--- title: "What Elite Performance Actually Costs" episode: 139 podcast: "The LeanScale Podcast" publisher: "LeanScale" guest: "Miles Kirkpatrick" guest_title: "Chief Revenue Officer, SITE Technologies" date_published: 2026-10-14 date_modified: 2026-10-21 duration: 00:54:43 word_count: 10340 topics: ["sales-leadership", "outbound-sales", "enterprise-sales", "sales-compensation", "revenue-operations", "brand-positioning"] canonical_url: https://www.leanscale.team/knowledge/podcast/miles-kirkpatrick-site-technologies-what-elite-performance-actually-costs/ source: "LeanScale Knowledge Hub — https://www.leanscale.team/knowledge" license: "Free to quote and cite with attribution to The LeanScale Podcast." --- # What Elite Performance Actually Costs _Miles Kirkpatrick on the panic attack that changed how he works, finding a 45-minute peak window, decision velocity versus flip-flopping, promoting a commercial roofer to run customer success, and building pipeline with points of view instead of sequences_ **Episode 139 · The LeanScale Podcast** Miles Kirkpatrick, Chief Revenue Officer, SITE Technologies · Hosted by Anthony Enrico Published October 14, 2026 · Updated October 21, 2026 · 00:54:43 Canonical: https://www.leanscale.team/knowledge/podcast/miles-kirkpatrick-site-technologies-what-elite-performance-actually-costs/ **Topics:** Sales Leadership · Outbound & Sales Development · Enterprise & Public-Sector Sales · Sales Compensation · Revenue Operations · Brand & Positioning ## Executive summary Miles Kirkpatrick is Chief Revenue Officer at SITE Technologies, a Chicago company of about 50 people that uses drones, satellite imagery and AI to tell commercial property owners what condition their roofs, pavement and facades are in before problems become capital expense. He built SITE's go-to-market function from nothing: when he arrived there was no pipeline, no collateral and no process, and he set up Salesforce himself over a weekend. Before SITE he was CRO at Productiv, ran Central US and Canada at Sprinklr from pre-IPO to public, and held sales leadership roles at Salesforce. Before tech he played competitive golf, including a run at it professionally. The first half of the conversation is about what sustained high performance costs. For years Miles opened his laptop before 6 a.m., worked a full day in the office, went back to the laptop after dinner and added a couple of hours every weekend. He describes himself as someone who succeeds by outworking people rather than by talent. Layered on a stressful job, events in his personal life and COVID, that routine ended in the first panic attack of his life. He could not breathe and thought he was dying. He did not want medication, and his employer at the time offered executives one-on-one sessions with a coach, Neha. That started a practice he has kept up almost daily for more than seven years. The practice is concrete. Most mornings he sits in a dark room and plays a 30-minute recording of guided meditation and breath work, then goes straight to the hardest thing on his list. For him, roughly 5:30 to 6:30 a.m. is the window where he does his best work, and he tells his team that peak performance means finding their own window, not performing from eight to five. He names the warning sign he missed: if everything you do is giving to your job and your team and nothing fills you back up, you are setting yourself up for a crash. Years later his doctor told him his blood pressure was the best it had ever been and his resting heart rate the lowest. Anthony Enrico frames the lesson for high performers: keep doing what the job requires, and build recovery in as part of performance. The second half turns to running revenue at an early-stage company. Miles's top rule for his team is decision velocity: decide with limited data, commit, and pivot without drama if the call was wrong. He compares it to golf, where you hit only a few shots the way you planned and have to play the next one anyway, and aims to be right 70 percent of the time. He is candid about what missed: comp plans that don't yet satisfy both reps and the CFO, and PR spending that came before the market understood the category. His best decision was promoting Jack, a commercial roofer of ten years who had never done customer success, to build and run the CS team, which Miles calls a differentiator in enterprise sales. On pipeline, Miles says high-volume sequencing no longer works. SITE writes points of view for specific buyers, sends them with handwritten notes, hosts quarterly customer dinners, gets invited into private commercial real estate groups and publishes real content on LinkedIn, including a short interview series and a weekly property observation. Signals inform the points of view, but people write them. He closes on RevOps, which at SITE has so far been "me on a Sunday", and lists the work ahead: pricing and packaging, contract structure, quoting, territories and rep capacity. ## Key takeaways 1. **Being in the zone is available at a desk, not only on a golf course** — Miles describes the zone from competitive golf: seeing the shot before you hit it, then watching your body execute it. He assumed that state belonged to sport and found he was wrong. With a daily practice built around morning breathing exercises and mindset preparation, he aims to reach the same state at work and to stay in it for more of the day. _Why it matters:_ He frames peak performance as doing three, four or five times your normal output for longer periods. The goal is not working more hours but spending more of them in that state. _For:_ Sales Leaders, Revenue Executives, Founders 2. **The crash came from years of compounding load, not one bad day** — For years Miles worked from before 6 a.m., through a full office day, again after dinner and for a couple of hours every weekend. He says panic attacks build over time from many choices, sometimes with one event that triggers them. In his case an already stressful job, events in his personal life and COVID came on top of that routine, and the result was the first panic attack of his life. _Why it matters:_ He believed at the time that constant focus on closing deals and hitting the number was simply what leaders did. He now says it is what leaders heading for burnout do. _For:_ Sales Leaders, Revenue Executives, Founders 3. **Find your own peak window and protect it** — Most mornings Miles does 30 minutes of recorded guided meditation and breath work in a dark room, then starts immediately on the hardest task of the day. He finds the next 30 to 60 minutes are his most productive, roughly 5:30 to 6:30 a.m. He tells his team that peak performance does not mean peaking from eight to five. It means finding the hours when you do your best work, whether that is 5:30 a.m. or 10:30 p.m. _Why it matters:_ The window has to be defended. With two young children he is up at 5:15 and is considering 4:45, and he says it only works because his wife, who also does breath work, gives him the space and he gives her the same. _For:_ Sales Leaders, Revenue Executives, Founders 4. **The warning sign: giving everything and refilling nothing** — Asked what he could have noticed before the panic attack, Miles names one indicator above the others. If you look at your day and find no time for yourself or your family, nothing that gives you energy back, and everything goes to your job, coworkers and team, you are setting yourself up for a crash. _Why it matters:_ Anthony hopes no listener needs a physical event to make the change. Miles's test is simple enough to check now: is there any part of the day that fills you back up? _For:_ Sales Leaders, Revenue Executives, Founders 5. **Recovery is part of performance, and the trade-off beats rigid boundaries** — Miles doesn't believe in hard rules like no email after five, because sales sometimes means a call at 9 p.m. or work on vacation. Instead he makes a trade: he will do whatever it takes to hit the number, and he will also take his 45 minutes in the morning and a day off when he needs one. He frames it as a long game. Crushing it for five or ten years and then burning out is not worth it if you never see your kids. _Why it matters:_ Anthony's summary: keep doing what's necessary and add recovery to hit the performance you expect. When people say they have no time, he asks what TV shows they watch. Miles gives his own example of choosing 30 minutes in the sauna over an episode of TV, and reports that his blood pressure and resting heart rate are now the best they have been. _For:_ Sales Leaders, Revenue Executives, Founders 6. **Build room for honest conversation, flexibility and reflection into the team** — Miles describes himself as a human first and a boss second. His team is told it can talk to him about anything. Work is outcome-driven, so people run their own calendars without asking permission as long as the work gets done and they are present when needed. Every quarterly business review presentation starts with self-reflection on what happened, why and what to do better, and he has brought meditation sessions into QBRs. _Why it matters:_ He admits he was not this kind of leader early in his career, when in-office cultures expected people at their desks from eight to six. He calls self-reflection a core part of peak performance because you can't improve without looking back at what just happened. _For:_ Sales Leaders, Revenue Executives, Customer Success 7. **Know what size of company you thrive in** — Miles tells his team that much of success comes from finding the right size of company. He says he would probably not do well at a company of 50,000 or 75,000 people, and he has repeatedly seen people from large companies struggle at a company of about 50 like SITE. The difference is pace and comfort with incomplete information. _Why it matters:_ People who need all the data before deciding struggle at a startup. That gap is why decision velocity became his first rule. _For:_ Sales Leaders, Revenue Executives, Founders 8. **Decision velocity is not flip-flopping** — Miles's number one rule for his team is decision velocity. In a roadmap meeting with product, CS, sales, trades, engineering and executives, nobody knows for certain which features will drive the most revenue. There are early indications but never all the data. The team makes a decision for stated reasons, commits with conviction, and if it proves wrong, pivots and commits to the new direction with the same conviction. Spinning and asking for one more data point is worse. _Why it matters:_ Golf taught him this: in 18 holes you hit perhaps three or four shots the way you intended and still have to play the next one. The aim is to be right about 70 percent of the time, which leaves room for wrong calls. Anthony adds a guest's poker analogy: you have to bet without seeing the other hand. _For:_ Sales Leaders, Revenue Executives, Founders 9. **Bets that missed: comp plans and early PR** — Comp plans keep Miles up at night. He wants a plan account executives see as a chance to make a lot of money and the CFO sees as fair and aimed at the right behaviors, and SITE's contracting situations created cases he didn't anticipate. Separately, SITE invested in PR too early: the agency did good work, but buyers did not yet understand solving the problem SITE's way, so the spend was only marginally helpful. _Why it matters:_ On comp, the intent is to build something that works for both sides, and he plans to redo it next year. Anthony notes the added difficulty of moving from seat-based to usage-based models. On PR, Miles's lesson is that it works once a category is understood, not while you are still educating an entire industry. _For:_ Revenue Executives, Sales Leaders, Founders, Marketing Leaders 10. **The best hire for customer success had never done the job** — One of Miles's first moves at SITE was to stand up customer success. He promoted Jack, a commercial roofer for ten years who had never worked in CS, and let him run with it. Miles calls it the best decision he has made at SITE: Jack completely owned the function and changed how SITE operates. _Why it matters:_ Miles's reasoning is that a sales organization can't succeed without strong CS counterparts, because they drive expansion and keep and grow revenue. Anthony, who ran CS before RevOps, notes that many CROs on the show never mention customer success, yet teams that invest in it get results. _For:_ Customer Success, Revenue Executives, Sales Leaders 11. **In the enterprise, named CS people are a selling point** — Miles tells enterprise buyers that, beyond the service, they get named people who will sit with them, help them use the platform, answer calls when they have questions, and are measured on helping them get value. He says he would demand that as an enterprise customer and does not understand why more vendors don't offer it. _Why it matters:_ Because SITE asks customers to change how they have done something for years, it has to prove value every day. CS is how that proof gets delivered after the sale. _For:_ Customer Success, Sales Leaders, Revenue Executives 12. **Prove value with storytelling and business value cases** — SITE's pitch is that customers should do something a new way when the old way has worked for years. To answer "why wouldn't I keep doing it the old way?", the team worked with an outside storytelling consultant on its story and invested heavily in business value cases, taking clients through the exercise of showing how SITE drives value for their organization. _Why it matters:_ Miles says this is required when selling to the enterprise and that he hasn't fully nailed it yet. He describes SITE as big on fundamentals and expects much else to follow if they are done well. _For:_ Sales Leaders, Revenue Executives 13. **Pipeline comes from points of view, not sequence volume** — Miles says the old method of sending lots of sequences as a math problem no longer works. SITE's most successful pipeline effort is writing a point of view for a specific buyer: what SITE thinks, how it can drive value, and proof points. Miles writes them too. They are packaged with handwritten notes. SITE also hosts a customer dinner about once a quarter in major markets (a recent Chicago dinner had eight to ten customers and prospects discussing commissioned research), gets invited by customers into private commercial real estate industry groups, and works with influential people in the industry who drive leads. _Why it matters:_ SITE does look at signals and uses them to inform points of view, but people write them. Miles calls it quality over quantity and notes the irony of returning to what sellers did ten years ago in the age of AI. _For:_ Sales Leaders, Marketing Leaders, Revenue Executives 14. **Real content starts conversations, and engagement beats follower counts** — SITE runs a short LinkedIn interview series, A Mile with Miles, with three-minute unscripted conversations with influential people in commercial real estate. Every week it also publishes an observation of the week: something its trades team found while analyzing a building's parking lot, roof, facade or landscaping with SITE's in-house AI tools, plus the recommended fix. Readers reply with how they would have fixed it. SITE also commissioned research and placed its first print ad, in Thesis Driven, using a real photo rather than AI. _Why it matters:_ Compared with its competitors, SITE's LinkedIn engagement is far higher even though its follower growth is lower, and Miles says engagement is what they are after. Anthony's read is that AI has oversaturated digital marketing, so old-school channels are working again. _For:_ Marketing Leaders, Sales Leaders, Founders 15. **Early RevOps is the CRO on a Sunday** — When Miles started at SITE, two colleagues followed him there and there was nothing in place: no pipeline, no collateral, no process. He set up Salesforce over a weekend. SITE won enterprise customers early, before it had built the infrastructure, so RevOps was Miles on a Sunday going through data. The CFO has since taken on much of it and finance has added help. _Why it matters:_ The next stage for SITE's go-to-market is a real RevOps function covering pricing and packaging, contract structure, quoting, territory assignment and rep capacity. Anthony adds that airtight data and a narrative built on it were what RevOps did for his own company's exit and valuation. _For:_ RevOps Leaders, Revenue Executives, Founders ## Frameworks ### Decision Velocity: Aim to Be 70 Percent Right (27:18) **Definition:** Make decisions quickly with limited data, commit to them with conviction, and pivot without drama if they prove wrong. Aiming to be right about 70 percent of the time, rather than 100 percent, is what makes speed possible. Miles separates this from flip-flopping. Each decision is made for stated reasons and pursued with conviction. A pivot is a new committed decision based on new information, not a reversal for its own sake. What he wants to avoid is spinning and repeatedly asking for one more data point. He traces the mindset to golf, where most shots miss in some way and the only choice is to play the next one. ### Find Your Peak Window (10:04) **Definition:** Peak performance is not being productive from eight to five. It is finding the specific periods of the day when you do your best work and spending them on the hardest task. Miles primes his window with 30 minutes of recorded guided meditation and breath work, then starts immediately on the hardest thing on his list. His most productive time is roughly 5:30 to 6:30 a.m. He tells his team their window might be 10:30 at night, and he backs that with outcome-based flexibility over calendars. ### The Give-and-Refill Check (17:49) **Definition:** If everything in your day goes to your job, team and other people and nothing fills you back up, you are setting yourself up for a crash. Miles offers this as the main warning sign he missed before his panic attack, which he describes as the result of accumulated choices rather than a single day. The fix is not lower effort but deliberate recovery: time for yourself or your family that restores energy. ### The Trade, Not the Boundary (22:41) **Definition:** Instead of rigid boundaries that sales will force you to break, commit to doing whatever the number requires and, in the same breath, commit to the recovery you need. Miles finds boundaries like "no email after five" unrealistic in quota-carrying work and compares them to New Year's resolutions. His version: he will work at 8 p.m. or for five hours on a Sunday if needed, and he will also take his 45 minutes each morning and a day off when he needs it. Anthony adds that most people who say they have no time are watching several TV shows. ### Point-of-View Pipeline (41:40) **Definition:** Build pipeline by proactively sending a specific buyer a written point of view (what you think, how you can drive value for them, and proof points), rather than running high-volume sequences. Miles applies his own rule as a buyer: he gives time to anyone who brings a point of view that could matter to his business. SITE's sellers, Miles included, write points of view and send them with handwritten notes. Signals inform them, but people write them. He calls it SITE's most successful pipeline effort and pairs it with quarterly customer dinners, private industry groups and industry influencers. ### Self-Reflection First QBRs (15:33) **Definition:** Every QBR presentation starts with the presenter reflecting on what happened in the quarter, why it happened and what they will do better. Miles treats reflection as a core part of peak performance: you won't improve without looking back at what just happened, good or bad. He has also brought meditation sessions into QBRs. ## Quotes _Speakers inferred from an undiarized transcript — verify before attributing._ > "When I had one, I literally couldn't breathe. I felt like my chest was caving in on itself. I had no idea what was happening. I felt like I was dying." > > — Miles Kirkpatrick, The LeanScale Podcast Ep. 139 (07:36) > "To be a peak performer, it doesn't mean that you have to be a peak performer between eight and five. It means that you've got to find the periods of time throughout the day that you are the most productive." > > — Miles Kirkpatrick, The LeanScale Podcast Ep. 139 (10:04) > "In order to be different, in order to be elite, you have to do the things that others are unwilling to do." > > — Miles Kirkpatrick, The LeanScale Podcast Ep. 139 (12:27) > "I'm a human first and then a boss second." > > — Miles Kirkpatrick, The LeanScale Podcast Ep. 139 (14:19) > "You're never going to get better if you don't reflect on what just happened, good or bad, and how we're going to move forward from that." > > — Miles Kirkpatrick, The LeanScale Podcast Ep. 139 (16:08) > "If all you're doing is giving to other people, to your job, to your coworkers, to your team, to others, others, others. If that's all you're doing, you are setting yourself up to have a crash." > > — Miles Kirkpatrick, The LeanScale Podcast Ep. 139 (18:11) > "At the time I thought that was what leaders did. That was just what you do, right? And now I've realized that that's what leaders at burnout do." > > — Miles Kirkpatrick, The LeanScale Podcast Ep. 139 (18:44) > "You crush it for five years and then ten years and then you burn out and you can't ever do it again. You never see your kids. At what cost? Is it worth it?" > > — Miles Kirkpatrick, The LeanScale Podcast Ep. 139 (19:51) > "I don't think it's, hey, don't do the things necessary. It's, you also have to incorporate recovery to help you hit your performance that you expect." > > — Anthony Enrico, The LeanScale Podcast Ep. 139 (24:07) > "My number one thing for my team is decision velocity." > > — Miles Kirkpatrick, The LeanScale Podcast Ep. 139 (27:18) > "What's worse is spinning and never making a decision or always asking, well, can we get that data point?" > > — Miles Kirkpatrick, The LeanScale Podcast Ep. 139 (29:29) > "If you are waiting to be 100 percent right and want to be 100 percent right of all your decisions, that to me is an impossible feat. But could you be 70 percent right?" > > — Miles Kirkpatrick, The LeanScale Podcast Ep. 139 (31:27) > "If there's the one thing that keeps me up at night more than anything, it's how do I build the best comp plan?" > > — Miles Kirkpatrick, The LeanScale Podcast Ep. 139 (32:58) > "That's probably the best decision I've ever made at SITE, was promoting Jack and letting him run with it." > > — Miles Kirkpatrick, The LeanScale Podcast Ep. 139 (37:06) > "I feel like it's this lost art or a lost department that people haven't been investing in. But the teams that do always get results." > > — Anthony Enrico, The LeanScale Podcast Ep. 139 (38:19) > "I will give you time if you come with a point of view, and I think it can drive impact for my business." > > — Miles Kirkpatrick, The LeanScale Podcast Ep. 139 (41:54) > "In the age of AI, we're doing things like we used to do 10 years ago, but maybe that's the cycle we're on, right?" > > — Miles Kirkpatrick, The LeanScale Podcast Ep. 139 (42:44) > "I just think AI has completely oversaturated the majority of any digital marketing that you've been doing in the past." > > — Anthony Enrico, The LeanScale Podcast Ep. 139 (48:40) > "Rev ops is me on a Sunday trying to go through some of the data and figure some stuff out." > > — Miles Kirkpatrick, The LeanScale Podcast Ep. 139 (50:22) ## Practical advice by role ### Sales Leaders - Make decision velocity an explicit team norm: decide with the data you have, state the reasons, commit, and pivot without blame if it turns out wrong. - Judge outbound by quality, not volume. Write a point of view for a specific buyer with proof points and send it with a handwritten note. - Use signals to inform outreach, but have people write the message. - Run outcome-based schedules: people manage their own calendars as long as the work gets done and they are present when needed. - Open each QBR presentation with self-reflection on what happened, why and what will change. - Watch for reps and managers whose whole day goes to the job with nothing that restores them. That is Miles's main burnout warning sign. ### Revenue Executives - Find your own peak window and spend it on the hardest task of the day, not on email and meetings. - Pair hard work with deliberate recovery rather than relying on boundaries the job will force you to break. - Design comp plans to pass two tests at once: reps should see real upside and the CFO should see fair incentives for the right behaviors. Expect contracting edge cases to break the first version. - Hold PR spend until buyers understand the category. Paying to educate an entire industry early may be only marginally useful. - Hire for the person, not the résumé. SITE's best CS leader was a commercial roofer who had never done the job. ### Customer Success - Treat CS as a revenue function that sits alongside sales and owns expansion and retention. - In enterprise deals, introduce named CS people during the sale as part of what the customer is buying. - When the product asks customers to change a long-standing way of working, plan to prove value every day after the sale. - Consider domain experts from the customer's industry for CS roles. Knowing the customer's world can matter more than CS experience. ### Marketing Leaders - Publish real, unscripted content: short interviews with industry figures and recurring observations from your own data or field work. - Measure content by engagement and conversation, not follower growth. - Host small customer and prospect dinners around commissioned research about once a quarter in major markets. - Look for invitation-only industry groups your customers belong to and ask those customers to bring you in. - Test offline channels like print. Expect the first one to be harder to produce than it looks. ### RevOps Leaders - At an early-stage company that lands enterprise customers before building infrastructure, expect a backlog of pricing and packaging, contract structure, quoting, territory and rep-capacity work. - Build airtight data and a narrative supported by it. Anthony credits that with helping his own company's exit and valuation. ## AI takeaways **Thesis:** Miles's go-to-market at SITE runs against the automation trend. AI is part of the product and of internal analysis, but outreach and content stay human-written because AI has made automated digital marketing crowded and easy to ignore. - **** — - **** — - **** — - **** — **Agent & automation ideas** - A research agent that gathers signals and proof points on a target account into a draft brief for the seller writing a point of view. - An agent that turns field-analysis findings into candidate observation-of-the-week posts for a human to choose and edit. - A comp-plan simulator that runs proposed plans against past contract structures to find edge cases before rollout. ## Operations takeaways ### Revenue operations - **.** - **.** - **.** - **.** - **.** ### Pipeline & marketing ops - **.** - **.** - **.** - **.** - **.** - **.** ### Customer operations - **CS was one of the first things Miles built.** Standing up customer success was among Miles's first moves at SITE, because sales can't succeed without CS counterparts who drive expansion and keep and grow revenue. - **Hire for the person and the domain.** SITE's CS leader was a commercial roofer for ten years and had never done CS. Miles calls promoting him the best decision he has made at SITE. - **Named CS people help win enterprise deals.** Miles introduces specific CS people to enterprise buyers as part of the offer: people who will sit with them, take their calls and be measured on the value the customer gets. - **A neglected function that still pays off.** Anthony notes many CROs on the show never mention customer success, yet the teams that invest in it get results. ## Metrics mentioned | Value | Metric | Context | | --- | --- | --- | | 7+ years, almost daily | Breath-work practice | How long Miles has kept up the practice that began after his panic attack. | | 30 minutes | Morning routine length | Recorded guided meditation and breath work before starting the hardest task of the day. | | About 5:30–6:30 a.m. | Peak window | The 30 to 60 minutes after the routine that Miles finds most productive. He wakes at 5:15 and is considering 4:45. | | 70% | Decision accuracy target | Miles's standard for decision velocity: being right on 70 percent of decisions is very successful, and waiting to be 100 percent right is impossible. | | 3–4 per 18 holes | Golf shots that go as planned | Miles's illustration that most shots miss in some way and you still have to play the next one. | | About 50 people | SITE Technologies headcount | Miles's figure for SITE's size, which he contrasts with companies of 50,000 to 75,000. | | 10 years as a commercial roofer | CS leader's prior experience | Jack had never done customer success before Miles promoted him to build and run it. | | About 1 per quarter; 8–10 attendees | Customer dinner cadence and size | Dinners in major markets. The recent Chicago dinner had eight to ten customers and prospects. | | 3 minutes | Interview length in A Mile with Miles | Each unscripted LinkedIn interview with a commercial real estate figure. | | About 3 years | Time building SITE's GTM | Miles's own account of how long ago he and two colleagues started building SITE's go-to-market from nothing. The show notes give 2024 as his start year. | ## Entities mentioned - **SITE Technologies** (company) — Miles's employer, where he is CRO and built the go-to-market function from scratch about three years before recording by his account (the show notes say he joined in 2024). A Chicago company of about 50 people using drones, satellite imagery and AI to assess the condition of commercial property portfolios, selling to the enterprise. Its customer success team, points-of-view pipeline motion, customer dinners, LinkedIn content and first print ad are all discussed. · https://www.leanscale.team/knowledge/company/site-technologies/ - **Thesis Driven** (company) — Commercial real estate publication where SITE placed its first print ad, built around a real photograph rather than AI imagery. ROI was still to be determined at recording. · https://www.leanscale.team/knowledge/company/thesis-driven/ - **Microsoft** (company) — Used by Miles as an example of a very large organization, in contrast to a company of about 50 people like SITE, when explaining that people should know what size of company they thrive in. · https://www.leanscale.team/knowledge/company/microsoft/ - **Anthropic** (company) — Cited by Anthony, alongside OpenAI, as a company he has heard pays sellers high base salaries with only a small variable component. · https://www.leanscale.team/knowledge/company/anthropic/ - **OpenAI** (company) — Cited by Anthony, alongside Anthropic, as a company he has heard pays sellers high base salaries with only a small variable component. · https://www.leanscale.team/knowledge/company/openai/ - **LeanScale** (company) — Anthony's company and the producer of the podcast. Anthony mentions that the show's transcripts are available through LeanScale's MCP when he notes how few CROs on the show mention customer success. · https://www.leanscale.team/knowledge/company/leanscale/ - **Miles Kirkpatrick** (person, guest) — Chief Revenue Officer at SITE Technologies; previously CRO at Productiv and VP of Central US and Canada at Sprinklr. · https://www.leanscale.team/knowledge/guest/miles-kirkpatrick/ - **Anthony Enrico** (person, host) — Co-founder of LeanScale and host of The LeanScale Podcast. · https://www.leanscale.team/knowledge/guest/anthony-enrico/ - **Salesforce** (tool, CRM) — Miles held sales leadership roles at Salesforce earlier in his career. At SITE, with no infrastructure in place, he set up Salesforce himself over a weekend. - **LinkedIn** (tool, Social Platform) — SITE's main content channel, home to the A Mile with Miles interview series and the weekly observation of the week. Miles says SITE's engagement there is far higher than its competitors', even though follower growth is lower. - **Clay** (tool, GTM Data / Enrichment) — Mentioned by Miles as shorthand for signal-based, automated marketing that SITE deliberately does not rely on. Anthony separately cites Clay's subway ad campaign as one of his favorite offline campaigns from a tech company. ## FAQ **Q: What warning signs come before burnout for sales leaders?** A: SITE Technologies CRO Miles Kirkpatrick, who had his first panic attack after years of overwork, says the clearest warning sign is a day where everything goes to other people: your job, coworkers and team, with no time for yourself or your family that gives you energy back. He describes panic attacks as building up over time from many choices, sometimes with one event that triggers them. Before his, he thought constant focus on closing deals and hitting the number was simply what leaders did. He now calls it what leaders heading for burnout do. **Q: How can a high performer avoid burnout without working less?** A: Miles Kirkpatrick's approach is a trade rather than a rigid boundary. He will do whatever the job requires, including a late call or a few hours on a Sunday, and he also commits to recovery: a 30-minute guided breath-work and meditation routine most mornings, a day off when he needs it, and choices like a sauna session instead of an episode of TV. Host Anthony Enrico sums it up as keeping up the necessary work while adding recovery to reach the performance you expect. Miles has practiced this almost daily for more than seven years, and his doctor recently told him his blood pressure and resting heart rate were the best they had been. **Q: What is decision velocity and how is it different from flip-flopping?** A: Decision velocity, as Miles Kirkpatrick runs it at SITE Technologies, means making decisions quickly with limited data, stating the reasons, committing with conviction and moving forward. If the decision proves wrong, the team pivots and commits to the new direction with the same conviction. Flip-flopping is changing direction without that commitment. Miles considers the alternative worse: spinning and repeatedly asking for one more data point. His standard is to be right about 70 percent of the time, which he considers very successful, because waiting to be 100 percent right is impossible. **Q: Why should a CRO invest in customer success early?** A: Miles Kirkpatrick stood up customer success as one of his first moves as CRO at SITE Technologies because a sales organization can't succeed without strong CS counterparts: they drive expansion and keep and grow revenue. In enterprise sales it is also a differentiator, because he can introduce buyers to named people who will help them use the platform and whose job is to make sure they get value. He calls promoting a former commercial roofer with no CS experience to run the function the best decision he has made at SITE. **Q: How do you build B2B pipeline when outbound sequences stop working?** A: At SITE Technologies, CRO Miles Kirkpatrick replaced volume sequencing with higher-effort plays. Sellers, Miles included, write a point of view for a specific buyer with proof points of how SITE can help, and send it with a handwritten note. Signals inform the point of view, but people write it. SITE also hosts a customer dinner about once a quarter in major markets around commissioned research, joins invitation-only industry groups through its customers, works with industry influencers, and publishes real content on LinkedIn, including short unscripted interviews and a weekly observation from its own building analyses. Miles calls points of view SITE's most successful pipeline source. **Q: When is a startup too early to invest in PR?** A: Miles Kirkpatrick's experience at SITE Technologies is that PR helps once buyers understand the problem and the category. SITE invested in PR while it was still trying to educate an entire industry on a new way of assessing commercial property. The agency did good work, but the result was only marginally helpful. His lesson is that the product and industry need to reach a level where buyers know who you are and understand solving the problem your way. **Q: What does RevOps look like at an early-stage company that lands enterprise customers first?** A: At SITE Technologies, CRO Miles Kirkpatrick set up Salesforce himself over a weekend, and RevOps was him going through data on Sundays. SITE won enterprise customers before building infrastructure, so the work came afterwards. The CFO has taken on much of it and finance has added help. The next stage is a full RevOps function covering pricing and packaging, contract structures, quoting, territory assignment and rep capacity. ## Timeline - **00:00** — Cold open + intro - **01:23** — Seeing the shot before you hit it: being in the zone - **05:28** — Hitting the wall: the first panic attack - **09:02** — The 30-minute morning routine and the 5:30 a.m. peak window - **17:10** — The warning signs before the crash - **27:55** — Decision velocity vs. flip-flopping - **31:53** — Bets that missed: comp plans and early PR - **36:14** — The best decision: a commercial roofer runs CS - **40:47** — Pipeline: points of view, handwritten notes, customer dinners - **49:16** — RevOps is "me on a Sunday" - **53:08** — Wrap ## Related episodes - **Ep. 54: The Hidden Cost of Hustle Culture** (Jack Jackson (ShelterZoom)) — Another look at what constant grinding costs operators, alongside Miles's account of years of overwork ending in a panic attack. · https://www.leanscale.team/knowledge/podcast/jack-jackson-hidden-cost-hustle-culture/ - **Ep. 32: The RevOps Poker Game** (Spencer Hodgson) — The poker guest Anthony refers to: making bets without full information, which is the core of Miles's decision velocity. · https://www.leanscale.team/knowledge/podcast/spencer-hodgson-revops-poker-expected-value/ - **Ep. 63: Customer Success as a Competitive Advantage** (Maranda Dziekonski (Fexa)) — Tying customer success to revenue, the case Miles makes for building CS early and putting named CS people in front of enterprise buyers. · https://www.leanscale.team/knowledge/podcast/maranda-dziekonski-customer-success/ - **Ep. 28: Run CS Ops like a Pro: The 5 Things Every CS Operation Needs to Have** (Adrian Diaz (Findem)) — How to build a customer success function from scratch, which SITE did under a leader who had never done CS before. · https://www.leanscale.team/knowledge/podcast/adrian-diaz-cs-ops/ - **Ep. 84: From Fortune 1 to 100 Person Startup: A CRO's Bet on Creative** (Gabby Stoller (Big Happy)) — Another CRO moving from a large company to a small one and betting on creative and offline channels, comparable to SITE's print ad and real content. · https://www.leanscale.team/knowledge/podcast/gabby-stoller-cro-bet-on-creative/ - **Ep. 69: Inside the Mind of a Modern CRO** (Brett Kelly (Inovonics)) — A modern CRO's view of leadership and RevOps, for comparison with Miles's human-first approach and his RevOps-on-Sunday reality. · https://www.leanscale.team/knowledge/podcast/brett-kelly-modern-cro/ - **Ep. 136: There Is No APAC Playbook: Going International, Then Walking Away** (Bhavik Vashi (Siro)) — Another CRO episode from the same run on making high-stakes calls with incomplete information. ## Full transcript _Machine-transcribed and not diarized; speaker attribution is inferred._ _Transcript only, as a separate file: https://www.leanscale.team/knowledge/podcast/miles-kirkpatrick-site-technologies-what-elite-performance-actually-costs/transcript.md_ ### 00:00 — Cold open + intro **[0:00]** If you are waiting to be 100% right and want to be 100% right of all your decisions, that, to me, is an impossible feat. **[0:08]** But could you be 70% right? If you make 70% of your decisions are correct, I think you're going to be pretty damn successful. **[0:18]** My guest today is Miles Kirkpatrick, Chief Revenue Officer at Site Technologies, the Chicago company using drones, satellites and AI to tell commercial property owners what condition their roofs, **[0:29]** pavement and facades are actually in before any of it turns into a capital expense. **[0:35]** Is the ability to take a step back a luxury that you've earned by investing that? **[0:41]** I mean, you crush it for five years and then 10 years and then at what cost? Is it worth it? **[0:48]** I don't think it's, hey, don't do the things necessary. It's, oh, you also have to incorporate recovery to help you hit your performance that you expect. **[0:56]** Because a lot of times, I don't have time. I don't have time. **[1:00]** Okay. What TV shows are you watching? You know, maybe don't do that. **[1:05]** We actually had a person on the podcast who played some professional poker and you have to make bets. **[1:12]** And bets mean you don't know all the data. You don't know what that other person's hand is, but you have to play. ### 01:23 — Seeing the shot before you hit it: being in the zone **[1:23]** So you described being in the zone to me during our prep session as seeing the shot before you hit it. **[1:29]** And then your body just goes and does exactly what it needs to do. **[1:33]** When did you first realize the same thing was available to you at a desk? **[1:38]** Well, Anthony, first off, I appreciate you having me on the podcast. **[1:44]** Yeah. So let's talk about being in the zone. So I think if you've played athletics or it doesn't have to be athletics, any sort of thing that is competitive, **[1:52]** for any length of time, you probably have experienced something where you envisioned the outcome and then you went and did that outcome. **[2:02]** You accomplished that outcome and you're like, wow, this is easy. Like, why can't it always be like this? **[2:08]** So I played competitive golf for a number of years, you know, at a high school college, tried my hand professionally for a number of years. **[2:16]** And there's a few times where I was in the zone where essentially you would see yourself doing something. **[2:22]** You would see the outcome. You would see the seven iron, you know, trailing a couple of yards right to left and landing by the pin and spinning back. **[2:28]** And, you know, you would see that shot and then you would go execute. And so I call that being in the zone. **[2:33]** And if you look at some of the best athletes in the world, they have also experienced times where they're able to put themselves in that. **[2:40]** And that's when they have the triple doubles like the throw for 350, 400 yards in a game, like whatever that may be, like that's them being in the zone. **[2:48]** I didn't really equate that to the professional world, like being able to do that in kind of what we do day to day now, but I was wrong and you can. **[2:59]** And I want to attribute a lot of this to I have been working on, I would say, professional development, peak performance, trying to put myself in the zone or that mindset. **[3:10]** I've been, you know, doing this practice and it is a practice because this is like an everyday deal. **[3:15]** I've been doing it now for over seven years, almost daily. **[3:20]** I'm going to say I wish it was every day, but geez, with a couple of kids, things get a little things get a little harder, say almost daily. **[3:27]** And I want to attribute a lot of this to my coach, Neha, who will have to tag in the comments. **[3:34]** But she is amazing and has completely changed my life and how I kind of see myself, how I act, how I prepare for the day. **[3:43]** And so a lot of what we do is about doing things in the morning, exercises. **[3:48]** We do breathing exercises in the morning, kind of a mindset prep, if you will, to get ready for the day, but also put yourself in a position where you can be at your best. **[4:01]** You can be in the zone for a period of time and hopefully over time, more of the hours of the day so that you can do your best work. **[4:12]** So that was a really long answer, but essentially really what we're trying to do is put yourself in with the right mindset to be able to do 3x, 4x, 5x, what you would normally do for longer periods of time. **[4:25]** And that's peak performance. And if you can do that, then you can get more done, you can be more effective, you can have more of an impact. **[4:32]** So the whole challenge, the goal is to how am I a peak performer for longer? And there's things that you can do to help you get in that mindset and be able to do it. **[4:43]** Well, and I think I'm a former athlete as well. And I think some of those moments are pretty obvious if you've had that experience in the past. **[4:51]** But I've also really felt that in my professional life as well. And there have definitely been days where it's like, okay, I spent seven hours pretty much doing nothing. **[5:02]** I'm on autopilot through meetings, I'm kind of scanning my inbox in Slack, but I didn't really do anything. **[5:08]** And then all of a sudden there's a spark of creativity and in one hour I did more than almost seven. **[5:12]** So I would love to get into specifically like what you can do and how, but before that, I think what maybe drove the inspiration is when you said you hit that wall in life. ### 05:28 — Hitting the wall: the first panic attack **[5:28]** Yeah. Yeah. So let's talk about why, right? Let's talk about how, because a lot of times, you know, with anything, like you don't really change until you have a moment in time that like forces you to change. **[5:39]** When you have to, or you have to change. Right. And so there was a long period of time where, you know, I can remember this vividly. **[5:48]** And a lot of this was kind of during COVID too. So, but I would get up in the morning, I'm an early riser, like I would get up before 6am. **[5:57]** First thing I would do, go in, flip open the laptop and just start grinding and start working. **[6:03]** And I would go six to eight or six to 730, you know, kind of get ready for work, go into the office, work, work, work all the way through, come home, say, hey, how you doing? **[6:12]** Kiss your wife, have dinner, back on the laptop. And that was rinse and repeat. And then, oh, by the way, let's, let's factor in a couple hours on the weekend. **[6:20]** And that was rinse and repeat for years. Just because, you know, I believe, and I still do believe this to some extent, but like I'm, you know, I don't view myself as some extraordinary talent. **[6:32]** I view myself as being successful, just because I'm kind of willing to do what other people aren't. And for me, that's working harder than most folks. **[6:40]** And, you know, I, I think that's always been kind of my differentiator, even when I was playing golf, like I was certainly not the most talented by any means, but I was just willing to spend more time doing it. **[6:54]** And so I tended to, you know, you know, kind of rise because of that. But anyway, so, so if you start layering in, you know, days and days and months and months of this same routine, **[7:08]** and then and then kind of drop on top of that an extremely stressful job that you're in anyway, and then drop on top of that, you know, some things that happen in my personal life and then drop on top of that COVID. It just kind of all came together. **[7:24]** And for me, what that manifested in was a panic attack. And if you've never had one before, you don't know what they are. **[7:36]** And when I had one, I literally like couldn't breathe, like I felt like my chest was caving in on itself. I had no idea what was happening. I felt like I was dying. **[7:47]** I mean, it was it was a once in a lifetime experience that I absolutely hope never happens again. And it was like kind of in that moment, I was like, I have to figure out what's happening to me and I have to do things differently because like, I don't want to do this again. **[8:02]** And for me, medication wasn't an option. Like I just just kind of fundamentally try to live my life without medication of any kind. So I needed to find another way. **[8:12]** And I was lucky enough to work at a company at the time that really prioritized mental health. And and we had a program with Neha, where executives at the company could see her one on one. **[8:27]** And, you know, I said, yeah, sign me up. I let's go. Let's see if this see what's happening here. I just, you know, more so just wanted somebody to talk to about it. **[8:37]** And that started kind of this seven year journey of trying to be better, use breath work as a mechanism to alleviate stress, as a mechanism to put yourself in the right mindset that you can go out and attack your day. **[8:57]** And so you talked about so that's what happened, right? That's when it happened. What happened? How I'm addressing that is something I do every morning. ### 09:02 — The 30-minute morning routine and the 5:30 a.m. peak window **[9:07]** Well, gosh, I wish I could say every but we'll say most, most mornings. And it's basically a routine that I do. **[9:16]** It's recorded on my phone. And I sit in a dark room. And I play this recording. And it's basically a 30 minutes of a guided meditation and breath work where it's taking you through different types of breathing exercises that you do. **[9:33]** And so that's what I do every morning. And when I'm done with that, what happens is you have kind of a mental clarity around, you know, you're very calm in that state. **[9:44]** Like you're kind of your mindset is you're clear, you're kind of focused on what needs to happen. **[9:48]** And I have found that when I do that, and then immediately start kind of the hardest thing I have to do, or like, you know, the kind of jump right into work, that I'm able to be the most productive in that 30 to 45, 60 minutes of time. **[10:04]** And so for me, and I tell my team this all the time, it's like, to be a peak performer, it doesn't mean that you have to be a peak performer between eight and five. **[10:12]** It means that you've got to find the point in time, the periods of time throughout the day that you are the most productive. **[10:18]** Maybe that's at 1030 at night. Maybe it's at 530 in the morning. For me, it's between the hours of 530 and 615 to 630 in the morning, like that is like my peak time. **[10:31]** And so I get more done and more productive in that peak time and have the most clear thought, because I'm kind of doing this kind of program. **[10:40]** It takes a lot of intentionality to carve out that 30 minutes. **[10:44]** I think a lot of people would look at that and say like, oh, do I have 30 minutes to do this? **[10:49]** How have you adjusted the rest of your schedule or investment time to carve out this time? **[10:59]** And have you felt the pressure to give up on investing this time, too? **[11:06]** It sounds a lot easier when you don't have two kids. When you have children, it gets really difficult. **[11:14]** So, in fact, I was telling my wife the other day and also, I would say that there is no way that I could ever do this if I didn't have a really strong supportive partner. **[11:25]** And my wife has also actually recently gotten into breath work and so she gets it. **[11:30]** And so we both have to be pretty intentional about giving each other the space to go do these things, because we know that we're better in our marriage, **[11:38]** we're better in the office, we're better with our kids, when we're able to do these things. **[11:42]** So it's like trying to make sure the other person can have their moment to go do this. **[11:47]** But I was telling her, I was like, I think I maybe have to get up earlier. **[11:50]** Like, I'm up at 515 and maybe I got to move that to 445 so that I can get this stuff in because one of my sons is getting up earlier. **[11:59]** So he loves to come and sit next to dad while while I'm doing my work. **[12:03]** And so he's just kind of so it's I love it. **[12:06]** I mean, it's just like you can't trade those moments in nor would I. **[12:09]** So but maybe I've got to get up a little bit earlier to get the stuff that I need to do in before that happens. **[12:15]** So, yeah, there's definitely an intentionality that happens. **[12:18]** It's not easy by any means. **[12:19]** But I think, again, going back to my previous point, it's like in order, I truly believe like, you know, maybe you can put this on my billboard or on my gravestone. **[12:27]** But it's like, you know, in order in order to be different, in order to be elite, like you have to do the things that others are unwilling to do. **[12:35]** And so if that means doing those things, then, geez, I guess we got to go do those things because, you know, it's that's how you're going to be different. **[12:43]** That's how you're going to be better. **[12:46]** Is there anything else that you've reconstructed in your workday, how you approach work, how you approach performance? **[12:55]** Sounds like breath work has been a really, really important piece of that. **[12:59]** Are there other things that you took a step back at and redesigned? **[13:04]** Yeah, I think that so clearly a big advocate of men's mental health and also just mental health in general. **[13:11]** I think it's we are living in pretty unique time with the covid, with, you know, the shutdown with social media and kind of this like **[13:23]** you never know what's real and fake and it's just right in front of our face all the time. **[13:27]** So I think that there's a really there's a lot of like mental health issues that are happening right now. **[13:31]** And I think that giving people the space to talk about it, I think is really important. **[13:35]** So, yeah, there's some things that we do kind of on my team that I think are really important. **[13:41]** I'll give you a couple. The first, I think, is space just to be able to talk. **[13:45]** So, you know, like we are, I hate to say that any team in an organization is or any is a family because we're not. **[13:56]** We are a high performing team, but it's important that that team has the ability to have open conversations about what is working, **[14:05]** what's not working, what's making you feel a certain way versus that. **[14:08]** Like it's important that we are humans first. And so we have those conversations. **[14:12]** So I've been very open with my team around, you know, being able to come to me and have conversations about whatever it is they want to talk about. **[14:19]** And I'm a human first and then a boss second. **[14:23]** But going along with that is freedom to work when you need to work. **[14:28]** So at the end of the day, we're outcome driven. **[14:30]** It doesn't mean that you need to be in your seat from eight to five. **[14:32]** Like I understand people have things outside of work that are more important like family first always. **[14:37]** So if you have things you need to do, if you have children's pick up at two thirty and your turn to go do that thing, then that's OK. **[14:45]** Like we structure our day around an outcome that we need to drive. **[14:49]** And that doesn't mean necessarily working from eight to five. **[14:51]** So first off, first and foremost, it's like as long as you're getting your jobs done, as long as you are here at certain times when I need you, like you have flexibility. **[15:00]** You don't need to ask me. You have flexibility to kind of run your calendar. **[15:04]** And I don't think I was I think that's becoming more common. **[15:08]** But I certainly don't think that I was that type of leader where I was OK with that when I started my career. **[15:13]** I was definitely not that person. **[15:14]** So I think I think it was very common culturally where that was not OK. **[15:19]** I mean, I I had in office cultures where, yes, you're expected to be there from eight to probably six. **[15:27]** And then you still don't you might get looped into something still when people are at the office. **[15:31]** So that was common. **[15:33]** So that's one. We do a lot of self-reflection. **[15:36]** In fact, we have our Q.B.R. tomorrow. **[15:39]** And the first thing that every person does when they give their Q.B.R. presentation is self-reflection. **[15:47]** I think it's really important that we take a step back. **[15:51]** We take, you know, kind of pull yourself up a little bit like give me a macro understanding of like what happened. **[15:57]** Why did it happen? What are we going to do to be better? **[15:59]** Those kind of things like it's a very much a self-reflection aspect of of what we do. **[16:04]** I think that that is a really important part of peak performance. **[16:08]** Like you're never going to get better if you don't reflect on what just happened good or bad and how we're going to how we're going to move forward from that. **[16:16]** So those are a couple of things. **[16:17]** I'm also a huge advocate of talking to my team about breathing and breathwork and yoga and meditation and those kind of things to kind of put yourself in that mindset. **[16:27]** In fact, we've brought in, you know, we've had some meditation experiences during my Q.B.R.s. **[16:33]** And, you know, I'm not sure if people get out of those sessions like what the hell did we just do. **[16:38]** But, you know, that's OK. I'm kind of like that. **[16:41]** So it's all right. You know, I've got some I've got a few crystals on my desk laying around. **[16:45]** So, you know, we just we we open the door to that stuff. **[16:49]** Being in sales is a crazy, crazy gig like, you know, you got to be a little nuts to be in this in this business. **[16:54]** So we can do those things that kind of make it, you know, make ourselves be better. **[16:58]** Then so be it. I think that's great. **[17:01]** I'm in Arizona, which Sedona famously some of your crystals probably came from. **[17:07]** Yeah, I'm from there. ### 17:10 — The warning signs before the crash **[17:10]** I am I was hoping you could maybe walk us through. **[17:13]** I hope nobody listening to this has to get to the point where they're having a physical experience like a panic attack **[17:21]** to realize that they need to make a change up until that point. **[17:26]** Were there any signs that you could have seen to help start to steer the ship a different way **[17:33]** or anything you'd recommend people to look out for? Yeah. Yeah. **[17:36]** Well, first, I think it's, you know, to me, panic attacks don't happen. **[17:40]** Just, you know, one day like it's a culmination over time. Right. **[17:43]** It's like a lot of life choices kind of leading up to certain things. Right. **[17:46]** And maybe you have like one event that kind of triggers it. **[17:49]** So for me, I think it's you got to have a balance of you have to do things for yourself. **[17:54]** I think that's probably the first and foremost. **[17:56]** If you're looking at what you're doing throughout the day and you do not have time for yourself or your family **[18:02]** that is giving you basically energy, power, filling you up, you know, preparing you for what you're challenging. **[18:11]** If all you're doing is giving to other people, to your job, to your coworkers, to your team, to others, others, others. **[18:18]** If that's all you're doing, you are setting yourself up to have a crash. **[18:22]** There has to be a moment where you fill yourself back up, like where you are giving yourself something that you can kind of recharge. **[18:30]** So I think that's like probably the number one indicator. And that was me. **[18:34]** I would wake up and go to bed and all I was thinking about was how are we going to close these deals? **[18:39]** How am I going to get my team to my number? Like that's all I was thinking about always. **[18:44]** And, you know, at the time I thought that was like what leaders did. **[18:50]** That was just what you do, right? **[18:52]** And now I've realized that that's what leaders at Burnout do. **[18:56]** And I needed to change. **[18:59]** I always wonder this. It seems like it works for a while. **[19:04]** And the people who do that, like you're doing these things and you're getting rewarded for it, **[19:10]** is the ability to take a step back at this point or rearrange things or have different priorities, **[19:18]** a luxury that you've earned by investing that? **[19:21]** Or do you think if you were to go back, you could have been even more productive if you kept yourself from that Burnout phase? **[19:30]** Wow, I guess we'll never know. But I think you're right. **[19:35]** I mean, there was a period of time where I crushed it. **[19:39]** And I was like, well, this is working. Keep doing it. Double down. **[19:46]** But at what cost? **[19:51]** I mean, you crush it for five years and then ten years and then you burn out and you can't ever do it again. **[19:58]** You never see your kids. At what cost? Is it worth it? **[20:03]** So I think that's the question that I think that a lot of folks have to answer. **[20:07]** And so I think, you know, I'm in this for the long game, not for the next six months. **[20:13]** Right. So if we wanted longevity do this, that's why I need to make the change. **[20:17]** And I'll give you a proof point. This is this, you know, I'm trying not to make this TMI here, but I'm pretty open person. **[20:24]** I think it's important. I went to the doctor the other day and, you know, it's great now. **[20:30]** They have like, you know, years of your medical history that they can just pull up and look at the charts and the graphs and that kind of stuff. **[20:36]** And, you know, when I started going to the doctor, only doing these annual physical, you know, seven or eight years ago, **[20:41]** it's very clear to see like what my blood pressure was, like what my oxygen and my blood was, all those things. **[20:47]** And it wasn't like I wasn't borderline, you know, bad, but I mean, it was definitely high. **[20:54]** And I went back this time was last week and she's like, what, what are you doing different? **[21:00]** So what do you mean? Said, well, your blood pressure is the best it's ever been. Your oxygen, your blood, like is, you know, **[21:08]** your heart, your resting heart rate is the lowest it's ever been. **[21:11]** And, you know, I'm certainly not working out more because with two kids and a full time job, it's that's difficult. **[21:19]** But I think that what I'm attributing it to is like the ability to be able to do these things and to practice over time. **[21:27]** And I think kids have something to do with it, too, like, you know, but they're, to me, an immediate stress relief, **[21:32]** stress relief, just being able to spend time with them. So highly recommend that. **[21:35]** Although it can also be very stressful, but it's kind of a different kind of stress. **[21:39]** I'm a believer in this stuff. I think it really works. **[21:41]** But my ability or I think the ability to be able to kind of take a step back and do more things for yourself, **[21:46]** like will have, I think, a profound impact on you as a person, but it will also impact medically. **[21:53]** And I've seen it firsthand by seeing those results. **[21:58]** Yeah, it definitely is. It's tough to squeeze in. I have young kids, myself, six, four, one and a half. **[22:05]** We have another one on the way in about six weeks. **[22:07]** Congratulations. **[22:09]** Thank you. **[22:10]** You're right in it. **[22:11]** But I'm right in it. Thank God I have a home gym. I do get to squeeze in a couple workouts. **[22:17]** But yeah, very, very difficult to find that time when you have a high stress career plus building a family. **[22:24]** Where else do you feel like, hey, there's opportunities to carve things out? **[22:29]** Are there certain boundaries that you should be setting at work? **[22:31]** Are there certain things you should be looking for in your opportunities? **[22:35]** What else can people do to help guard that and give them self longevity in their career? **[22:41]** Yeah, to me, it's about routine. You know, boundaries are tough for me because, like, you know, you set a boundary. **[22:49]** It's like, I can never break this boundary. **[22:51]** Well, in the world of sales and quarters and years and things like that, you know what, sometimes you got to work on a vacation. **[23:01]** Sometimes you got to take a call at nine o'clock at night. It's just kind of like what you got to do. **[23:07]** It's difficult for me to draw a line in the sand. I will not answer emails after five o'clock. **[23:11]** This isn't Germany, you know, where they shut email servers off or take a month off. **[23:17]** We work. That to me is kind of like, I don't do that. It's kind of like New Year's resolutions type of a thing. **[23:26]** But what I do think is important is knowing that and knowing, hey, listen, I'm going to do everything I have to do to move this forward, **[23:34]** to hit our numbers, to, like, you know, do what I have to do. But I'm also going to spend time for myself. **[23:42]** I'm also going to take the day off when I need it. I'm also going to spend 45 minutes in the morning and do these things. **[23:48]** I'm also going to do that. So I think to me, that's a trade off. **[23:51]** It's like I'm going to work as hard as I need to do to get to where we need to go. **[23:56]** And if that means I got to work at seven thirty eight o'clock at night, if that means I got to work five hours on a Sunday, fine. **[24:02]** But I'm also going to do these other things for me. Right. No. **[24:07]** And I think that's a good formula for a high performer listening to this, too, because I don't think it's hey, don't do the things necessary. **[24:14]** It's you also have to incorporate recovery to help you hit your performance that you expect. **[24:20]** And a lot of times I don't have the time. I don't have time. OK, what TV shows are you watching? **[24:26]** And people, like, rattle off like three TV shows. I'm like, right. Well, there you go. You know, maybe maybe don't do that or watch one or something. **[24:35]** You know, it's like my wife and I like TV, you know, for us, like it's like we might catch an episode, maybe one or two episodes a week, maybe. **[24:43]** You know, and that's like a luxury for us. But like like last night we were sitting there like, what do you want to do? **[24:48]** Like, you know what? Let's go. We just got an infrared sauna. Huge fan of that. Oh, nice. Love that huge. Yeah, amazing. **[24:56]** Right. So we won the sauna for 30 minutes and like meditate, you know, so it's it's could have watched an episode of whatever. **[25:04]** Well, we went and did the sauna and said so I think it's just kind of like making better choices with the times that you have open and just kind of going to do those things. **[25:12]** As you've gotten into sight, you have a new perspective, a new approach, you have a new way of organizing your time and some capabilities that maximize your performance. **[25:24]** Where have you seen that in this new journey with all the skills you've acquired recently, too? **[25:30]** Well, sight is a really interesting story. You know, I think I tell my team all the time this and I think that this is really important that a lot of being successful is finding out what company or what size company you do well in. **[25:50]** OK, like, are you the kind of person that does really well at Microsoft and a huge organization or do you do really well at a company who's really small and having those different skill sets. **[26:04]** Are important and understanding where you thrive is really important because if you drop me into, you know, name some company that's 50,000, 75,000 people, I'm probably not going to do well. **[26:19]** It's just not who I am. Right. And vice versa, if you drop somebody at a huge company into a company like sight, which is like 50 people. **[26:30]** I'm not going to say they're not going to do well, but it's going to be different for them. Right. It's a different thing that you're doing. **[26:36]** I've seen that person not do well. So I've seen that happen time and time again. Yeah. Like, I mean, it's it's definitely a different animal. **[26:45]** Like we, you know, you have to just move at a pace that is just so uncomfortable for people that at large organizations. **[26:52]** And I just I hear this. Yeah. Well, we move fast. Now, not as fast as what you have to move as a startup. **[26:58]** You just don't. And you have to be so comfortable with it that it's just another day. **[27:02]** You know, and I see people that really struggle on that because they just can't wrap their heads around not having all of the data and then make a decision. **[27:13]** It's like if you're waiting for all of the data to help inform this decision, you're you're what do you? **[27:18]** You're never going to make a decision ever like our my number one thing for my team is decision velocity. **[27:26]** That's like, you know, maybe I'll get that tattooed on my arm. But like to me, that is like the most important thing that we do is make decisions fast. **[27:37]** Because when we make the decision, then we are either right or if we're wrong, that's OK, because we can change and then pivot and then move forward. **[27:46]** But making those quick decisions with not a lot of data is something that you have to be incredibly comfortable with at a startup. ### 27:55 — Decision velocity vs. flip-flopping **[27:55]** Can we can we double click there for a little bit because I think I understand the nuance between decision velocity and flip flopping and just changing things. **[28:05]** I've seen I've seen what that looks like. And then I've seen like, OK, this is a productive way of making decisions quickly. **[28:12]** Can you help draw the distinction between those two things? **[28:17]** Yeah, so I'll give you an example, like so today, you know, we had a product meeting where we got on the phone with all the leaders from the product team, the CS team, the sales team, our trades team, the engineering team, executives like. **[28:30]** And we're laying out the roadmap for the next six months, three months, six months, and we're talking about what our priorities are. **[28:38]** Like, what are we going to go build, like certain things that we're going to go build? **[28:42]** It's like, OK, go to market team like of these things, like what's going to drive the most revenue? **[28:48]** Now, do we know? **[28:52]** No. Do we have early indications? Yes. **[28:57]** Do we have all of the data? Absolutely not. No, no way to. **[29:02]** But do we have to make a decision and believe in it for what, you know, for the reasons that we stated and then move forward in that direction? **[29:09]** We absolutely do, because if we don't, we're just going to sit here and spin around and not really do anything. **[29:16]** And that's worse. Right. **[29:18]** So just we make the decision, have conviction, go forward. **[29:21]** If we get down the path and it wasn't correct, OK, then we pivot and go to another direction and have conviction to go down that path. **[29:29]** But like what's worse is spinning and never making a decision or always asking, well, can we get that data point? **[29:36]** Can we get that data point? Can we go get this thing and then that thing? **[29:39]** It just you're just never going to get it. **[29:42]** And so we have to make decisions based on limited data. **[29:44]** And that I think is very uncomfortable for certain people, but other people thrive in it because they're they're willing to make mistakes. **[29:52]** They're OK with it. And I think I'm just one of those people that's OK with it. **[29:57]** Like I think maybe playing golf early in my career, like. **[30:02]** I mean, in golf, like if you go out and play around 18 holes, like you might hit might hit three or four shots how you wanted to. **[30:09]** Everything else is a miss it into some capacity. Now, the guys on tour just miss it in a very much smaller margin. **[30:17]** Right. So they're able to continue to play. **[30:19]** But most of the time you're not hitting things the way you want it to. You're making mistakes. **[30:23]** But what are you going to do? You sit there and dwell on it or are you going to go hit the next shot? **[30:29]** Right. So it's like it's that kind of mentality, I think. And some people might disagree with me and that's OK. **[30:35]** But for me in way we move, that's the way we operate. **[30:40]** And I think some people can get super frustrated with me because I'm like, all right, so we made a mistake. **[30:44]** So we'll just pivot and do something different. Well, why do we make that mistake? **[30:47]** Well, because it was based on the best data we had at the time and we had to make a call. **[30:50]** So we made it and we move forward. **[30:54]** The best metaphor for this I've heard we actually had a person on the podcast who played some professional poker. **[31:03]** And you have to make bets and bets mean you don't know all the data. **[31:09]** You don't know what that other person's hand is and you don't know what they're going to do. **[31:12]** Totally. So but you have to play. **[31:15]** You got to play. You got to play. Yeah, no, you're absolutely right. **[31:18]** And so we just try to make I think what paralyzes you is to try to be 100 percent right all the time. **[31:25]** That's just impossible. **[31:27]** If you are waiting to be 100 percent right and want to be 100 percent right of all your decisions like that to me is an impossible feat. **[31:36]** But could you be 70 percent right? **[31:39]** If you make 70 percent of your decisions are correct, I think you're going to be pretty damn successful. **[31:45]** And so for us, it's like, can we be 70 percent right? **[31:49]** And it gives you some grace to make a wrong decision. ### 31:53 — Bets that missed: comp plans and early PR **[31:53]** Absolutely. At at site, what are some of the bets that you've made? **[32:01]** And in particular, I'm always curious because I feel like we're going through such a such a change with how people are going to market, **[32:08]** how sales is operating, how marketing is operating, how people are building pipeline and closing deals. **[32:13]** It just feels like it's dramatically changing every day. **[32:16]** What are some bets that you feel like you're making that are paying off and ones that maybe you wish you would have avoided? **[32:22]** Where do I start? **[32:26]** The ones I've waited, I think, are definitely more top of mind just because they're easier ones to remember. **[32:32]** Yeah, they're the ones I remember. **[32:36]** I. **[32:39]** She's all right. **[32:40]** Well, I'll give you a couple of examples. **[32:41]** Right. You asked. **[32:42]** Let's give let's give some real examples. **[32:45]** Comp plans. **[32:48]** And team structure. **[32:52]** I don't think I nailed it. **[32:54]** You know, it's like the complaints to me are so difficult. **[32:57]** It's so difficult. **[32:58]** Like if there's the one thing that keeps me up at night more than anything is like, how do I build the best comp plan? **[33:05]** The ones that the account executives look at and they're like, oh, yes, I can make a lot of money here. **[33:12]** This is totally fair. **[33:13]** Like I love this and then your CFO can also say, I love this comp plan. **[33:19]** This is going to like this is completely fair. **[33:22]** This does what it needs to do for the business. **[33:24]** We're incentivizing the right behaviors. **[33:26]** Perfect. **[33:27]** How do you create that plan? **[33:29]** And that has been difficult because there are just so many, at least in our business, **[33:36]** so many unique, interesting situations that arise from a contracting perspective that like, I just don't think we anticipated. **[33:46]** And it's just it just made it difficult, I will say. **[33:49]** So definitely have not nailed comp plans. **[33:51]** Like if I could go back and redo it now with the information I had, I would. **[33:55]** So I guess that's what we do next year. **[33:56]** But that has been that has been a big time challenge, I think, for us. **[34:00]** Well, it's a very difficult one. **[34:02]** It's a very difficult one. **[34:03]** And especially, yeah, a lot of these tech companies are moving from seat based platform base. **[34:08]** It's a little bit easier. **[34:09]** Like, OK, here's the annual contract value. **[34:12]** Ship the rep 10 percent to usage based. **[34:16]** You're trying to forecast things. **[34:17]** You don't want to tie someone down to like an annuity plan, but also you don't want to overpay. **[34:22]** It's it's a very, a very difficult time for Siro's writing complaints right now. **[34:27]** Yeah, totally. **[34:28]** Or then let's just take commission out of it. **[34:30]** I mean, there's a lot of companies like anthropic and open AI that I don't know the intricacies of the plan. **[34:35]** But I've heard directionally, hey, we're just going to pay you a lot of money and maybe we'll give you a very small variable component of your salary. **[34:44]** So just screw it. **[34:45]** We're not going to do that anymore. **[34:46]** You know, it's so it's it's definitely a hard one. **[34:49]** Definitely haven't solved it. **[34:51]** But I think the important thing is like when I tell my team and I think, you know, I tell my colleagues and the executive team, it's like we're trying to create. **[34:59]** We're trying to create this thing that works for both parties and that's hard. **[35:02]** So we're the intent is good here. **[35:05]** We're trying to appease both individuals. **[35:07]** We're trying to make this thing the best it can be. **[35:10]** We're just you know, this is a difficult time for us to create those. **[35:13]** There's a lot of a lot of moving parts. **[35:15]** So I think that's one that's been difficult. **[35:18]** I think we and I'm going to preface this to say this is no fault of this organization. **[35:25]** I think we tried PR and invested in PR when we were too early. **[35:30]** I just I don't think we spent a lot of time on it. **[35:34]** And again, no fault to this organization. **[35:35]** They did a great job. **[35:36]** I just don't think we were right. **[35:37]** We were at the right stage. **[35:38]** I think we just we we took a swing on something that we thought would potentially help us. **[35:43]** It was marginally helpful. **[35:44]** But I just I think we were just weren't at the right stage. **[35:46]** And so I think we that was one thing that, you know, for the learnings, I think you need to be at a certain level. **[35:51]** I think the product in the industry I think has to be a certain level of like where buyers kind of know who you are and understand. **[35:59]** Like they need to have a little bit more of an understanding of like solving the problem this way. **[36:03]** I think we were trying to like completely educate an entire industry on something. **[36:09]** And I think we were just a little early. **[36:10]** So I'm not sure those PR dollars really worked for us at that time. ### 36:14 — The best decision: a commercial roofer runs CS **[36:14]** Some things that did work and are continuing to work is one of the first things I did was stood up a customer success team inside of site. **[36:24]** And you might say, well, what does that have to do with sales? **[36:27]** And I would respond to everything. **[36:30]** We were incredibly lucky to have an individual at site. **[36:33]** His name is Jack O'Connor. **[36:35]** And I will there's some things I believe firmly. **[36:40]** And I believe that Jack O'Connor is one of the most incredible people I've ever met in my life. **[36:45]** And I get a little emotional. **[36:47]** I talk about my team like this, but he is. **[36:49]** He's completely changed how we operate from a CS perspective. **[36:52]** The guy's an amazing person. **[36:54]** He has, you know, never done CS before in his life. **[36:57]** The guy was a commercial roofer for 10 years. **[37:00]** Never done it. **[37:02]** Completely owned that function like change the game. **[37:06]** And so that's probably the best decision I've ever made at site was promoting Jack and letting him run with it. **[37:12]** That's that's a good decision. **[37:14]** And what why that matters so much is because we would never be successful as an organization as a, you know, as a revenue team as a sales organization. **[37:26]** If we didn't have unbelievable CS counterparts working alongside us, right? **[37:31]** Because they're the ones that drive expansion. **[37:33]** They're the ones that help us keep the revenue and grow the revenue. **[37:37]** It's pretty incredible thing. **[37:38]** So those two teams working side by side is really is really a cool thing to watch happen. **[37:45]** And so that was by far the best decision I made. **[37:48]** You know, it's interesting. Yeah. **[37:50]** I ran CS before I did RevOps. **[37:53]** So I kind of that was like my first go to market leadership type of role. **[37:58]** And at the time it had a ton of attention. **[38:00]** There are like huge conferences on customer success, dedicated tools. **[38:04]** It was like a whole thing. **[38:05]** It's having a whole moment. **[38:06]** And I have found many CROs and you can go rip the transcripts off of our MCP and get the receipts for it. **[38:17]** Don't even mention customer success. **[38:19]** And I feel like it's this lost art or a lost department that people haven't been investing in. **[38:24]** But the teams that do always get results. **[38:28]** Totally. **[38:29]** It's what's happening. **[38:31]** Yeah, I don't know. **[38:32]** I really don't know. **[38:33]** But it's a game changer, especially when you sell to the enterprise, which we do. **[38:38]** It's for us, it was such a differentiator where I could tell somebody, hey, not only are we going to provide this great service to you, but see this person. **[38:48]** His name's Jack. **[38:49]** His name's Vinny. **[38:50]** His name's Matt. **[38:51]** They're going to sit with you and they're going to help you use this thing. **[38:56]** And you can call them when you want to call them and you have questions. **[38:58]** And their job is to help you get value out of the platform. **[39:01]** And I don't know why more people don't do that. **[39:04]** It is, especially in the enterprise, like I would demand it if I was an enterprise customer. **[39:09]** But it has been a real differentiator for us. **[39:12]** We are at site. **[39:16]** Basically, we are telling people a new way to do something. **[39:21]** Hey, you used to do it this way. **[39:23]** It's worked for you for years. **[39:26]** We think you should do it this way now. **[39:29]** Okay, sounds great, guys, but why wouldn't I just do it that way? **[39:33]** So we have to prove value every day. **[39:37]** And so we've invested a lot in our ability to tell our story. **[39:43]** We've used folks, and I'm going to give a plug for somebody because I think they're fantastic, but an individual named Dan Mayer does not work for site. **[39:52]** He has a company called The Sale Cycle. **[39:54]** He's fantastic. **[39:55]** And he has helped us build a story and work on our storytelling abilities, and that's helped dramatically. **[40:04]** But we also have invested a lot in business value, creating business value cases, going through that exercise, taking our clients through it to say this is how we drive value for your organization. **[40:17]** And when you're selling to the enterprise, that stuff's required. It just is. And we will continue to do that. **[40:26]** I believe it's a differentiator. I believe it's a right way to do something. **[40:30]** Yeah, I mean, I don't think we've nailed it yet. I still think that there's better things that we can do it better than we've done. **[40:35]** But we will continue to do those things because I think those are fundamental to selling, and we're a big fan of the fundamentals here. **[40:42]** So let's go do those things really well, and I think a lot of things will take care of themselves after that. ### 40:47 — Pipeline: points of view, handwritten notes, customer dinners **[40:47]** Makes a ton of sense. On the pipeline front, I've seen a lot of companies struggle because a lot of the methods in which they would build pipeline in the past are having significantly diminishing returns as of recent. **[41:03]** How are you finding new logos, building pipeline? What methods are you using to get in front of your market? **[41:11]** Yes, in fact, we've been having a lot of conversations recently about this. **[41:15]** So the old methods, hey, I'm going to send a bunch of sequences out, and it's a math problem, basically. It doesn't really work anymore. **[41:28]** So we're doing, I think, three things that I think are somewhat unique. **[41:35]** I don't know if they're unique, but these are the plays that we're running. **[41:40]** Okay, the first play is I'm a big believer that if you are going to get my time on the phone, and I get a lot of people to reach out to me, come with a point of view. **[41:54]** I will give you time if you come with a point of view, and I think it can drive impact for my business. If you spend the time to create it. **[42:05]** And so we create a lot of point of views. Hey, here's what we think. Here's how we can drive value for you. Here's proof points. **[42:13]** We will proactively go to people and say, this is how we think we can help you. And that has proven probably to be our most, our probably most successful pipe gen effort. **[42:23]** It's not quantity, it's quality, where us as salespeople, I'll put myself in that category because I also write point of views. And we will go to our buyers and say, this is how we think we can help you. **[42:35]** And we'll actually create and spend some time on something. We write handwritten notes. We will package up the point of views and send it to people. **[42:44]** Like in the age of AI, we're doing things like we used to do 10 years ago, but maybe that's the cycle we're on, right? Maybe that's what you have to do now. **[42:53]** So we will do stuff like that. We do a lot of, we'll do customer dinners. We try to do one a quarter in major markets where we just had one in Chicago where we had I think eight to 10 customers and prospects we got together. **[43:06]** We had a great conversation. We talked about some industry research that we commissioned. **[43:10]** So we love to get people together and start a conversation. So we do that. **[43:15]** We've also spent a lot of time trying to get into these secret squirrel groups that exist in commercial real estate. And then if you know, you know, but you're part of these groups. **[43:27]** And we're going to one next week in Fort Worth. And I can't even mention it by name because it's so secret. I'm kidding. **[43:33]** It's basically like this group of folks that get together and, you know, they get together and talk about a lot of issues that are really pressing to their industry. **[43:42]** And there's been a few vendors that get invited to go to these things and we're lucky to be one of them because we have some customers that really think what we're doing solves a lot of problems. **[43:51]** And they invite us to go and we go there and we have great conversations and it's a great way to meet new clients. **[43:58]** So we do that. And we've worked with a couple folks who helped drive leads for us that are really influential in the industry. **[44:06]** So those are some of the things that we're doing. But if you notice in those, I think four tactics I said, I didn't mention signal based advertising, you know, marketing via clay or, you know, like whatever that may be. **[44:19]** Like, do we look at signals? Yes. Do we use it to inform a point of view? Yes. **[44:26]** But are we creating that point of view in seven people? Also, yes. So it's not as I think other folks are really just taking this automation route. **[44:35]** We're taking more of like, let's be more thoughtful about our outreach because we think that matters more. **[44:42]** I'll give you another one. If you're interested, I guess you can follow our LinkedIn if you really want to see this. **[44:49]** I love the concept of starting conversations and like real content, like real content, real use cases, real conversations. **[44:59]** And so we're doing a couple of things on LinkedIn. I started a video series. I, you know, it's fledgling at best, but hey, we're we're we're dedicated to making it better. **[45:08]** It's called a mile with miles. And I'm interviewing really influential people in commercial real estate. It's a three minute interview. **[45:15]** So we just started that, but it's a real conversation with real people. It's not scripted. **[45:20]** Like we do very minor editing. Most of the editing we do is because I mess up doing the intro most of the time. **[45:26]** So so like that's the editing we do. It's the hardest part. That's the hardest part is the hardest part. **[45:31]** Once you get rolling, you're good. Right. It's the hardest part. So we do that. **[45:35]** But then the other thing we do is every week we publish something called an observation of the week where our team we're doing analysis of commercial real estate buildings. **[45:44]** We're looking at the parking lots. We're looking at the roof. We're looking at the facade. **[45:47]** We're looking at the landscape and we see things and we make recommendations for hey, this is how you should fix certain things. **[45:53]** And so we always catch things that we see that are super interesting that our trades team who does a lot of the analysis using some AI tools that we have built. **[46:04]** They kind of start a conversation like how would you recommend we fix this or why did this happen? **[46:08]** And so we'll use some of that data to start a conversation. **[46:11]** Hey, we saw this. This is what we recommended. And lo and behold, you know, we get a lot of conversation around. **[46:17]** Well, this is how I would have done it. What about this? Or did you think about this? **[46:20]** And and that's the kind of stuff that we want. We want to start conversations. **[46:24]** And if you look at we're just looking at this the other day where we look at our LinkedIn versus our competitive set. **[46:29]** It's it's super interesting to me to look at like our engagement numbers are off the charts compared to our competitors. **[46:36]** You know, our new follower metrics like are not as high as competitors like that's not we're in the game for what we're in the game for is to drive engagement to produce really high quality content. **[46:47]** And I think if you look at the board been doing that's that's working. **[46:52]** Well, I think the old school has become in the new school. **[46:55]** I'm seeing a lot of the trends that you're you're sharing. **[46:58]** And I mean, a lot of it is just having intentionality behind what you're doing and being authentic and being organic. **[47:06]** And first of all, you're solving a real problem. If you are, then building content and certain conversation should be relatively straightforward. **[47:13]** I'll tell you, I think it is harder and it's hard for effort. Yeah, I mean, we we did a print ad the other day. **[47:22]** So ROI TBD on this print ad. But let me tell you, you know, that could be a podcast in itself around getting a couple digital marketers. **[47:32]** I'm going to loosely call myself a marketer, although marketing does report to me like, again, I'm I have a great team that does great work. **[47:42]** But getting us in a room to say, hey, let's produce a print ad was difficult. **[47:48]** And did we do it? Yeah. And it's coming out in the magazine in thesis driven. **[47:52]** Brad Hargrave's magazine really excited about it. **[47:54]** It was kind of like I got to design like a vision and then we kind of like brought this vision to life in a print ad. **[48:00]** So but I mean, that was that was hard. It was like probably and we didn't use AI, by the way. **[48:06]** We actually took the photo. And so it was I'm excited to see how it does. **[48:10]** But it was it was a very difficult thing that we did, which we did not anticipate was going to be difficult. **[48:16]** Well, I think that's very cool. Some of the some of my favorite campaigns have been like subway ad campaigns from tech companies like Clay did a really good job at that one. **[48:26]** I've seen some really billboard ads and I actually recently saw some people taking out TV ads. **[48:34]** So I mean, we're going real, real old school and a lot of these things, but I do think they're working. **[48:40]** I just think AI has completely oversaturated, like the majority of any digital marketing that you've been doing in the past. **[48:47]** I completely agree. So, you know, we've also done some some like white paper stuff where we've commissioned research and done those things. **[48:54]** So it's like that that's to me is more valuable. **[48:56]** It's like we'll give people something real to talk about, like real content, real data. **[49:00]** Like we want to be real. We want to be authentic. **[49:03]** We're we're dealing with properties that are in the built world. **[49:07]** They're real structures. And so we want to have real conversations around around the buildings that we're helping to helping to diagnose and solve. ### 49:16 — RevOps is "me on a Sunday" **[49:16]** The last thing I was hoping to pick your brain about is how you partner with RevOps or think about making investments in RevOps and what that means to you and the go to market team in the grand scheme of things. **[49:30]** Would love to hear your perspective on that. **[49:31]** Yeah. I don't know if we're unique in this. **[49:37]** OK, I'll give you my journey. And if our CFO Thomas listens to this, he's he's going to chuckle. **[49:44]** And I told him this when he started. I was like, listen, man, when we started three years ago, I came over with two guys that followed me. **[49:53]** And I you know, I every day I thank my lucky stars that those two guys came with me, Evan and Corey, because they didn't have to. **[50:01]** And they did. And they've stuck with it. And we've done some really great things. **[50:05]** And I'm forever grateful that they did that. But we didn't have we we had nothing. **[50:12]** I set up a sales force over the weekend. We didn't have pipeline. **[50:17]** We didn't have collateral. Like we had nothing. We had no process. We had nothing. **[50:22]** And so over the last like three years, we've built it all. And so I told Thomas when he started, I was like, listen, man, rev ops is me on a Sunday trying to like go through some of the data and figure some stuff out. **[50:32]** And we like site was really blessed to have like a ton of like enterprise customers, like really early. **[50:36]** But like we didn't like build the house. We just kind of like went out and got all these customers. **[50:40]** And so which is great proof point. But then we had to build like a bunch of the infrastructure. **[50:45]** So nobody will tell you that we need better support, technology, infrastructure and rev ops than me because we do in a lot of it. **[50:56]** I've just been trying to do and now Thomas has been doing since he started. He's done a fantastic job. **[51:00]** He's really good at it. And we just hired some some additional help in finance to help us. **[51:06]** But that's kind of think the next journey, the next evolution for site in our go to market function is to be a really great rev ops organization. **[51:13]** And we just, you know, we'll get there. We're just not we're not there yet. So what does rev ops mean? **[51:18]** Well, it means we got to go look at our pricing and packaging. **[51:21]** We got to go look at how we're contracting like optimal contract structures. **[51:24]** We need to look at how we're quoting. You know, we need to look at how territories are assigned. **[51:28]** We need to go look at, you know, rep capacity and really what that number should be. **[51:34]** All of those things like we need to go do a deeper analysis. **[51:37]** We're starting to do a lot of that analysis now. So we have kind of a cursory level of like what it is. **[51:42]** But for us in our journey, that's probably the thing that we need to get. **[51:48]** Well, there's a lot of things, but it's one of the things that we need to get better at as an organization. **[51:54]** Yeah, and it's always tough. It's like a you have to moneyball it at the beginning and then try to figure it out. **[52:01]** Yeah, I like that. But but I think once you get to a certain stage, my first time getting into rev ops, **[52:07]** I transitioned from customer success to rev ops right after a series B at a company and our CRO walked in. **[52:14]** He's like, hey, who owns all the tools and who's going to help me with the forecast and who doesn't? **[52:20]** Right. And I was like, well, I kind of been doing some of this just because like customers are most of the revenue. **[52:25]** We have the biggest team. And he's like, you're not customer success anymore. You're rev ops now. **[52:29]** I'm like, OK, sounds good. What is he? But what does that do? **[52:34]** I had to go look it up like, what am I supposed to be doing? **[52:38]** But I think the biggest thing that I recognized is what it was able to do for our exit and valuation when we had airtight data, **[52:49]** narrative supported by that data and a really strong story. And we could make you're still making bets, **[52:57]** but you had more data to feel better about the bets you were making. **[53:00]** Yeah, no doubt. **[53:02]** That's always kind of stuck with me like that, that experience of what rev ops can help do. **[53:07]** I agree. ### 53:08 — Wrap **[53:08]** Miles, thank you so much. This has been amazing. **[53:11]** I really appreciate the depth that you went to on your personal story, **[53:15]** as well as shedding some light on what I know a lot of people listening are probably going through right now. **[53:21]** And I hope they take this as a sign to make those changes in their lives, **[53:26]** to help stay in the game as long as possible and at a healthy pace and reduce any of the cost in their personal life as well. **[53:34]** And I also appreciate everything you're doing at site. I love the approach that you're taking to go to market. **[53:40]** I love the ways you're building pipeline, engaging with your market, building things that matter, **[53:44]** having an opinion and showing up in the market with it and also the vision you have for the future. **[53:50]** So I appreciate everything you share at any operator here is going to learn something from this episode. **[53:54]** And can't wait to see what you incite do next. **[53:57]** Thanks, Anthony. I appreciate it. And the last thing I'll say is, you know, very insightful questions. **[54:03]** I think a lot of podcasts are a lot of fluff, but you asked some really pointed questions, so I appreciate that. **[54:09]** And, you know, I want to make myself available to people. **[54:15]** Like if you have some questions, if you're maybe struggling a little bit, you know, I'm an email. **[54:24]** I'm a LinkedIn message away and I'm happy to make some time to talk. **[54:28]** I really appreciate that. And I'm sure there's a lot of people listening who would like to take you up on that. **[54:33]** So thank you for leaving that invitation and absolutely appreciate your rolling with the questions the entire time. **[54:38]** Thanks, man. --- _LeanScale Knowledge Hub. Free to quote and cite with attribution to The LeanScale Podcast (https://www.leanscale.team)._