--- title: "Fall in Love With the Buyer, Not the Product" episode: 146 podcast: "The LeanScale Podcast" publisher: "LeanScale" guest: "Zach Rego" guest_title: "Chief Revenue Officer, Triple Whale" date_published: 2026-10-27 date_modified: 2026-11-09 duration: 00:50:00 word_count: 9786 topics: ["sales-leadership", "pricing-packaging", "ai-in-gtm", "outbound-sales", "sales-enablement", "gtm-strategy"] canonical_url: https://www.leanscale.team/knowledge/podcast/zach-rego-triple-whale-fall-in-love-with-the-buyer/ source: "LeanScale Knowledge Hub — https://www.leanscale.team/knowledge" license: "Free to quote and cite with attribution to The LeanScale Podcast." --- # Fall in Love With the Buyer, Not the Product _Zach Rego on starting Triple Whale's sales team from an Airtable of 2,000 names, why a CRO should still sell every flagship launch, moving AI pricing from credits to good-better-best, why first managers should do the job first, and taking personalization to the craziest degree_ **Episode 146 · The LeanScale Podcast** Zach Rego, Chief Revenue Officer, Triple Whale · Hosted by Anthony Enrico Published October 27, 2026 · Updated November 9, 2026 · 00:50:00 Canonical: https://www.leanscale.team/knowledge/podcast/zach-rego-triple-whale-fall-in-love-with-the-buyer/ **Topics:** Sales Leadership · Pricing & Packaging · AI in GTM · Outbound & Sales Development · Sales Enablement · GTM Strategy ## Executive summary Zach Rego is Chief Revenue Officer at Triple Whale, the AI operating system for commerce used by more than 60,000 brands, where he leads sales, partnerships and marketing. He joined four and a half years ago as the company's first head of sales and found an Airtable of 2,000 waitlist names, no enrichment, no playbook, and one rep he had brought with him from Unstack. Between them they ran roughly 250 demos in the opening sprint. Today the sales team is roughly 40 people including managers, across the US and international markets, alongside 11 or 12 SDRs and a partnerships function, and he is still on demos. In those first weeks the priority was collecting revenue: the co-founders ran demos and chat support sent out payment links because there was no self-serve sign-up. But Zach had already whiteboarded roughly today's org structure when he interviewed, so he changed the form questions after the first 25 to 50 calls, stood up HubSpot, built a lead score and added enrichment, all so he could route leads by segment and forecast headcount later. He still sells every flagship launch, starting with existing customers, because whoever makes the pricing decision should feel the friction first. The rule he reached after what he calls a lot of failed experiences is to loop in the AE, let them own discovery, and take the demo and pricing himself. Anthony Enrico calls AI pricing the biggest go-to-market challenge in B2B SaaS and AI today, and Triple Whale has been through several rounds of it. Charging credits for an AI workflow builder inhibited usage because customers feared hitting the limits. Selling AI as an add-on made the sales process convoluted. The company has landed on good-better-best, with AI in every package and tiers that differ by models and token rates, and Zach accepts that it eats into margin. He looks at margin blended across heavy, middle and light users, and calls an internal head of pricing and packaging one of the best hires the company has made. The title comes from his career. Selling to Fortune 500 CIOs never felt right, selling to entrepreneurs at WordStream did, and he decided he would only sell to people he would want to have a beer with. On hiring, he leaned on his network for the first reps, then had a new manager do outbound himself for months before building a team around him. In interviews he looks for progression inside one company, digs into short stints, and treats severance requests before day one as a red flag. New reps are on the phone within two weeks and learn through peer-to-peer coaching matched to their gaps. The last section covers AI and pipeline. Triple Whale runs its own BI on its own product, moved someone into a go-to-market engineering role in RevOps, and has built a morning account list, transcript-based handoff documents and a podcast scraper that surfaces gifting ideas. Zach is still working out how much should be top-down versus bottoms-up, because reps produce both AI slop and remarkable event handouts. His conclusion is that personalization has to go to the craziest degree and that in-person is mission critical. The episode suits CROs, founders, RevOps leaders and sales managers working through AI pricing and pipeline in 2026. ## Key takeaways 1. **Fall in love with the buyer, not the product** — Zach started in IT consulting services, calling IT directors and CIOs at Fortune 500 companies. He was successful but never enjoyed the conferences or the dinners. At WordStream he loved talking to the entrepreneurs he sold to and came off demos inspired, and he decided he would never work somewhere he wasn't excited after hanging up with a prospect. At Triple Whale he sells to e-commerce brands he can buy from himself. _Why it matters:_ If you spend eight to ten hours a day talking to a buyer, Zach says you should want to sit down and have a beer with them, and he calls this a big part of Triple Whale's success. Anthony adds the career case: staying in one pond compounds your network and value, while many sellers just chase the sexiest or best-funded product. _For:_ Sales Leaders, Revenue Executives, Customer Success 2. **Collect the dollars first, but capture the data next year's org needs** — Early on, the waitlist held emails, first names and a couple of form data points. Zach recalls his first rep doing about 140 demos and himself 109, while the co-founders ran demos and chat support sent people links to pay because there was no self-serve sign-up. What he did add quickly was data: new form questions after the first 25 to 50 calls, HubSpot, a lead score and enrichment. _Why it matters:_ Zach asked what data he would need 12 months out to route SMB and mid-market leads to separate teams and to forecast reps by segment. The form changes he made then are close to the questions Triple Whale still asks today. _For:_ Founders, RevOps Leaders, Sales Leaders 3. **The CRO should still sell every flagship launch** — Triple Whale usually launches new features to existing customers first, often with some exclusivity or preferred pricing, and Zach demos them himself or with the product manager and tests pricing on the call. For a recent automated media buying product he aimed for five demos in a week while the team ran five more, then reviewed all of them to refine discovery, pricing and which customer stories landed. _Why it matters:_ Zach says the person making the pricing decision needs to go and try to sell it, because the feedback loop is much faster. When the product reaches the wider team, he can explain the decisions from the ground rather than as something a few executives agreed on in a room. _For:_ Revenue Executives, Sales Leaders, Founders 4. **Stay in the deal without taking it over** — Zach admits he has pissed people off or lost a deal by not looping in an AE and then letting follow-up slip. He says his boss, the company's COO and a co-founder, now sees deals drag on four weeks longer when no rep is involved. The division of labor he landed on: the AE owns discovery, and he takes the presentation and pricing, where he expects the most friction. _Why it matters:_ Anthony contrasts this with two failure modes: the CRO who flies in to slam-dunk deals and the ivory tower CRO who writes messaging that never meets the market. Letting the rep own part of the call keeps the executive close to the market while someone else handles the next steps. _For:_ Revenue Executives, Sales Leaders 5. **Credits quietly inhibited AI usage** — Triple Whale launched an AI workflow builder, similar to Gumloop but specific to its industry, and charged in credits as others in that category did. It worked okay, but customers were fearful of hitting the limits. The company then adjusted the value of credits and stopped worrying about margin, to get usage and value to customers. _Why it matters:_ Zach describes a choice between protecting margin and chasing usage. Triple Whale followed the AI labs: get as much usage as possible, make the product critical infrastructure, and expect the rest to take care of itself. _For:_ Founders, Revenue Executives 6. **Put AI in every plan rather than selling it as an attachment** — Selling a base package with an AI add-on made the sales process too convoluted and risked AI becoming an afterthought. Triple Whale moved to good-better-best with AI in all packages. The base Foundation plan gets chatbot-style usage with limited models and token volume, plus one-time or recurring top-ups. The next tier gets a more preferred token rate and all of the models. A percentage of the single fee is allocated to tokens, and Zach says they are not really trying to take much margin there. _Why it matters:_ Zach says they started at good-better-best and ended up back there after a bunch of stops in the middle. All-model access has a downside, since customers burn tokens using a top model for a simple question, so routing matters. A new AI product is now testing a different value metric, which would be the company's fourth round of AI pricing. _For:_ Founders, Revenue Executives, Marketing Leaders 7. **Judge AI margin blended, not by your heaviest users** — Asked whether finance set a margin floor, Zach says roughly, and illustrates with an example: perhaps 20% of customers use all of their tokens and sit at the floor, a middle group does slightly better, and the bottom group uses far less. Blended, he says, the margin looks quite good. _Why it matters:_ If you only looked at the top users, Zach says the margin would look pretty bad for a SaaS company. He accepts that the approach eats into margin and believes that is fine while the company grows with customers. _For:_ Revenue Executives, Founders, RevOps Leaders 8. **Hire a dedicated owner for pricing and packaging** — Triple Whale had hired consulting firms, run external surveys, iterated internally and set up internal task forces. It then hired a head of pricing and packaging from a consulting background, who reports to the COO and biz ops rather than sales. Six months in, Zach can't believe how much the company relies on him and calls it one of its best hires. _Why it matters:_ Zach would put out a job req around the point a Series A company starts refining pricing and working on NDR. With AI speeding up feature releases, he doesn't want teams slowed down by figuring out pricing, and he expects pricing to change far more often than in legacy SaaS. _For:_ Founders, Revenue Executives 9. **Your first reps should be people who won't let you fail** — Zach thinks four of the first six reps came from his network, and the next four came from a manager's past teams. He says that at the very early stage you need people who will not let failure be an option because they want to succeed for you. He believes almost all of them are still at Triple Whale four and a half years later. _Why it matters:_ Adding managers is where he says team-building gets really hard. Referrals from people you trust still work well, but the next step is testing people by putting them on the infrastructure you need to scale. _For:_ Founders, Sales Leaders 10. **Make a new manager do the job first** — After about a year on inbound alone, then a partner ecosystem, Triple Whale decided to go outbound. It hired a manager who had run a team of eight and had never really done outbound, and told him he would start by doing it himself. From October through the end of January he worked like an SDR with very little success. In February a lot of demos hit, and by March he had four of the most senior reps and four new SDRs. _Why it matters:_ That team is now the company's biggest, and he leads the SMB, mid-market and upper mid-market commercial groups. Zach's advice is to build the infrastructure you need around someone who has personally proved the job can be done. _For:_ Revenue Executives, Sales Leaders, Founders 11. **Interview for progression and an appetite for upside** — Zach digs into resumes with 11 or 12 month stints, asking why each move happened and what success looked like. He wants progression inside one company, such as SDR to AE or a move into a new segment, because it shows someone has dealt with change. He treats negotiating severance or a ramp quota bonus before starting as a red flag, and would much prefer candidates ask about accelerators. Anthony looks for one three-to-four-year run somewhere. _Why it matters:_ Zach also tries to scare sales candidates out of the job, citing incredibly high quotas, aggressive growth targets and a product that keeps changing. Someone unwilling to fight through change will probably be looking again nine months in. _For:_ Sales Leaders, Revenue Executives 12. **Get new reps on the phone within two weeks** — Triple Whale puts new AEs to work within about two weeks on its database of free-product accounts, including thousands that never had a demo or are closed lost. They test messaging, record Looms and learn where to look in the product. Zach says some reps have hit a full monthly quota in four weeks. Ramp schedules vary by team, and with a 45-day SMB sales cycle he says those reps should theoretically be starting to hit full quota by day 90. _Why it matters:_ Throwing reps into demos quickly produces game tape for managers to refine. Zach also spends time with newer reps between day 60 and 90 on demo review and coaching, which helps him understand their process. _For:_ Sales Leaders, RevOps Leaders 13. **Match reps peer to peer by strength** — Zach pairs a rep who is weak at something, such as the pricing pitch, with the person who does it best in the company. Long-tenured reps with known strengths do this coaching, and he says they gain from it too, because you learn a lot when you tell someone how to do their job. _Why it matters:_ Anthony says getting the team to manage the team produces the best results and means less intervention. Zach adds that senior people who coach should be treated well and told their work is valued, since it takes time from their day-to-day. _For:_ Sales Leaders, Revenue Executives 14. **AI in go-to-market needs both top-down and bottoms-up, and taste** — A RevOps team member moved into go-to-market engineering and builds workflows such as a morning account attack list for every salesperson and a skill that reviews transcripts and creates an implementation handoff document. The podcast-scraping idea for gifting came from Zach. From the bottom up, he sees some reps producing AI slop and others building excellent hyper-personalized event handouts. He says he has had a really hard time deciding which model it should be, and they have tried a little of both. _Why it matters:_ Anthony's point is that leaning into AI meaningfully takes taste and an understanding of what good looks like. Triple Whale also runs its BI and analytics on its own instance, using the AI its customers use as often as it can. _For:_ RevOps Leaders, Revenue Executives, Sales Leaders 15. **Personalization has to go to the craziest degree** — After seeing a band's tour poster behind a high-value prospect on a podcast, Triple Whale sent a signed record from that band. It sends cookies from one of its customers, branded Triple Whale and paired with a case study about that customer, to offices unprompted. A rep found 10 target prospects on an event's attendee list, read their quarterly earnings and handed each a personalized AI-built infographic. _Why it matters:_ Zach now approves events he would never have funded five years ago. A two-day Berkshires resort workshop for 25 prospects from New York drew skepticism from the CFO, and the first deal closed four weeks later. Anthony's view is that the lazy first-name LinkedIn message or email might kill your brand. _For:_ Marketing Leaders, Sales Leaders, Revenue Executives ## Frameworks ### Fall in Love With the Buyer, Not the Product (22:54) **Definition:** Choose where you work by who you get to sell to, not by which product is hottest, because the buyer is who you will spend eight to ten hours a day with. Zach compares selling to Fortune 500 CIOs, which he never enjoyed, with selling to entrepreneurs at WordStream, startup founders at Unstack and e-commerce brands at Triple Whale. His test is whether you would want to sit down and have a beer with the person. He does not criticize sellers who move between hot data companies and make a lot of money, but says he doesn't want to sell to that buyer. ### Capture Data for the Org You Will Build (04:36) **Definition:** Before you can hire the team, decide what the team will look like, and collect today the data you will need to route and forecast for it. Zach whiteboarded roughly the current org structure when he interviewed. He refined form questions after the first calls so leads could later go to SMB or mid-market teams, added an e-commerce-specific enrichment source even before using all of it, and built a lead score so he could forecast how many reps each segment would need. ### Sell the Launch Yourself First (06:21) **Definition:** Whoever sets the pricing and positioning for a flagship launch should sell it first, starting with existing customers, before rolling it out to the sales org. Zach and the product manager demo the new product and test pricing with existing customers, often with some exclusivity or preferred pricing. The team runs its own calls in parallel, and all the calls are reviewed together. In one recent case the process ran about two weeks, while the team was trained on features first and on discovery, demo and pricing as those were refined. ### Split the Call With the AE (13:11) **Definition:** When an executive joins a sale, the AE owns discovery and the executive takes the presentation and pricing, then the roles shift over time. Zach learned through failed experiences that he drops follow-up when he runs deals alone. Discovery can be somewhat scripted and lets a rep find their voice. He keeps the demo and pricing because that is where he expects the most friction and needs to uncover value for the prospect, and over time the rep takes on parts of the demo. ### Good-Better-Best AI Pricing (16:56) **Definition:** Include AI in every package and differentiate tiers by feature versions, available models and the rate card for tokens, with token top-ups on top. Triple Whale reached this model after trying credits and an AI add-on. The base Foundation plan offers chatbot-style usage with limited models and token volume. The next package gets a more preferred token rate and every model. Customers pay one fee, a percentage of which is allocated to tokens, and can add one-time or recurring top-ups. ### Blended Token Margin (18:50) **Definition:** Assess AI margin across the whole customer distribution of heavy, middle and light token users instead of looking only at those who use everything. Zach's illustration is that perhaps 20% of customers use all their tokens and sit at the margin floor, a middle group does slightly better, and a bottom group uses far less. Blended, the margin looks quite good, while the top users alone would look pretty bad for a SaaS company. ### The Manager Does the Job First (32:20) **Definition:** Hire the leader for a new motion, then have them do the individual work personally until it is proven, before building the team around them. Triple Whale's outbound manager had never really done outbound. He spent about four months working as an SDR with very little success, began to see demos hit in February, and by March had four senior reps and four new SDRs. Zach also uses this as an answer to how to test people: put them into building the infrastructure you need to scale. ### Strength-Matched Peer Coaching (40:37) **Definition:** Pair a rep who is weak in one part of the sale with the colleague who is strongest at it, so both sides improve. Zach's own best learning came from listening to people strong where he was weak. He matches a rep with the best pricing pitch in the company to one who struggles with it, and says the coach learns too, because telling someone how to do the job makes you examine it. ### Top-Down Versus Bottoms-Up AI (44:37) **Definition:** Go-to-market AI can come from leadership-designed infrastructure or from reps experimenting on their own, and Triple Whale has tried a little of both. Zach's top-down example is his idea to scrape podcast episodes for gifting research, and a go-to-market engineer in RevOps builds shared workflows. His bottoms-up examples range from AI slop decks to a rep's personalized infographics for an event. He calls the choice a big discussion that he has had a really hard time with. ### Personalization to the Craziest Degree (46:07) **Definition:** Basic personalization no longer works, so outbound has to go far beyond it with research-driven gifts, in-person events and tailored artifacts. Zach says some prep and personalization has always been needed, but you've got to go so far now. Triple Whale's examples include signed records, cookies from a customer paired with that customer's case study, personalized AI infographics at events, and a two-day resort workshop for 25 prospects. ## Quotes _Speakers inferred from an undiarized transcript — verify before attributing._ > "The lazy, hey first name LinkedIn and emails like, that is, you might as well not send them. I think that might kill your brand." > > — Anthony Enrico, The LeanScale Podcast Ep. 146 (00:00) > "I think in-person has become so mission critical and personalization is going to need to go to like the craziest degree to work." > > — Zach Rego, The LeanScale Podcast Ep. 146 (00:39) > "It was a very scrappy, "How do we collect as many dollars as we can?" We'll figure out the rest later motion." > > — Zach Rego, The LeanScale Podcast Ep. 146 (03:12) > "I always had the vision of, what does 12 months from now look like when I hire people? What data do we need to collect today so that one day I can route SMB leads to our SMB rep or mid-market to our mid-market team, et cetera." > > — Zach Rego, The LeanScale Podcast Ep. 146 (04:36) > "If you're making that decision, you need to go and try to sell it because the feedback loop is going to be so much faster for you to iterate and you'll know where the friction points are." > > — Zach Rego, The LeanScale Podcast Ep. 146 (07:35) > "You don't want an Ivory Tower CRO either, who's coming up with messaging that they think sounds good to themselves, pushing it to the team, but it's not really resonating with the market." > > — Anthony Enrico, The LeanScale Podcast Ep. 146 (11:40) > "If I had just looped in an AE, that deal closes because they'll handle the follow-up." > > — Zach Rego, The LeanScale Podcast Ep. 146 (12:21) > "I'll let the expansion sales rep do the discovery. I might add a couple things in there, but I want to do the presentation and the pricing because I feel like that's where we're going to hit the most friction and need to uncover the value for the prospect." > > — Zach Rego, The LeanScale Podcast Ep. 146 (13:29) > "It worked okay, but it actually inhibited usage. People were fearful of hitting the limits." > > — Zach Rego, The LeanScale Podcast Ep. 146 (15:12) > "There's a benefit and a downside to that, in that customers are blowing themselves up when they're like, Opus 5.5 max, and then ask a question, like, "How many sales did I have today?"" > > — Zach Rego, The LeanScale Podcast Ep. 146 (17:56) > "One of the best hires we've made is an internal pricing and packaging leader." > > — Zach Rego, The LeanScale Podcast Ep. 146 (19:24) > "Obviously you want the product to be good, but if you're in sales or CS or any go to market function, even marketing, whoever you are trying to get in front of, or you have to talk to for eight to 10 hours a day, you want to be able to sit down and have a beer with them." > > — Zach Rego, The LeanScale Podcast Ep. 146 (25:22) > "I don't want to sell to that person. I want to enjoy my day to day." > > — Zach Rego, The LeanScale Podcast Ep. 146 (27:32) > "So I think when you're in that very early stage, you kind of need people who will not let failure be an option because they want to succeed for you." > > — Zach Rego, The LeanScale Podcast Ep. 146 (31:32) > "When we interview now, I try to scare people out of the job as best as I can from a sales rep perspective, because this is not an easy place to work." > > — Zach Rego, The LeanScale Podcast Ep. 146 (34:13) > "I like to see progression within a company. I want to see someone that was an SDR and got promoted to an AE of the company and maybe moved into a new segment has dealt with change within the same company." > > — Zach Rego, The LeanScale Podcast Ep. 146 (35:32) > "I would much prefer someone be asking me about how do I get into accelerators? What are your accelerators look like, right, as opposed to, what's the severance before you've started?" > > — Zach Rego, The LeanScale Podcast Ep. 146 (38:00) > "We give them some runway, but we throw them into demos as fast as we possibly can and get game tape." > > — Zach Rego, The LeanScale Podcast Ep. 146 (40:15) > "I think anytime you can get the team managing the team, you're going to see really, really good things happen." > > — Anthony Enrico, The LeanScale Podcast Ep. 146 (41:59) > "And then we have bottoms up where I have a bunch of sales rep creating some AI slop outputs that I'm like, please don't ever create a deck like that again." > > — Zach Rego, The LeanScale Podcast Ep. 146 (45:27) ## Practical advice by role ### Revenue Executives - Sell each flagship launch yourself first, starting with existing customers, so pricing and positioning are tested before the wider team carries them. - Bring an AE into any deal you run, and let them own discovery and the follow-up. - Look at AI margin blended across heavy, middle and light users rather than judging it by the customers who use everything. - When you start a new motion, have the leader you hire do the work personally until it is proven, then build the team around them. - Budget for in-person events you might once have rejected, and report early deal results back to finance. ### Founders - Keep process light while you are collecting early revenue, but decide what data you will need to route and forecast later and start capturing it. - Look first to people who know and trust you for your earliest sales hires. - Include AI in every plan if an add-on would make the sale convoluted or turn AI into an afterthought. - Consider a dedicated pricing and packaging hire around the point you start refining pricing and working on NDR after a Series A. - Choose markets and buyers your team will genuinely enjoy talking to all day. ### Sales Leaders - Probe every short stint on a resume: why the move happened and what success looked like at that company. - Favor candidates who have progressed inside one company and dealt with change there. - Treat a request to negotiate severance before starting as a warning sign, and notice who asks about accelerators instead. - Tell candidates plainly how hard the job is, including quotas, growth targets and product change. - Put new reps on the phone within about two weeks on unworked and closed-lost accounts so managers have game tape early. - Pair reps with the colleague who is strongest at the skill they lack, and thank the senior people who take that on. ### RevOps Leaders - Revise form questions after the first 25 to 50 calls based on what makes a good account, with future routing in mind. - Look for an enrichment source specific to your vertical, and build a lead score when inbound demand outstrips the people who can work it. - Use segment data to forecast how many reps you will need in each segment before you hire. - Consider moving someone inside RevOps into a go-to-market engineering role to build shared workflows such as a daily account list and implementation handoffs. ### Marketing Leaders - Use early launch demos to learn which positioning, features and customer stories land before writing the broader launch assets. - Mine public material such as podcast appearances for personal details that make a gift feel thoughtful. - Replace first-name personalization with something researched, or don't send it. - Hold AI-generated assets to a standard of taste, and be direct when output is slop. ## AI takeaways **Thesis:** Zach treats AI as something to price for usage, even at a cost to margin, and to use in go-to-market for personalization that would otherwise be impractical. The open question he names is how much of that work should be led from the top versus invented by reps. - **** — - **** — - **** — - **** — - **** — - **** — - **** — **Agent & automation ideas** - A morning account attack list delivered to every salesperson, as Triple Whale already sends. - A handoff skill that reviews sales transcripts and drafts the implementation handoff document. - A research agent that scrapes podcast transcripts about a prospect and proposes personalized gift ideas. - An event-prep agent that matches an attendee list to target accounts, reads quarterly earnings and drafts a personalized one-page infographic. - A model router that sends simple customer questions to cheaper models to protect token budgets. ## Operations takeaways ### Revenue operations - **.** - **.** - **.** - **.** - **.** - **.** ### Pipeline & marketing ops - **.** - **.** - **.** - **.** - **.** - **.** - **.** ## Metrics mentioned | Value | Metric | Context | | --- | --- | --- | | More than 60,000 | Brands using Triple Whale | Anthony's introduction and the show notes. | | 2,000 names | Waitlist when Zach started | An Airtable with emails, first names and a couple of form data points. | | About 250 | Demos in the opening sprint | Zach recalls his first rep doing about 140 and himself 109. The show notes round this to roughly 250. | | 6–8 a day, about 110 a month | First rep's demo pace | Zach's recollection, and a pace he knew was not sustainable. | | About 40, including managers | Sales team size | Across international and US markets. | | 11 or 12 | SDR team | Across all of Triple Whale's markets. | | 5 reps | Expansion sales team | The team that handles all upsells into the base and goes first on new products. | | 3, with a 4th in progress | AI pricing iterations | Zach's count, with a new AI product testing a different value metric. | | About 4 of the first 6 | Early reps from Zach's network | The next four came from a manager's previous teams. Zach believes almost all are still at Triple Whale four and a half years later. | | About a year | Inbound-only period | Before Triple Whale built its partner ecosystem and then started outbound. | | About 4 months | Outbound manager's time as an SDR | October through the end of January with very little success, before demos hit in February. | | Within 2 weeks | Time before a new rep is on the phone | Prospecting into the free-product database. | | 45 days | SMB sales cycle | With reps theoretically starting to hit full quota by day 90. | | 25 prospects, 2 days, first deal in 4 weeks | Berkshires event | A resort AI-strategy workshop for New York prospects, with another deal in legal at the time of recording. | | A few million to $100M+ in 3–4 years | Customer growth Zach cites | Zach's description of some Triple Whale clients, including a supplement company. | ## Entities mentioned - **Triple Whale** (company) — Zach's employer, the AI operating system for commerce used by more than 60,000 brands. Its attribution product is the backbone of its data infrastructure. It has about 40 sellers including managers, an expansion team of five, 11 or 12 SDRs and an agency partnerships function, and runs its own BI and analytics on its product. · https://www.leanscale.team/knowledge/company/triple-whale/ - **WordStream** (company) — Where Zach sold a Google ads management platform to mostly SMB and mid-market customers and found he loved talking to entrepreneurs. Per the show notes he spent seven years there, rising from rep to general manager of the global agency business. A sales manager he later hired at Triple Whale worked alongside him there. · https://www.leanscale.team/knowledge/company/wordstream/ - **Unstack** (company) — Zach's previous company, where he implemented HubSpot, sold to mostly startup founders and operators, and hired the rep he brought with him to Triple Whale. Per the show notes he led sales and marketing there and it was later acquired by Elastic Path. · https://www.leanscale.team/knowledge/company/unstack/ - **Anthropic** (company) — Zach's example of the usage-first approach to AI: wanting as much usage as possible and expecting to bring down cost per token over time. Its Opus model is also his example of customers using a top model for a simple question. · https://www.leanscale.team/knowledge/company/anthropic/ - **MongoDB** (company) — Part of Zach's example of a career moving from one hot data company to the next, which he says can make a lot of money but isn't the buyer he wants to sell to. · https://www.leanscale.team/knowledge/company/mongodb/ - **Snowflake** (company) — Named with Mongo and Databricks in Zach's example of sellers moving between hot data companies. · https://www.leanscale.team/knowledge/company/snowflake/ - **Radian Capital** (company) — Hosted the New York CFO summit where Anthony says the biggest topic was how to price AI features and full AI solutions. · https://www.leanscale.team/knowledge/company/radian-capital/ - **LeanScale** (company) — Anthony's company. He says he presented on getting your data model ready for AI at a CFO summit, and that selling to CROs, CMOs, RevOps leaders and founders is his favorite market he has worked in. · https://www.leanscale.team/knowledge/company/leanscale/ - **Zach Rego** (person, guest) — Chief Revenue Officer at Triple Whale and its first head of sales; previously seven years at WordStream and led sales and marketing at Unstack. · https://www.leanscale.team/knowledge/guest/zach-rego/ - **Anthony Enrico** (person, host) — Co-founder of LeanScale and host of The LeanScale Podcast. · https://www.leanscale.team/knowledge/guest/anthony-enrico/ - **Airtable** (tool, Database / Spreadsheet) — Where the 2,000-name waitlist lived when Zach started: no enrichment, no data, and a brief to go attack it. - **HubSpot** (tool, CRM) — Zach quickly stood up HubSpot, which he had implemented at Unstack, to organize the list, create tasks, begin collecting data and build a lead score. - **Store Leads** (tool, Data Enrichment) — An e-commerce-specific data enrichment tool that Triple Whale adopted early and still uses. Zach says almost every e-commerce SaaS company uses it. - **Gumloop** (tool, Workflow Automation) — Zach's comparison for Triple Whale's AI workflow builder, which was similar but specific to its industry. Triple Whale followed the same credit-based pricing and found it inhibited usage. - **Loom** (tool, Video Messaging) — New Triple Whale AEs record Looms as part of early prospecting into the free-product database. - **Databricks** (tool, Data Platform) — Named with Mongo and Snowflake in Zach's example of sellers moving between hot data companies. ## FAQ **Q: What does "fall in love with the buyer, not the product" mean?** A: It is Triple Whale CRO Zach Rego's advice for choosing a sales career. If you will spend eight to ten hours a day talking to someone about their business, he says it should be someone you would want to sit down and have a beer with. He enjoyed selling to entrepreneurs at WordStream far more than selling to Fortune 500 CIOs earlier in his career, and he now sells to e-commerce brands he can buy from himself. He doesn't criticize sellers who chase the hottest product, but says enjoying his buyers matters more to him and has been a big part of his team's success. **Q: Should a CRO still run sales demos?** A: Triple Whale CRO Zach Rego says yes, especially for flagship launches. He launches to existing customers first and demos the product himself or with the product manager while testing pricing. His argument is that whoever makes the pricing decision should go and try to sell it, because the feedback loop is much faster, the friction points become obvious, and he can explain decisions to reps from direct experience rather than as something executives decided in a room. **Q: How can a sales executive join deals without stepping on the AE?** A: Zach Rego of Triple Whale says the AE should be looped in from the start and should own parts of the process, because executives drop follow-up. He usually lets the rep run discovery and takes the presentation and pricing, where he expects the most friction. He admits that going solo has cost him deals, and says his co-founder and COO has seen deals drag four weeks longer without a sales rep involved. **Q: Why can credit-based pricing hold back AI adoption?** A: When Triple Whale priced its AI workflow builder in credits, CRO Zach Rego says it worked okay but actually inhibited usage, because customers were fearful of hitting the limits. The company then adjusted credit values to favor usage over margin. It also found that selling a base package plus an AI add-on made the sales process too convoluted, so it later moved AI into all of its plans. **Q: How does Triple Whale price its AI today?** A: Triple Whale uses a good-better-best model with AI included in every package. According to CRO Zach Rego, the base Foundation plan offers chatbot-style usage with limited models and token volume, with one-time or recurring top-ups available. The next package gets a more preferred token rate and access to all models. A percentage of the single fee is allocated to tokens, and Zach says the company is not really trying to take much margin on them. He also said a new AI product was testing a different value metric at the time of recording. **Q: How should you think about margin on AI features when usage varies?** A: Zach Rego of Triple Whale suggests looking at the whole customer distribution. In his illustration, perhaps 20% of customers use all of their tokens and sit at the margin floor, a middle group does slightly better, and a bottom group uses far less, so blended margin looks quite good. Looking only at the top users would make margin look pretty bad for a SaaS company. He accepts that this approach eats into margin while the company grows with its customers. **Q: When should a company hire a head of pricing and packaging?** A: Triple Whale CRO Zach Rego says he would put out a job req around the point a Series A company has money to scale and needs to refine pricing and work on net dollar retention. Triple Whale had used consulting firms, external surveys and internal task forces before hiring its own head of pricing and packaging, from a consulting background, who reports to the COO and biz ops. Zach calls it one of the company's best hires, because AI is speeding up feature releases and pricing needs someone thinking ahead. **Q: What are red flags when interviewing sales reps?** A: Zach Rego, CRO of Triple Whale, looks closely at resumes with 11 or 12 month stints and asks why each move happened and what success looked like. He prefers progression within one company, such as SDR to AE or a move to a new segment. A candidate who negotiates severance or a ramp quota bonus before starting is a red flag for him. He would much rather they ask how accelerators work. Host Anthony Enrico adds that he looks for at least one three-to-four-year run somewhere. **Q: How quickly should new sales reps start selling?** A: At Triple Whale, new AEs are put on the phone within about two weeks, prospecting into free-product accounts that have not had a demo or are closed lost. CRO Zach Rego says some reps have hit a full monthly quota in four weeks. Ramp schedules vary by SMB, mid-market and enterprise team. With a 45-day SMB sales cycle, those reps should theoretically be starting to hit full quota by day 90, and managers use early demos as game tape. **Q: What outbound personalization is working as AI raises the bar?** A: Triple Whale CRO Zach Rego says personalization now has to go to the craziest degree. His company has sent a signed record based on a band poster seen behind a prospect on a podcast, sent cookies from a customer paired with that customer's case study, handed out AI-built infographics based on each target's quarterly earnings at an event, and hosted 25 prospects for a two-day resort workshop in the Berkshires, whose first deal closed four weeks later. Host Anthony Enrico says lazy first-name LinkedIn messages and emails might kill your brand. ## Timeline - **00:00** — Cold open + intro - **01:12** — Day one: an Airtable of 2,000 names and one rep - **05:56** — Why the CRO still takes demos - **13:43** — How to price AI when the economics have changed - **19:24** — Why they hired a head of pricing and packaging - **22:35** — Fall in love with the buyer, not the product - **26:51** — Chasing the hot product vs. staying in one pond - **30:19** — Hiring: why the first reps came from his network - **34:48** — Interview red flags: job hops, no progression, severance asks - **42:36** — AI in GTM: top-down or bottoms-up? - **46:07** — Personalization to the craziest degree - **48:36** — Wrap ## Related episodes - **Ep. 91: Why Outcome-Based Pricing Is a Trap for Most AI Companies** (Roee Hartuv (Winning by Design)) — A pricing and packaging specialist on how AI broke SaaS unit economics, the backdrop to Triple Whale's move from credits to good-better-best. · https://www.leanscale.team/knowledge/podcast/roee-hartuv-outcome-based-pricing-trap/ - **Ep. 132: The Token Bill Came Due: What Comes After the AI Pilot Phase** (Anish Chadalavada (Gradial)) — The buyer's side of token costs, next to Zach's account of customers burning tokens on top models and the margin that comes out of. - **Ep. 107: Why Circle's Co-Founder Ran 1,500 Sales Demos Before Hiring a Single Rep** (Andy Guttormsen (Circle)) — Demos as a product and brand engine from a co-founder, alongside a CRO who still demos every flagship launch. - **Ep. 120: AI Made Outreach Worthless. Events Are What's Left** (Alex Reynolds (Vendelux)) — The case that in-person replaces cheap AI outreach, matching Zach's two-day Berkshires workshop and view that in-person is mission critical. - **Ep. 137: 90% of Reps Don't Prep: The LEGO Booth Playbook** (Shani Shoham (OpenObserve)) — Memorable event tactics and a CRO owning sales and marketing, close to the personalized infographics and combined role Zach describes. - **Ep. 123: Stop Hiring GTM Engineers. They Already Work For You.** (Ryan Vanshur (Handle)) — Finding builders inside the existing team, as Triple Whale did when it moved someone within RevOps into go-to-market engineering. - **Ep. 142: How to Sell Against Claude: Differentiation Is a System** (Simon Kirk (Orbital)) — A revenue leader's approach to interviewing AEs and sales leaders, to compare with Zach's focus on progression and appetite for upside. ## Full transcript _Machine-transcribed and not diarized; speaker attribution is inferred._ _Transcript only, as a separate file: https://www.leanscale.team/knowledge/podcast/zach-rego-triple-whale-fall-in-love-with-the-buyer/transcript.md_ ### 00:00 — Cold open + intro **[0:00]** But the lazy, hey first name LinkedIn and emails like, that is, you might as well not **[0:09]** send them. **[0:10]** I think that might kill your brand. **[0:11]** So if you're going to do something, then you got to really take it to that next level. **[0:15]** My guest today is Zach Rigo, Chief Revenue Officer at Triple Whale, the AI operating **[0:20]** system for commerce used by more than 60,000 brands. **[0:24]** So it was very scrappy, how do we collect as many dollars as we can? **[0:29]** We'll figure out the rest later, motion. **[0:31]** I think if you're making that decision, you need to go and try to sell it because the **[0:36]** feedback loop is going to be so much faster for you to iterate. **[0:39]** But I think in-person has become so mission critical and personalization is going to need **[0:43]** to go to like the craziest degree to work. **[0:48]** You said fall in love with the buyer, not the product. **[0:55]** What did you mean by that? **[0:56]** If I'm going to spend 9-10 hours a day talking to someone about their business, I would want **[1:02]** to just sit down and have a beer with and have that discussion. ### 01:12 — Day one: an Airtable of 2,000 names and one rep **[1:12]** Four and a half years ago, somebody handed you an air table with 2,000 names in it. **[1:17]** No enrichment, no data, said go attack it. **[1:20]** Walk me through that first week. **[1:22]** What did you actually do on day one? **[1:24]** Yeah, so our founders were incredibly scrappy and our CMO at the time was just amazing at **[1:31]** generating demand. **[1:33]** We had actually launched a wait list for a product that was just coming to fruition as **[1:37]** I started, which is our attribution product today. **[1:40]** It's kind of the core backbone of our data infrastructure. **[1:44]** I brought one sales rep with me, so when I left Unstack, I had just hired a sales rep **[1:47]** there. **[1:48]** It happens to be one of my best friend's little brothers. **[1:50]** I didn't want to leave him because basically me and him were the only folks on the sales **[1:54]** team at the time and asked the CEO at Unstack if I could bring it with me. **[1:58]** He was like, "Yeah, sure." **[1:59]** I asked the CEO at Triple Well if I could bring it with me. **[2:02]** He was like, "Yes, of course. **[2:03]** We need someone." **[2:05]** We just attacked the list. **[2:06]** We had emails and first name and a couple data points from the form. **[2:11]** It was just how can we reach out to as many folks as fast as we possibly can to get demos **[2:16]** booked as well as manage the inbound pipeline. **[2:20]** We started to stand up HubSpot because I had implemented that at Unstack to try to organize **[2:24]** that, create tasks, and start to create some semblance of data collection where we could **[2:28]** potentially build a lead score. **[2:32]** Between Brantley, the first sales rep and I, I think he did 140 demos. **[2:35]** He was doing six or eight demos a day. **[2:39]** It was crazy. **[2:41]** I think I did 109. **[2:43]** Then we quickly started to see who's our ICP, where should we start to focus things, and **[2:49]** who should we maybe not go after anymore on this list. **[2:54]** Very quickly stood up HubSpot, built a lead score, and had to hire salespeople. **[2:58]** We put a job posting up instantly. **[3:01]** Sales were really coming in at that time between our two co-founders doing demos and our chat **[3:06]** support team just sending people links to pay and sign up. **[3:10]** We didn't even have a self-serve sign-up flow at the time. **[3:12]** It was a very scrappy, "How do we collect as many dollars as we can?" **[3:16]** We'll figure out the rest later motion. **[3:20]** I think some people, they try to play business early in that stage and get too much process **[3:25]** in place and too many things when, "Hey, it's kind of Wild West gunslinging stage right **[3:30]** now. **[3:31]** We just got to get out there and get it done." **[3:34]** What are some of the things that you did during that time that you think, "Hey, this was the **[3:42]** right fit of process," but made sure we weren't acting bigger than we were at the **[3:47]** time? **[3:48]** Yeah. **[3:49]** I think a couple really quick changes was, "What data do we want to collect on the form?" **[3:54]** As we quickly learned, what was a good brand for us to talk to in those first 25, 50 calls, **[4:00]** it was like, "Okay, we've got to change our form strategy here on what data we're collecting." **[4:04]** Actually, the changes we made then are pretty similar to the same form questions we asked **[4:08]** today for booking a demo or a guide download or a webinar. **[4:13]** We very quickly refined that process on what do we want to collect because it was just **[4:17]** going to become, how do we want to route these leads to different sales teams over the course **[4:22]** of time? **[4:23]** That was one. **[4:24]** It's like, you should be thoughtful about how you want the team to look in the future. **[4:28]** When I interviewed for the job here, I actually white-boarded out, I would say, roughly where **[4:32]** we are at today from a sales org structure with a couple small changes. **[4:36]** I always had the vision of, what does 12 months from now look like when I hire people? **[4:41]** What data do we need to collect today so that one day I can route SMB leads to our SMB rep **[4:46]** or mid-market to our mid-market team, et cetera. **[4:50]** That was a big part. **[4:51]** Then the other one was enrichment. **[4:52]** What tools are available to us that we can start to, if we have email and we have website, **[4:57]** get some of the other data points because I knew I needed to refine a lead score. **[5:01]** We were getting so much inbound demand at the time with so few people to fulfill it, **[5:08]** that getting data enrichment was very, very important to us. **[5:11]** Interestingly enough, there was a tool that's specific to the e-commerce space that had **[5:15]** started spinning up around that time that was perfect for us. **[5:18]** It was called Store Leads. **[5:19]** We still use it today. **[5:20]** Almost every e-commerce SaaS company uses it. **[5:23]** Just to collect additional data points, we didn't really do anything with it to start, **[5:26]** but it was more just like, how do we start to get our ducks in a row so when the time **[5:29]** is right and I do start hiring, I can at least forecast, I need three reps in this segment **[5:34]** and six reps in this segment because it was not going to be sustainable for Brantley to **[5:37]** do 110 demos a month for very long. **[5:41]** Although he did make a ton of money in those first few months and we tried to write commission **[5:45]** plans and get really scrappy on some of that stuff as well, which was a fun and challenging **[5:49]** time. **[5:50]** Those are good problems to have. **[5:53]** Those are champagne problems. **[5:54]** Yeah, 100%. ### 05:56 — Why the CRO still takes demos **[5:56]** One of the things I find really interesting is that you still, to this day, even after **[6:00]** you've grown, scaled, you have the team in place, you're still doing quite a few demos. **[6:06]** What's the logic behind that? **[6:08]** We launch a lot of new products, which is awesome. **[6:13]** I've worked for companies that are very strategic about how they want to build and their release **[6:16]** schedule is once a quarter and we launch new things daily, it feels like now. **[6:21]** When we have these kind of flagship launches, I still like to see how the market's going **[6:26]** to react to it. **[6:27]** We're figuring out pricing. **[6:28]** We're figuring out packaging. **[6:30]** I lead marketing, so we're figuring out how we want to position it. **[6:33]** What kind of case studies do we need and customer stories do we need? **[6:37]** We typically always start by launching new features to existing customers and giving **[6:41]** them some sort of exclusivity to either preferred pricing or whatever, but I'm going to demo **[6:47]** you the product or me and the product manager are going to demo you the product and take **[6:51]** you through it. **[6:52]** Then I'm going to test some pricing on you and see what I can get. **[6:56]** We do that as recently as this week, we've launched a new product that our expansion **[7:00]** sales team, which does all upsells into our base, is going to market with. **[7:06]** This morning, I was literally working on refining the demo process with the sales leader and **[7:10]** now I'm getting on demo starting in the next few days and we'll start to hone that craft **[7:15]** and adjust pricing, which is a hypothesis right now. **[7:19]** This will work and that's just me and a few other people banging our heads and saying, **[7:23]** "Hey, we're going to try this." **[7:24]** I think especially with AI, we're on our third iteration of AI pricing. **[7:28]** This will actually be our fourth. **[7:30]** This is an AI product we're bringing to market. **[7:32]** We're trying a different variable for pricing here, a different value metric. **[7:35]** When you're doing that, I think if you're making that decision, you need to go and try **[7:38]** to sell it because the feedback loop is going to be so much faster for you to iterate and **[7:44]** you'll know where the friction points are. **[7:46]** You'll know what assets you'll need to arm the team with and then when you do roll it **[7:48]** out to the broader sales org, most of those questions are answered. **[7:52]** There's still ... Sales reps love to ask questions about things that are changing or different. **[7:56]** There will still be things unanswered, but I think I can have some confidence on why **[7:59]** we made the decisions we did and explain them from a boots on the ground perspective as **[8:03]** opposed to a few executives sat around a room and said, "This is what's best for us and **[8:08]** we think it's going to work with customers," and sales reps go figure it out. **[8:11]** I think that's just a really hard way to collect feedback and make change quick. **[8:17]** I'm going to want to get into pricing and packaging because that's a really big topic **[8:20]** right now, so I want to table that for a second. **[8:23]** I do want to get back to ... How big is the team right now? **[8:28]** How many reps roughly are on the team? **[8:31]** Yeah, so total sales-specific reps is between international and US-based, it's roughly 40 **[8:41]** with managers, a few managers across those various segments. **[8:45]** We also have partnerships, which works through our agency network, which reports up to me. **[8:49]** That's a big part of our business is driven by either agencies leveraging our platform **[8:54]** internally or referring us customers, and then we have a solid-size SDR team between **[9:00]** all of our markets that's roughly 11 or 12 SDRs as well. **[9:06]** Practically speaking, with a team of that size and scale, how do you actually get in **[9:12]** and do some of the demos? **[9:13]** Are you getting some of the inbound? **[9:15]** Are you targeting a few of the ones? **[9:17]** Are you writing shotgun with a few reps? **[9:19]** I think it's ... I'm always interested in the balance of being in the weeds and then **[9:26]** letting the team run, not stepping on toes, but not losing touch. **[9:32]** How are you managing that right now? **[9:34]** Yeah, so again, we start with existing customers when we're trying to launch a new product. **[9:41]** Something is somewhat ironed out. **[9:43]** I'll do a shotgun ride along with most of the expansion sales team. **[9:49]** Typically I'll start with one or two reps. **[9:51]** We have five on that team, so start with two and let them kind of get in with the executive **[9:54]** team on what we want to roll out, what it's going to look like, pick some target lists **[9:58]** with them, do some outreach from myself specifically to them with the AEC seed, and book the calls. **[10:06]** Then, more recently, if we set up an inbound router, which is a pop-up in our app of, "Hey, **[10:11]** we've got ... You've been picked to kind of check in beta this feature, which I'd like **[10:15]** to book a call," I just get added to those as we go. **[10:18]** Listen, my goal is to get, in this case, the more recent one, which is our automated media **[10:23]** buying product, I'm trying to get five in the next week, so not a massive amount. **[10:27]** The team's also doing five and I'm analyzing those calls, but part of it is like, "Can **[10:33]** I go in and test the messaging or refine the messaging or come up with new talk tracks **[10:37]** or positioning for the pricing," while the team's also going to market with it and getting **[10:40]** more data points. **[10:41]** Then, in aggregate, we look at everything and see how can we refine what discovery looks **[10:46]** like, how we should position pricing, what features we should lean in on, which customer **[10:50]** stories are resonating the most. **[10:52]** That's kind of where we're at and hope to be at by the end of next week. **[10:55]** It's like a two-week process of us kind of really going deep on that. **[11:02]** In parallel right now, we're training the new sales team on the product itself, what **[11:06]** the features do. **[11:07]** Then, next week, we're starting to roll out. **[11:10]** Here's the discovery process. **[11:12]** Here's the demo process. **[11:13]** Here's how we pitch pricing. **[11:14]** That'll be last because that's the one that I think we're farthest behind on right now **[11:18]** in getting reps and real buy-in from brands. **[11:22]** Yeah, I'm just making sure it's like, "Oh, Zach's not flying in slam dunking deals on **[11:27]** his own and then building out a territory for himself," because I feel like I've seen **[11:33]** that version of a CRO flying in and trying to do that. **[11:38]** It's like, "Hey, I could have done that on my own." **[11:40]** I feel like that's a really good, healthy way of, compared to you don't want an Ivory **[11:46]** Tower CRO either, who's coming up with messaging that they think sounds good to themselves, **[11:53]** pushing it to the team, but it's not really resonating with the market. **[11:57]** Just think finding that balance is super challenging and it feels like you've kind of cracked the **[12:02]** code on that. **[12:03]** Yeah, I've tried to. **[12:04]** I mean, listen, no doubt I've pissed people off or lost a deal because I didn't manage **[12:08]** it appropriately and I didn't loop in an AE. **[12:11]** It's humbling, right? **[12:12]** It's good to go back to that of like, "Oh, I can do this. **[12:15]** It's easy." **[12:16]** Then my follow-up's horrible or I get sidetracked because I got other things going on. **[12:21]** I'm like, "If I had just looped in an AE, that deal closes because they'll handle the **[12:24]** follow-up. **[12:25]** They'll handle the next steps." **[12:28]** It took me a lot of failed experiences to find that out and we've gotten to a really **[12:33]** good spot. **[12:34]** Even like our COO and my boss, Max, is one of our co-founders. **[12:38]** He was the first salesperson when we were building this thing. **[12:42]** He's starting to get back into it now, which has been fun, but he even sees it now where **[12:45]** he doesn't loop in a sales rep and that deal starts to drag on for four weeks longer than **[12:50]** it should. **[12:51]** I'm like, "Did you follow up with them?" **[12:52]** I'm starting to do the micromanaging that you have to do as a sales manager to him and **[12:56]** he's like, "I should have looped in a sales rep." **[12:58]** I think we all know at this point we're going to drop the ball here, so it's best to do **[13:03]** it, in my opinion, alongside the salesperson and even let them own some parts of the process. **[13:11]** Just like if you brought in a brand new sales rep, I almost always let them own Discovery **[13:15]** because you can somewhat script a Discovery flow for them and it feels a little robotic **[13:20]** but it allows them to find their voice, but I'm going to do the demo and I'm going to **[13:24]** do the close and then the next time you're going to do the demo of this feature and this **[13:27]** feature. **[13:28]** We do a lot of that as well. **[13:29]** We're like, "I'll let the expansion sales rep do the Discovery." **[13:32]** I might add a couple things in there, but I want to do the presentation and the pricing **[13:35]** because I feel like that's where we're going to hit the most friction and need to uncover **[13:39]** the value for the prospect. **[13:41]** I love it. **[13:42]** I love it. ### 13:43 — How to price AI when the economics have changed **[13:43]** One question going into pricing and packaging. **[13:48]** I think this is the biggest go-to-market challenge CRO, CMOs, founders, CFOs are having in B2B **[13:58]** SaaS and AI today is how do we price and package this stuff when the economics have completely **[14:05]** changed. **[14:06]** A couple of weeks ago, I was at a CFO summit with Radian Capital, so I was in New York, **[14:12]** full room of CFOs, we were presenting on getting your data model ready for AI, but probably **[14:19]** the biggest topic for the rest of the event was talking about how to price AI features, **[14:25]** full AI solutions. **[14:27]** I was wondering if you could maybe walk through. **[14:30]** I know there's not a silver bullet. **[14:31]** I know there's not a one size fits all. **[14:33]** I know there's not one answer, but I would love to just hear the thought process. **[14:38]** What did you ask, what did you test, and what were some of the hypotheses that you had that **[14:47]** led you through the process to how you ultimately ended up pricing and packaging? **[14:51]** Yeah. **[14:52]** Listen, we look for inspiration to a lot of folks that had tried and changed and iterated. **[14:58]** At the time, we had launched a product that was similar to a gum loop, but very specific **[15:02]** to our industry, so a workflow builder for AI tasks. **[15:09]** They charged off of credits, so we tried to charge off of credits. **[15:12]** It worked okay, but it actually inhibited usage. **[15:17]** People were fearful of hitting the limits. **[15:21]** That put an interesting discussion at play of where do we want to be in this? **[15:25]** Do we want just incredible usage and let the usage metrics, which is the approach that **[15:29]** Anthropic and everyone else has taken, like Anthropic's losing $80 billion. **[15:33]** They don't care. **[15:34]** They just want as much usage as possible, and they'll figure out how to bring down the cost **[15:37]** per token over time. **[15:39]** We were like, "Okay, we don't want to inhibit usage, so what do we do next?" **[15:42]** Then we started adjusting credit value to where like, "Hey, let's whatever. **[15:47]** We don't need to worry about margin on this. **[15:48]** Let's just get usage and value to customers." **[15:52]** Then we found that the sales process is just too convoluted. **[15:54]** I'm trying to sell this base package, and you can add on this AI attachment that you **[15:58]** can build off of. **[16:00]** We didn't want it to be an afterthought. **[16:01]** We wanted it to be integrated in all plans and really become more AI forward. **[16:06]** Listen, we're on our third version of an AI product. **[16:10]** We had a chatbot in 2024 that was unique to us and our data set and our customers. **[16:14]** We were very early to that space and credit to our CEO, AJ, for pushing that very early. **[16:20]** We redid our entire data infrastructure to support AI and normalized all of our data **[16:26]** across billions of rows of different data points across every ad channel, every SKU, **[16:31]** everything that you would need to know as an operator way before anyone else in our **[16:36]** space did. **[16:37]** We knew we could get usage. **[16:38]** We knew if we priced appropriately, we'd get a lot of usage. **[16:41]** We knew we wanted to be kind of AI forward and more learned from the AI kind of labs **[16:46]** and leaders of like, "Let's get as much usage as we possibly can and make this just **[16:51]** critical infrastructure to our customers, and the rest of it will take care of itself." **[16:56]** We decided more recently to kind of do a good, better, best pricing model, which is like **[17:01]** we started there and then we somehow ended up back there after a bunch of different stops **[17:04]** in the middle where AI is included in all packages, but you unlock different versions **[17:09]** of features and different, I would say, like rate cards around what a cost per token roughly **[17:16]** would be, but we're not really trying to take much margin on tokens. **[17:20]** In our foundation package, which is our base plan, you get AI usage, but it's more chatbot. **[17:25]** You can ask our chats questions. **[17:26]** You could build maybe a dashboard or a report out of it, but you're going to be limited **[17:30]** in the models you can use, and you're going to be limited in the volume of tokens you **[17:35]** have included in your package. **[17:36]** You can always add one-time top ups or recurring top ups. **[17:41]** Our next package, you get a more preferred rate on tokens. **[17:45]** You're going to get more usage as a percentage of what you pay us. **[17:48]** You pay us one fee, a percentage of that is allocated for us paying for tokens, and you **[17:54]** get access to all of the models. **[17:56]** There's a benefit and a downside to that, in that customers are blowing themselves up **[18:00]** when they're like, Opus 5.5 max, and then ask a question, like, "How many sales did **[18:07]** I have today?" **[18:08]** It's like, "Please don't do that." **[18:11]** Routing is important, and thinking about what your task you're trying to accomplish there **[18:14]** is really important, but that's the approach we've taken. **[18:18]** It eats into our margin, and again, we believe that is fine, and we want to grow with our **[18:25]** customers around using our product in the right ways to scale their business and provide **[18:30]** them as much value as we can, and we'll figure out the rest from there. **[18:34]** Without revealing any real numbers, did you and the finance team think about having a **[18:40]** floor of what the margin needed to be and working backwards from that, and then just **[18:44]** having like, "Hey, this is an acceptable range as long as we can model, most of the **[18:48]** customers will fall within here?" **[18:50]** Yeah, roughly, and I think you got to look at it as like, if you look at all of your **[18:55]** customers that buy these packages, whatever, 20% are going to use all of their tokens. **[19:04]** Yeah, those ones, they're going to be maxed out on the floor of the margin, but then you're **[19:09]** going to have this middle of the pack that's going to make margins slightly better, and **[19:12]** then you're going to have this other like bottom, the people that just aren't using **[19:15]** nearly as much, and blended, the margin will look quite good. **[19:19]** If you only looked at the top users, your margin is going to look pretty bad as like **[19:22]** a "SAS" company, right? ### 19:24 — Why they hired a head of pricing and packaging **[19:24]** So I think it is a bit of a model there, and listen, one of the best hires we've made is **[19:30]** an internal pricing and packaging leader, you know, he's our head of pricing and packaging. **[19:35]** We had hired consulting firms before, we had done external surveys before, we've iterated **[19:40]** on pricing a bunch internally, we've created internal task force. **[19:44]** Finally, we were like, this is like going to be critical infrastructure, it will be **[19:48]** a leg up to us. **[19:50]** And we just hired someone from a great background, awesome resource. **[19:53]** He's actually out right now for his wedding and honeymoon, and I'm like, just can't believe **[19:59]** how much we rely on him just six months later of him starting, where it's like, that is **[20:03]** a super important hire right now, in my opinion. **[20:07]** You can't have our guy, but I would be looking for someone in that realm, because it's going **[20:12]** to keep you nimble, and it's going to allow it to not be a distraction, but always be **[20:15]** top of mind for you. **[20:17]** Where? **[20:18]** I actually haven't had a CRO have that particular role on their team. **[20:22]** Maybe I've seen it in really, really scaled out companies, like near public sized companies. **[20:32]** What type of background are you looking for? **[20:34]** Did he have pricing and packaging experience before, or did you have a transferable skill? **[20:40]** Yeah, he's not on my team. **[20:43]** Obviously, I spend a ton of time with him and we're bouncing ideas off of each other. **[20:47]** He reports into the COO and kind of the more like biz ops teams. **[20:53]** Yeah, he actually had, he came from like more of a consulting background. **[20:58]** And there's a bunch of firms out there, you know, most SaaS companies have hired one at **[21:01]** some point in their time, you know, I would say Series A, you're kind of like, I got some **[21:07]** money to go scale. **[21:08]** You got to start to refine that, figure out how you get some NDR. **[21:11]** You know, when you get to that point, I'd put a job wreck out, like at this point in **[21:18]** the game, you know, being able to iterate on pricing every six months, or you're going **[21:22]** to be launching features faster than you ever have before with AI, you know, in the engineering **[21:27]** and product world, you don't want to be slowed down by figuring out pricing, like you want **[21:32]** someone who is thinking about that, you know, before you know, skate to where the puck is **[21:37]** kind of thing, like you got to know where you want to be, and have someone that's always **[21:43]** like living and breathing what that looks like for every product you're launching. **[21:47]** Makes a ton of sense. **[21:48]** And I do think the difference now, like you mentioned, it's the cycle time where the velocity **[21:55]** of new features, new products, new things that will be a forcing function to adjusting **[22:00]** your pricing and packaging. **[22:02]** Also release of new models, new AI capabilities that you can leverage. **[22:07]** It may change the economics. **[22:08]** You may adjust pricing that can give you a bigger advantage. **[22:11]** I agree. **[22:12]** I think you're going to need to be tweaking this so much more often than you did in the **[22:17]** legacy SaaS world. **[22:20]** And I think it's a good investment. **[22:23]** And if you can get your pricing and packaging nailed down, right, the return on that is **[22:27]** immense. **[22:28]** Insane. **[22:29]** Insane. **[22:30]** There's such great value can be attributed to that. ### 22:35 — Fall in love with the buyer, not the product **[22:35]** One of the things you talked about during our prep session that I thought was really, **[22:38]** really interesting, because it is a little contrarian to how a lot of people navigate **[22:44]** their careers. **[22:46]** You said fall in love with the buyer, not the product. **[22:52]** What did you mean by that? **[22:54]** Yeah, listen, I, you know, I started my career in IT consulting services where I was basically **[23:02]** calling IT directors and CIOs of Fortune 500 companies all day and getting hung up on often. **[23:10]** And when I connected, you know, the only objective that the person on the other end of the phone **[23:14]** had was to make me look like a dumb sales guy, which they did quite often. **[23:18]** Like, I was successful at that job, but I never enjoyed the conferences. **[23:25]** You know, I never enjoyed when I was taking, you know, the IT director from XYZ company **[23:31]** out to dinner, like, it was fine. **[23:33]** But it was like, I kind of always wanted to love who I was selling to and talking to them. **[23:39]** Like, if I'm going to spend nine, 10 hours a day talking to someone about their business, **[23:45]** their goals, what, how they want to grow personally, professionally in their business. **[23:50]** I want it to be someone that like, I would want to just sit down and have a beer with **[23:53]** and have that discussion with at all times. **[23:56]** And when I joined word stream, it was like, I loved calling our customers or our prospects, **[24:04]** right? **[24:05]** Like, it was like, I enjoyed the conversations. **[24:06]** I enjoyed the demos, you know, we were selling a Google ads management platform at the time **[24:12]** to mostly SMBs and mid markets, but a lot of entrepreneurs and there were businesses **[24:16]** I would like get on off the phone with and I'd be like, that's insane. **[24:20]** Like that felt like an episode of Shark Tank, like this guy is brilliant or, you know, she **[24:23]** built this amazing business that you would never think about. **[24:26]** I remember one where it was like, they sold, you know, crib sheets. **[24:30]** The margins on crib sheets are insane. **[24:33]** A crib is only, you know, this big and like, it's always the same size. **[24:37]** And I was just like blown away. **[24:39]** I was like the whole business around crib sheets is just crazy. **[24:42]** And like, I was so inspired after every demo and I was always like, I will never work for **[24:47]** a company where I'm not selling to somebody that when I hang up the phone, I'm like, that **[24:52]** was awesome. **[24:53]** Like I am so excited. **[24:54]** And I think, you know, Unstack, I was selling to mostly startup founders and operators and **[24:59]** it was awesome. **[25:00]** I got to see like some really cool companies were customers of ours early and I grew to **[25:04]** become like pretty awesome businesses. **[25:06]** And at triple whale, similarly, like we're selling to e-commerce brands that I'm a customer **[25:11]** of a lot of them, you know, or every one of our prospects I've, I can go and buy from, **[25:16]** for myself or my wife or my kids or whatever. **[25:19]** And that gets me really excited and I love it. **[25:22]** Obviously you want the product to be good, but if you're in sales or CS or any go to **[25:26]** market function, even marketing, whoever you are trying to get in front of, or you have **[25:31]** to talk to for eight to 10 hours a day, you want to be able to sit down and have a beer **[25:35]** with them or play around to golf with them in my case, right? **[25:38]** Those are the things I like to do in my spare time of preferably a beer and golf at the **[25:42]** same time. **[25:43]** Usually hand in hand. **[25:44]** Yeah, yeah, yeah, exactly. **[25:46]** But I want that, right? **[25:47]** Like I want my prospects, I want to be excited to invite them to an event and that's a rings **[25:51]** true here for sure. **[25:52]** And it's been a big part of our successes. **[25:54]** I think everyone on our sales team kind of loves and is excited about who they're reaching **[25:58]** out to. **[25:59]** No, I think that's really, really insightful and my personal experience, I've worked in **[26:09]** companies that have sold to a number of industries, but this is my favorite one. **[26:13]** And I don't know if I recognized that it's because I get to talk to CROs, CMOs, heads **[26:19]** of RevOps, founders of companies I'm really excited about every single day, multiple times **[26:24]** a day. **[26:26]** And I think there's a lot of compounding that happens during that time too. **[26:32]** So if you build a bigger network with people that are similarly connected or have similar **[26:38]** problems and you continue to grow to be more and more valuable over time as well in that **[26:45]** particular industry or function, I think a lot of people miss out on that. ### 26:51 — Chasing the hot product vs. staying in one pond **[26:51]** And I think they're just chasing what's the sexiest product on the market right now, who **[26:57]** got funded the most, especially in sales roles, like really, really chasing that when, hey, **[27:03]** you could actually build a pretty fruitful, substantial career if you kind of hang in **[27:09]** a pond for a while. **[27:11]** Yeah. **[27:12]** 100%. **[27:13]** Listen, there's nothing wrong with going from Mongo to Snowflake to Databricks to whatever **[27:20]** the next up and coming data warehouse company is because you're going to make a ton of money. **[27:25]** And I know a lot of those guys and they've had amazing careers and have made a ton of **[27:31]** money. **[27:32]** I don't want to sell to that person. **[27:35]** I want to enjoy my day to day. **[27:36]** I do all right. **[27:37]** I'm happy with where I'm at. **[27:38]** But like, I think it's just, you know, people are, people are motivated by different things. **[27:42]** And I love entrepreneurship. **[27:43]** You know, both of my parents were entrepreneurs, like they scared me out of it, which is why **[27:47]** I've always done like the, the next riskiest thing, which is work for very early stage **[27:52]** startups without starting anything on my own outside of a little mobile golf simulator **[27:56]** business. **[27:57]** And it's just, I love talking to entrepreneurs all day. **[27:58]** I'm super inspired by them. **[28:00]** And I think that's, you know, every podcast I listen to is talking to entrepreneurs for **[28:04]** the most part. **[28:05]** And I get that, that gets me expired up and doing demos feels like I'm doing a podcast **[28:10]** episode or an episode of shark tank and I'm one of the sharks asking them, what's your **[28:14]** CPA? **[28:15]** How did this business get here? **[28:16]** You know, where are the flaws? **[28:17]** How can we help? **[28:18]** You know, I think that's really fun and interesting. **[28:20]** So I don't think it's too far off being, being in the early stage, you might as well **[28:27]** be the entrepreneur, especially when everything changes so much, you have to reinvent, go **[28:32]** to market differently, come up with a new product. **[28:35]** I mean, if you're right there in a series, a company, it's almost, you might as well **[28:38]** been there from the beginning. **[28:41]** So it is an exciting time. **[28:42]** I think there's a lot of energy around it and it attracts really, really smart and interesting **[28:49]** people to come into that. **[28:52]** And then you can really feel the impact every day too. **[28:55]** So you know, and I'm sure you're feeling this in the sales process too, when you're working **[29:00]** with somebody like that, you could be helping them fully change how they're running their **[29:05]** business. **[29:06]** A hundred percent. **[29:07]** Those are the best. **[29:08]** We have, we have clients that have gone from a few million dollars in revenue to a hundred **[29:12]** million plus. **[29:13]** And it's like over three or four years, one, I'm always like, what the heck am I doing? **[29:18]** They just built a supplement company in three years to a hundred million. **[29:21]** But you know, it is, it is amazing to watch and you just see these folks and then they **[29:25]** spin up another business. **[29:26]** Like they have, they've cashed out, right? **[29:28]** They're done, but they're starting from zero again. **[29:31]** They got a new idea they're going to run with. **[29:33]** And it always just blows my mind. **[29:34]** I'm like, I am not sprinting fast enough and like that's, there's a, there's a guy Zach **[29:39]** who really inspiring started an agency, started this brand, started that brand, started another **[29:45]** brand. **[29:46]** Just won't stop. **[29:47]** It's like, he's just loves doing it. **[29:50]** It's like, that's really, really inspiring. **[29:52]** Yeah. **[29:53]** I heard a quote that was some people play to not lose. **[29:58]** Some people play to win. **[30:00]** Some people play for fun. **[30:01]** They're not even in it for the money or whatever, like, yeah, they're nice trophies and accolades, **[30:06]** but they just have fun building new things, birthing something into existence and seeing **[30:12]** it through. **[30:13]** And I think it's really exciting to watch when people do that. **[30:17]** Yeah. **[30:18]** It's amazing. ### 30:19 — Hiring: why the first reps came from his network **[30:19]** I would love to get into one of the areas that I think is one of the most difficult **[30:26]** things to do as a CRO and that is building your team and hiring sales reps. **[30:34]** Where I found it to be so difficult is one, people who are in sales interview very, very **[30:42]** well. **[30:43]** Uh, they're good. **[30:44]** They're good at selling at least themselves. **[30:47]** And I found it hard to know if they're going to be successful in their role for the long **[30:51]** run. **[30:52]** What is your approach to hiring, ramping and retaining your best reps? **[30:59]** Yeah. **[31:00]** Listen, hiring, we were very fortunate early on that we, we brought in a bunch of people **[31:07]** we knew for the most part, you know, I brought our first sales rep with me. **[31:10]** It was one of my best friends, little brothers, he, my best friend is now the director of **[31:14]** our measurement product, which is our, one of our most important products. **[31:17]** Um, so he's on our product team. **[31:20]** The first five or six of the first six sales reps we hired, I think four of them came from **[31:25]** my network and then we hired a manager and the next four came from previous experience **[31:31]** working with him. **[31:32]** So I think when you're in that very early stage, you kind of need people who will not **[31:37]** let failure be an option because they want to succeed for you. **[31:41]** Like there is a relationship there that is strong enough that they're like, we're going **[31:45]** to figure this shit out together. **[31:46]** Right. **[31:47]** And that's really, I think important in those early days and almost, I think all of those **[31:51]** guys are still with us for four years later, four and a half years later. **[31:54]** So that's one, I think in the early days, it's like, who can you rely on from your network **[31:58]** that you trust and that trust you as you're hiring and you having to add managers. **[32:03]** I actually think that's where it gets really hard in kind of building a team is like, who's **[32:08]** the first manager you want to bring in to either take over some of these, you know, existing **[32:13]** reps and build that, that function out, um, or to attack a new market. **[32:18]** How do you want to build that infrastructure out? **[32:20]** So you know, one thing that we did in our early days is when we were going to build **[32:25]** like an outbound motion and we had, we relied on inbound for, I would say like a year only. **[32:33]** And then we started to build out our partnerships ecosystems and then we were like, okay, we, **[32:37]** we've got enough brand awareness. **[32:38]** We should start going outbound. **[32:39]** Uh, we hired a manager. **[32:41]** We had actually poached a few of his reps, was an early hiring cohort. **[32:45]** He was kind of left standing at the other company going, all my best reps just left **[32:48]** for this, called us up and was like, Hey, I'm interested in joining. **[32:52]** I was like, Hey, we're, we need to build out an outbound motion. **[32:55]** If you want to join as a manager, I will hire you as a manager, but you're going to start **[32:59]** by doing outbound on your own and figuring out the infrastructure we need to get this **[33:03]** right and he came in in October, I believe, and you know, basically from October through **[33:11]** the end of January, just did outbound as if he was an SDR to figure it out with very little **[33:18]** success. **[33:19]** February, he had a lot of demos hit and by March, he had a team of, uh, you know, four **[33:25]** of our most senior reps and had hired four SDRs to go to market. **[33:29]** And now it's our biggest team in the company and he leads, you know, our SMB mid market **[33:35]** and kind of upper mid market commercial is what we call it teams. **[33:38]** But he came in like from a manager, managed a team of eight to I'm going to be an SDR. **[33:42]** He had never really done outbound figured it out and has built an amazing organ and **[33:48]** process and hired, you know, great managers underneath him. **[33:50]** And I think to answer your question on like, how do you figure that stuff out? **[33:54]** I think one find people you trust to refer as best you can, which I think everyone knows **[33:58]** that works well, but find ways of testing out and putting them into building the infrastructure **[34:04]** that needs to scale as quickly as you can. **[34:07]** In the case of Jordan, like, you know, we brought him in to do the job. **[34:09]** We wanted to prove out and built around him. **[34:13]** You know, when we interview now, I try to scare people out of the job as best as I can **[34:17]** from a sales rep perspective, because this is not an easy place to work. **[34:20]** We have incredibly high quotas. **[34:22]** We have, you know, aggressive growth targets as a company. **[34:27]** It's an ever moving and evolving product. **[34:30]** And I don't want anyone that's not ready for that because it is going to be hard. **[34:35]** But when you succeed, you'll win in a big way. **[34:38]** And a lot of our reps have and, you know, there's a lot of places that validate that **[34:43]** and that people are very happy here and do, do really great work. ### 34:48 — Interview red flags: job hops, no progression, severance asks **[34:48]** Do you have any interview judo moves that can help you suss out assuming you get to **[34:54]** the point, I mean, with 40 reps, I don't, some people have had to come in that weren't **[35:00]** necessarily referred any advice for a CRO or VP of sales that's trying to build out **[35:07]** a team and interviewing people that might not be connected to the company. **[35:12]** Yeah. **[35:13]** You know, things that I look for a lot is a lot of it's on, I think, on paper, like **[35:19]** the resume itself, you know, you see so many resumes now where people have jumped around **[35:24]** in 11 months, 12 months, you know, I'm very loyal. **[35:26]** My resume is like three companies over 15 years. **[35:32]** And I like to see progression within a company. **[35:35]** I want to see someone that was an SDR and got promoted to an AE of the company and maybe **[35:39]** moved into a new segment has dealt with change within the same company. **[35:43]** So I spend a lot of time when I look at a resume that does not have that. **[35:46]** That's usually what I pick out a lot is why did these moves happen? **[35:50]** What were the reasons for it? **[35:51]** What was your success, you know, at the companies in 11 months when you decided to leave? **[35:56]** You know, some of that is out of reps control, but I think especially over the last six years **[36:00]** and COVID and layoffs and all of this that's happened, you're seeing people bounce around **[36:04]** a lot. **[36:05]** I think both on their own accord and then things that, you know, happened at the company, but **[36:08]** it's important to really dig there. **[36:10]** So I look a lot for progression within one company, like did they figure stuff out to **[36:16]** move to the next spot? **[36:17]** Did they deal with change, you know, where they were an enterprise sales rep and moved **[36:21]** into new markets or something else? **[36:22]** Like, I like to see that because that's what's going to happen here. **[36:26]** And if you're not willing to fight through that, you know, you're in nine months from **[36:31]** down the road from here, you're probably going to be looking because we're making some change **[36:35]** that has to happen. **[36:37]** Yeah. **[36:38]** And I think I'm looking for something similar. **[36:40]** It's like COVID did create some weird nuances, I think everybody working remote, it became **[36:48]** a little bit easier to move around to, but I am looking for like, did you have one, three **[36:54]** to four year run somewhere? **[36:56]** Just one. **[36:57]** You didn't have to be at every one. **[36:58]** You bounced around a couple of times here, but was there a place where you could just **[37:02]** like sink your teeth into it, really go through a ride with the company? **[37:08]** I'm usually looking for something like that too. **[37:09]** And I think it's really telling. **[37:10]** I think the people who, cause you don't want to hire someone who's just going to be around **[37:14]** for eight to 12 months. **[37:16]** I mean, by the time you get them ramped and trained and somewhat productive, they're on **[37:21]** their way out. **[37:22]** It's, it's not a good formula. **[37:24]** A hundred percent, a hundred percent. **[37:26]** The other red flag I try to look for, which I think has become really common and I see **[37:30]** a lot of the like sales gurus putting this out there is the, they're like negotiating **[37:36]** severance before they've started or they're negotiating some sort of like ramp quota bonus **[37:41]** from the jump. **[37:42]** Like that's a great, like I just, I want to be asking for upside. **[37:47]** I want to be figuring out how I get more upside. **[37:50]** I don't ever want to present that I'm looking to protect the downside so much. **[37:56]** Those things are like, I understand it from a business perspective, but always seem like **[38:00]** I would much prefer someone be asking me about how do I get into accelerators? **[38:04]** What are your accelerators look like, right, as opposed to, you know, what's the severance **[38:08]** before you've started? **[38:09]** It's like, ah, you've had two stops and you're asking about what severance looks like. **[38:13]** It's like, okay, let's maybe not progress here. **[38:16]** It's kind of like the business prenup like, yeah, sure. **[38:21]** Maybe it makes sense. **[38:22]** And I don't know, maybe for a few couples, you have reasons why you need to do that. **[38:26]** But as a rule of thumb, yeah, are you, why are you going in with the exit package already **[38:32]** ready to go? **[38:33]** 100%. **[38:34]** 100%. **[38:35]** One of the things you mentioned too, because I'm curious once you make the hire, then what **[38:40]** is, what does the first 90 days look like? **[38:44]** And how do you suss out if there's someone who should stay on the team or not? **[38:49]** And the way you phrased it, I thought it was interesting. **[38:51]** Hire people who will bang their head against the wall for 90 days. **[38:55]** What did you mean by that? **[38:57]** How do you assess that period of time? **[38:59]** Yeah. **[39:00]** So I think like Jordan was a great example of that, where we hired a manager and made **[39:03]** him an SDR and then allowed him to build out an SDR in our mid market team, which is like, **[39:06]** Hey, do the job. **[39:07]** You're going to have to figure out how to scale. **[39:09]** You know, from an IC perspective, uh, we put people on the phone very quickly, like within **[39:14]** two weeks, we're trying to get them, uh, prospecting into our database. **[39:19]** So we have, um, a kind of a free product that has a ton of data. **[39:24]** We've got, you know, thousands of them at this point that are sitting and have not had **[39:28]** a demo or have had a demo of it didn't close and are closed loss now. **[39:31]** We assign those to, you know, the eighties very early and allow them to start test messaging, **[39:36]** record loom, start to understand where to look within the product and put them on the **[39:40]** phone within two weeks. **[39:41]** Um, and we have reps that have like hit their full quota in, in four weeks, um, for the **[39:48]** month and we work out monthly quotas, but you know, you'll be blown away by some, how **[39:51]** quickly some reps can take action, you know, on the database and really find value that **[39:56]** was untapped before. **[39:58]** And then, you know, within 90 days, our, our ramp schedule depends on the team. **[40:01]** So we've got an SMB, a mid market and enterprise team. **[40:04]** All of them have slightly different ramp schedules. **[40:05]** You know, our SMB sales cycle is 45 days. **[40:08]** So like if you're on a ramped rotator by day 60, theoretically by day 90, you should be **[40:13]** starting to hit full quota. **[40:15]** And so we give them some runway, but we throw them into demos as fast as we possibly can **[40:20]** and get game tape. **[40:21]** And then, you know, managers are responsible for really refining that. **[40:25]** I usually will spend some time with newer reps kind of between day 60 and 90 doing a **[40:29]** demo review, um, and some coaching and refinement just to dip my toes and get to know them a **[40:35]** little bit more, understand their process. **[40:37]** And then I think the other one that we spend a lot of time on is peer to peer coaching. **[40:40]** I think like some of my best learnings always came from listening to people who were really **[40:46]** strong in areas that I'm weak. **[40:48]** You know, one of those people we hired as a sales manager here, uh, you know, he was **[40:51]** a rep that worked alongside me at word stream and he was just like, could sell anything **[40:55]** to anybody. **[40:56]** You know, one of the guys that could just talk to a wall and like convince them that **[41:00]** they needed something. **[41:01]** And I'm not that person. **[41:03]** Like I was very much always selling on, I would say like you can sell on logic or emotion. **[41:07]** The best salespeople kind of can do a bit of both where they can build the ROI model, **[41:11]** but they're also just so emotionally in tune with what, um, people are looking for or what **[41:17]** makes them excited and they're exciting people to listen to. **[41:21]** You know, Gleb was one of those people. **[41:23]** So we do a lot of peer to peer coaching where I'll match, you know, Anthony's not strong **[41:26]** at this portion pricing, you know, I'm going to match him with a person who does the best **[41:30]** pricing pitch in the entire company and have them work together on that. **[41:33]** Um, and we have some reps that have been with us for a really long time where we know where **[41:37]** they're very strong and allow them to do some peer to peer coaching, which is great for **[41:41]** them because you learn a lot when you tell someone how to best do their job. **[41:46]** I feel like when I was first sales manager, I was like, you know, I keep telling the reps **[41:49]** to do this, but I didn't really do this. **[41:50]** I just know it's the right thing to do. **[41:52]** Um, and I think it helps sales reps a lot when they start coaching people one-on-one **[41:56]** on certain processes. **[41:59]** I think anytime you can get the team managing the team, you're going to see really, really **[42:04]** good things happen. **[42:05]** Of course, like top down vision, but if you can get the team helping each other or holding **[42:10]** each other accountable, uh, that's when I've seen the best results. **[42:14]** Um, and you don't have to intervene as much. **[42:16]** Yeah. **[42:17]** Yeah, it's, it's great. **[42:18]** And if you have senior people, you can rely on for that, like treat them well and make **[42:22]** sure that they know that that is, uh, you know, you're very thankful for their work in **[42:27]** those areas that take away from their day to day, but are, are additive and helpful **[42:31]** and a lot to the organization. **[42:34]** Absolutely. ### 42:36 — AI in GTM: top-down or bottoms-up? **[42:36]** One last topic. **[42:37]** I was hoping to pick your brain on, this has been an interesting year, 2026 really seems **[42:42]** when AI has become ubiquitous across go to market teams. **[42:47]** I would love to hear maybe two things, two things, because I think it's impacted these **[42:54]** two areas the most one, how people are generating pipeline. **[42:59]** A lot of the outbound plays have needed to be shifted, changed in order to remain effective **[43:05]** over time. **[43:07]** And a lot of companies are struggling with building pipeline and getting in front of **[43:12]** their prospects in a meaningful way that makes them want to engage and get them to a demo. **[43:17]** And then the other is how are you leveraging AI as a go to market team? **[43:23]** And are you leaning on rev ops to help you implement AI workflows systems, manage the **[43:30]** data? **[43:31]** And what does that look like? **[43:33]** It's a great question. **[43:35]** We use, I think we're, we're relatively advanced from like an AI usage perspective. **[43:40]** We've looked at a bunch of external tools, we've tested a few. **[43:44]** We've built a lot of internal processes using our own kind of AI infrastructure. **[43:49]** So all of the kind of our BI and analytics are actually on a triple will instance. **[43:55]** So our own internal AI that our customers use, we actually use as often as we possibly **[44:01]** can. **[44:03]** And we do have a rev ops team, we do lean on them a lot. **[44:07]** We did move someone into like a go to market engineering role within that team. **[44:11]** So he is building workflows, you know, we have a morning account attack list that gets **[44:16]** sent to every salesperson. **[44:17]** We've got a handoff skill that basically allows us to review transcripts, create a handoff **[44:22]** document for, you know, implementation. **[44:25]** We've got one that scrapes podcast transcripts to try to find nuggets of information about **[44:29]** the prospect to come up with gifting ideas. **[44:32]** So we've tried to create a bunch of automations that work across the business. **[44:37]** I think what is, what I've had a really hard time with, and I think is a really like big **[44:43]** discussion and we've tried a little bit of both is, does this need to be top down or **[44:47]** bottoms up? **[44:49]** Meaning, like, am I the one coming up with the AI infrastructure? **[44:52]** Like I'm the one that came up with the podcast thing, I was like, Hey, let's build this and **[44:55]** like, let's scrape some podcast episodes and see what we can find out about prospects and **[44:58]** do some really personalized gifting because personalized gifting has worked well for us **[45:02]** from an outbound perspective. **[45:04]** Someone sent me this car because they saw this car in my background. **[45:08]** It's like, that was a nice gift. **[45:09]** It was really thoughtful. **[45:11]** It worked really well. **[45:12]** We've done the same thing where like we look in the back of a podcast episode and we see **[45:16]** a poster for a band on tour and we sent the very high value prospect, a signed record **[45:22]** of that from that band. **[45:24]** So that works really well. **[45:25]** So like that's tops down. **[45:26]** Right. **[45:27]** And then we have bottoms up where I have a bunch of sales rep creating some AI slop outputs **[45:31]** that I'm like, please don't ever create a deck like that again. **[45:34]** And then I have some that are like incredible and building, you know, really hyper personalized **[45:40]** handouts for events. **[45:41]** I was at an event last week where there's a bunch of enterprise prospects there. **[45:46]** The sales rep went through the attendee lists, found the 10 that were on his, you know, prospecting **[45:51]** and target audience lists that were going to be in attendance, reviewed all of their **[45:55]** quarterly earnings and created a personalized infographic using AI for each of them and walked **[46:01]** around the event and handed him to the people and you could see the people that he was handing **[46:04]** him to being like, can you believe what this guy just gave me? ### 46:07 — Personalization to the craziest degree **[46:07]** So I think, you know, what's going to become really mission critical here is personalization **[46:12]** and you know, being in person is really critical. **[46:15]** Personalization has been, I think to us like the one thing that you need to lean on more **[46:19]** and more and obviously that has always been the case, I think with email or phone calls, **[46:22]** you want a little bit of prep and personalization, but like you've got to go so far now. **[46:27]** So you know, we're sending cookies to the office that are branded as triple whale from **[46:30]** one of our customers with a case study about that customer. **[46:33]** And that's just like unprompted. **[46:34]** We're just sending them to people's offices, working very well. **[46:38]** Personalized gifting like the mention of like looking in the background or listening to the **[46:41]** podcast episode. **[46:42]** We're doing in-person events that like from a budget perspective, five years ago, I would **[46:49]** have never approved, but now it's like, all right, we got to take this swing. **[46:52]** Like we did an event at an amazing resort in the Berkshires and we took a bunch of prospects **[46:58]** from New York, drove them out to this event in a big limo bus and it's 25 of them and **[47:04]** spent two days at a very expensive resort going over their AI strategy and a bunch of **[47:10]** different kind of workshops on AI. **[47:12]** And then allowed them to have a bunch of time for events, time for the spa, whatever it **[47:16]** was, just kind of unplug and it was expensive. **[47:20]** The CFO was not, he's like, this isn't going to work. **[47:24]** I need to say we closed our first deal from it just four weeks later today. **[47:28]** That's what I'm talking about. **[47:29]** Sent it right to the CFO. **[47:30]** We got one down. **[47:31]** We got legal in another. **[47:32]** We got a couple more that I'm feeling really, you know, um, but I think in-person is going **[47:37]** to become so mission critical and personalization is going to need to go to like the craziest **[47:42]** degree to, uh, to work. **[47:45]** And that's, that's what we've tried to lean in on as much as we possibly can. **[47:49]** Yeah. **[47:50]** And I think to your point, the bar has just been raised, so you still have to work just **[47:56]** as hard. **[47:57]** You still have to be as creative as you can be, but the lazy, Hey, first name LinkedIn **[48:04]** and emails, like that is, you might as well not send them. **[48:09]** I think that might kill your brand. **[48:11]** So if you're going to do something, then you got to really take it to that next level. **[48:14]** And I think only the companies that are doing that are really building pipeline in the space **[48:19]** right now and leaning into, leaning in into AI in a meaningful way and in a way where **[48:27]** you have taste like the person who was building this infographics, you have to have some taste **[48:31]** and understanding of what good looks like so that it's actually helpful. ### 48:36 — Wrap **[48:36]** Zach, thank you so much for sharing everything you did in the podcast. **[48:40]** It just is really refreshing to hear tactical, practical blocking and tackling advice that **[48:47]** you're that you're experiencing in the CRO position. **[48:51]** And especially taking it to the beginning of, Hey, do the job that you're managing and **[48:56]** don't lose touch. **[48:58]** Find a way to get involved. **[48:59]** Keep doing demos. **[49:00]** Keep talking to customers. **[49:01]** Keep talking to prospects. **[49:03]** I love the way you do it without stepping on anyone's toes and you do it in a really **[49:08]** helpful and productive way. **[49:11]** And also when it comes to hiring, look for those people who can stand for the long haul. **[49:16]** Okay. **[49:17]** Did you have a stint? **[49:18]** Have you gone through a few times where you've had some progression in your role? **[49:23]** And I think all of your advice on how to use AI in 2026 for go to market is really, really **[49:28]** strong. **[49:29]** You have to step it up. **[49:31]** You have to be creative. **[49:32]** You have to take personalization to a level you didn't even know personalization could **[49:36]** go to. **[49:38]** And that is the recipe for success in 2026. **[49:42]** Zach, thank you so much for being on the podcast, can't wait to see what you and Triple Whale **[49:46]** do next. **[49:47]** Awesome. **[49:48]** Thank you, Anthony. **[49:49]** Everyone please connect with me on LinkedIn or X at Zach Rego, excited to connect to everybody. --- _LeanScale Knowledge Hub. Free to quote and cite with attribution to The LeanScale Podcast (https://www.leanscale.team)._