | | 12 months to 9 months | Cycle compression example | Anthony's example: pulling deals into this year can move a fundraise from an 80% growth rate to 2x, worth potentially tens of millions in valuation. | | 8+ | Engaged buyer contacts | Engaging eight or more people in a deal sharply raises the likelihood of moving from stage three to stage four. | | $100K+ | Scrutiny threshold | Above this, a deal gets scrutinized; at millions there's a committee to prepare for. | | 50% | Close probability for a deal that hasn't slipped | Tim's example of discounting a deal in a board forecast based on prior-quarter slippage. | | 3 days to 2 days | Legal request response time | The kind of internal SLA trend Imubit's head of RevOps proposed measuring. | | 1% per stage per quarter | Stage improvement compounding | Across a seven-stage process, incremental quarterly gains add up to significant impact over a year. | | +5 points ≈ +$5M | Conversion lift value | Anthony's example on a $20 million plan with enough pipeline to feed it. | | 10–15 pieces a week | Content experiment volume | Short content pieces Tim's marketing team ran for a month; traffic rose, lead volume did not. | | 1 call to 2–3 calls, 60-day horizon | Discovery extension | An example change with an agreed time horizon for seeing its effect. | | $500K to $1M+ per year | Imubit license value | Per the show notes, Imubit's deals in license alone. | ## Entities mentioned - **Imubit** (company) — Tim's current company, which sells closed-loop AI process optimization to refineries and chemical operators at half a million to over a million dollars a year in license. It is a global hybrid company that communicates internally only through Slack, records calls with Otter, doesn't use its own product for go-to-market, and runs an internal app store where employees publish the agents they build. Its head of RevOps built the Slack deal desk. · https://www.leanscale.team/knowledge/company/imubit/ - **Sama** (company) — Where Tim ran global sales in computer vision and data labeling, according to the show notes. The $29.4M deal he describes was a computer vision and data labeling deal: a $20K pilot with a German global manufacturer, maker of everything from refrigerators to car parts, that needed to keep pace with competitors on self-driving components. · https://www.leanscale.team/knowledge/company/sama/ - **Regrow** (company) — Where Tim was CRO, selling carbon verification into Nestlé and Unilever, according to the show notes. Not discussed in the conversation itself. · https://www.leanscale.team/knowledge/company/regrow/ - **TGI Fridays** (company) — Where Tim worked as a server in college, during a rebrand that cut a thick menu to two sides — drinks and food, around five items each — on research that too many options stress guests out. He uses it as his model for curating what buyers see. · https://www.leanscale.team/knowledge/company/tgi-fridays/ - **The Cheesecake Factory** (company) — The byword for a menu with too many options — Tim compares TGI Fridays' old menu to it, and Anthony says those menus stress him out. · https://www.leanscale.team/knowledge/company/cheesecake-factory/ - **DocuSign** (company) — The signature request everyone refreshes at the end of a stalled deal; the example of what happens after a seller has handed the buyer everything and has nothing left to do. · https://www.leanscale.team/knowledge/company/docusign/ - **LeanScale** (company) — Anthony's company. He cites having run RevOps at three companies and LeanScale engagements with hundreds more as the source of his belief that small conversion and time-in-stage improvements add up quickly. · https://www.leanscale.team/knowledge/company/leanscale/ - **Tim Yandel** (person, guest) — · https://www.leanscale.team/knowledge/guest/tim-yandel/ - **Anthony Enrico** (person, host) — Co-founder of LeanScale and host of The LeanScale Podcast. · https://www.leanscale.team/knowledge/guest/anthony-enrico/ - **Slack** (tool, Team Messaging) — Imubit's only internal communication channel as a global hybrid company, and the home of its deal desk: a Slack flow that routes commercial, product and services questions to approvers and pings Tim with approve yes or no, replacing two-hour weekly meetings. - **Gong** (tool, Revenue Intelligence) — One of the conversation-intelligence tools Tim has used for forecasting — reading buyer and champion language directly rather than relying on a rep's happy ears. - **Otter** (tool, Conversation Intelligence) — Records Imubit's internal and external calls; the listener agent in the employee-built collaboration workflow draws on those recordings. Tim also names it alongside Gong as a forecasting input. - **Claude** (tool, AI Assistant) — Tim says he's in Claude more hours than he cares to admit, building things he wouldn't otherwise know how to; Anthony uses it to run a short list of daily processes well. - **OpenClaw** (tool, AI Agent) — Anthony says he was one of the first on it, with a server rack of Mac minis at home — the peak of the phase he later pulled back from. ## FAQ **Q: How do you find a critical event in an enterprise software deal?** A: Tim Yandel, CRO at Imubit, points out that software has no natural deadline, unlike recruiting, where a candidate on the market is a perishable asset. The seller has to find the critical event inside the buyer, and the one that moves deals is usually personal: a promotion from being a first mover, or the risk of being replaced by someone who does innovate. In his $29.4M deal, a $20K pilot became a program once it reached a buyer whose career depended on it. The ROI case was built afterwards to back that up. For forecasting, a real critical event carries a consequence of no action. If it can move by quarters, it isn't one. **Q: Why do most enterprise deals end in no decision?** A: Tim Yandel says about 85% of enterprise deals are lost to no decision rather than to a competitor, and the cause is fear of messing up, or FOMU. At a large, traditional company, attention can be a risk rather than a reward, so doing nothing feels safest. Adding urgency or more ROI tends to add fear and make things worse. What helps is diagnosis rather than prescription: acting as an advisor who has run this deal many times, knows the buyer's worries, and can show how other customers got past them. **Q: How should you forecast large enterprise deals?** A: Assume every enterprise deal slips at least a quarter, and when forecasting to a board, assume a deal that hasn't slipped yet will. Tim Yandel keeps deals out of best case and most likely unless there is a credible compelling critical event, and doesn't trust inherited historical cycle data if close-lost discipline was weak. He reads buyer and champion language in call recordings rather than relying on rep optimism, discounts probabilities using prior-quarter slippage, and presents the result to the executive team as a shared forecast, inviting their challenge. **Q: How do you ask a buyer whether they've approved a deal this size before?** A: Don't ask it as a yes-or-no question; Tim Yandel calls that the dangerous question. Assume experience and ask them to tell the story instead: I'm sure you've closed deals like this before, so what was the last process of similar size like, and what did you learn? If nothing comes to mind, it's their first one, which is fine. Treat it as a journey you're on together. The answer tells you whether you need to build the business justification with them. That matters because deals over about $100K get scrutinized, and multi-million-dollar deals go to a committee. **Q: Why do enterprise deals stall at stage three?** A: Stage three is usually the technical deep-dive, and deals stall there because sellers rush discovery to reach it and then show the buyer everything at once. After that the buyer has all the information and the seller has lost control. Tim Yandel recommends going slow to go fast. Spend more time in discovery finding the pain and the critical event. Earn access to each new stakeholder. Tell your own technical team what to say: if the product has 20 worthwhile things, mention no more than three. **Q: What is the best way to use RevOps in an enterprise sales motion?** A: Use RevOps as a systems-thinking partner and force multiplier, not as data wranglers. At Imubit, Tim Yandel's head of RevOps replaced two-hour weekly deal-desk meetings with a Slack flow. It routes commercial, product and services questions to the right approvers, and Tim gets a simple approve-yes-or-no ping. The team also measures response time on internal requests such as legal, and tracks the trend from three days to two. The end buyer isn't the only thing RevOps can measure, and improving the seller's own internal speed makes the customer's buying experience predictable. **Q: How can AI agents in Slack avoid becoming noise?** A: Add a filtering step before anything reaches people. At Imubit, an employee replaced a collaboration tool with two agents. A listener agent draws on recorded calls and Slack and proposes task and status updates. A scrutinizing agent then rejects the weak items before anything posts. Tim Yandel says he switches off about half the bots he builds because they annoy his sales team, and this pairing is what kept one running. More generally, he says to curate: pick a few important jobs for AI to do well, not dozens of outputs nobody acts on. ## Timeline - **00:00** — Cold open + intro - **01:08** — Recruiting to software: the perishable asset - **02:57** — The $20K pilot that became a $30M deal - **05:19** — It's not FOMO, it's FOMU — deals lost to no decision - **07:12** — Revenue athletes vs. chess players - **16:18** — Diagnosis, not prescription — why urgency backfires - **17:58** — Stage three is where deals stall - **27:43** — Forecasting when every deal slips - **30:30** — What actually counts as a critical event - **31:36** — "Have you approved a deal this size before?" — how to ask it - **40:44** — More internal selling than external selling - **44:11** — RevOps as a force multiplier: the Slack deal desk - **46:29** — Measuring internal SLAs and building revenue athletes inside - **48:56** — Baseball, Moneyball, and the long season - **51:51** — The data and the story - **55:14** — Leading indicators and measurement gates - **01:01:18** — AI in go-to-market: the internal app store and the scrutinizer agent - **01:08:15** — The TGI Fridays menu and why less is more - **01:14:00** — Wrap ## Related episodes - **Ep. 80: Why Enterprise AI Deals Die After the Buyer Says Yes** (Scott Sinatra (Wisq)) — Another CRO on how enterprise AI deals stall inside the buyer's organization — the no-decision risk Tim traces to fear of messing up. · https://www.leanscale.team/knowledge/podcast/scott-sinatra-ai-sales-trap/ - **Ep. 81: Sell to the Blocker, Not the Champion** (Leigh Gross (Synctera)) — A different angle on mapping power in an enterprise deal, alongside Tim's org-chart-to-power-chart exercise and the champion with a personal stake. · https://www.leanscale.team/knowledge/podcast/leigh-gross-compliance-killed-my-deal/ - **Ep. 6: Why Your Forecast Is Broken** (Anthony Enrico (solo)) — Anthony's own case on forecast discipline, which Tim's critical-event gate and slippage-adjusted probabilities put into practice for enterprise deals. · https://www.leanscale.team/knowledge/podcast/why-your-forecast-is-broken/ - **Ep. 88: Why AI Won't Close Your Biggest Deals** (Michael Kiernan (Nextdoor)) — A CRO's view that the largest deals are won through human judgment and relationships — the same thing Tim describes in finding the personal motivation behind a $29.4M contract. · https://www.leanscale.team/knowledge/podcast/michael-kiernan-nextdoor-ai-wont-close-deals/ - **Ep. 77: RevOps Is Your Secret Weapon: From Order-Taker to Strategic Advisor** (Pete Shelton (Fullcast)) — Tim uses the same phrase for RevOps and makes the same argument: treat it as a strategic thought partner, not data wranglers. · https://www.leanscale.team/knowledge/podcast/pete-shelton-revops-secret-weapon/ - **Ep. 27: Hypothesis-Driven RevOps: Operate Like a Top-Tier Consultant** (Pratz (Origin)) — The method behind Tim's advice to form several hypotheses, pick the shortest learning cycle, and agree the metric and time horizon before testing. · https://www.leanscale.team/knowledge/podcast/pratz-hypothesis-driven-revops/ - **Ep. 34: Pipeline Is a Vanity Metric** (Guy Rubin (Ebsta)) — Goes with Tim's view that a fake pipeline is an empty pillow to sleep on, and that deals asking to wait quarters should be closed out. · https://www.leanscale.team/knowledge/podcast/guy-rubin-ebsta-benchmark-report/ ## Full transcript _Machine-transcribed and not diarized; speaker attribution is inferred._ _Transcript only, as a separate file: https://www.leanscale.team/knowledge/podcast/tim-yandel-imubit-20k-pilot-30m-deal/transcript.md_ ### 00:00 — Cold open + intro **[0:00]** My guest today is Tim Yandell, Chief Revenue Officer at Inubit. **[0:04]** What makes Tim worth listening to is that he has run both, **[0:07]** and he is blunt about the trap hiding inside the strategic sale. **[0:11]** You don't have anything that people kind of grab onto. **[0:13]** So connecting the two is really the job. **[0:15]** I rounded up the 30 million from 21. **[0:17]** I'm just kidding. **[0:18]** But it was actually 29.4 million. **[0:20]** When you're fundraising and doing things like that, **[0:23]** the difference between an 80% growth rate and 2Xing **[0:26]** is potentially worth tens of millions to your evaluation. **[0:29]** So it's not a small thing to say, hey, we close this in December versus March. **[0:35]** What's the big deal? **[0:36]** You have the chiseled revenue athlete, **[0:39]** and then you have the more of the chess player, **[0:41]** or if you will, it might be lazy and fat behind the chessboard, **[0:45]** but very strategic mentally. **[0:47]** I know I have like 18 sessions open right now, **[0:50]** but am I actually doing anything productive? **[0:53]** Am I actually moving the needle forward? **[0:55]** Dive as deep as you can, **[0:57]** but not so deep that you forget what the job you're supposed to be doing. ### 01:08 — Recruiting to software: the perishable asset **[1:08]** Tim, walk me through how you went from recruiting to closing a-- **[1:12]** I can't believe I'm going to say this number-- **[1:14]** a $30 million deal and what you had to do differently in that type of sale. **[1:22]** Yeah, thanks for having me. **[1:23]** I'm looking forward to discussing a little bit more. **[1:25]** I rounded up the $30 million from '21. **[1:27]** I'm just kidding, but it was actually $29.4 million, **[1:32]** but I did do a little rounding. **[1:33]** $30 million sounds a little bit better than that. **[1:36]** The journey was a lot of discovery on not only just closing a big deal, **[1:41]** but just the difference in solution selling, **[1:44]** which is in the recruiting side of things, **[1:46]** more of the consultive type of work into you're selling not a person, **[1:50]** but an actual product. **[1:53]** And so a lot of learnings there in particular, **[1:58]** but one in particular is when you're in recruiting, **[2:01]** you have a perishable asset, if you will. **[2:03]** You have someone that's on the market for a period of time **[2:06]** and they're going off the market. **[2:08]** And so you have this natural critical event **[2:11]** that surfaces from all your deals that you do. **[2:15]** The longer you take, the more that Anthony is looking for another job **[2:19]** and he changes his mind and this is logic sense. **[2:22]** When you're selling software, **[2:24]** there is no critical event that's naturally aging. **[2:26]** So you got to find it within the person you're talking to. **[2:30]** And once you find it, which is really, really the point of enterprise sales, **[2:35]** you continue to ensure that you're reminding **[2:38]** and you're kind of surfacing all of your conversations around that event. **[2:42]** So that is one of the big things that drives enterprise sales in particular, **[2:49]** but also just software sales in general and difference on that. **[2:53]** Ultimately, that was kind of the conversation that led to the $30 million deal. ### 02:57 — The $20K pilot that became a $30M deal **[2:57]** It started on a pilot, which was a small 20K pilot to prove out the technology is working. **[3:05]** And then it started to kind of surface the bigger problem in particular. **[3:08]** And this one was with a global manufacturing company **[3:12]** that makes all types of products from refrigerators to car parts located in Germany. **[3:16]** You could probably close down on who that could be. **[3:23]** But it was specifically computer vision and data labeling in particular. **[3:28]** And one of the pricing items that they needed to do **[3:30]** was relevancy in the manufacturing space. **[3:32]** So they didn't get outpaced by the competitors' parts on self-driving components in cars. **[3:39]** And so it turned into like a science project at first, **[3:44]** which is, "Hey, let's test out this cool technology." **[3:46]** But once it got to the right person with the right message of, **[3:50]** "Do you want to be a first mover on this, or do you want to be a fast follower?" **[3:56]** And the benefits of a first mover, because they could answer either way. **[4:00]** The benefits of a first mover was clearly outweighed why. **[4:03]** And it turned to be more of a personal kind of achievement **[4:07]** for the person we were dealing with **[4:08]** on how they are going to get promoted within their global organization. **[4:11]** And so it's not just a critical event of, **[4:14]** "Hey, if we don't do this, then my budget gets pushed naturally." **[4:18]** It was a personal kind of motivation that ended up being **[4:21]** like the emotional tenet of driving that deal forward. **[4:24]** And then you just back it up with ROI after that. **[4:26]** But that personal kind of critical event is pretty key. **[4:29]** It's very hard to find. **[4:30]** And then kind of bringing it back into the recruiting angle, **[4:33]** personal motivation is what every decision is made out of, **[4:37]** whether your software or services or recruiting. **[4:41]** And so rooting that out and kind of marrying it between all of them is pretty key. **[4:45]** I think you uncovered something I never really heard articulated that way, **[4:49]** where oftentimes these big enterprise deals are massive career movers for people. **[4:56]** And if you do a good job and you get implemented quickly **[4:59]** and show the value that you know your solution can show, **[5:02]** that can expedite their promotion within the organization. **[5:06]** And I think that's a huge level. **[5:08]** I've seen that happen a ton of times with products that I have supported **[5:12]** in the enterprise phase, where that person becomes a hero **[5:16]** once they do a full implementation and it goes successful. ### 05:19 — It's not FOMO, it's FOMU — deals lost to no decision **[5:19]** It could go the other way too. **[5:21]** Could go the other way too. **[5:22]** And I think that in enterprise, 85% of deals don't get closed loss to competitors. **[5:31]** They get lost to no decision. **[5:34]** And the reason why deals get lost for indecision **[5:39]** is because it's not FOMO, which I'm sure you've heard. **[5:44]** It's FOMO, which is fear of messing up. **[5:47]** And when you're selling to these large organizations that are traditional in nature, **[5:53]** my motivation at a fast growing technology company **[5:58]** to get exposure and attention is very different **[6:01]** at a brick and mortar company that's been around for hundreds of years, **[6:05]** where it's almost the opposite. **[6:07]** Attention isn't a good thing, and it depends on the culture as well. **[6:12]** So it's not always a promotion. **[6:14]** Sometimes it's like, if you don't do this, if you don't innovate, **[6:18]** you might actually get replaced by someone who does. **[6:20]** Like an outsider coming in, like a digital nomad coming from another industry **[6:25]** into your safe zone. **[6:27]** So if you're not pushing yourself, it's the other way around, right? **[6:30]** So it's all what resonates with the individual. **[6:32]** But I guess the key is find out what that root cause of personal motivation **[6:38]** and emotional driver is with the right person. **[6:42]** And that's kind of like finding your champion, **[6:45]** because you can do that at someone at the wrong level and does nothing. **[6:48]** But once you do that, then it's no longer your deal. **[6:52]** It's their deal. **[6:53]** It's their decision. **[6:55]** And you're just here to help them out and making sure that they're doing **[6:58]** all the steps necessary to get the deal done. **[7:01]** Yeah. It's like you get on the same team as them presenting it to the organization. **[7:05]** I think whenever you can build that type of relationship, **[7:09]** they can help move those along quicker. **[7:11]** Yep. Yep. ### 07:12 — Revenue athletes vs. chess players **[7:12]** One of the things you're talking about during our prep session, **[7:15]** you described salespeople who are in high velocity motions. **[7:20]** And I would put recruitment in there absolutely as a high velocity motion, **[7:24]** plus the urgency on both sides of the marketplace that you're running. **[7:28]** You say they turn into revenue athletes. **[7:30]** So, Juan, I would love for you to define what does a revenue athlete look like, **[7:35]** and then apply that mindset that you can pick up there and bring to the enterprise world. **[7:41]** Yeah. If you think about high velocity teams, **[7:46]** the month ends, the deals go, some of them die, some of them win. **[7:50]** You learn something with every interaction. **[7:52]** They're quick, iterative. **[7:54]** You just have more at bats to refine. **[7:57]** And almost like the losses don't hit as hard. **[8:00]** The wins don't mean as much as well. **[8:03]** But it's like the drug. **[8:05]** You get the dopamine hits and you get that going. **[8:08]** And so, I mean, the bullpen environments, **[8:12]** that's why I have music in the background. **[8:14]** I grew up in that environment. **[8:15]** The more stimulation, the better. **[8:18]** But in an enterprise, you don't have as many at bats, **[8:21]** and you don't have a lot of lessons to learn from. **[8:24]** And then, arguably, if you wait to win loss, it's so long. **[8:30]** If your sales cycle's eight months to 18 months, then how fast are you learning? **[8:36]** And then if you're also kind of holding on the deals **[8:38]** that are already lost because of indecision, **[8:40]** the buyer just doesn't want to tell you that they're not going to go with you. **[8:43]** They're just kicking the can down the road. **[8:46]** You end up kind of lying to yourself. **[8:48]** So, yeah, revenue athletes are the ones who are, **[8:51]** they don't take it personally, they're machines, right? **[8:53]** They're just chiseled and they're ready to go. **[8:58]** But they're also not very strategic in nature because of that. **[9:02]** There's no reason to be. **[9:03]** I'm not saying that high-velocity teams are dumb by any means, **[9:07]** but there's pros and cons. **[9:10]** You have the chiseled revenue athlete, **[9:13]** and then you have the more of the chess player, **[9:15]** or if you will, there might be lazy and fat behind the chess board, **[9:19]** but very strategic mentally. **[9:22]** So, I think that to avoid that, you have... **[9:26]** Well, the problem in that is you don't have the urgency **[9:30]** that a high-velocity seller would have naturally, **[9:33]** and you kind of can rest on your laurels. **[9:34]** And as an organization, you kind of sit back on your heels a bit **[9:38]** because you have time. **[9:39]** Like, "Oh, we didn't get the proposal out on Friday." **[9:41]** Well, it's okay. **[9:42]** We can get it next week. **[9:44]** The deal's not going anywhere because we have an eight to 18-month sales cycle. **[9:48]** So, you end up getting lax on that point. **[9:52]** But I'd argue that, especially this day and age, **[9:55]** when you're selling an AI solution, of course, **[9:58]** but when there's so much innovation happening outside, **[10:02]** it's not just hitting high-velocity low-sale cycle products. **[10:06]** It's also coming to the enterprise. **[10:08]** If it's not evident, it's going to be evident very soon. **[10:11]** And so, if you're not ready for prime time, **[10:14]** speed is going to come to you whether you like it or not. **[10:17]** And so, looking at things like how fast does it take to you to get an NDA out? **[10:23]** How fast does it take internal deal-desk conversations to happen? **[10:28]** When you look at different metrics you can learn from, **[10:30]** from a revenue ops perspective, **[10:32]** how many times are we single-threaded versus multi-threaded? **[10:35]** Are we at the right level? **[10:36]** You can have several conversations in a week with a deal **[10:41]** that doesn't move from stage to stage, **[10:43]** but now it's likelihood to move from stage three to stage four goes up highly **[10:49]** because you've engaged eight-plus buyers or eight-plus people in that process. **[10:54]** So, I think it's all like different tells that you can look from in the data. **[10:59]** And it kind of comes down to what are you really looking at for efficiency? **[11:03]** And why you should never accept that it's strategic sales. **[11:06]** So, let's just go the old-fashioned way and whiteboard things **[11:10]** and just wait for things to come to us. **[11:13]** You still have to make sure that you're up to snuff mentally **[11:15]** and then also physically with the athlete analogy coming back. **[11:21]** Well, and I think a lot of companies don't realize the opportunity that they can capture. **[11:26]** Let's take that 12-month sales cycle type of deal. **[11:31]** If you can compress that to nine months, **[11:33]** you can make sure you close even more deals within this year **[11:37]** versus it slipping into the next. **[11:39]** And then that's stacked up onto your growth rate for that particular year. **[11:43]** When you're fundraising and doing things like that, **[11:45]** the difference between an 80% growth rate and 2Xing **[11:49]** is potentially worth tens of millions to your evaluation. **[11:53]** So, it's not a small thing to say, **[11:55]** "Hey, we close this in December versus March. What's the big deal?" **[11:59]** No, it is a big deal. **[12:00]** It's a huge deal for your enterprise value. **[12:03]** And as you know, the longer you let things just wait, **[12:06]** the less likely it are to close to. **[12:08]** And then your mechanism is not just... **[12:11]** It's not land, really, because your addressable market with your big logos is great. **[12:15]** But the days of closing $30 million land deals, **[12:19]** it's few and far between. **[12:20]** Those land deals, even the one I just told you, was an expand deal. **[12:24]** If you count pilot as a land, right? **[12:27]** And the most important thing is what kind of expansion flywheel are you building? **[12:32]** And so, the time to close, it doesn't have to be like... **[12:35]** Maybe it's 18 months because you're asking for too much upfront. **[12:39]** Maybe you can close something in 90 days and have like, **[12:43]** as opposed to 500k pilot or first year deal, you do a 20k pilot. **[12:49]** And in that 20k pilot, you automatically set them up **[12:51]** for an expansion into a $5 million deal because of that. **[12:55]** So, it's all about how you break up your own sales process **[13:02]** and just try things and be creative with things **[13:05]** to see what works for the buyer you're selling to. **[13:09]** Which is an interesting thought because if you land smaller, **[13:13]** I'm certain the conversion rate of that bigger deal **[13:17]** is going to be much, much higher if you have an opportunity to prove it out. **[13:21]** And that should be moved up forward **[13:24]** than if you tried to land the entire thing in the first go. **[13:28]** So, I think that land and expand motion in the enterprise world. **[13:32]** Seeing how you can build that in not only helps you close a little bit early, **[13:37]** but even the big deal that you have in your head of what it should be, **[13:40]** that should expedite that potential and improve the conversion rate too. **[13:44]** Yeah, absolutely. **[13:45]** And it has some semblance of can you get a higher velocity learning moment at least. **[13:53]** Having some discipline of saying like, if we're talking **[13:57]** and you're buying what I'm selling and you say, this sounds great Tim, **[13:59]** but I need a couple more quarters for whatever reason. **[14:05]** And so I'm like, okay, sounds good. **[14:08]** So what's your next, I mean, obviously I'm going to try to convince you not to wait, **[14:11]** but are you close, you should close loss that deal. **[14:15]** It's dead, right? **[14:16]** Because it's two months or three months or two quarters, whatever it might be. **[14:20]** That's a learning moment. **[14:21]** So how do we, so the point is, it's like learning close loss. **[14:25]** And so it gives attention to the actual, you know, **[14:29]** you know, retro of what you could have done to made you not want to wait two quarters **[14:35]** and having those moments where you can have some sort of a recognition and learning in earlier ways. **[14:42]** But a lot of enterprise, I mean, I've done this taking over enterprise teams **[14:47]** and they have just this, their sales cycle is 18, 24 months, **[14:52]** but that's only because they don't have the rigor of actually closing things **[14:55]** when they should be closed, right? **[14:56]** They just kind of hold onto these weird things and their pipeline meetings. **[14:59]** And I don't know if it's like a pillow that helps them sleep at night **[15:03]** or something like that with their big, huge pipeline. **[15:05]** But if the, if the pipeline is fake, then that's an empty pillow to sleep on, right? **[15:12]** I don't know if some reps understand how easy it is to see through all of that. **[15:17]** And nobody goes to president's club on their pipeline. **[15:20]** Yeah. **[15:20]** So you might as well close it out, keep it clean and then focus **[15:23]** on the things that matter and can actually close. **[15:25]** Yeah. Yeah, I agree. **[15:28]** What one thing on the speed too, I'm wondering your perspective on this. **[15:33]** Let's assume, Hey, it's going to take 12 months **[15:36]** and these little bottlenecks of the NDA, the proposal, scoping out the, **[15:41]** the POC, if there is one or something like that. **[15:43]** Let's assume that doesn't ultimately move the needle on the closed date. **[15:49]** I still think very few things signal competence more than speed. **[15:55]** So when somebody asks you for a proposal and you can get it to the same day or next day, **[16:01]** or somebody asks for the NDA and you ship it right away or get it turned around right away. **[16:05]** I think even just the perception of your company's ability to execute on whatever **[16:12]** you're trying to sell could really be elevated if you run the process **[16:16]** really professionally and have speed baked up. ### 16:18 — Diagnosis, not prescription — why urgency backfires **[16:18]** Yeah. Well, I think what do you, what are you signaling with that? **[16:23]** I've done a lot of deals like this. You're not the only one, you know, **[16:28]** and I will help you in that back to that same point of fear of messing up. **[16:33]** It becomes less of a fear if I'm dealing with someone who's done this many times **[16:38]** and it's about diagnosis and it's not about prescription. **[16:42]** It's like, I know exactly what you're going through. **[16:45]** I've done it before. I can spend more time, you know, and I'm not going to have to push you **[16:50]** because it's okay, you're going through this stuff, so have all the other 10 other customers **[16:55]** before you, worried about data wrangling or not being perfect or whatever it might be. **[17:01]** And so that ends up being like, you end up kind of taking fear away from the deal. **[17:07]** And so I would actually say if you end up, if you don't do that and if you get into **[17:12]** advisor mode where it's not about me, it's about you, and then you push urgency, **[17:19]** you're actually just pushing more fear onto the person who doesn't want to make a decision. **[17:25]** And that critical moment becomes this like unsurmountable, like fear moment that they **[17:31]** just can't get past. And so you end up kind of perpetuating a little bit of the problem **[17:37]** because of that. So I would say it's like, you know, it's not about more urgency, **[17:43]** it's not about more ROI, that stuff can backfire a lot if you don't get to the emotional driver **[17:51]** of why this deal or why you, why us, why it works, and it makes sense in an emotional way, ### 17:58 — Stage three is where deals stall **[17:58]** not just a rational one. Are there any tactical or practical areas in the sales cycle in that **[18:06]** enterprise world that you think, systemically, some of these companies just are so slow **[18:12]** at doing X, Y, or Z that you think you could come up, come in and just speed some of those up? **[18:20]** Yeah, I think that stage three, you know, I don't care what sale you're in, **[18:25]** but it's always stage three. It doesn't matter, it's where the pipeline bundles up. **[18:32]** But in all seriousness, it's like, I think people rush the first stage is usually discovery call, **[18:40]** second stage is a demo of the product itself, stage three is like when it's getting into **[18:45]** the real stuff, right? And there's always this obsession where, you know, moving from stage one **[18:52]** to stage two to stage three, as quickly as possible, speeds up the deal. When it's not **[18:59]** necessarily the case where you spend more time on discovery, and less time on like the later stages, **[19:05]** you know, that's really what matters, to kind of, you know, go slow to go fast kind of thing, **[19:11]** and setting that up, where you have so many moments of that you can skip through and just **[19:17]** really find that pain point, finding that critical event at the beginning, why should you actually **[19:23]** get more stakeholders involved? Because the moment you get more stakeholders involved on your side, **[19:28]** the more you get kind of out of control of what is actually being said in the narrative, and **[19:32]** potentially wasting a lot of other people's time as well. So you're almost protecting not only their **[19:37]** time, but you're architecting the deal of like, of I want you to speak to this person, and you've **[19:42]** earned the right to speak to them, as long as you bring in another person that you want to speak to **[19:47]** that matches a little bit of the leveling as well. And so it's a little bit of that chest match back **[19:52]** and forth of architecting the flow of that. And once it's out of your hands as a seller, and given **[19:57]** into like the technical side of your organization, you get a lot of folks internally that can, you **[20:03]** know, crap on your deal before you get that further, then you have to have your stuff ready to go to **[20:09]** get exposed internally to say not only why should we spend time with it, why should you spend your **[20:14]** time with a technical persona internally? And how can you convince how can what do I want you to **[20:20]** actually say, say these three things, don't say these 20 things, right? These are the if you have **[20:25]** 20 things in your product that are worthwhile, just say no more than three. And these are the **[20:30]** three things I want you to focus on. And you know that because you've already done your discovery **[20:35]** ahead of time. So I don't know, I think that that's probably the stage that things stick, **[20:41]** because once you show everything, then you basically gave everything to the person you're **[20:47]** talking to that. So that third stage or that technical stage where you're getting more deep **[20:51]** dive is pretty crucial, because then you pretty much are giving a lot of the control over to **[20:56]** the buyer at that point in time, because they know everything about your product. And now it's up to **[21:00]** them. You know, so piecemealing information at the right stage in the right time is pretty critical. **[21:08]** I think that's an interesting way to think about it, like intentionally titrating the process out **[21:13]** a little bit. So that way, you can keep the engagement throughout, because I have seen this **[21:19]** happen too. And I think it's what you're alluding to, like you do an amazing presentation, amazing **[21:24]** technical review. And then there's going to be a three month process where there's really nothing **[21:28]** left for you to do. And we're just waiting for decision time, if they're doing technical reviews, **[21:32]** or whatever red tape they have to go through internally. And then if you're not manufacturing **[21:37]** ways to engage in a relevant way, I think it could really lose the momentum along the way, **[21:45]** let alone what other like booby traps are going on behind the scenes on their side, the person, **[21:51]** your point of contact leaves, new initiatives happen, who knows what could happen. So I think, **[21:57]** I don't know if you've seen where, okay, we have to manufacture some engagement and urgency, **[22:02]** you end up having to do that with what information you think is applicable to the person, you know, **[22:08]** so and and the people and multi threading. And you have to figure out ways to keep the conversation, **[22:14]** you know, relevant. Otherwise, you're just kind of I've never had I've never had a deal where you **[22:19]** just say, okay, they have everything they need. And you haven't talked to them and in more than **[22:27]** 30 days, and the deal as promised, comes in, you know, on time, your inbox and DocuSign is there. **[22:34]** Yeah, it's like I've been refreshing the DocuSign link for every single day. Don't worry. There's **[22:39]** nothing else we can do. I mean, that's it. You get that from forecast calls with, with salespeople, **[22:44]** because it's like they've run out of ideas. You like because you gave them everything, you know, **[22:50]** you've lost completely control of your deal. And you give that power to folks, because you just **[22:54]** want to answer everything, all their questions, you know, and you're more on the receiving end, **[22:58]** as poor as you're not driving the deal at all. So and you missed that whole point, you missed that **[23:04]** whole, that moment you can play into doing deals, especially critical ones, you miss it because you **[23:11]** just undervalued your time at the beginning of the sales process by trying to get to the technical as **[23:18]** quickly as possible. And when you undervalue your time in the deal, then so will the person you're **[23:23]** talking to and the stakeholders and they just say, okay, so Tim's or whoever the rep is, they're just **[23:28]** kind of a person that gets people together. They're the scheduler, you know, I really want to talk to **[23:33]** this person. And I have to go through means for an end is this this seller that I got to talk to, **[23:39]** because you never developed the relationship, you never became valuable at that point in time and **[23:43]** just gave it up too quickly. Any and I know it probably depends on every org and exact product **[23:50]** and everything. But any way or tactics that you recommend slowing the process down so you can go **[23:59]** fast. I like the way you put it that way, like slow, smooth, smooth as fast, Navy SEAL type of thing. **[24:03]** But any any tactics you recommend to just help set that environment up? **[24:11]** I think that it kind of manifests into like a mutual clothes plan in some way, shape or form. **[24:19]** Once you get to a spot where it seems like it seems like we want to continue this conversation, **[24:23]** right? I'm not going to like preempt this and say like you need to buy by this date. But you know, **[24:27]** if we're if you find the critical event and you can find you can tie that to an actual date that **[24:33]** you can commit to and doesn't have to be like etched in blood by any means. But it's something **[24:42]** that you can start saying, okay, so this is how I think this can go. What do you think? I mean, **[24:47]** next call, we talk about this bringing this person work your way backwards almost from the from the **[24:53]** critical event of like getting legal involved and all that kind of stuff to get that go live date **[24:59]** actuality in existence. You can even say like I know we said September 1st is the date we want **[25:04]** to go after. Most likely it's going to slip, but let's just try to hold ourselves accountable to **[25:09]** what that date is. And then you kind of go backwards from there and it shows kind of what **[25:16]** we said earlier. It shows that you've done this many times before and you're in complete control **[25:21]** of how to buy your solution. And it's not like, all right, I'm the buyer, I'm going to put you **[25:27]** into this buying process of mine, I'm going to vet you with 15 different vendors. And that's **[25:32]** just the worst spot to be in because you know, you're not going to be able to stand out from the **[25:37]** competitors or your buying process because you've lost that control. I think it's just being **[25:42]** intentional and mindful of like, before you talk to what, let's say you do a first discovery call, **[25:48]** you get this action, you spot exactly who's who in the zoo that makes the decision at that company. **[25:53]** You say, okay, Anthony doesn't have the budget, but he's going to be a champion. And you kind of **[26:00]** do like a power and org chart internally with maybe someone else that can think through this **[26:05]** with you. I'd love to collaborate with someone else. And like, if you're with another rep, say, **[26:10]** hey, can we just go back and forth and see if we can architect some deals together? And it could be **[26:15]** early stage for years, but you just go through your org chart, and then you kind of turn that **[26:20]** org chart into a power chart. Who has the influence and the authority? Who is your business **[26:25]** champion? Who has influence and no authority based on what you're seeing? What does this person look **[26:30]** like in terms of similar buyers who bought that? Can you bring that use case to the table and say, **[26:36]** you sound like a lot like this company. Their challenge was X, this is how they solved it with **[26:42]** Y. Does that resonate with you? And then you get that kind of, yeah, that seems to be really, **[26:47]** really interesting. So you just kind of establish credibility that you've seen deals like this **[26:50]** before, and you saw challenges that are applicable to them. And you go, this is how this deal was **[26:54]** done. This is how we kind of manifested it. Usually they had trouble at this area. Legal **[26:59]** was a pain in the ass. How's your legal team? And they're like, oh, yeah, my legal team is a pain in **[27:04]** the ass too. And you can kind of like, you know, warm that up in that way. So I think it's just kind **[27:08]** of going through that confidence. And if you haven't done a deal before, if you're a new rep **[27:13]** at a company, then try to steal someone else's story, you know, and then just act like you've **[27:17]** done it before as well. And just trying to figure out the steps and the people and pace of that **[27:21]** process where you can make that. So I think that's, I think it's just kind of figuring out when to, **[27:29]** when to limit the exploration and get to a spot where you're actually ready to move forward with **[27:34]** the deal itself. Otherwise exploration and decision and steps could take a long, long time if you're ### 27:43 — Forecasting when every deal slips **[27:43]** not in front of how many are appropriate for the deal you're trying to do. One thing I want to go **[27:49]** into that I think is really difficult for teams to figure out is forecasting in the enterprise **[27:55]** world. I don't know how on earth you forecasted the $30 million deal. I don't know what that looked **[28:00]** like in your CRM, but how do you, cause this is very different than high velocity. You go back, **[28:06]** you have all the historical data, you can run your conversion rates, you can run your cycles **[28:11]** in the grand scheme of things. You're going to be able to keep it pretty tight when you have **[28:15]** hundreds of deals coming through the door. What's your approach to forecasting when the deals are **[28:20]** that big? I mean, the deals are going to slip. I think that's what you have to assume, you know, **[28:26]** at least a quarter. And so even if the seller is great at what they do and their high confidence, **[28:34]** it depends on who you're forecasting to. If you're forecasting to a board, then you have **[28:39]** to take into account that if it hasn't slipped once, it's going to slip. And so minimally. **[28:46]** And so I think you take that into account. Of course you would want to look at prior data, **[28:49]** but typically enterprise software companies that I've been a part are really poor at data hygiene. **[28:56]** To the point we were talking about earlier. And plus it's someone else's data story. So if you're **[28:59]** a CRO or you're out of RevOps, you're joining a company, the data story that was told before, **[29:08]** it could be a lot of different things. Like the rigor of closed loss, like I said earlier, **[29:11]** could be completely out the window. And so that sales cycle is no longer something you can trust. **[29:15]** So it's like, is it, this deal is set to close in six months, but yet the data says we've never **[29:20]** closed a deal in six months. It's like, well, does the data tell you that it hasn't closed in six **[29:24]** months because you've been holding onto opportunities or, you know, and you're just more rigorous. **[29:28]** So you have to, you got to take into account that deals will slip. I would also kind of be **[29:35]** relentless on, I mean, I've been forecasting using like gong or otter and having that **[29:44]** tell me the story of what the behavior of the buyer, the champions are. Are they using language **[29:50]** itself that is being kind of transposed because you're dealing with a rep that has happy years? **[29:58]** On the other end, are you dealing with a rep that's super pessimistic that doesn't want to **[30:01]** put anything in the forecast because they feel like that's kind of, I only put deals in the **[30:06]** forecast when it's like, illegal. I'm like, well, great, that gives me no visibility into anything. **[30:11]** So thank you very much. So those are like the opposite of your pipeline stuffers. So I can run **[30:18]** both ways. And so just like an honest assessment of how, why things are going to close. And I think **[30:25]** it's you as a sales leader or RevOps leader, depends on that be very black and white objective ### 30:30 — What actually counts as a critical event **[30:30]** of what needs to happen. What is the critical event? When is that critical event? What happens **[30:36]** if that critical event is not hit? So if it can move, you know, if it moves a couple of weeks or **[30:43]** month or two, then, you know, it still can be a critical event. But if the critical event **[30:47]** can move quarters, it's not a critical event. And there's no consequence of no action. So that's **[30:53]** what a compelling event is. So it's, it would be nice to have, you know, this, this new thing, **[30:59]** you know, it'd be nice to have a new car. But do I need to have it? And if I don't have it, **[31:05]** by this point in time, I'm out of my lease or whatever it might be like, those are, those are **[31:09]** critical events. And so deals don't get forecasted without a credible compelling critical event. **[31:17]** And they don't get into best case or most likely without it. So, you know, be rigorous with **[31:24]** whatever methodology you're using. And ensure that you have, you know, whatever it is, it could be **[31:30]** spiced, it could be med pick could be whatever it is, but critical event needs to be there. ### 31:36 — "Have you approved a deal this size before?" — how to ask it **[31:36]** I like that. And it's really clear and tactical for someone to have another one that you've **[31:41]** mentioned before. I like this as a qualifying question, and I'm curious, best way to artfully **[31:48]** ask someone you're in a sales process with, but when you ask the buyer, have you ever personally **[31:54]** gotten a deal this size approved before? And I think that could go one or two ways. It could be, **[32:01]** yes, of course. Okay, good. Check that box. How do you handle it when they say no? First, **[32:05]** I want to even how to ask it. How do you ask it where it doesn't sound like it's going to come **[32:09]** off wrong? And then if they say no, what do you do? Let them, I mean, yes or no question is the **[32:19]** dangerous question. So I think it's like, tell me about, I'm sure you've closed deals like this **[32:24]** before. Like, what was the last process you went through that was a similar, similar magnitude in **[32:28]** terms of price? You know, any learnings from that. And you can usually spot like, let me think. **[32:38]** Yeah, nothing really comes to mind. It's like, it's okay. This is your first one. No big deal. **[32:45]** But make it exciting for them. You know, it's a journey that they're on with you. And I think **[32:48]** that's the end result of you being the shepherd in the sales process or the evaluation process **[32:58]** is be like, it's fine. Not everyone has, you're new in your role or whatever it might be like, you **[33:04]** know. So you can commiserate with them and say like, I'm not looking to kind of expose you. I'm **[33:09]** just trying to figure out business justification is a big thing for any kind of deal. But once you **[33:17]** hit over $100k, you know, it becomes scrutinized and let alone millions of dollars. I mean, that's **[33:23]** the whole committee of people you have to be prepared for. And so if you have someone that says, **[33:29]** I'm going to do the business justification for this, and you're not a part of that conversation, **[33:36]** that person must be a very sophisticated buyer. And you can even say that it's like, wow, okay, **[33:39]** you're doing this by yourself. Most people I'd work with, I work with them on the business **[33:43]** justification because you know, this is a high ticket item. So you must have done a lot of these. **[33:50]** How many have you done? You know, and you know, you can kind of feel it off from there. So I **[33:54]** wouldn't say it's a scripted way of asking it. It's just feel it out. But don't be like, have you **[34:00]** done this before? You know, don't go directly to the chase. No, that's a much more artful way **[34:08]** of asking the question. And I think I've seen some people going through their qualification list **[34:15]** and can ask a lot of these things in an off putting way. But I actually like the way you positioned it **[34:20]** that actually puts them on a pedestal in a way. And it's like, I'm just assuming you have the **[34:26]** experience. So no problem. I'd love to hear how you did. And I think that's a really good way **[34:30]** of getting that answer. Yeah, you don't want to put them on a pedestal where they're above you, **[34:34]** but you want to put them at the level that they're your chat, you're talking with them, **[34:37]** right? So there's a mutual respect. Exactly. Anything else in forecasting that you can think **[34:44]** of that just helps you tell the story to the CEO, tell the story to your board during a board meeting, **[34:55]** tells a story during a fundraise potentially, what types of things do you want to make sure you have **[35:00]** in your forecast if your deals are of that size? Well, if you're dealing with, well, you mentioned **[35:06]** quite a few different audiences there. But if you're talking to a board or investor in general, **[35:15]** I mean, they want to make sure that you have, they want to make sure that you're data centric. **[35:20]** That's for sure. You can't just be I've done this before, this is my Rolodex. I'm a seller for 20, **[35:26]** 30 years, you know, that bravado doesn't go very far at all. So you need to have data and a firm **[35:33]** handle of what the data is telling you. So I've run into traps early and just said, all right, **[35:39]** I'm a data first CRO, here's the data. It's obvious to me, you know, this is what the this is what it's **[35:44]** saying. You have to have a story behind the data. Otherwise, you're kind of screwed. They can make **[35:54]** assertations of what this data is saying, when you don't have like a way a command of it. So it's like **[36:01]** not going too far into how you've done it. But like, I've broken this data based on cohort date. **[36:07]** And why am I doing cohort is because I found that doing it this way is not the way **[36:12]** to kind of get the you know, it's like so it's show a little bit of double clicking. **[36:17]** Show a little bit of the hey, when I use this close percentage in this in this forecast **[36:22]** likelihood, this is kind of the way I've discounted a little bit where I've used **[36:27]** prior quarter slippages. And because this deal hasn't slipped once, I'm assuming that it's a 50% **[36:36]** close probability at this quarter, because it's most likely going to slip based on the data we've **[36:40]** had. And so I think it's like, it's the it's the power behind the thought behind the data itself **[36:47]** on how you're presenting, especially for board that gives them confidence, at least, but listen, **[36:53]** every board is different. So that's there's not like, I'm not here saying I've got the silver bullet **[36:58]** for board conversations. It's always something you could take you should take very seriously **[37:01]** at if you're if you're presenting in front of a board. And if you're presenting in front of **[37:07]** an executive team, I think it's I think it's less being I found more success when you present a **[37:18]** forecast by asking and getting clarification from your executive team around the table their input. **[37:26]** And it's not the Tim show. It's not the CRO show saying this is my forecast. Look at how beautiful **[37:31]** it is and how likely it is to close. It's a our forecast as an executive team. It's a I am just **[37:37]** like the tip of the spear getting one angle from the sellers, but you manage a team and you manage **[37:42]** a team. And so some people on your team are on calls as well. You may be on calls as well. The **[37:47]** CEO might be engaged a couple call. What's your read? You know, do you think we're reading this **[37:51]** this deal correctly? Or how would you forecast this? I think that's the that's how I've seen **[37:56]** more success. And you can get and I find myself, you know, recently in the past six months, even **[38:04]** you get in. If you don't do it in a collaborative way, you kind of get defensive about it **[38:09]** naturally. You know, and so people poke questions like, I mean, Anthony, you're not you're not in **[38:14]** these deals. Like, why are you asking me questions about my forecast? You know, it's like this is **[38:19]** it's almost like you find your ego getting into it. It's like, like, this is my deal. Do I go into **[38:23]** your like product roadmap? And do I say I actually do, but whatever. But do I poke holes in it? **[38:30]** I'm like, yeah, I guess they do. But you know what I mean? Like, you get a little defensive **[38:34]** on it. So just watch yourself. And if you go into it with a collaborative spirit, you find yourself **[38:38]** being less defensive, because what do you have to be defensive about? It's like, you're forecasting **[38:43]** what these sellers have told you. So it's like, why should you have pride and ownership of what **[38:48]** you've been handed? You do your diligence, you put your rigor on it. But ultimately, don't take it **[38:53]** personally when someone starts to poke holes in it. Well, it sounds like product didn't invite you **[38:58]** in to have some recommendations on the roadmap. So that's that's their fault, I think. Yeah. I mean, **[39:03]** invite. Yeah. I just shoe more myself into these like, let me just be a fly in the wall in your **[39:09]** roadmap session. Let me just hear what hear what you're getting through. Yeah, we should be shipping **[39:13]** these things 10 times faster. I don't know what's going on around here. Yeah, well, it's always it's **[39:18]** always the caveat with product, which is like, it's like, oh, you want this? Well, then this is going **[39:22]** to go. It's like why everything is a trade off, right? So you want the sandwich, then you're not **[39:26]** going to be able to have a drink with it. I'm like, everything is a trade off. So I think that's **[39:31]** super important to get to flip it around because the CRO position, oh my goodness, that that is the **[39:38]** hardest job with the most risk in all startup world. And usually it feels like they're on an **[39:47]** island expected to just go make magic happen, go make it rain and makes a bunch of money and **[39:53]** go do it. And if you don't do it, it's all your fault. But I would love when I've seen some CRO's **[39:59]** just get like destroyed when they're isolated and put in their own. And just like you said, **[40:05]** start to get defensive and start like, yeah, take it as a personal attack. But I've seen some CRO's **[40:12]** turned into a real collaborative effort and then puts the right amount of pressure on everybody **[40:16]** else. Like, hey, yeah, product gets involved in big deals or CFO needs to come in to get some **[40:23]** special type of pricing going on for this or make it figure out a POC or form something new. And **[40:28]** the CEO needs to take ownership on some strategy that we're having. So when that happens, **[40:35]** I think it's so much more productive and then you're all focused on the right things. Hey, **[40:40]** how can we just do the right things that give us the best shot at winning? ### 40:44 — More internal selling than external selling **[40:44]** I 100% agree. I think it's also might be a lesson between the high velocity seller and the **[40:50]** enterprise seller, which is you have more internal selling to do than external selling, **[40:57]** getting the team aligned on what you're trying to do. And kind of mentioned to it earlier, but **[41:02]** you don't get a gold star and say, oh, wow, so this is a deal that Tim just closed by himself **[41:09]** and he got no help ever. And if anything, if I'm a board member or an executive that says, **[41:16]** okay, so no one else sniffed this deal out, then I'm actually more concerned. I have more concern **[41:21]** in this deal than I previously did because it was done with one person as opposed to several. **[41:25]** So if it works against you, then why not be collaborative on this stuff? And if you're **[41:33]** buying something that has a significant value, they're buying you as a company, not just a **[41:39]** product. And that partnership goes a lot further than just what they're buying today. So the **[41:43]** confidence in the people behind the product is key. So you're kind of like showcasing within **[41:50]** without it being like a, you know, exploration, endless exploration, be articulate about who **[41:58]** on the executive team you want to bring in based on the size of the deal and what their role would **[42:02]** be. And that's applicable to that. And so you're not doing this deal by yourself, you know, and **[42:06]** you're doing it in a way where you can have a collaborator and map the power in the company, **[42:12]** leverage them to say like, Hey, I think you got along with Joe at this company and you kind of **[42:18]** match their persona a little bit. So why don't you, you know, develop that one-to-one relationship, **[42:23]** Anthony, and ping that person. And this is what I would do. So you're kind of like a puppeteer, **[42:27]** right? Behind your own kind of team. I mean, it just happened yesterday. We had a workshop with **[42:35]** potential customer that, you know, of course is taking some time. It's in legal right now. And so **[42:39]** it's been in legal for the last three months. You know, we did like a product roadmap workshop **[42:44]** session with their product person as well. And so I'm like, you guys jammed a little bit on that **[42:49]** conversation. So, you know, my head of product, I'm like, why don't you send them a text or an **[42:54]** email and saying, Hey, we'd love to kind of go a little bit further on this conversation if you're **[43:00]** up for it. And it helps build momentum and keep that momentum while legal is doing what, who knows **[43:06]** what they're doing right now, but not signing my contracts. So, you know, you can be architecting **[43:11]** that way. They're out there eating bonbons, just not caring. Yeah, looking at their massive stack **[43:18]** of contracts to go through, you know, it's like, wow, it's getting really big right here. It's, **[43:22]** I wonder how big it can go. Good time for me to go on vacation. This is **[43:27]** exactly. No, I think, I think that's really helpful in turning sales into a team sport. And **[43:36]** that's a good way for people to think about it too. Like the more velocity, the more individualistic **[43:40]** it can likely be. And then the more enterprise, the more team oriented that whole process really **[43:45]** needs to be one component of the team. I think a lot of people have when they're thinking of **[43:52]** departments like rev ops, I think there's a lot of index and orientation to the velocity sales **[44:00]** type of environment. And I think a lot of the work they do tends to become obvious there. **[44:06]** I've done rev ops and enterprise environment, so I have a good idea. But from your perspective, ### 44:11 — RevOps as a force multiplier: the Slack deal desk **[44:11]** where has rev ops helped the enterprise motion the most? And where are you using rev ops to **[44:19]** get the most leverage out of your team? Oh, I mean, like, rev ops has always been my secret **[44:25]** weapon, partly because I hate doing rev ops myself. And so, you know, you look at, you know, **[44:30]** what brings you joy and what brings you frustration and identify that's usually a strength and a **[44:36]** weakness. So you might think that you're good at rev ops, but if it brings you no joy, it's probably **[44:40]** because you can't just admit to yourself that you're just not rev ops material. They're a **[44:44]** force multiplier. And if you treat them like, you know, data wranglers or just a means to an end, **[44:52]** then that's what you get. But they're a strategic lever on how to advance your business. And just **[44:56]** because they can't do it in turn rates or turn rates on like high velocity metrics and just **[45:01]** manage it that way and give me a whole of the data story so I can tell it when I board, then **[45:06]** you got to have a thought partner in that area where it's almost like, am I thinking of things **[45:10]** the right way here? How kind of systems internally can we build in rev ops to make us more effective? **[45:17]** My rev ops person is the person that makes it a reality. Is there a way where we don't have to do **[45:23]** weekly deal desk meetings that last two hours? Like, what can we do? What can we get ahead of **[45:30]** time? And what's one way we can use Slack and just make sure that everything goes through deal desk **[45:35]** appropriately, where we don't have to do CPQ. We don't have to do any of that kind of stuff. **[45:38]** We just build like some sort of a system that says, all right, Tim, it's you need to look at **[45:43]** this portion of the deal because it's a commercial thing. And then it goes to this person who's in **[45:49]** product and this person that's in like services. And then it goes ultimately to the CEO to **[45:54]** to look through. And then, you know, just explain that problem. Like we have a fully articulated **[45:59]** deal desk motion on Slack where it's just like, I just get pinged and it says approve yes or no. **[46:04]** Here's what I need to know without actually opening the entire contract, although I can, **[46:07]** if I want to see the whole deal. But if I need to kind of get back an approval matrix, then, **[46:13]** then, you know, he designed a system that just does that. So systems thinking is kind of the **[46:19]** the way I look at it. It's like, I need a systems thinking person where I can look at the data, **[46:25]** of course, and talk about strategy. But like, you know, come to the table and say like, he's the ### 46:29 — Measuring internal SLAs and building revenue athletes inside **[46:29]** one, my head of RevOps, Jack Volkoff, you can look him up on LinkedIn. And I hope no one recruits **[46:35]** him because of this podcast. But he comes up with the ideas of like, hey, I just was thinking, **[46:40]** I'm like, wouldn't it be interesting to measure the response time on SLAs that we have on legal **[46:46]** requests? And I wonder if we can kind of build a little bit of a trend saying like, you know, hey, **[46:50]** this month, we've gone down from three days to two days, or this many hours to this many hours. And **[46:57]** so that's a that's a way to kind of get, you know, revenue athletes within your own organization. And **[47:03]** so, yeah, I would think it's not just, it's not about buyers themselves. The end buyer isn't the **[47:10]** isn't the only mechanism for measuring RevOps. It could be internal signals that you can make sure **[47:16]** that you get into like, you know, rigor and get into a spot where you're offering a customer a **[47:22]** great experience, because the buying process and the way that they get back to a customer about **[47:28]** certain things is programmatic, systematized. And you're kind of taking the creativity to another **[47:34]** level where it's something that's predictable. So yeah, I think RevOps is super crucial. **[47:42]** I've always liked when I've seen really good duos with CROs, heads of RevOps, **[47:48]** and they kind of turn into your chief of staff a little bit, maybe like your COO of the startup **[47:54]** that you mentioned. And I love the way you put it, they turn your strategy into reality, and they **[48:00]** can execute against it. And I think a lot of the leverage too, if you can help your sales team **[48:07]** reduce that sales cycle a little bit, increase conversion rate a little bit, hold a little bit **[48:12]** more pipeline than they could before, and be a little bit more efficient, that leverage compounds **[48:18]** pretty quickly, even with a small sales team. And yeah, I think you keep it lean, keep your sales **[48:24]** team fed really well, keep their pipeline healthy, and not turn into this bloated sales org if you **[48:31]** have RevOps in order. Yeah, I mean, if you have like a, if you have a seven stage sales cycle, **[48:37]** a sales process, and you incrementally every quarter improve each one of those stages by 1%, **[48:44]** you know, and you look at that over a year, you're making some significant impact. And just because **[48:49]** you don't see, you know, if high velocity of deals, I mean, that those rates really add up. ### 48:56 — Baseball, Moneyball, and the long season **[48:56]** I am a baseball fan. And not because I just like the sport itself, because I like going to games, **[49:03]** I mean, outside, and you know, it's turned into a good thing with my kids. But because baseball is so **[49:08]** frickin long, the season is so long, there's so many games, and it's the only sport that you, **[49:13]** even the best teams in baseball, they lose more than 50 60 games a year. And so they've, they **[49:20]** they've experienced failure. And then every team that wins the World Series goes through a period **[49:25]** of time in the season, where they've just sucked, you know, and there's there's that drought. And **[49:31]** it's kind of how you get out of that drought that really defines your season. And I feel like that's **[49:38]** a good analogy for business, especially in the enterprise space, where, you know, it's you got **[49:45]** to learn, you got to improve, you got to take your losses, and you got to kind of learn from them, **[49:49]** and you got to keep on going, because it's a long ass season ahead. And it's not about just burning **[49:53]** out in a month, and just kind of making your your number in a quarter, it's about the whole, **[49:58]** whole year. And in most cases, it's multi years. And you know, it's a significant test of time. **[50:05]** I think it's a great metaphor, especially just saying discipline to the fundamentals as you go **[50:09]** through. And even when you're doing the right thing, sometimes bad things happen. So you have to **[50:15]** kind of roll with that as you go along. Yep, exactly. And so your rev ops, and enterprises **[50:20]** like moneyball, right, it's kind of like, look at all the stats and look at all of it, the different **[50:25]** components of like, it's not just three point percentage, and how many threes that you got to **[50:29]** do, but like, walk rate on base percentage steel, I did this this war metric that it's going around, **[50:36]** which is wins above replacement, which I'm, I still don't quite understand how they do that. **[50:40]** But that's a metric as well. But it's like, it's pretty cool stuff. So there's countless ways to **[50:46]** break down that game and stats and numbers that a lot of folks don't necessarily appreciate. **[50:52]** Yeah, I've kind of become obsessed with it. Because like, I ran red ops for three companies, **[50:57]** then at lean scale, we've, we've done engagements with hundreds of companies. And I think you just **[51:04]** see when you see those conversion rates go up a little bit, when you see time and stage reduce a **[51:09]** little bit, when you see, hey, let's get rid of a couple sellers that really aren't producing, **[51:15]** and then amplify the ones that are doing a really good job, like these little micro improvements **[51:22]** all across the go to market life cycle just add up to so much. I don't think people realize like, **[51:27]** if you're on a $20 million plan and assume you have enough pipeline to feed it, if you can **[51:32]** increase your conversion rate by five points, that could mean another $5 million into your **[51:39]** overall year. So the numbers get pretty big pretty quickly. And just being like a blood hound, **[51:46]** looking for those areas that can get improved, we'll just keep that thing going. Yep. Yep. ### 51:51 — The data and the story **[51:51]** It's a force multiplier. One thing I want to make sure we get to the data in the story. **[52:00]** If you have one, you might as well not have anything. You really need both to come together **[52:05]** really well. My CRO that I worked with that company, he would always say, if you torture **[52:12]** the data enough, it'll tell you anything you want it to. And that was kind of his phrase around it. **[52:17]** But I think tell me more about that and some of the venues that you need to be prepared for too. **[52:25]** Well, we went to the board conversation. I think that's one of them. I mean, if you don't connect, **[52:29]** if you have the story with no data, then there's no story that's relevant. If you have the data **[52:34]** without the story, then you don't have anything that people kind of grab onto. So connecting the **[52:40]** two is really the job. And, you know, one of the things that you can get to an example of like, **[52:49]** you know, 40 to 60% of losses are due to no decision. And then if you don't have a story **[52:58]** as to what that signals, then what does that mean? It's like, so why? Okay, so great. So 40 to 60 of **[53:07]** your percent of your losses are moving to no decision. And if you don't have a compelling **[53:11]** reason or a few different theories as to why that is and how you're going to fix it, **[53:17]** you're on the wrong path. And not only the board conversations, like, I mean, at the end of the day, **[53:20]** who cares? It's like, are you doing the right job? Are you looking at the data at the right way? **[53:25]** Are you double clicking to say, okay, so how do we kind of fix that? And what are the reasons why **[53:32]** that is the case? What are we doing, not doing in the discovery call that we could be doing more? **[53:36]** Okay, let's try that. Now, how do we measure whether that whether we're on the on the right **[53:42]** path? And how can we do that in a quick way, where we don't have to wait six months to see if we did **[53:48]** the right thing to begin with? What are the metrics we're looking for? And so you kind of like double **[53:53]** and triple click into that and say like, okay, well, then and this is where you need, where I need at **[53:58]** least someone who is who is inquisitive and can interrogate the data, not to tell a better story, **[54:05]** but what you're trying to really solve for. And what are you trying to measure improvement on? **[54:10]** And the data is the data. So then you make your assumptions as to why that is. And then you make **[54:14]** some points as to how to fix it. And then you get to how are we going to measure improvement, **[54:19]** which is somewhere we can iterate quickly on. We don't have to wait too long for that data to come **[54:24]** back to know that we're on the right path or the wrong path. So we can kind of pivot necessarily. **[54:30]** That's hard. It sounds much easier on a podcast to do than in a white boarding session, **[54:40]** not only to come up with those metrics, but come up with those gates of measurement to say, **[54:44]** when do we expect to see results of whether it did anything or not? And so if it's two weeks, **[54:50]** is it a month? Let's make sure we have that kind of concrete agreement amongst us, whoever's in this **[55:00]** decision tree. And then at that point at a time, we do either do more of it or less of it based on **[55:04]** what it's doing. Because in the enterprise sales cycle, as you mentioned, you may not know what ### 55:14 — Leading indicators and measurement gates **[55:14]** you're doing is working in the closed one metric. What are you measuring to see if what you're doing **[55:22]** is having an effect? Is it just further up the funnel? Are there more subjective things that **[55:29]** you're taking a look at as well? What are some things that you've had experience with where you **[55:34]** say, hey, yeah, this is giving me leading indicators that that change we made in enablement, **[55:38]** that change we made to positioning is actually working? I took over marketing for a bit. By the **[55:44]** way, if you want to have the hardest job out there for relevancy, I feel bad for CMOs. So CMOs are **[55:52]** pretty tough. So at least I have a scoreboard that everyone knows on CMOs. It's like I have **[55:59]** a scoreboard, but people believe it is another story. But anyway, so when I took over marketing, **[56:06]** it was the theory of like, okay, so paid search is the way that every marketer gravitates to, **[56:13]** as to how they're getting the lead volume, which I fundamentally think has been completely disrupted **[56:19]** based on AI, but whatever. And so we went through a theory of like, let's just organically write, **[56:25]** this is maybe a year ago, year and a half ago, when LLMs were kind of, now everyone's doing it, but **[56:32]** let's write 10 to 15 popcorn pieces a week of content. And these are like top 10 things that **[56:42]** manufacturers do in this industry that has, you know, have maybe a little bit to do with us, **[56:47]** but not like it's not our pitch, right? And let's run it for a month. And then, you know, **[56:54]** you get the traffic rates, and you can just look at it very, very explicit, like saying, **[56:58]** I don't have to have leads or opportunities be the thing we're solving for. Right now, **[57:03]** I'm just trying to say, do they give people more to the website? And then that gate was successful. **[57:08]** Yes, it does. Okay, cool. So let's look at lead volume. Is that increased as well? No, it didn't. **[57:13]** Okay, well, then that probably has to go with content and the quality of the content itself, **[57:17]** and maybe call to action, so you can play around with it there. So what probably you're trying to **[57:22]** solve, it's not the whole thing, to your point of like small improvements in the wholesale cycle **[57:27]** need to be it. So if I'm improving this point of the sales process, then what am I looking at, **[57:34]** as far as a success, it could be like, I want to, we're going to extend the discovery period of time **[57:39]** to two to three calls from one call. And because of that, we think it's going to impact either the **[57:45]** next session, or maybe it's the stage three, what I was talking about. And so the time horizon for **[57:52]** that is we expect that to be 60 days. And so that's our kind of line in the sand to kind of go **[57:58]** forward from there. So I think it's really applicable to like, what you're trying to solve **[58:03]** for. And if it's close loss to note, like how do we get things to move in stage three faster? It's **[58:10]** not like more do more things in stage three, as the only answer, it could be a answer, it could be a **[58:16]** answer to do. And you could have a theory to say, yeah, let's do more things in stage three. But it **[58:20]** could be like, well, let's look at the other things. And let's part in interrogating the data that I **[58:23]** think is valuable, where it's like, if I have an opinion, or I come, all right, Anthony, I have an **[58:28]** opinion, stage three, win rate or duration of that stage itself needs to be needs to be improved. **[58:38]** So really reduce the sales cycle from stage two to stage four, this is how we're going to do it. **[58:42]** We're going to have a new demo or whatever workshop that we're going to introduce here. **[58:47]** And without someone that can kind of check me to say like, okay, that's one element of doing it, **[58:51]** but but can we look at the stage before? Or have we looked at the stage before that not accepting **[58:56]** the first kind of solution as the solution. So you have a problem, you should have several solutions **[59:02]** to that problem. And they all could be right. And don't do all of them because you want people to **[59:07]** measure which one was actually effective, right? So we're going to say, let's start with this one. **[59:11]** And because we feel like it has the shortest learning cycle. And so that's the one you pick **[59:16]** with. And then, you know, it's a do we have an agreement that this is the measurement that we **[59:20]** want to get to. So I don't know, that's kind of the the internal negotiation that you do through **[59:27]** these things. And again, I feel like a lot of this stuff is much easier said than done, you got to be **[59:31]** very rigorous, and kind of be mindful of this stuff, almost like put like a little banner in your home **[59:36]** office that says, you know, don't accept the first data story that you have try to interrogate multiple. **[59:43]** No, it's very difficult to do in real time, especially because you were mentioning, like, **[59:48]** often, if you're trying to do an experiment, that you're going to change one factor and see how it **[59:52]** goes. Sometimes you don't have the luxury of just waiting. So you might have to do three factors at **[59:56]** once. Maybe you don't do 10, but you have to do a couple things. And then you need to bring in some **[1:00:01]** judgment, like, okay, do we think it had an effect, the data says this, but what do we think drove the **[1:00:07]** biggest impact? So, but I think just even having that approach of, I'm not gonna wait to see what **[1:00:13]** close one is, let's start looking for leading indicators. Let's lead with a hypothesis. Hey, **[1:00:18]** we think this thing will affect this other thing. Let's do it, commit to it, and then measure it, **[1:00:24]** and then come back and did it work? I don't know. Maybe we need to change it. Yeah, yeah. But yeah, **[1:00:30]** as you mentioned, easy to say in a podcast. It's tough to do it real time every day in the field. **[1:00:36]** Yeah, it's try to be as black and white as you can, you know, I think that the best part about **[1:00:40]** data is you can you shouldn't be in love with the solution that you put in place. You can be very **[1:00:45]** objective with it. And, and again, easier said than done, but if you're like so positive about **[1:00:54]** this changing it, then you kind of you have to try it. But but just watch your enthusiasm for this **[1:01:00]** fixing it. You know, because you might be like, Oh, no, I definitely think it's going to work. And **[1:01:04]** then you're gonna you can interrogate the data in a way that's like, Oh, no, I think it's working, **[1:01:08]** but it's not actually doing the conversion that we said it was going to do. So, you know, **[1:01:14]** be objective. I've had to walk that one back a million times. And then my excuse goes, well, ### 01:01:18 — AI in go-to-market: the internal app store and the scrutinizer agent **[1:01:18]** it's good for the brain. So let's just keep doing it. So the other thing that's obviously creating **[1:01:23]** lots of leverage, lots of noise is AI and go to market. And there's so many different applications. **[1:01:29]** What are you seeing being effective ways of leveraging AI? And maybe what are some **[1:01:35]** ineffective ways to? Yeah, I mean, we're in the AI industry ourselves, that's what we sell. And so **[1:01:40]** it's kind of an interesting, you got to dog food it a little bit and kind of be kind of AI native. **[1:01:46]** And so we don't use our own solution for go to market. Unfortunately, that'd be kind of cool. **[1:01:50]** So we are leveraging all types of things to build different solutions internally. So even like **[1:01:58]** rebuilding, we have like an internal app store, where we've had folks within the organization **[1:02:05]** be able to kind of build different skills and apps that solve challenges. And I think one of the cool **[1:02:12]** things about that is connecting the dots on like someone from another department. And if you don't **[1:02:17]** go into like, here's a skill that fixes my problem. But this is kind of what I did to build it is **[1:02:25]** sometimes the most interesting thing that I can see, like there was one example where someone's **[1:02:29]** like replacing an internal tool, I'm not going to say what the tool is, but it's like a collaboration **[1:02:34]** software that we use for quite some time. And he's like, I think we can actually replace it, **[1:02:42]** because part of the problem is, you know, filling out this collaborative software is some of the **[1:02:47]** issue. And so if we have a listener agent, which is on Otter, all of our internal calls are being **[1:02:53]** recorded, as well as external calls, we have so much information we're sitting on. We have Slack **[1:02:58]** as a tool, we communicate exclusively internally, because we're a global hybrid company. And so all **[1:03:03]** the information is there. And so it's not a matter of just like, you know, setting the different tasks. **[1:03:09]** So he created an agent that automatically creates the tasks and builds this collaboration thing and **[1:03:14]** does automatic updates. And that's not noisy in Slack. And one of the reasons I picked this one in **[1:03:21]** particular is because I said, like, how do you make this not noisy? Because I build these bots **[1:03:26]** all the time, or these agents, and half the time I turn them off, because they annoy the hell out of **[1:03:31]** my sales team. And, and he has this like, he talked about like a listener agent, and then like a **[1:03:39]** scrutinizing agent, and then before it goes even to him, they talk to each other. And so you have a **[1:03:44]** guy, you have an agent that scrutinizes the listening agents, the listening agent kind of pulls up, **[1:03:49]** here's everything that happened this year, it's everything that we should have posted. And then **[1:03:54]** the scrutinizer basically just like, calls bullshit on half the stuff before it actually go. I'm like, **[1:03:58]** that's a brilliant thing to do. He had a better way of saying it like, than scrutinizer or bullshit **[1:04:03]** artists. But I like that description. Well, that's what I titled my agents. I called them, you know, **[1:04:10]** dummy and smart, I don't know. But, but you end up kind of having these workflows, you say, I can **[1:04:16]** build that same logic in all of my workflows. And my man, so I think that internally, not everyone's **[1:04:25]** going to do this, right? So but internally, by creating an avenue of folks that do that have a **[1:04:30]** curious mind and have that builder mentality, and have that in and provide like an avenue for people **[1:04:38]** to publish what they've done. So people can can not only just reuse it for what they need to do, **[1:04:43]** but repurpose it and and build it and make it their own. And further it in another function is super **[1:04:49]** cool. So I think that there's so many different cases where you can create more work for yourself **[1:04:56]** and more insights. And are you actually doing anything with that stuff? Like, so there's a lot **[1:05:00]** of busy work you're doing, but AI is supposed to make make you more efficient. So is it making you **[1:05:05]** more efficient? I think questioning that aspect of it is pretty, pretty key. But ultimately, like, **[1:05:13]** it's a way for me to be more effective than ever before by just making sure that I'm consistent **[1:05:20]** with my management style and, you know, and, you know, you're making canonical docs and what you **[1:05:25]** want to stand for and making sure you check yourself and you're in on decisions you make, **[1:05:30]** make sure it's fair and consistent with whatever you did. And if I'm deviating, then I need to call **[1:05:35]** it out. So there's like coaching mechanisms that you can use internally to make you a better leader. **[1:05:41]** So I don't know, I think that my I can go on and on about all the different ways of deploying it. **[1:05:47]** But I'm in, I'm in Claude, more, more hours than I care to admit, in terms of how we and I'm **[1:05:55]** hammering things through. And for me, I've this is the funnest I've had at building stuff, because **[1:06:00]** I don't have to know, I don't have to do things that I have no idea how to do like, like, back to **[1:06:05]** the building mentality, I still need my systems thinker, though I'm not trying to replace that **[1:06:09]** person by any means, because that brain is much different than my brain still, regardless of what **[1:06:14]** AI in between human in the loop is centered. So we kind of balance each other out on things that **[1:06:21]** things that can work. And it's cool. It's cool stuff. Oh, my gosh. Well, you're talking to like, **[1:06:26]** one of the most AI pill people over here token maxing, I was one of the first people on open **[1:06:32]** Claude getting a server rack of Mac minis in my house here. And all that money gone to waste. **[1:06:40]** 100%. It was fun, though. But I think what you there was a point where I had to go, **[1:06:49]** am I just messing around here? Like, I don't have like 18 sessions open right now. But am I am I **[1:06:55]** actually doing anything productive? Am I actually moving the needle forward? And I found like, I was **[1:07:01]** like, I don't really know what this is to like, oh, my gosh, I'm like doing 16 hours a day. I can't **[1:07:05]** even like get out of the terminal here. And now I'm like, Okay, we're sober about it. There's like **[1:07:09]** 10 things I have to do every day. And Claude can make sure I do them really, really well. There's **[1:07:14]** some really important things that we have to do for our customers. There's some real important **[1:07:18]** processes that we have to run. But it's like five things. And now we can just take a look at unstructured **[1:07:23]** data really well, that's really difficult or boring to manipulate before. Now we can just make **[1:07:27]** sure we're not missing anything. And I think when you get into that mode where you're like, okay, **[1:07:32]** yeah, I have some like, five to 10 supercharged processes that are consistent, I'm iterating on, **[1:07:39]** but all the core jobs are still the same. So like doing a podcast, before AI, I still had to prep **[1:07:46]** with the guest, make a storyboard, meet with the guest, send follow up, get everything written on **[1:07:52]** social media, turn it into external content and then post. So the job isn't different. Now I can **[1:07:58]** just do some of it a little bit faster and a little bit higher quality. Yeah, exactly. But I am, I **[1:08:04]** think it, you know, it's funny, it's things you said is whittling it down to actual decisions you can make **[1:08:09]** is the key thing. And I've known this for quite some time, even going back when I was in college, ### 01:08:15 — The TGI Fridays menu and why less is more **[1:08:15]** I worked at TGA Fridays. And so TGA Fridays before, right after I'm in the server. Oh, **[1:08:24]** you're in there. You're in there. Yeah, there you go. Hard knocks. But they had a huge initiative and **[1:08:30]** it sticks with me to this day. I haven't been to a TGA Fridays in a long time, but I'm assuming their **[1:08:36]** menu is like this, but their menu used to be a huge book. And then you had the flair and all **[1:08:42]** that kind of stuff. It was a lot. So they just went through a whole rebrand when I joined, **[1:08:46]** they took their menu down from, you know, I don't know, I think it was like the cheesecake menu, **[1:08:50]** which is like 60 pages of stuff. And they turned it into two sides, one's drinks and one's food. **[1:08:55]** And the food was, you know, appetizers, entrees, desserts, whatever it might be. And they had like **[1:09:00]** five things of each. And what that kind of signals and they had tons and tons of research is like, **[1:09:05]** if you have so many options, you're stressing the person out. And then they end up saying like two **[1:09:11]** things. They end up kind of like, oh, they flipped through the menu and it's just this one. Or they **[1:09:14]** just asked the server, what should I get? Because they don't, as much as we want more information, **[1:09:20]** we don't actually want more information. We just want to make the right decision. And so when you **[1:09:25]** think about that, tying it back to go to market and how you help people through the buying process. **[1:09:31]** The idea isn't like, Anthony, we had a great conversation about our technology, **[1:09:34]** cool, I'll send you some materials and I send you 12 different things to look at. **[1:09:40]** I'm not going to, you're not going to look at them. But if I give you one thing to look at, **[1:09:45]** you're going to look at it. And if I demo 20 different features, **[1:09:49]** none of them are going to resonate. But if I send three different features that I think are impacting **[1:09:53]** to you, then I actually am catering that. So how can you take this human psychology and going back **[1:09:59]** to recruiting, you have to know human psychology to be a good recruiter. If you don't, you're going **[1:10:03]** to be a sucky recruiter. And so human psychology is how people make decisions in general. And so **[1:10:10]** by doing that, you need to make sure you really fall in love with human behavior, **[1:10:16]** human decision making, and ensure to cater that experience to them by not more as more, right? **[1:10:24]** Less is actually more and more impactful, and you'll become more memorable because of that. **[1:10:30]** Do you know what my favorite dining experience is? **[1:10:33]** Don't tell me Cheesecake Factory. **[1:10:36]** Omakase. **[1:10:37]** Oh, there you go. Yeah. **[1:10:39]** I just want to be told what we are having for dinner. You know the products better than I do. **[1:10:44]** Just have the chef serve up whatever is best here. I love walking in and not needing to make **[1:10:50]** a decision. I'm like decision fatigue throughout the whole week. I can't even choose one more **[1:10:55]** thing. So if you can just lay out all your best stuff for me and I can enjoy it, that's my favorite **[1:11:00]** way to go to dinner. Oh, I understand. Yeah, it's totally great, especially if these like just, **[1:11:05]** I'm trying to have a great experience. And they're like, how hungry are you? I'm like, **[1:11:09]** perfect question. Yes, it's always high. So just get it going. As hungry as you've ever seen. **[1:11:18]** No, but I think tying it back to AI though, it's like, oh my goodness, **[1:11:23]** you can just spin yourself in circles for hours, days, weeks. And it feels productive. It feels **[1:11:30]** like you're doing a lot like the TJ Friday's menu, the Cheesecake Factory. Those menus stress me out, **[1:11:34]** by the way, too. It feels like it's more valuable because you have more things on it, **[1:11:39]** but it, but it's not. It's what's valuable is being intentional, the curation of everything. **[1:11:46]** It's so important. And I think after probably everyone needs to go through their like discovery **[1:11:52]** phase, like just dive deep, just go get lost in cloud for a little bit. But when you come out of **[1:11:56]** it and the dust settles, then it's like, okay, I still have the same job that I have to do. **[1:12:03]** And a lot of it's not replacing any of the work that I have to do, by the way, it just kind of **[1:12:06]** like created more work for me. And now just be intentional about how you use it and then **[1:12:11]** get the leverage out of it. Yeah, exactly. That's that's really it. But yeah, dive, **[1:12:15]** dive as deep as you can, but not so deep that you forget what the job you're supposed to be doing. **[1:12:24]** It feels like a lot of people are in like the third level of inception and they don't even **[1:12:28]** remember what they're doing anymore. Yeah, they forget the world that they're in. Yeah, **[1:12:32]** it's, it's crazy. But you know what, I think that what it's all it's just supporting that we're **[1:12:39]** going to find humans are find more things to do and then how to change jobs for themselves and **[1:12:45]** whatnot in the process. So I mean, I wouldn't be like the social media manager that existed is **[1:12:51]** no longer a job, right. And so you can be fearful about that. Well, now it's replacing social media **[1:12:58]** jobs. But then you think about, well, how long is the job social media manager been existence? **[1:13:03]** Not very long. So that in itself is a new concoction of what we can do. And there'll be new **[1:13:09]** jobs that we come across and those wonderful get replaced as well. And so onwards we go. **[1:13:16]** Yeah. And at the core of it, it was probably still like every business needs to build product **[1:13:22]** or build a service, deliver it, internal operations, sales, marketing. Yeah. Like **[1:13:30]** doesn't matter. Whatever, whatever was dressed up on the top, like social media manager, like, **[1:13:35]** okay, you're still the marketer, probably project manager, probably like those type of roles. And **[1:13:40]** there's just gonna be other things. Now you're managing AEO or something. And yeah, like if you **[1:13:45]** had that experience, it's still gonna be transferable to other things. Yeah. Just dive in. Don't be **[1:13:49]** fearful, right? Just dive in and figure it out. Otherwise you might be the one being replaced **[1:13:55]** and you're going to have to do it without a job. So, so just dive in while you're while you can. ### 01:14:00 — Wrap **[1:14:00]** 100%. Well, Tim, this has been awesome. Thank you for everything you shared. I really, **[1:14:08]** really appreciate the insights on all things enterprise because I think it's a very difficult **[1:14:13]** game to play. I haven't met anyone yet who's closed a $30 million deal. That's like entire **[1:14:19]** company's worth of revenue, which is incredible. And I'm happy that we got to go through that story. **[1:14:24]** And I really liked the perspective on how to leverage RevOps in that environment too, **[1:14:28]** because it just has such a brand of being high leverage in that high velocity environment. **[1:14:34]** But arguably you might even get more out of a RevOps team in that enterprise environment. **[1:14:39]** And I think knowing how to deploy that and then all things AI, I think it obviously here to stay. **[1:14:46]** So get plugged in with it. Start using it. Don't be afraid. Probably going to get lost in the **[1:14:54]** journey, but just come back up and get your feet on the ground and keep trudging forward with **[1:14:57]** whatever the work you were doing. So anyway, appreciate having you on the podcast today. **[1:15:03]** Before I let you go, just best way to get in contact with you and the current company you're **[1:15:08]** working at now. LinkedIn is probably the best way to reach out. So otherwise that's tim.yandel@imibit.com **[1:15:18]** is my email. So curious to hear anything. Anyone who wants to reach out with more would be great. **[1:15:25]** Well, thank you so much, Tim. Appreciate it again and can't wait to see what you do next. **[1:15:31]** Thanks, Anthony. --- _LeanScale Knowledge Hub. Free to quote and cite with attribution to The LeanScale Podcast (https://www.leanscale.team)._