--- title: "Why the Best CROs Don't Come From Sales" episode: 86 podcast: "The LeanScale Podcast" publisher: "LeanScale" guest: "Jerry Brooner" guest_title: "Four-Time CRO (most recently CRO at Levelpath)" date_published: 2026-06-08 date_modified: 2026-07-22 duration: 00:57:40 word_count: 10520 topics: ["sales-leadership", "mergers-acquisitions", "ai-in-gtm", "enterprise-sales", "gtm-strategy", "revenue-operations"] canonical_url: https://leanscale-knowledge-hub.netlify.app/podcast/jerry-brooner-best-cros-dont-come-from-sales/ source: "LeanScale Podcast Knowledge Hub — https://leanscale-knowledge-hub.netlify.app" license: "Free to quote and cite with attribution to The LeanScale Podcast." --- # Why the Best CROs Don't Come From Sales _Jerry Brooner on four exits, the secret pre-IPO roadshow, the truth about startup equity, and why every revenue leader should be building their own agents_ **Episode 86 · The LeanScale Podcast** Jerry Brooner, Four-Time CRO (most recently CRO at Levelpath) · Hosted by Anthony Enrico Published June 8, 2026 · Updated July 22, 2026 · 00:57:40 Canonical: https://leanscale-knowledge-hub.netlify.app/podcast/jerry-brooner-best-cros-dont-come-from-sales/ **Topics:** Sales Leadership · Mergers & Acquisitions · AI in GTM · Enterprise & Public-Sector Sales · GTM Strategy · Revenue Operations ## Executive summary Most CRO stories are told through the multiples. Jerry Brooner's is told through the decade before the multiples — the years he deliberately spent NOT carrying a quota. A four-time Chief Revenue Officer, Jerry stood up the strategic enterprise team at Dropbox and rode it through the IPO, was founding CRO at Scout RFP through its acquisition by Workday, took Enable from Series A to unicorn as president of global field operations, and most recently drove 4X ARR growth as CRO of AI-native procurement platform Levelpath. But before any of that, he rotated on purpose through operations, marketing, partnerships, consulting, sales ops, and product. He calls himself a 'late CRO,' and his thesis anchors the episode: the leaders who move revenue understand the whole business, and the traditional sales-only track is increasingly a disadvantage in a modern GTM org. The bet paid off because it gave him range. Sitting with LeanScale co-founder Anthony Enrico — who shares an equally non-linear path from social media to product training to hospital-system FP&A to RevOps — Jerry turns that range into concrete advice for operators: start in a BDR seat to learn the most undervalued skill of the AI generation (picking up the phone and getting a stranger to talk to you), stay in every role at least a year because a job with no hard parts isn't teaching you anything, and hunt for 'achievement over tenure' when you read a resume. His counsel to young operators is a spine you can build a career on. The middle of the conversation is a rare, candid tour of the exits themselves. Jerry recounts the brutal first three months at Dropbox when his 10-years-of-SAP enterprise playbook stopped working, and the pivot that saved it: stop attacking Box head-on (an all-enterprise incumbent whose strengths you can't beat), get selective on collaboration-heavy accounts like media, CPG, and retail, pick off two or three divisions, then unite them under one executive with a security-and-cost case. He demystifies the 'secret roadshow' before every IPO — execs on different jets, an app where bankers signal buy-or-pass and you watch the book oversubscribe in real time — and argues that an acquisition is actually harder than an IPO, because the acquirer audits every contract, approval, and pipeline metric, then runs a full systems-and-org integration an IPO never forces. Then he gets blunt about equity. Startup equity is 'monopoly money' until a change of ownership: it is literally worth zero until an IPO or acquisition, secondary sales are rare and board-gated, and in a buyout the investors get paid first — so if the equity is your primary reason for joining a startup, go work at a big technology company instead. Anthony matches it with his own Emailage arc ($4M to ~$40M ARR, a ~$500M LexisNexis exit that closed in the first days of COVID) and the day-one integration machine that detonated the Salesforce instance. The shared message: know the facts before you bank your career and family on a number. The final act is the most forward-looking: every revenue leader should be building their own agents today. Jerry insists AI is a monumental shift you must adopt, but pushes back hard on the headcount-doom narrative — OpenAI and Anthropic are the biggest hirers of enterprise sellers right now (Anthropic's CMO from ServiceNow, its CRO from Slack), so AI lifts the ceiling and changes the roles and skill sets, it doesn't shrink the team. He walks through his own 'Pykey' pipeline-review agent that replaced grilling AEs for numbers with signal-driven strategy calls, and both operators land on 'the new analog': lead with deep domain expertise and your own thinking on paper, then use AI to fill gaps and propel execution — because clean data architecture, not the model, is the hairiest and most durable part of the whole thing. Who should listen: founders, CROs and aspiring CROs, RevOps and GTM operators, and anyone weighing startup equity or trying to separate the real AI-in-GTM signal from the slop. ## Key takeaways 1. **The best CROs understand the whole business — not just how to sell** — Jerry deliberately rotated through operations, marketing, partnerships, consulting, sales ops, and product before ever carrying a quota, betting that the leaders who move revenue are the ones who understand what actually affects revenue end-to-end. He calls himself a 'late CRO' and treats it as one of the seminal decisions of his career. _Why it matters:_ Aspiring revenue leaders should engineer range early. A pure sales-track resume is increasingly a disadvantage; empathy for and literacy across ops, product, partnerships, and marketing is what lets a CRO orchestrate a whole revenue engine. _For:_ Revenue Executives, Sales Leaders, Founders 2. **Start in a BDR seat — picking up the phone is the most undervalued skill of the AI generation** — Jerry's advice to young operators (and his own daughters) is to spend a year in outbound/BDR work. Nobody loves it, but getting a stranger who isn't supposed to talk to you to actually engage is a fundamental skill that's atrophying as people default to email, Slack, and chat — and it matters more, not less, in the AI age. _Why it matters:_ Build human-conversation reps early in a career, and don't let AI tooling become an excuse to never talk to people. The skill compounds into every later revenue role. _For:_ Founders, Sales Leaders, RevOps Leaders 3. **Stay at least a year in every role — a job with no hard parts isn't teaching you anything** — Jerry pushes back on serial short stints: unless there are bad actors or something is genuinely wrong, you should stick out a role for at least a year (sometimes two) and learn the skill, because every good job has hard parts and the hard parts are the growth. When hiring, he indexes on achievement and increasing responsibility, not raw tenure. _Why it matters:_ Treat 'this is hard' as a signal to stay and learn, not to leave. Resumes should show progression and mission-moving stints, not a pattern of exits at the first friction. _For:_ Founders, Revenue Executives, RevOps Leaders 4. **Convert PLG to enterprise by uniting divisions, not attacking whole accounts** — At Dropbox, Jerry's SAP enterprise playbook failed for three months. The fix: get selective on collaboration-heavy segments (media, CPG, retail), land two or three teams or divisions, then unite them under one executive with a combined security, collaboration, and cost case — rather than walking into a large account cold with 'we have your data and a bunch of small teams.' _Why it matters:_ A product-led motion becomes an enterprise motion by aggregating bottoms-up adoption into a top-down executive narrative. Right-size the account list to where your PLG strengths already have a foothold. _For:_ Sales Leaders, Revenue Executives, Marketing Leaders 5. **Don't battle on a competitor's strengths — if you're in that cycle, you're in the wrong cycle** — Jerry's costly early mistake at Dropbox was chasing Box head-on in all-enterprise accounts where Box's security and enterprise functionality were unbeatable. His team's mantra became: if we're in a competitive cycle against Box, one of us is in the wrong cycle, and it's probably us. Know your weaknesses so you can avoid the fights they define, and double down on the ICP that values your strengths. _Why it matters:_ Positioning is account selection. Don't try to fix weaknesses to win a competitor's game; find the customers whose priorities match your differentiated strengths and concentrate there. _For:_ Sales Leaders, Marketing Leaders, Revenue Executives 6. **There's a secret roadshow before the public one** — Before the well-known IPO roadshow, there's a private trial run: execs flying separately on different jets to a non-event event, pitching bankers who signal buy-or-pass on an app so the company can watch the book oversubscribe and the price move in real time before the S-1 debut. The feedback gets baked into the real roadshow. _Why it matters:_ The public IPO narrative hides a lot of pre-work. Leaders eyeing that milestone should understand the private dress rehearsal — and the discipline that precedes it — long before the bell rings. _For:_ Founders, Revenue Executives 7. **Operate like a public company a year before you are one** — Dropbox ran forecasting, pipeline, hiring, and performance management as if it were already public for a full year ahead of the IPO — because Wall Street hates surprises. Jerry keeps those practices to this day as baseline hygiene and discipline: monthly and weekly cadence, audit trails on everything, no surprise raises or hires. _Why it matters:_ Public-company rigor is good operating rigor at any stage. Installing the cadence and audit trail early makes the eventual transition a non-event rather than a scramble. _For:_ Revenue Executives, RevOps Leaders, Founders 8. **An acquisition is harder than an IPO** — Jerry found the Workday acquisition of Scout RFP materially harder than the Dropbox IPO: the acquirer audits every contract, approval, and pipeline metric to make sure the revenue is durable, and then — unlike an IPO — runs a full integration of systems, org, and process. Anthony's LexisNexis/Emailage experience matched it: day-one reporting-line changes and a forced Salesforce-into-Siebel migration. _Why it matters:_ Plan the integration, not just the deal. The buyer's diligence and post-close systems/org integration are where the real work and the real risk to the revenue engine live. _For:_ Founders, Revenue Executives, RevOps Leaders 9. **Startup equity is monopoly money until a change of ownership** — Equity is worth literally zero until an IPO or acquisition. Secondary sales are rare, board-gated, and usually capped at a small slice; in a buyout, investors are paid first, so if the number isn't big enough your equity can be nothing. If money is your primary reason for joining a startup, Jerry says go work at a big technology company, where you'll likely make more, more consistently. _Why it matters:_ Weight equity realistically when making a life decision. Join a startup for impact, environment, and learning; treat the equity as upside on a lottery ticket, not a bankable plan. _For:_ Revenue Executives, Founders 10. **Know your equity clauses — but don't confuse them for the real risk** — Double-trigger acceleration and change-of-role protections are standard and worth having (single triggers are essentially extinct), but Jerry argues they matter less than being realistic about how much equity you have and what it can or can't do. Bravado about negotiating equity terms is often poor advice from people who haven't been through an arc. _Why it matters:_ Get the protective clauses, then anchor your decision in the sober math of your actual stake — not in a story about the terms you negotiated. _For:_ Revenue Executives, Founders 11. **AI lifts the ceiling and changes the roles — it doesn't shrink the team** — Jerry rejects the 'reduce revenue teams by 99% and get $10M per AE' fantasy. Evidence: OpenAI and Anthropic are the biggest hirers of enterprise sellers right now (Anthropic's CMO came from ServiceNow, its CRO from Slack). Teams aren't shrinking — the roles and skill sets are changing, and RevOps is getting more technical, not less important. If a seller could reliably close $10M, you'd want more of them, because no company doesn't want more revenue. _Why it matters:_ Frame AI as capacity and capability expansion, not headcount reduction. Reinvest productivity gains into more people and more ambitious motions, and expect the roles to demand new AI and data fluency. _For:_ Revenue Executives, RevOps Leaders, Founders 12. **Every revenue leader should build their own agents — with expertise as the propellant** — Jerry says you can literally ask Claude to teach you to build an agent and then do it; if you haven't built one once or twice you can't grasp the power, scope, or how to make it correct. His 'Pykey' pipeline-review agent surfaces deal signals (stalled activity, deals sitting in stage two ~30% longer than winners) so Monday calls become strategy instead of number-reciting. The best AI leverage comes from deep domain expertise used as a propellant — the 'new analog' of putting your own thinking on paper first, then using AI to fill gaps, not to generate ideas you can't defend. _Why it matters:_ Hands-on agent-building is now a core revenue-leader competency, and clean data architecture — not the model — is the hairiest, most durable part. Point an LLM at a messy Salesforce or HubSpot instance and it will hallucinate; fix the data pipeline first, then layer agents, subagents, and workflows. _For:_ Revenue Executives, RevOps Leaders, Sales Leaders ## Frameworks ### The 'Late CRO' Thesis (01:27) **Definition:** Deliberately rotate through operations, marketing, partnerships, consulting, sales ops, and product before ever carrying a quota, so you understand everything that actually affects revenue — rather than reaching the CRO seat straight up the sales track. Jerry's core claim is that the leaders who move revenue understand the whole business, and a modern GTM org increasingly disadvantages the pure-sales CRO. The diverse foundation is what gives a revenue leader range, empathy across departments, and the judgment to know what they don't know. ### Achievement Over Tenure (and the One-Year Rule) (06:36) **Definition:** Stay in every role at least a year (sometimes two) to actually learn the skill, and when hiring, evaluate candidates on increasing responsibility and achievement rather than raw time-in-seat. A job with no hard parts isn't teaching you anything; the hard parts are the growth. Jerry looks for progression and mission-moving stints on a resume, acknowledging timelines are compressing but still rewarding people who marinated long enough to move something monumental. ### PLG-to-Enterprise Conversion (Unite the Divisions) (11:33) **Definition:** Convert a product-led motion into an enterprise motion by getting selective on collaboration-heavy segments, landing two or three teams or divisions, then uniting them under one executive with a combined security, collaboration, and cost case. At Dropbox, walking into large accounts with the old SAP playbook failed. The winning motion aggregated bottoms-up PLG adoption into a top-down executive contract, choosing accounts (media, CPG, retail) where the product's collaboration strengths already had a foothold. ### The 'Wrong Cycle' Rule (Don't Battle on a Competitor's Strengths) (16:25) **Definition:** If you find yourself in a competitive cycle defined by a competitor's strengths, one of you is in the wrong cycle — and it's probably you. Know your weaknesses so you can avoid the fights they define, and concentrate on the ICP that values your strengths. Chasing Box head-on in all-enterprise, high-security accounts cost Jerry time, people, and losses. The lesson: don't try to fix weaknesses to win a competitor's game; double down on the strengths and the customers who appreciate them. ### The Secret Roadshow (17:37) **Definition:** A private trial-run roadshow before the public IPO roadshow: executives travel separately to a low-profile event and pitch bankers who signal buy-or-pass on an app, letting the company watch the book oversubscribe and the price move before the S-1 debut. The feedback from the secret roadshow is baked into the real one. It's the hidden dress rehearsal behind the celebrated bell-ringing, and it reflects the year of public-company-grade discipline that precedes an IPO. ### An Acquisition Is Harder Than an IPO (27:02) **Definition:** An acquisition demands the acquirer audit every contract, approval, and pipeline metric to validate revenue durability, and then run a full integration of systems, org, and process — a burden an IPO never imposes. Jerry found the Workday/Scout deal materially harder than the Dropbox IPO; Anthony's LexisNexis/Emailage experience matched it, with day-one reporting changes and a forced CRM migration. The deal thesis is the easy part; integration is where value and risk live. ### Equity Is Monopoly Money Until a Change of Ownership (31:33) **Definition:** Startup equity is worth literally zero until an IPO or acquisition. Secondary sales are rare, board-gated, and usually capped; in a buyout, investors are paid first, so if the exit isn't large enough your equity can be nothing. Jerry uses this to reset expectations: join a startup for impact, environment, and learning, not primarily for the equity. If money is the main driver, a big technology company will likely pay more, more consistently. ### Every Revenue Leader Should Build Their Own Agents (43:14) **Definition:** Revenue leaders should personally build at least one or two agents (you can ask Claude to teach you) so they understand the power, scope, and correctness constraints well enough to manage AI-driven GTM — the same way understanding marketing and ops makes you a better revenue leader. Without hands-on reps you can't grasp what agents can and can't do or how to make them correct. Jerry's 'Pykey' pipeline agent is the exemplar: it surfaces deal signals so pipeline reviews become strategy instead of number-reciting. ### Expertise as Propellant (The 'New Analog') (53:43) **Definition:** Lead with deep domain expertise and your own thinking captured on paper first — not with AI-generated first-draft language — then use AI to fill gaps and propel execution rather than to create ideas you can't defend. The best AI leverage comes from operators who have taste and context in the domain. The 'new analog' is doing your own thinking before you prompt; and beneath all of it, clean data architecture is the hairiest, most durable part of extracting value. ## Quotes _Speakers inferred from an undiarized transcript — verify before attributing._ > "The ones that I found that really had an impact on their business understood the whole business." > > — Jerry Brooner, The LeanScale Podcast Ep. 86 (02:06) > "One of the fundamental skills people are lacking, especially younger generations, is the ability to pick up the phone and call somebody — and even more so now in the AI age, that's a fundamental skill." > > — Jerry Brooner, The LeanScale Podcast Ep. 86 (05:22) > "As long as you are learning something in your job, you should stay there and learn that skill." > > — Jerry Brooner, The LeanScale Podcast Ep. 86 (07:10) > "It taught me how to converge at volume and velocity product-led growth into an enterprise sales motion." > > — Jerry Brooner, The LeanScale Podcast Ep. 86 (10:53) > "My mantra that my team became: if we're in a competitive sales cycle against Box, one of us is in the wrong cycle — and it's probably us." > > — Jerry Brooner, The LeanScale Podcast Ep. 86 (16:25) > "Don't improve your weaknesses. Ignore your weaknesses. Know what they are, and then be like, I'm not going to go there." > > — Jerry Brooner, The LeanScale Podcast Ep. 86 (16:25) > "Everyone knows the roadshow. But before any of that happens, there's a secret roadshow — every exec is flying on different jets, it's like an event somewhere that's not really an event." > > — Jerry Brooner, The LeanScale Podcast Ep. 86 (18:12) > "You've got to tell Wall Street about everything, or things go bad. No one loves surprises — no one — but especially Wall Street." > > — Jerry Brooner, The LeanScale Podcast Ep. 86 (20:39) > "That acquisition process was a whole lot harder than the IPO process. A whole lot harder." > > — Jerry Brooner, The LeanScale Podcast Ep. 86 (24:48) > "It is literally worth zero to you until there's a change of ownership. It is funny money — it is monopoly money until there's an exit." > > — Jerry Brooner, The LeanScale Podcast Ep. 86 (31:33) > "If you're going to a startup just for the money, you should go work at a big technology company, because in the long run you will probably make more money consistently." > > — Jerry Brooner, The LeanScale Podcast Ep. 86 (29:55) > "The investors get their money first. And if the buyout isn't large enough, your equity will be nothing and you'll get bought out." > > — Jerry Brooner, The LeanScale Podcast Ep. 86 (34:17) > "You can get on Claude and say, tell me how to build an AI agent, and it will walk you through it — and you're going to actually do it." > > — Jerry Brooner, The LeanScale Podcast Ep. 86 (43:58) > "I'm not of the opinion that you're going to reduce the revenue teams by 99% and get $10 million per account executive. If anyone looks at OpenAI and Anthropic, who they're hiring — they are the biggest hirers of enterprise sales teams right now." > > — Jerry Brooner, The LeanScale Podcast Ep. 86 (45:16) > "People used to think I was nuts because I'd update ICP twice a year. With Clay now, I can update it weekly — literally weekly." > > — Jerry Brooner, The LeanScale Podcast Ep. 86 (45:55) > "If I could get a salesperson who could close $10 million, why wouldn't I want more of them to close even more? There's no company in the world that doesn't want more revenue — not one." > > — Anthony Enrico, The LeanScale Podcast Ep. 86 (47:18) > "If you just throw an LLM on your entire Salesforce or HubSpot instance, it's going to hallucinate insanely. All of these data architecture problems are really the hairiest part of the whole thing." > > — Anthony Enrico, The LeanScale Podcast Ep. 86 (49:19) > "There is absolutely no excuse for lack of execution nowadays. No excuse." > > — Jerry Brooner, The LeanScale Podcast Ep. 86 (53:11) ## Practical advice by role ### Founders - Build public-company-grade discipline a year before you need it — monthly and weekly forecasting, pipeline, hiring, and performance cadence with audit trails on everything — so an IPO or acquisition is a non-event, not a scramble. - Plan the integration, not just the deal: an acquisition forces a full systems-and-org integration that an IPO never does, and that's where the revenue engine is most at risk. - Be honest with candidates about equity — it's monopoly money until a change of ownership, and investors get paid first in a buyout. Recruit on impact, environment, and learning, not on a lottery-ticket number. ### Revenue Executives - Engineer range before (or after) the CRO seat: the leaders who move revenue understand ops, product, partnerships, and marketing, not just how to close. - Don't fight competitors on their strengths — if you're in a cycle their strengths define, you're in the wrong cycle. Concentrate on the ICP that values what you're uniquely good at. - Reinvest AI productivity into more capacity and more ambitious motions. If a seller could reliably close $10M, you'd want more of them — the team doesn't shrink, the roles change. ### RevOps Leaders - Fix data architecture first: normalize the CRM, stand up transcription and data-movement pipelines, then layer agents, subagents, and workflows — point an LLM at a messy instance and it will hallucinate. - Build at least one or two agents yourself so you understand their power, scope, and correctness limits; a pipeline-signals agent can turn Monday reviews from number-reciting into strategy. - Use tools like Clay to move ICP from a twice-a-year spreadsheet slog to a weekly refresh with intent and signal data — the cadence of RevOps work is compressing fast. ### Sales Leaders - Convert PLG to enterprise by uniting divisions: land two or three collaboration-heavy teams, then bring one executive a combined security, collaboration, and cost case — don't cold-walk a whole account. - Adjust fast in a new motion: expect the first few months of a transplanted playbook to fail, A/B test, and be willing to try a creative idea when something isn't working. - Push early-career reps into a BDR seat for a year to build the phone and human-conversation skills that AI makes more valuable, not less. ### Marketing Leaders - Treat positioning as account selection: sharpen the ICP toward customers whose priorities match your differentiated strengths instead of chasing accounts an incumbent already owns. - Feed the modern GTM machine with Claude-based harnesses (including design for creative) on top of clean data — and expect ICP and messaging cycles to compress from yearly to weekly. ## AI takeaways **Thesis:** AI is a monumental shift every revenue leader must adopt hands-on, but it lifts the ceiling and changes the roles and skill sets rather than shrinking the team. The durable moat isn't the model — it's clean data architecture and operators with deep domain expertise who use AI as a propellant for execution. - **Build your own agents** — You can ask Claude to teach you and then actually build one. Without one or two hands-on reps you can't grasp the power, scope, or correctness constraints — the same way doing ops and marketing makes you a better revenue leader. - **More AI means more people, not fewer** — OpenAI and Anthropic are the biggest hirers of enterprise sellers right now (Anthropic's CMO from ServiceNow, CRO from Slack). If a seller could close $10M, you'd want more of them — teams don't shrink, roles change. - **Data architecture is the hairiest part** — Point an LLM at an un-normalized Salesforce or HubSpot instance and it hallucinates insanely. Fix transcription pipelines, data movement, and CRM normalization first, then layer agents, subagents, workflows, plugins, and skills. - **Expertise as propellant, not creation** — The best leverage comes from operators with taste and context. Use AI to fill gaps and propel execution — not to generate ideas you can't defend. Slop shows up fast when people can't defend their own work. - **The new analog** — Start by putting your own thinking on paper (typed, not AI-drafted), then bring AI in. Deep domain expertise plus AI compounds; AI-first with no expertise produces defensible-looking noise. **Agent & automation ideas** - A pipeline-review agent ('Pykey'-style) that runs every Monday and surfaces per-deal signals — stalled activity, no customer reply in two weeks, deals sitting in stage two ~30% longer than historical winners — so reviews become strategy instead of AEs reciting numbers. - A weekly ICP-refresh agent (Clay-powered) that ingests wins, losses and loss reasons, industry/region/persona research, and intent signals to keep ICP current instead of a twice-a-year spreadsheet project. - A transcription-to-CRM pipeline that normalizes call data and auto-populates the CRM so downstream agents have a clean, queryable dataset to reason over. - A GTM ops agent that generates SOWs, scopes engagements, and builds per-project deploy configurations pushed to Salesforce via CLI — the way LeanScale now runs delivery. ## Operations takeaways ### Revenue operations - **RevOps gets more technical, not smaller.** As products launch and new regions open faster than ever, RevOps must set up systems that scale and stay agile — the function becomes more important and more technical in the AI era. - **Data architecture before agents.** Normalize CRM data and stand up transcription and data-movement pipelines first; only then can agents, subagents, workflows, plugins, and skills produce reliable insight instead of hallucination. - **The AI ops / RevAI engineer is now critical.** Whatever you call it — revenue AI ops, AI engineer — the person who owns the lights-out data architecture and agent stack becomes one of the most important seats in the org. - **Compressing cadence.** Work that used to run yearly (ICP, messaging, motion changes) now runs weekly; RevOps has to build for a much faster refresh cycle. - **Public-company hygiene is baseline.** Monthly/weekly forecasting, pipeline, hiring, and performance cadence with audit trails is good operating discipline at any stage, not just pre-IPO. ### Pipeline & marketing ops - **Signal-driven pipeline reviews.** A pipeline agent that surfaces deal signals (activity gaps, stage aging, response cadence) replaces grilling AEs for numbers and turns the call into strategy on how to win and move deals. - **Stage aging as a leading indicator.** Deals sitting in a stage ~30% longer than deals that historically won from it are a concrete, automatable risk signal worth flagging every Monday. - **The first agent won't be great.** Jerry's first pipeline agent lacked his gut feel, but building it taught him the concept; with help it improved fast — and it unlocked the next two or three agents around the go-to-market machine. - **No excuse for poor execution.** Once you can prompt your way to capabilities that used to need engineers and budget, the ceiling of what's possible lifts and the bar for execution rises. ## Metrics mentioned | Value | Metric | Context | | --- | --- | --- | | 4 (as a four-time CRO) | Jerry's exits | Dropbox (IPO), Scout RFP (Workday), Enable (Series A to unicorn), Levelpath — the arc behind his operating lessons. | | 4X ARR | Levelpath growth | ARR growth Jerry drove as CRO of the AI-native procurement platform. | | 2 people | Dropbox enterprise team start | Jerry started the strategic enterprise team with two people among an org that was otherwise all engineers and self-service. | | Founding CRO, ~employee 52 | Scout RFP tenure | Jerry joined as the founding CRO to build the revenue machine that led to the Workday acquisition. | | 6 vs. 19 stages | Sales-stage complexity gap | Scout RFP ran 6 sales stages; Workday ran 19 — and a 38-step pricing-change process — illustrating the friction a startup absorbs in an acquisition. | | ~$4M → ~$40M ARR · ~$500M exit | Emailage trajectory | Anthony's company before LeanScale; a ~$500M sale to LexisNexis that closed in the first days of COVID. | | ~1 in 1,000 | Startup exit odds | Jerry's framing of how rare the champagne-in-Times-Square outcome is; secondary offerings are rarer still (~1 in 10,000 companies). | | $500M ARR | Clio ARR milestone | The LeanScale customer just crossed the half-billion ARR mark. | | ~30% longer in stage two | Stalled-deal signal | An example signal Jerry's pipeline agent surfaces — deals sitting in stage two roughly 30% longer than deals that historically won from that stage. | | $10M per AE | Productivity-vs-headcount fantasy | The '99% smaller team, $10M per AE' scenario Jerry rejects — if a seller could close $10M, you'd hire more of them, not fewer. | ## Entities mentioned - **Dropbox** (company) — Jerry stood up the strategic enterprise team (starting with two people among all engineers) and led it through the IPO, converting a self-serve PLG motion into an enterprise sales motion. · https://leanscale-knowledge-hub.netlify.app/company/dropbox/ - **Box** (company) — Dropbox's all-enterprise competitor; Jerry's 'wrong cycle' lesson — an incumbent whose security and enterprise strengths a PLG-born company shouldn't fight head-on. · https://leanscale-knowledge-hub.netlify.app/company/box/ - **Callidus (CallidusCloud)** (company) — Where Jerry went through his first IPO earlier in his career; later acquired by SAP. · https://leanscale-knowledge-hub.netlify.app/company/callidus/ - **Scout RFP** (company) — Jerry was the founding CRO (roughly employee 52) and built the revenue machine that scaled ASP, velocity, and logo count to a Workday acquisition. · https://leanscale-knowledge-hub.netlify.app/company/scout-rfp/ - **Workday** (company) — Acquired Scout RFP to add sourcing/procurement to its new financials suite — its largest acquisition at the time — and ran a low-friction integration (Jerry contrasts Scout's 6 sales stages vs. Workday's 19 and a 38-step pricing-change process). · https://leanscale-knowledge-hub.netlify.app/company/workday/ - **Enable** (company) — Where Jerry served as president of global field operations, helping take the company from Series A to unicorn status. · https://leanscale-knowledge-hub.netlify.app/company/enable/ - **Levelpath** (company) — Jerry's most recent role as CRO of the AI-native procurement platform, where he drove 4X ARR growth. · https://leanscale-knowledge-hub.netlify.app/company/levelpath/ - **SAP** (company) — Where Jerry spent roughly a decade running large enterprise deals (the playbook that initially failed at Dropbox); also his experience as an acquirer, and the eventual acquirer of Callidus. · https://leanscale-knowledge-hub.netlify.app/company/sap/ - **Siebel Systems** (company) — Where Jerry was acquired by Oracle; its legacy CRM also appears as the system LexisNexis migrated Emailage's Salesforce instance into. · https://leanscale-knowledge-hub.netlify.app/company/siebel-systems/ - **Oracle** (company) — Acquired Siebel Systems, where Jerry worked. · https://leanscale-knowledge-hub.netlify.app/company/oracle/ - **Emailage** (company) — Anthony's company before LeanScale; he was VP of RevOps and took it from ~$4M to ~$40M ARR through a ~$500M exit to LexisNexis that closed in the first days of COVID. · https://leanscale-knowledge-hub.netlify.app/company/emailage/ - **LexisNexis Risk Solutions** (company) — Acquired Emailage; Anthony cites its day-one integration machine — reassigning reporting lines and forcing a Salesforce-into-Siebel migration — as the concrete difference between an acquisition and an IPO. · https://leanscale-knowledge-hub.netlify.app/company/lexisnexis/ - **Anthropic** (company) — Cited as one of the biggest current hirers of enterprise sales teams (CMO from ServiceNow, CRO from Slack) — Jerry's evidence AI isn't shrinking GTM teams; also referenced for its secondary-market equity controversy. · https://leanscale-knowledge-hub.netlify.app/company/anthropic/ - **OpenAI** (company) — Cited alongside Anthropic as one of the biggest hirers of enterprise sales teams right now — evidence against the AI-headcount-collapse narrative. · https://leanscale-knowledge-hub.netlify.app/company/openai/ - **ServiceNow** (company) — The company Anthropic hired its CMO from — Jerry's example that frontier AI labs are aggressively hiring GTM leadership. · https://leanscale-knowledge-hub.netlify.app/company/servicenow/ - **Slack** (company) — The company Anthropic hired its CRO from — more evidence AI labs are building, not cutting, enterprise GTM teams. · https://leanscale-knowledge-hub.netlify.app/company/slack/ - **Mistral AI** (company) — A LeanScale GTM-ops customer that has raised billions; cited by Anthony as an example of implementing AI solutions inside high-growth companies. · https://leanscale-knowledge-hub.netlify.app/company/mistral-ai/ - **Clio** (company) — A LeanScale customer, Vancouver/Burnaby-based legal software that just crossed the $500M ARR mark. · https://leanscale-knowledge-hub.netlify.app/company/clio/ - **LeanScale** (company) — Anthony's firm, doing GTM ops / RevOps for B2B SaaS and AI companies since 2021, deep with CROs and heads of RevOps; now uses AI to build SOWs, scope engagements, and generate per-project deploy configs pushed to Salesforce via CLI. · https://leanscale-knowledge-hub.netlify.app/company/leanscale/ - **Jerry Brooner** (person, guest) — Four-time CRO (Dropbox, Scout RFP/Workday, Enable, Levelpath) who spent a decade in ops, marketing, and partnerships before ever carrying a quota. · https://leanscale-knowledge-hub.netlify.app/guest/jerry-brooner/ - **Anthony Enrico** (person, host) — Co-founder of LeanScale and host of The LeanScale Podcast. · https://leanscale-knowledge-hub.netlify.app/guest/anthony-enrico/ - **Claude** (tool, AI Assistant) — Jerry's on-ramp to agent-building ('get on Claude and say tell me how to build an AI agent'); Anthony notes Claude is 'winning' on the best business suite of harnesses for enterprise use cases. - **Claude Code** (tool, AI Dev Tool) — Cited by Anthony among the Claude harnesses companies are increasingly leveraging for business use cases. - **Claude Cowork** (tool, AI Agent Platform) — Referenced by Anthony as one of the Claude work surfaces companies are adopting. - **Claude Design** (tool, AI Design) — Cited by Anthony as a Claude capability companies use for marketing creative. - **Clay** (tool, GTM Data / Enrichment) — What lets Jerry update ICP weekly instead of twice a year — pulling intent, signals, and account movement that used to take heavy spreadsheet analysis. - **Salesforce** (tool, CRM) — The CRM detonated and migrated during acquisitions (Emailage into Siebel), the instance that will hallucinate if you point an LLM at it un-normalized, and the target LeanScale pushes deploy configs to via CLI. - **HubSpot** (tool, CRM) — Cited alongside Salesforce as an instance that will 'hallucinate insanely' if you point an LLM at it before solving the data architecture. ## FAQ **Q: Why does Jerry Brooner say the best CROs don't come from sales?** A: Because the leaders who most effectively move revenue understand the whole business, not just how to close. Jerry deliberately rotated through operations, marketing, partnerships, consulting, sales ops, and product before ever carrying a quota — a 'late CRO' path he credits for giving him the range, cross-department empathy, and judgment that a pure sales-track resume often lacks in a modern GTM org. **Q: How do you convert a product-led growth motion into an enterprise sales motion?** A: Jerry's Dropbox lesson: don't walk into large accounts cold with the old enterprise playbook. Get selective on collaboration-heavy segments (media, CPG, retail), land two or three teams or divisions bottoms-up, then unite them under a single executive with a combined security, collaboration, and cost case. You aggregate PLG adoption into a top-down enterprise contract rather than attacking a whole account at once. **Q: What is the 'secret roadshow' before an IPO?** A: It's a private trial-run roadshow that happens before the well-known public one. Executives travel separately to a low-profile event and pitch bankers who signal buy-or-pass on an app, letting the company watch the book oversubscribe and the price move before the S-1 debut. The feedback is baked into the real roadshow, and it reflects the roughly year of public-company-grade discipline that precedes an IPO. **Q: Why is an acquisition harder than an IPO?** A: In an acquisition, the acquirer audits every contract, approval, and pipeline metric to confirm the revenue is durable, and then — unlike an IPO — runs a full integration of systems, org, and process. Jerry found the Workday/Scout RFP deal materially harder than the Dropbox IPO, and Anthony's LexisNexis/Emailage experience matched it, with day-one reporting-line changes and a forced Salesforce-into-Siebel migration. **Q: How should you value startup equity in your compensation?** A: Treat it as monopoly money until a change of ownership. Equity is worth literally zero until an IPO or acquisition; secondary sales are rare, board-gated, and usually capped; and in a buyout investors are paid first, so if the exit isn't large enough your equity can be nothing. If money is your primary reason for joining a startup, Jerry advises working at a big technology company instead, where you'll likely earn more, more consistently. Join a startup for impact, environment, and learning. **Q: Will AI shrink revenue and RevOps teams?** A: No — Jerry argues AI lifts the ceiling and changes the roles and skill sets, but doesn't shrink the team. His evidence: OpenAI and Anthropic are among the biggest current hirers of enterprise sellers (Anthropic's CMO came from ServiceNow, its CRO from Slack). If a seller could reliably close $10M, you'd want more of them. RevOps in particular is getting more technical and more important, not smaller. **Q: Why should every revenue leader build their own AI agents?** A: Because without one or two hands-on reps you can't grasp what agents can and can't do, their scope, or how to make them correct — and you'll struggle to manage AI-driven GTM. You can ask Claude to teach you and then build one. Jerry's 'Pykey' pipeline agent surfaces deal signals so Monday reviews become strategy instead of AEs reciting numbers, and it unlocked the next agents around his go-to-market machine. **Q: What's the biggest prerequisite for getting value from AI in go-to-market?** A: Clean data architecture. Point an LLM at an un-normalized Salesforce or HubSpot instance and it will hallucinate insanely. The hairiest, most durable work is the data infrastructure — transcription pipelines, automated data movement, and CRM normalization. Only once that's solved can you layer agents, subagents, workflows, plugins, and skills. And the best results come from operators using deep domain expertise as a propellant, not asking AI to create ideas they can't defend. ## Timeline - **00:00** — Cold open and intro - **01:57** — The 'late CRO' thesis: why Jerry avoided sales for a decade - **05:54** — Where young operators should start (and how long to stay) - **11:33** — Inside Dropbox's IPO and the PLG-to-enterprise pivot - **17:04** — The Box lesson: don't battle on a competitor's strengths - **19:32** — The secret roadshow nobody talks about - **22:35** — What actually changes after the IPO bell rings - **24:48** — From founding CRO at ScoutRFP to the Workday acquisition - **27:02** — Why an acquisition is harder than an IPO - **33:09** — The hard truth about startup equity - **46:56** — Why Jerry would never do anything besides startups - **47:18** — Every revenue leader should be building their own agents - **55:30** — Jerry's pipeline review agent (the most actionable AI use case) - **57:44** — Why AI lifts the ceiling but doesn't shrink the team ## Related episodes - **Ep. 95: Why AI Means More RevOps Hires, Not Fewer** (Jimmy O'Halloran, VP of GTM Strategy & Operations at New Relic) — The direct sibling to Jerry's 'AI lifts the ceiling, doesn't shrink the team' thesis, from a RevOps operator's vantage point. · https://leanscale-knowledge-hub.netlify.app/podcast/jimmy-ohalloran-new-relic-revops-consumption-revenue/ - **Ep. 85: Why AI + GTM Engineers Can't Replace RevOps** (Tessa Whittaker) — Another counter to the AI-headcount-collapse narrative — AI and GTM engineers augment the operating layer rather than replacing it. · https://leanscale-knowledge-hub.netlify.app/podcast/tessa-whittaker-ai-gtm-engineers-revops/ - **Ep. 87: What M&A Really Does to a Revenue Team** (Chris Heller) — Extends Jerry's 'acquisition is harder than an IPO' point with a deeper look at GTM M&A and integration. · https://leanscale-knowledge-hub.netlify.app/podcast/chris-heller-why-most-acquisitions-fail/ - **Ep. 88: Why AI Won't Close Your Biggest Deals** (Michael Kiernan, CRO at Nextdoor) — A CRO's take on the limits of AI in enterprise selling — pairs with Jerry's signal-vs-slop, humans-still-close view. · https://leanscale-knowledge-hub.netlify.app/podcast/michael-kiernan-nextdoor-ai-wont-close-deals/ - **Ep. 89: The AcuityMD Enterprise Playbook** (Alex Wakefield) — Companion on enterprise selling and PLG-to-enterprise motion mechanics that Jerry lived at Dropbox. · https://leanscale-knowledge-hub.netlify.app/podcast/alex-wakefield-acuitymd-ceo-to-cro/ - **Ep. 92: Rebuilding Outbound in the AI Era** (Mica, Ample Market) — Extends Jerry's 'pick up the phone / start as a BDR' point into modern AI-assisted outbound. · https://leanscale-knowledge-hub.netlify.app/podcast/mica-ample-market-outbound-agents/ ## Full transcript _Machine-transcribed and not diarized; speaker attribution is inferred._ _Transcript only, as a separate file: https://leanscale-knowledge-hub.netlify.app/podcast/jerry-brooner-best-cros-dont-come-from-sales/transcript.md_ ### 00:00 — Cold open and intro **[0:00]** 4-time Chief Revenue Officer Jerry Bruner has built and scaled revenue organizations through some of the defining moments in modern enterprise tech. He stood up the Strategic Enterprise team at Dropbox and led it through its IPO, was founding CRO at Scout RFP through its acquisition by Workday, served as President of Global Field Operations at Enable from Series A to Unicorn Status, and most recently was Chief Revenue Officer at LevelPath, an AI-native procurement platform where he drove 4X ARR growth. But what makes Jerry's story different isn't the multiple scales and exits, it's how he **[0:43]** got there. Before he ever carried a quota, Jerry deliberately rotated through operations, marketing, partnerships, consulting, sales ops, and product, adding that a diverse foundation would make him a more effective revenue leader. In this episode, we get into why traditional sales track CROs may be at a disadvantage, what's actually changed in the modern GTM org as AI compresses the funnel, why Jerry believes every revenue leader needs to be building their own agents today, and the under-the-hood reality of taking a company through an IPO or acquisition, including what Jerry calls the secret roadshow nobody talks about. **[1:27]** Jerry, you've called yourself a very late CRO and said you went out of your way to do operations, marketing, partnerships, consulting, sales ops, and even product before getting into direct sales. What was the bet you were making, and looking back, did it pay off the way you expected? Thanks, Anthony, and thanks for that very tiny intro. I know what you said before I appreciate it. But when I was younger, I made a bet on the future growth of my career, and I think everyone should look at their goals and their career and what they want to do long-term and short-term. I didn't quite know exactly what leadership role I wanted to be ### 01:57 — The 'late CRO' thesis: why Jerry avoided sales for a decade **[2:06]** in. I knew I wanted to be a leader, and I knew that certain leadership roles had more prominence than others. Revenue, build something, sell something. Those are like the two big ones, and everything else is important, but not necessarily the same impact. So when I was looking at these roles, I said what makes great leaders in these roles? They normally came from not a traditional, like I was in sales and I did it the whole time. That's okay. I see a lot of people who are great at it, or I was only an engineer. They're really great leaders. The ones that I found that really had an impact on their business understood **[2:47]** the whole business. Now, not every single department and every single role, but they understood what affected their roles. So I was looking at revenue and saying what really impacts revenue? What really impacts revenue? And that would be operations, how you set up revenue from the very beginning, how you continue to maintain it. Talk about product, how you make sure from a revenue point of view, you're looking at that product and how you adapt it to the market you're going to and how you adjust it as it evolved to continue, especially in software. And then you talk about partnerships and the network. Nothing **[3:25]** gets sold by itself. There's always a partner, whether you're OEMing it, whether you're on a data center, whether you're integrating to it, nothing gets sold by itself. Consulting. There are a lot of consultants out there. A lot of really big companies out there. And they are always, always doing transformation projects. So you need to be part of those transformation projects. So how do you work that and optimize that? I look back at that as one of the seminal decisions in my career. And I look back and I think that really gave me, really gave me the platform by which I could grow in the revenue leadership. **[4:02]** It's a ton of sense. I share an eclectic background as well. Out of school, they threw the fresh kid out of college into managing the social media. So I found my way into marketing. I didn't know what I was doing, by the way, but they didn't either. Maybe I knew a little bit more. And worked my way into product training, got close to the product side of the house, attended sales, then left and went to a big hospital system to do operations and strategy where I got really good with financial planning and analysis. And then finally found a home in RevOps after a non-linear journey. And I've seen a ton of value myself too, giving **[4:43]** me that level of diversity and empathy for departments. I may not know the level of depth that a specialist would, but I know what I don't know. And I know when I need somebody in that seat. I'm curious, your perspective, somebody who might be early in their career, where do they start? Is there a department you say, hey, try to get in here first, spend X amount of time here. What would that roadmap look like to give somebody a really well rounded background? I think if I was, I have two young daughters and when they graduate from university with that, who fitted first thing I'll tell them is to go into being a VDR. If we have VDRs **[5:22]** by then or managing agent VDRs, whatever it is, I think one of the fundamental skills that people are lacking, especially younger generations as they grow up is the ability to pick up the phone and call somebody, ability to talk to somebody who you don't know you're supposed to and how to get them to speak to you. Like that is a great, you know, sending emails, sending Slack, sending chats. That's all great. But working with somebody, even now, even more so now in the AI age is a fundamental skill. So I would tell my kids to go do VDR work or some kind of, you know, outbound sales work for a year. And that's where I started. ### 05:54 — Where young operators should start (and how long to stay) **[6:01]** And you won't love it. I don't know anybody who loves being a VDR for that long, calling a hundred people or 20 people or doing research and getting told no a lot of times, but it built a great, great thing. And then you really have to figure out what you don't like as much as what you do like. Right. I knew I didn't like engineering. I tried to learn how to code. I couldn't do it. I wasn't very good at it. Right. Do you have a recommendation of how long you should hang in some of these roles? Is it one year, two year, three year? When do you feel like you've really absorbed the full experience to get the learnings that you need? **[6:36]** It's interesting because I see a lot of people come to me nowadays who say take on new roles and they say, I'm not happy. I don't like my boss. I don't like my manager. I'm leaving after X months. I understand that. Um, you should never be somewhere that, that you're, you're not emotionally happy or not bought in, but you also, you're never going to have a great job that you love every single day and jump out of it. There's going to be hard parts of your job. If they're not, if you're in a job and there's no hard parts, you're not learning and you're not expanding and you're not growing and that's not a great **[7:10]** job. So, so for me, I always say you should stick out everything at least a year and learn. See, unless it is, um, you know, a, something mentally wrong at the place, if it's a bad, like if there is a bad actors there, those are all like, you know, um, okay, get out quickly. But generally speaking, you should go to a job for a year and learn how to do it. And sometimes even two years, because yes, it's hard, but it'll get easier and then you'll learn something. As long as you are learning something in your job, you should stay there and learn that skill. Yeah. I think that's really good guidance. I there's a lot **[7:45]** of people who are moving quite a bit between jobs. And when we're looking at, um, when we're looking to hire, we're looking at, Hey, did somebody have a good stint somewhere? Like I like seeing, okay, you've done a couple one year, a couple of different roles, but did you do a good four year stint somewhere where you really moved up, marinated within something help move a mission forward? Because I think it can take around that time to do something like monumentally moving to the next stage of growth, moving through an acquisition, something like that. Um, I'm typically looking for that. I don't know if you're, if that **[8:23]** happens later, when, when do you think you slot those experiences? It's funny. I talked to my parents who have been at the same company for, I don't know, 70 years or 60 years. And they were like, why do you keep changing jobs? And I was at a company for 10 years, then four years. I see people nowadays and they're like, Oh, you've been there six months. That's a long time. I look for things and, and timelines might be compressed nowadays. Timelines are definitely compressed. Things are moving faster. So you might not get the four years. Um, you can look for someone I'm looking at resumes. I'm looking for achievement and constant, **[8:57]** um, achievements for people, right? Like, are they taking on new responsibility? Are they moving into new roles even within the same company? If you're keeping doing this, then your, your role is changing your learning skills and you're progressing in your career. That's a great signal to me. Well, and this experience has really landed you some very interesting and impressive go to market roles. I'm hoping we could dive into one, I think a household name being a Dropbox and then being there during the transition from private to IPO. There are so many people in this space that are aiming for that pinnacle of business **[9:40]** success and, and wanting to be there for that ride. And very few will ever go through that time period. I would love if you could take us back to that time period and what that transition was actually like. Yeah, it was, it was really an exciting time and it was definitely unique. I will say about it. Um, my wife thought I was out of my mind, literally out of my mind for going there. So Dropbox, when, when I started, it was all engineers and self-service on a website, right? They had a great product led growth. It's unbelievable. It was probably one of the first and best. They had it down and it was amazing. But when **[10:17]** they wanted to go to an IPO, you know, the bankers were like, you can IPO with, you know, you know, your biggest customer being Joe's sandwich shop on the corner with four users. Like, what are you talking about? You need to have some enterprise customers. So they went and found me. I had a couple of people. I knew that it worked there and I walked in to a, you know, start the strategic enterprise team with two people and everybody else was engineers. And it's two people are like, okay, how do we going to morph this product led growth motion to an enterprise contract with these accounts? And what do we have to do? **[10:53]** Because we needed, we all want an IPO. Nobody more than me wanted to get the IPO. So it was, it was really an exciting time and I'm really grateful for that opportunity. It taught me a lot. It taught me how to converge at volume and velocity product led growth into an enterprise sales motion, you know, pick off a bunch of teams at large companies and then go in and unite them with a larger contract. It was really, really exciting and really a great learning experience. And then being able to push the button and have that come and be in the square there with Dropbox every there was a experience that will live with me forever. **[11:29]** Yeah, it's a very unique and special experience that many people haven't gone through. I'm curious if maybe we could close the aperture on one of the experiences because I know a lot of companies that have a strong product led growth motion and they're looking to build that enterprise motion. How did you take the foundation? You had a Dropbox and convert it into an offering that was conducive to an enterprise motion and what did it actually take tactically? What did you have to do build teams you had to work with messaging you had to change? What did it look like to frame it up for an enterprise customer? ### 11:33 — Inside Dropbox's IPO and the PLG-to-enterprise pivot **[12:05]** Yeah, yes, Anthony. A couple things. First off, I made a lot of mistakes at the beginning. The first three months, like I did everything wrong and I'm really grateful for the leaders at Dropbox at the time, you know, my manager and the executive team because they worked with me and shared through this just just so report. So, you know, I had just come from 10 years at SAP doing enterprise deals at these large, large companies and I was taking basically the same playbook and moving it over and it didn't work. The first three months were really, really, really tough and I learned some really valuable lessons. Luckily, I adjusted **[12:44]** quickly and luckily our entire leadership team did and we said, OK, so we can't go head on into these accounts, these large accounts and and say we have a bunch of small teams and what what are you doing and we have your data that that won't work. So what's the benefit here and how do we do this? So one, we became very selective on the accounts we went after. Right. So what accounts would be willing to listen to us? Media, CPG, retail, all these have a lot of collaboration and a lot of file sharing. Right. That was great. The Olympics we did Saturday Night Live. These were great. So let's why don't we get a few of these teams **[13:26]** or a few of these divisions, right, and start circulating them. And once you get two or three divisions, then let's take an advantage in terms of both security, collaboration, sharing and cost to the executive in charge of it. And you need to go get one executive and then let's build the case instead of like just going to them with this to begin with. So, it was a lot of learning lessons. But what I would really take from that one, got to adjust quickly, got to adjust what's working, what's not working. A/B testing. Number two, you got to be willing to try something new, like it's not working for a couple months. **[14:01]** You know, someone comes with you with a crazy idea. Let's let's do it. And you got to get a little creative here when you're doing it. That normally works through it. So fortunate for us to do that. What were some of the big blockers when I imagine you go in, you have the playbook ready, you get the fresh pitch deck, the new messaging, you're meeting with the right person, and you get there. What fell flat? What was the first lesson that needed that adjustment that you're talking about? The first lesson was we went back and when I walked in, they said, "Okay, we need enterprise **[14:37]** accounts to go after them." And our competitor in the enterprise accounts was Boxx. And I was like, "Okay, let's go take Boxx head on in every one of their accounts." Now, Boxx had nothing but enterprise customers, nothing but enterprise customers. And they had all the enterprise functionality that they were looking for. High security, lots of things, but it wasn't as easy to use. But CIOs and chief security officers and CFOs didn't care about ease of use. So my first lesson, and it cost me a lot, was I'm just going to run after Boxx and I lost a lot. I lost a lot of people. It was a lot of time and energy **[15:12]** that I wasted going after that. And so that was the first lesson. So if you're battling in someone else's strengths, like that's not a good spot for you. You're not going to learn and you're not going to win a lot, right? So go back to your customer and go back to you. What are the customers I have? What are their strengths? Why are they looking at us? Why are they using us? Okay, great. What are similar customers? And even if they're larger or smaller, or how do I make sure that within that network, it's not directly taking on a, you know, defense company against Boxx for a government contract that's never going to work for a PLG started company. **[15:51]** No, I love that. I think oftentimes we focus on our weaknesses and what we need to improve when sometimes doubling down on the strength and just looking for the people who appreciate those strengths. So what's the ideal customer profile that values this thing that we're uniquely good at? And then funneling efforts there tends to be a better recipe for success unless you have some foundational things you need to improve. Of course, work on those. You don't want to have any fatal flaws, fatal weaknesses, but doubling down on your strengths tends to help people win. **[16:25]** Yeah, don't improve your weaknesses. Like, like ignore your weaknesses, right? Know what they are, then be like, I'm not going to go there. If I'm in a battle where these two things matter, like that's a weakness. Like we should not be in that. And my mantra that my team became if Boxx, if we're in a competitive sales cycle against Boxx, like one of us is in the wrong cycle, it's probably us. Like that shouldn't be, that's not our ICP. That's really sage advice. I'm wondering one of the unique moments going through, going through that IPO process. So people think about it. They hear about it. What is it actually **[17:03]** like? What is, what is the prep for the IPO? What happens when the bell is wrong? What happens directly after and what changes? Walking through that whole arc, I think would be really helpful for a lot of people listening. I was very fortunate earlier in my career to go through my first IPO at a company called Calidus. They got bought by SAP. I wasn't close enough to do it, but I remember the party and I remember everyone celebrating the bell ringing and I remember all that. I definitely remember, okay, this is what it's like to work at a company. I was like, ### 17:04 — The Box lesson: don't battle on a competitor's strengths **[17:37]** this is great. This is an unbelievable experience. This time it was much, much closer to it because I had the enterprise customers that had to go on the IPO. And it's really interesting because there's so much work before that happens, before anyone sees anything. And it really is. And it's like a trial run. They have a secret roadshow. Everyone knows the roadshow, right? Everyone knows the roadshow. Hey, they're going on a roadshow. They filed an S1. We're going to go on a roadshow and we're going to pitch our solution to all these bankers and they're going to buy it or not, right into it before the IPO, right? Before any of **[18:12]** that happens, there's a secret roadshow. It's the same thing. But when I say secret, I mean like, you know, every exec is flying on different jets on the calendars. It's like an event somewhere that's not really an event and people are like going in or out. I always had to take like the terrible three connection red eyes because I wasn't really like, you know, the CEO report, I was one away from the CEO report, but I was the strategy person or the strategy revenue person. So I had to get, you know, out there to it and it was really exciting and then they give you a lot of feedback and then you go and you prep it all and then **[18:51]** you go on the real and then you have your act together on and do it and they're pitching it. And I remember as we're doing the roadshow and they're coming, there's an app. There is that sign. There is an app and all the bankers would look into the presentation and they were either buy in or not on the app and you can see it counting. And this is before the IPO. So you can see how much oversubscribe or if your price is going up and you're like and a Dropbox, we were watching go up, up and up. And then the day the button put and they were, we were all in Times Square. And I remember after the button push, I went out **[19:23]** there, all my team was out there and it was just, it was, it was pandemonium. It was really exciting. And then, and then there was some champagne and wine after, as you can imagine. Really? Yeah, I wouldn't expect that. But it changes dramatically because now there are no more like, I'm going to miss my revenue number or I'm going to miss the margin number. You know, the amount of scrutiny on everything goes as I'm going to be hard because now you're in the public markets and everything's looking, looking at, you can't, you know, release a new product without telling the markets. You can't, you know, increase revenue or decrease ### 19:32 — The secret roadshow nobody talks about **[20:01]** it. You can't increase your attainment without warning. You got to tell Wall Street about everything or things go bad. So it became a lot of scrutiny. It was a lot of pressure after that. So post the champagne, sure that day was great. Wish I could have been there for it. But post the champagne, getting back to business as usual, underneath the scrutiny, what practically changed in your forecasting process and how you maybe manage your pipeline, manage your sales team. So knowing you had a lock in these numbers, was there just a litany of red tape that expanded from this or what helped keep that under control? Oh, **[20:39]** no, it actually was business as usual. And so we had been, for those who knew this was happening, which is about a year in the making before they asked one, we're like, okay, now we got the tight up. So our forecasting, our pipeline, our hiring, our performance manage, everything we did as if we were a public company for a year. And I keep those practices to this day because I think they're great hygiene and discipline and forecasting. So it didn't change, right? No one loves surprises, no one, but especially Wall Street. So we just started going in on a monthly and a weekly basis, you know, hiring somebody, it wasn't a surprise, **[21:15]** you know, raising our forecast. It wasn't a surprise. We did that a lot there, but you had to report a lot and you had to have a structure and you had to have the audit trail on everything. So there's a lot of people that I know are hoping to get to that pinnacle point and then keep the momentum growing as well. So I really appreciate you sharing that. I was hoping to get to it again. That's exciting. Yeah, all of us are. That's what we're all working towards. I want to compare that to your experience at Scout. So then moving into Scout, a little bit of a different seat. Now your chief revenue officer overseeing the entire **[21:53]** go to market organization. What was that build to exit arc like? And one thing I'm very curious about, what was the difference between going through the IPO process and then going through an acquisition process? That was another exciting moment. That was a lot harder. Just sort of, that was a lot harder. But let me start with what it was. So I'm, you know, taking the one seat, you know, the CRO seat, I was, I was the two seat before I'm through the idea of taking the one sheet. So I'd seen it, but I'd never had the full broad spectrum of owning everything, which included, you know, ops and success and implementation. I've always had ### 22:35 — What actually changes after the IPO bell rings **[22:35]** pieces of it, but this was the full end end. And by that, I mean, you know, a lot of people share with me. They want to be a CRO, a lot of people. And I think that's great. And I wish them the very best. But then when I speak to people and I'm like, okay, there's no, it's you, this is it, the whole company, when you're at a startup and you're a CRO and you have, you know, the revenue number, the customer success number, the customer for operates, all that, there's only one, one, you know, the buck stops with you and you just have to make sure that you're, you're good with that responsibility. And so I worked with a really great team there. **[23:12]** I think that was employee 52 or 53. I was our founding CRO and they had a lot of great ingredients. I saw a lot of great, they had an unbelievable product. They had some amazing customers, right? What they were missing, what they didn't have yet was they didn't have a machine, a revenue machine to scale it and to increase the, the number of customers, the average sales price and the velocity arc on this. And so we came together and that was, you know, the investors there were really terrific and the executive team. And, and, and we put together a two year run that, that was, was really gigantic and amazing with that ended **[23:52]** with, with work day, uh, you know, acquiring us. So the process preluding that time work day does the acquisition. Were you partnering with work day? Were there other potential suitors at the table? How did that whole situation orchestrate or did they just get aggressive and proactive about making it happen? Yeah. Um, they both, but so, so first they invested in our, in a previous round, a very small amount, and then they would start testing our software and doing it. So, you know, they had just introduced financials. They were an HCM company and introduced financials. **[24:31]** They didn't have a sourcing or procurement block and they're evaluating, I'm assuming at the time they're evaluating whether to build or, or buy it. And so after, you know, almost just about a year, I remember we were going to raise another fundraising round and, and, uh, we got the phone call from, uh, the CEO at the time and said, uh, don't raise that. I got an idea for you and it worked out great. Now that acquisition process was a whole lot harder than the IPO process, a whole lot harder. It was a one, it was a smaller org at the time, but two, they really like, ### 24:48 — From founding CRO at ScoutRFP to the Workday acquisition **[25:06]** every contract, every approval, every audit trail, every, you know, pipeline metric, everything that I've ever done, it was, it was mainly the revenue person and CEO, they wanted to know because they wanted to make sure that, you know, it wasn't, you know, one off land and they were going to get this revenue and, and great product going forward. There was, there was a lot of other secret meetings there too. Where's the executive team this afternoon? And, you know, you didn't tell your company and, and, you know, as even now, um, calendars are very open. So, so getting everyone **[25:39]** on the exact team out or even, you know, two or three of them out at the same time for two or three hours is a little hard. Yeah. Yeah. I walked through a similar scenario. I was at a company called email edge got acquired by Lexus nexus. I was there for four years. I was there from the 4 million ARR to about 40 million. And then we sold for half a billion. And that's relations. I'd say it was fantastic and amazing for everybody involved. Um, I'd like to say I, I helped, um, but also immaculate, but immaculate product market fit. Um, perfect timing on the exit. Just like, I felt like, Hey, really felt like we made the full arc and maximize the **[26:24]** opportunity. And leading up to that process was really interesting. Yes. Lots of secret executive meetings. There were a few other potential acquires on the table too, which created a little bit of competition, which was nice for the end outcome. And I think, uh, it was just very interesting. And one thing that happens in an acquisition that doesn't happen in an IPO. There's certain process changes that happened during IPO, of course, more scrutiny, uh, tighter processes, but you don't have to go through a full integration process. And I don't know about your experience, but that was Lexus. Nexus had a integration machine. They ### 27:02 — Why an acquisition is harder than an IPO **[27:03]** had a whole department and team day one. It was, here's your new boss. These execs on your, on your team are no longer here. Here's the new department you work in. Uh, yeah, I think that most of them were aware. I don't know if all of them were aware. Um, and then it was like, Hey, we're going to detonate your Salesforce instance and you're going to have to migrate everything into ours. So I just think that creates a whole new dynamic and experience versus an IPO. I don't know if you had a similar experience yourself. It was really, so I've been through, um, I've been the acquirer **[27:40]** before, both at SAP and then I was acquired at Oracle at Siebel systems. Very nice. So I, so I gone through it a couple of times and never at the, oh, I didn't realize you were at Siebel. I was actually when I was at Lexus Nexus and we got acquired, actually they were on Siebel. They loved our Salesforce instance, but they wanted to destroy it. So they like destroyed it, migrated into Siebel. And then we migrated to Salesforce and I led the Salesforce migration project. I've heard that a lot. We loved our Salesforce, we hated our Siebel. I heard that a lot. Um, **[28:13]** so it was, so fortunate, you know, Workday, I think there's a really unbelievable job. I think they were, um, they hadn't done major acquisition. That was their largest acquisition at the time. And they really put it up thinking for making us feel welcomed to, um, keeping our processes and our instances and everything in play and ensuring that we could be a nimble startup and still hit these revenue growth numbers without the clogs. I mean, I think one simple, I was speaking with the, the CRO at the time and, and he's like, how many, you know, sale stages you have? And I'm like, **[28:45]** six, how many of you have me? Like 19. I'm like 19. Very specific steps to get to it. He's like, do you want to see the process to change pricing? And like, he showed me the process, the workflow, and it was like 38. He's like, what's your process? And I'm like, I think of what it should be. And then I send out a message. And so it was, but they were really good about it. And it worked out really well for both sides. Oh, that's great. One, um, one thing too, after going through that, and then I've been at a few startups that went nowhere. Um, I'm curious your perspective on **[29:23]** equity in a company, how you should value that in your total compensation, especially for people maybe getting into the CRO seat for the first time. There's usually a big story that's, uh, told with the equity that you're getting in a company, but I'm curious how you approach that now after you've been through some of these rounds. First and foremost, you know, going at a startup, if you're going there just for the money, like I would, I would share with you that, you know, you should go work at a big technology company because in the long run, you will probably make more money **[29:55]** consistently. Um, the numbers on startups, you know, I worked at startup, not because of the, the, the compensation that most people shouldn't, I'd work because, you know, I love the environment. You make an impact. You can really know each other. Like, like these are, these are great reasons to work at a startup, but just cash because equity is a big part of it. And, and what people see is the IPOs and the people drinking champagne and, and everyone in times for it. And that's all true, but that is like one out of a thousand. That's literally, if you take all **[30:29]** the startups in the world, they're like one out of balance. You have to think, is this startup going to be the one out of a thousand, or is it going to be one of the other ones? And, and one of the other ones is at the end of, and I hear this a lot as well, you know, I spent, you know, three to five years at X company at all of this equity. I took equity instead of cash or lowered my OT. And, and then, you know, they're, they're going out of business or trying to pivot and it's not working. And, and, and that's tough, but that's the reality of it. So you have to **[30:59]** understand that going in. So my first thing would be like, hey, you just have to understand if, if it's for the money, um, and that's your primary thing, that's probably not a startup. It's probably not a startup. All right. And then if it is, if, if a startup is your thing and for all the reasons that I, we share to discuss and all the million of other reasons, yes, equity is a big part, but you have to understand, and it's a simple thing on equity until, until there's a change of ownership. There's no, no matter what the valuation is, it doesn't matter till there's a **[31:33]** change. And, and, and people, you know, the state that, you know, to, because I have equity, I can sell it on the market or sell it somewhere else, or I can get money for email. It's nothing. It is literally worth zero to you until there's a change of ownership. All right. And you get bought the IPO, you know, change of ownership. You might get a secondary on around a couple of times, but that's, that's rare. Like I've seen one in 10,000 companies give secondary offerings when they're fundraising around, it's up to their board. So, so you just have to know that going wise, **[32:07]** eye open and, and part of the pitch, and I do it too on, on interviewing people as I say, this is the valuation of our fundraising around. And this is what it was next time. So if you get equity at this, this is what it goes to. But I am also very deliberate. When I say, look, that doesn't mean you can get that money or someday it's going to be worth them. And it's complete zero. It is funny money. It is monopoly. I play monopoly with my kids a lot. It is monopoly money until there's an exit. So you have to think of what the change of ownership is. Is there going **[32:39]** to be an IPO? Is someone going to buy them? Is there going to be a fundraising around where they're going to let people, and they will never let you sell all your equity, but let you sell like 5% of it, 10% of like, so it's not, so you just have to make sure you're okay with that going into it. Because I think a lot of people just see the champagne and the cartwheels or hear the story. Do you always have a friend where the friend who was the first employee at Google or a friend who had a friend who go, but you never knew that person. I'm like, Oh, who was it? It was always **[33:08]** a friend of a friend, right? They were the office manager at Google and now they're a bazillionaire. And I hope that's true, but I've never known any of those people. No, 100%. You realize how rare it is. So we, at LeanScale, we work with B2B SaaS and AI companies. So we've worked with hundreds now. We've been around since 2021. We're deep in with the CRO and head of RevOps doing GTM ops for them. So we see lots of fundraising, tons of fundraising. I mean, people are raising 100 million plus multiple rounds doing a series B and series C within three to six months of each other. ### 33:09 — The hard truth about startup equity **[33:45]** But to your point, nobody's getting paid. Maybe the founder on secondary, they're the only ones who tend to get to do that. And then everybody else doesn't get the option or choice, but nobody's getting paid until that IPO or full acquisition happens. And it's got to be a strategic bio too. There's a lot of like half PE buyouts where nobody gets paid in those scenarios either. There's a lot. And that's an excellent point. And even worse, I didn't touch on, like there's chances you get buyouts because the investors get the money first. The investors, whoever invested, **[34:17]** they get their money first. And if the buyout isn't large enough, you'll get your equity will be nothing and you'll get bought out. So that reduces the chances even more. Excellent point. But that's it. I just want people to be known about that because I've had too many people I've spoken to that I put so many years into a company and they did it with a large buyout, which is why if it's the money and that's it, startup's probably not for you. That shouldn't be your main reason. It shouldn't even be number two. It should probably be a distant four or five. Yeah. And if you're indexing the value of that equity very high, you should reconsider why **[34:51]** you're making that decision. Don't let it have that strong of a weight in why you're moving somewhere. People share with me, they're like, they're all these secondary markets, high or forward. I'll just sell it there. That's actually not okay. They're like, you need to have your, if you were going to start up, the board has the right to approve it or not approve it. So just because even if you pay for it, and let's say you bought your shares and you've had them for years, even if you're still working there or not working there, that doesn't mean you can go sell it on **[35:23]** the secondary market. So it's a little thing that a lot of people don't know. I had someone coming to me the other day, they're like, I bought all my shares and then I wanted to sell them. And one, I couldn't find a buyer. And then number two, I got a notice from the board saying that you don't have the right to sell them on a market. So pull it down. Yeah. I know a lot of that's happening with people at Anthropic right now. That's kind of a big controversy happening. I met secondary. I heard about that. I heard about a house being sold for a Anthropic share. So what a great **[35:56]** company I hope that's the case. Yeah, it's wild. Absolutely wild times for them. One last question on this topic, just because I love the practical, the advice you're giving. I know sometimes you don't always have the negotiating power to do this, but are there any clauses you'd like to make sure are set in place for your equity agreement, single trigger, double trigger type of language, anything that helps protect that part of the plan? Yeah. I mean, I haven't seen a single trigger since 1999 or 2000. I've only heard of them mythically. I mean, double triggers are pretty **[36:37]** standard. Change of role is pretty standard. If they're going to, they hire you as a CRO and then they don't want you to be a CRO anymore. That's pretty standard. Or if a company, founders, sometimes they move or sometimes they get acquired by companies over there and they, you know, in different states or countries, and then they want you to do all these things are super important. I think they're less important than just being realistic about your equity and the amount you have and what it can or can't do. Because if you're making your life decision, which is a career and **[37:13]** family and that stuff on it, and you're banking on something, you should have all the facts on it. Yeah, I appreciate that. I think some people have this fake bravado around how they're negotiating their equity deals. I don't think it's the case. I think it's poor advice coming from people who don't necessarily know what they're talking about or have actually gone through some of these arcs. So I appreciate you sharing the real stories of what happens going through IPO, going through exits, and what those agreements mean at the beginning. And don't do it just for that. Make sure there's **[37:48]** so many other reasons why you should be moving to a startup or not. Yeah. Yes, I agree. Absolutely. Hopefully you'll get an exit like yours. All done. I didn't know that. Yeah. It was a, well, and after I was like, this is what startups are. Let's rock and roll. Let's go join Nolan. I'll do it again. Hop into the next one. It was easy. And then I quickly found out that's not the case. No, I actually knew. I remember sitting down. I was very close with the CRO, the CPO. We worked at company previous. So we all had a really good working relationship and friendship and we're **[38:28]** friends to this day. And I remember us being in the room like, hey, we're going to come back to this moment. We'd be in like a conference room trying to solve something. We're going to come back to this moment and really, really appreciate it. And we know we're living through the good times right now. And we know this is special. So I think we had a unique level of self-awareness that, hey, this isn't going to be forever. This is special. Let's soak it up while we're going through it. And it's unique that we're on this type of path. Was there champagne in that room **[38:56]** or bourbon or something stronger? You know what is most unfortunate? This whole thing happened during COVID. So, so here, I'll walk you through the timeline real quick. We kind of started the process late 2019. And I was the VP of RevOps at the time reporting to the CRO. So I came in for all the data requests, all the like, okay, we're spinning up the data room. We need this. We need to build the story, the deck. So all the data portions of what we were doing, I was supplementing and getting that in there. And so I knew what was going on. And we then in February, LexisNexis wrote **[39:41]** the letter of intent to acquire and we announced it publicly. And it was all out there. And then there was a 30 day period before everything closed. And then right in the middle of that is when the NBA started canceling all of their games because of COVID, everything started getting shut down all like everything. And we were all freaking out. We're like, oh no, no, two more days. They were like, are they are they going to not make this deal? And are they going to pull the plug? Are they weird? Everyone was on pins and heels waiting for that day to close. LexisNexis **[40:15]** didn't even stutter. They were like, yeah, why would we have not done this? So I don't think we had anything to worry about, but we all were worried. And then it was funny. It was like, the the day came. It's very operational, like hard to update it. OK, your shares have been purchased. Everybody had their like they had all of our bank account information. Checks just got deposited in everybody's bank accounts after the escrow did its thing. And and I just remember sitting in my house because it was COVID couldn't go to the office and popping champagne with my wife. That's it. We could all get together and have **[40:55]** have an event. And then we never really did because then it was like deep into COVID and people left. Then we're really just working at LexisNexis. It never felt like there was a right time to have it. So we didn't have that party. Let's do that. And and also, you know, your your your CRO. So so normally, normally of any change of ownership, executives like all the employees get paid immediately, but all the executives get paid like over a year or two depending. So they probably didn't celebrate as much because they were like, hey, I got to you know, I have my actual like all the money I've earned them over, **[41:28]** you know, over the next year or two years. Yeah, no. And they they anything they were great. Anything that wasn't vested yet, they converted to a vesting schedule and in their stock. So I think it was now now having more exposure. This was like the best experience possible. And they did it. They were really a class company doing the acquisition. They didn't try to mess with anything or take advantage of anyone. They were very fair during the whole time. Congratulations, because I've heard that and the workday story that I experienced are already. I've also been part of companies that acquired companies and did the other way. And by the other **[42:09]** way is, you know, you'd acquired it and, you know, you keep some of the sales people and then everyone else was gone within, you know, a month or three. So I've seen a lot of that, too, working on never experienced it. But, you know, I've seen it out there and I've had friends go through actual friends. Yeah. Yeah, it's tough. It's tough. So for those who are in a startup, just know what you're walking into very, very few end with that champagne. And if that's the only reason why you're doing it, then maybe do something else. And I'm going to just end with this. I know **[42:40]** you should have all the facts and all experiences. I would not do anything else. And if I had to go back and do it, then I would have started a startup for longer. I would never do anything else in my life. I get so much joy out of it and I think it's so fulfilling and rewarding and makes such an impact. I completely agree. Yeah. And you're making an impact every single day. I was hoping we could go into a little bit just to wrap up the conversation. One more topic that I think is on everybody's mind. And you mentioned something in the prep session that really stuck with me that **[43:14]** every CRO should be building their own agents for themselves. How are you seeing AI impact go to market? And this is a pretty big shift in this function right now. How are you seeing teams approach it? And what advice do you have? First of all, it's an unbelievably exciting time. Like really, really amazing what's going on. And you definitely have to adjust. There is no way around. I remember SaaS coming out and mobility. This is a monumental shift. And if you don't shift, you're going to be left out. And it's not a hardship. You just have to do it. And by a **[43:58]** hardship, I mean, it's not like quadratic equations where you're like, it's difficult to figure out, at least for me, difficult to figure out. Building your own AI agent, you can get on Claude and say, tell me how to build an AI agent and they will walk you through it. And you're going to actually do it. But much like I think if you're a revenue leader, much like going back and knowing how to do marketing and doing ops for a year. And if you don't have the fundamentals and basics on it, it becomes hard to manage it. Doesn't mean you have to build your own agents every day, **[44:31]** but if you haven't done it once or twice, you don't understand quite the power or what they can do or the scope of it or what can or can't or how to make it correct or not correct. That makes sense. And I think the revenue or the go-to-market motion is changing dramatically. And changing dramatically is the old SaaS model and the playbook. I think that's drastically different. I don't think, I'm not of the opinion that you are going to reduce the revenue teams by 99% and get $10 million per account executive. If anyone looks at OpenAI and Enthropic, who they're hiring, **[45:16]** they are the biggest hirers of enterprise sales teams right now. Those two companies are hiring. Look at the CMO they hired from ServiceNow and Enthropic. Look at the chief revenue officer they hired from Slack. They are hiring. So those are going to stay intact. But the skill sets and the roles are going to change. RevOps is changing. I'm sure you're seeing it. You now have these AI tools that are workflow and integration and updating. I remember people used to think I was nuts. People thought I was crazy because I would update ICP twice a year. Because updating ICP is **[45:55]** hard. You have to look at all your wins. That's an easy one. Look at your losses, but why did you lose? Then you have to research all the industries, the people, the region. You have to look at pipeline where it's coming. So you have to try to update ICP. It took a long time. It was hard. I know you've done it a lot, RevOps. It would be a lot of spreadsheet manipulation stuff. With Clay now, I can update ICP weekly. Literally, I can update it weekly. And it's easy. I can add a lot more information in terms of intent and signals and where people are coming from or leaving. So for me, things are changing dramatically. I'm assuming you're seeing **[46:35]** a lot of this in your RevOps org, right? What's the biggest one? What's your major life? Well, yes. Since we're doing GTM ops, RevOps for companies, we're working with companies like Mistral AI. They've raised billions of dollars. We're working for Clio. They just crossed the 500 million ARR mark. So we're working with the company. That's right, Vancouver-based. I've been to their Burnaby office quite a few times. ### 46:56 — Why Jerry would never do anything besides startups **[47:06]** And so, of course, we're implementing AI solutions across those type of companies. **[47:17]** On the curve of super high value of despair and then coming out with a sober attitude around what AI is, I'm also optimistic that it's not going to create these dramatic headcount cuts, even if-- let's assume you could reach a 10x productivity level, like you mentioned, with a salesperson. Great. Hire more salespeople. If I could get a salesperson who could close $10 million, why wouldn't I want more of them to close even more? There's no company in the world that doesn't want more revenue. I promise you, not one. Every company wants more revenue. No. And in the RevOps org, I don't think it ### 47:18 — Every revenue leader should be building their own agents **[47:57]** compresses there either. It's getting even more technical, even more difficult, even more important to be able to set up your systems to scale and have the ability to be agile as things change because things are changing so quickly. People are launching products faster than they've ever launched before. They're going to market in regions faster than they've ever done before. Some of these things-- and like you mentioned, hey, I would do my ICP twice a year. Some of these things you'd maybe do once a year, once every two years. Now the cadence is getting really, really compacted. So tactically, though, what am I seeing? Claude right now is winning, **[48:35]** so they have probably the best business suite of harnesses to leverage their model for business use cases. And I think we have really seen a dramatic increase of companies leveraging Claude, Claude code, Claude co-work, Claude design for marketing as well. And the biggest thing, which this never goes away-- well, fortunately for us, maybe-- but it's the data infrastructure and architecture. So in a sales example, how are we setting up the transcription pipeline to go feed the agents that we have? How are we setting up the data movement that's automatically **[49:19]** populating in the CRM? How are we normalizing the CRM data so that way we can actually get insights and query that data? So if you just throw an LLM on your entire Salesforce or HubSpot instance, it's going to hallucinate insanely. So all of these data architecture problems are really the hairiest part of the whole thing. And then once you get that solved, then you can start layering in the agents, subagents, workflows, plug-ins, skills to do some really amazing things. And if I'm looking at our own go-to-market motion, I mean, it's completely taken over-- how we create an SOW, how we scope an engagement, how we develop all of our **[50:04]** kickoff materials. We have apps for every project that we run. So now, oh, you're going to do-- we call it market map. It's kind of like ICP+. Market map-- OK, we'll go through all the questions, and then we'll build an entire deploy configuration that we can automatically push through the CLI to Salesforce. So we have seen dramatic gains in efficiency, but also keeping our quality consistent. All from the sales motion plus for us delivery is going to be very important. So I think it's going to be integrated at every single step. I think you're going to have to get **[50:40]** really fluent with the latest models and harnesses to get the most out of them. And you're going to have to have a lights-out data architecture to take advantage of any of this. And that's never going anywhere. And call it the AI ops, revenue AI ops, AI-- That's what we call it. --engineer. Whatever you call it, that person is now most critical in the world. And for example, I will give you an example. So pipeline calls are probably the thing that revenue leaders and AEs hate the most. Because you get on these calls, and you'd be like, how many meetings did you have? How many phone calls? What's your pipeline today? What's your **[51:20]** pipeline next quarter? What is it in three months? What's the source of this pipeline? What are your top deals? All this stuff. And it was hard. And now, and I did, and I created an agent, I created a pipeline agent that would, every Monday, every other Monday when we did it, that it would come every Monday to me. But every other Monday to everyone else, it would happen to be like, OK, here's your signal. Here's your signal. I call it Pykey. Here's your signal. Here's your signals on your deals. This one hasn't had an activity or a response in so long. This one has stayed in stage two 30% longer than other deals that have won in stage two. And it **[51:59]** would just automatically come to me and give me a summary. So then I wasn't grilling an AE. It was like, OK, what's happening on this deal? What can we do to help you? And they weren't explaining it and telling me stories. And so that to me, and by the way, the first agent wasn't very good. I was missing a gut feel, but I built that first agent. But conceptually, I understood what I needed to do, and then someone helped me, and it got much better. But think about that. No longer did we have to go through stuff. I didn't call an AE and have a label. I was like, OK, here's your deals that are **[52:31]** tracking well, hitting all the criteria that we have talked about, and it's moving. Great. Here's the ones that aren't moving and why they aren't moving. And I haven't seen an activity here, and this customer hasn't replied in two weeks when they replied 10 times. So you suddenly have all this stuff. So now you're talking about strategy on winning deals and strategy on moving pipeline and not reciting numbers or giving things. And this is done every Monday for me, but could be done daily or every other day and stuff. So what an advantage. There is absolutely no excuse for lack of execution nowadays. No excuse. No, none at all. And that's where **[53:11]** once you realize you have the capability to do certain things and then the ceiling of what is possible just lifts and lots of people have had this experience, you find yourself working even more because you're like, I wouldn't have even accepted that idea onto my plate because I would have automatically ruled it out because it would take millions of dollars of resources and engineers and people to, and now I can just put a prompt in and build this. Okay. Now I have the ability to do it. One thing you, the way you phrased it and mentioned it, I think it's important for people **[53:43]** to think about the best leveragers of AI have some deep expertise in the domain that they're leveraging the AI for. And I think that's intuitive, but a lot of people are leveraging AI for the creation of rather than propelling the execution forward. So in a lot of, if I'm doing anything, I like to start just in analog mode. Let me put all of my thoughts on paper because I have so much context and I know what Google is like and I have taste for this. You have to write it on paper. I type it into Google doc, Google, analog, meaning not leveraging AI to produce the **[54:24]** initial language. That's the new analog. That's what I was going to say. I was like, analog, wait a minute, pen and paper. No, not that I pull up my typewriter to start putting my ideas down. But I think getting your idea first and then leveraging AI to, Hey, fill in any gaps and then create these assets or create these things. That's when you get really, really good results. It's pretty easy to see slop out there or when people are presenting something as if it's their own and they can't defend their ideas. But if you have some deep expertise in something, **[54:58]** use it as the propellant. It's amazing what you can do with that. You have deep expertise. I've sat through millions of forecast calls, millions of deal reviews, pipeline. But if I hadn't built this agent and built what could happen, I couldn't think of the next two agents or three that now I'm optimizing a go-to-market machine around. Because now I'm like, okay, I can save time from this RevOps or RevAI leap or whatever we call it. For this agent, because I would ask them for the pipeline numbers, I'd be like, which deals are in stage two longer? I would be asking them. ### 55:30 — Jerry's pipeline review agent (the most actionable AI use case) **[55:37]** Now they don't do that. I can ask them for other things. And so it's really amazing. And that's why I think that the roles are changing. I don't think the teams are shrinking or everything. I think that the roles are just changing and the skill set. And then if you have that expertise, if you are a revenue leader and you're not able to do that or build a campaign yourself, I think you're going to really struggle. I think so too. I think so too. And then that's where tying this back to how you started, getting that diversity of experience and rolling up your sleeves and doing **[56:09]** some of the work in a variety of different departments and areas of the business can really give you that context too that helps leverage these things moving forward. Jerry, I really appreciate you being so open, honest, candid, vulnerable, going through real stories, IPOs, acquisitions, what it was like to go from a product led growth motion to an enterprise growth motion. And also the very timely advice on how to leverage AI and go to market. I think this episode has been packed with insights and I really, really appreciate you sharing these. Our audience is going to appreciate it. And I know I've learned **[56:53]** a lot listening. So I just want to thank you for being on the show. Can't wait to see what you do next. Any startups going to be lucky to have your experience there and always happy to have a return as things change in the future. And Anthony, I really enjoyed it too. And thank you for having me on. I'll definitely come back if you'll have me. And I really hope, and I mean this, I really hope people out there who listen to this, learn and don't make some of the mistakes I had or do better and build on what I've built because it's so much better out there if we can learn and help **[57:30]** each other. So thank you, Anthony. I hope this helps and I'm excited to share what's next shortly. - Amazing, thank you Jerry. - All right, bye Anthony. --- _LeanScale Podcast Knowledge Hub. Free to quote and cite with attribution to The LeanScale Podcast (https://www.leanscale.team)._