Your best buyers probably aren't the ones reading your LinkedIn posts. They're asking a question in a subreddit right now — and the first person who shows up with a real answer wins.

Shawn Tenam spent about a decade as a plumber before breaking into tech. SDR, founding BDR, deep on Clay, a stint at RevPartners, and then all-in on building go-to-market systems with Claude Code — including the Reddit engine that became Clearbox. Lila Rest is the product and engineering half: he'd already helped build an RB2B-style de-anonymization startup, told Shawn no the first time, then turned a sprawling ten-page prototype into the focused product Clearbox is today. He also quantized Google's Gemma 4 31B down to run on a consumer GPU — a model pulling 600k+ downloads a month on Hugging Face.

In this conversation with LeanScale co-founder Anthony Enrico, they make the case that Reddit is the most underrated channel in B2B — and that the reason it works is the exact same reason you can't automate it. Along the way: why Reddit is structurally incentivized to stay human when LinkedIn isn't, the karma gate, why you should never post your link, what happens to SaaS when anyone can build the product in a weekend, and the cost engineering that turns a $5,000/month AI workload into a $75/month one.

WHAT YOU'LL LEARNWhy Reddit is economically incentivized to stay human — and LinkedIn isn'tThe automation trap: why the more you automate a channel, the less trust you buildHow to work Reddit without getting banned — the karma gate, warmed accounts, and moderator riskWhy you should never drop your link until people ask for itThe "scroll and speak" method for building karma from zeroWhy five to ten genuine comments a day beats hundreds of automated onesWhy you don't need a backlink to get cited by ChatGPT, Claude, and GoogleHow Clearbox found 70 inbound leads in its first week using its own productThe cost-engineering moat: 95% of the intelligence for a fraction of the API billWhy SaaS is becoming a service business — and what that means for your moat

CHAPTERS00:00 — Cold open + intro01:44 — From plumbing to Claude Code: Shawn's origin story04:20 — Why Reddit, when LinkedIn is shouting into the void08:32 — The biggest misconceptions about Reddit09:07 — The automation trap: why AI kills trust14:47 — Why Reddit is structurally incentivized to stay human17:12 — Do less, in the right place: 70 leads in week one20:59 — The karma gate and the "scroll and speak" weekend27:03 — How to fail at Reddit: warmed accounts and bad research30:35 — You don't need a backlink to get cited35:08 — Reddit etiquette: post the problem, not the product42:00 — SaaS lost its moat — what replaces it?46:28 — The new SaaS model: distribution, cost, and speed51:06 — Anthony's take: SaaS isn't dead, it's becoming a service55:12 — The Gemma quantization story1:00:46 — Efficiency has a limit. Effectiveness doesn't.1:02:41 — Where to find Clearbox

ABOUT THE GUESTShawn Tenam and Lila Rest are the co-founders of Clearbox, a Reddit opportunity inbox that surfaces the threads where your buyers are already asking for what you sell. Shawn spent roughly a decade as a plumber before breaking into tech as an SDR and founding BDR, going deep on Clay and spending time at RevPartners before going all-in as a go-to-market engineer. Lila is the product and engineering half — he previously helped build an RB2B-style de-anonymization startup, and is the author of a quantized build of Gemma 4 31B that runs on a single consumer GPU.

ABOUT THE LEANSCALE PODCASTThe LeanScale Podcast is the show for GTM operators building the next generation of revenue infrastructure. Hosted by Anthony Enrico, co-founder of LeanScale.

▶ Learn more: https://www.leanscale.team▶ Try Clearbox: https://clearbox.to▶ Follow Anthony on LinkedIn▶ Follow Shawn on LinkedIn▶ Follow Lila on LinkedIn

#Reddit #RedditMarketing #RevOps #GTM #GTMEngineering #AI #B2BSaaS #ClaudeCode #Clearbox #LeanScale

Your pipeline isn't the biggest threat to your go-to-market. Neither is your product. It's the quiet attrition happening inside your own team — the people who checked out months before they ever handed in a resignation.

Luke Hoffmeister has worked nearly every seat in go-to-market — field, customer success, sales engineering, RevOps, sales training — and has spent the last two years bootstrapping a startup out of his own pocket. He has lived the problem he's paid to fix.

In this conversation with LeanScale co-founder Anthony Enrico, Luke makes the case that "you get what you pay for" is the most underappreciated line in talent strategy, that culture is follow-through and not free lunches, and that the best operators treat every role as a license to fix anything in the business.

WHAT YOU'LL LEARNWhy the most dangerous churn in your business is the kind no dashboard is trackingHow to spot an employee who is already gone — months before they resignWhy offering someone 20% more is life-changing to them and a rounding error to youWhat In-N-Out and Chick-fil-A understand about paying above market that most companies don'tWhy real culture is follow-through and keeping your word, not snacks and holiday partiesHow to run an all-hands that isn't a disciplinary session or a fake pep rallyWhy the best operators treat every role as a license to fix anything in the businessHow to hire for personality and potential instead of pedigreeWhy "hunters not hunting" is usually a data-entry problem, not a sales problemThe AI stack Luke runs — and why keeping the agents in line is a full-time job

CHAPTERS00:00 — Cold open + intro02:04 — The churn nobody tracks: internal, silent attrition03:42 — Losing a critical role: the ripple and the institutional knowledge04:45 — How to keep a finger on the pulse: listen, let people vent06:52 — "They're already gone": when someone checks out before they quit09:11 — The money conversation: 20% is life-changing, structure around raises10:05 — You get what you pay for: In-N-Out and Chick-fil-A11:04 — What culture actually is (and isn't)15:34 — Companies that model culture: Chick-fil-A, Series, Gary Vee, Buc-ee's20:47 — The doom loop and the professional-sports-team model22:29 — The honest all-hands: don't discipline, don't fake the pep rally24:53 — Don't send the blank Christmas card: mean it or don't27:20 — Self-awareness and needing a "cushion" as a leader28:37 — The eclectic GTM background: the through-line34:32 — A license to fix anything: not staying in your lane37:40 — Why RevOps is the home: it's a data-entry problem, not a sales problem40:03 — The AI stack: Cursor, ChatGPT, Update AI, Superhuman45:08 — Why AI needs more people, not fewer48:56 — Wrap

ABOUT THE GUESTLuke Hoffmeister runs revenue operations and sales training at HALOS Body Cameras, but the title undersells the range. He came up through the field and customer success, became a director of sales engineering, and now owns RevOps — which means he has worked nearly every seat in go-to-market. Technical enough to build his own software, Luke has spent the last two years quietly bootstrapping a startup of his own, funding it out of his own pocket and learning firsthand how every department of a business really works.

ABOUT THE LEANSCALE PODCASTThe LeanScale Podcast is the show for GTM operators building the next generation of revenue infrastructure. Hosted by Anthony Enrico, co-founder of LeanScale, we go deep with the operators, founders, and executives shaping how modern go-to-market teams are designed, scaled, and transformed.

▶ Learn more: https://www.leanscale.team▶ Follow Anthony on LinkedIn▶ Follow Luke on LinkedIn

#RevOps #GTM #GoToMarket #Culture #EmployeeRetention #Talent #Leadership #PeopleManagement #SalesTraining #CustomerSuccess #Hiring #AI #RevenueOperations #B2BSaaS #SalesEnablement #LeanScale #LeanScalePodcast

The customer spent two months evaluating quote-to-cash platforms — full-stack CPQ, billing, subscription management, sixty-thousand-dollar price tags. Derek Mogar built them a working CPQ inside HubSpot in two days, just to show them what advanced selling could look like. They took one look and asked: why don't we just use this?

That throwaway MVP is now the production system the entire sales team runs on. In this episode of the LeanScale Podcast, LeanScale architect Derek Mogar walks host Anthony Enrico through exactly how he did it — the two months of discovery, the four-step build, the guardrails, and the Claude Code build that turned a demo into a system dozens of reps run on every day.

This is the most tactical quote-to-cash conversation we've put out: where out-of-the-box tools stop being enough, how to configure, quote, bill, and recognize revenue without the wheels coming off, and the one thing most teams skip entirely — trust in the data. If you own CPQ, billing, or RevRec at a B2B SaaS company, this is the playbook.

WHAT YOU'LL LEARNHow Derek built a production-grade CPQ inside HubSpot in two days — and why the throwaway MVP became the real systemWhy the CPQ is the brain of the entire quote-to-cash system, not just a quote generatorThe four-step build: scenario selection, product configuration, commercial terms, and the review-and-discount stepWhy the biggest limitation of out-of-the-box quoting isn't features — it's the lack of guardrails on your repsThe three hardest problems he solved: co-termed expansions, honest churn, and the two-month overlap of an early renewalBuild vs. buy in the AI era: when to build custom and when an enterprise tool (DealHub, Subskribe) is the right callThe maintenance tax nobody talks about — the HubSpot serverless scare and who owns your CPQ at 2amHow billing software (Rillet, Maxio, Stripe) dictates the entire quote-to-cash architectureWhy trust and reliability in the data — not speed — is where most quote-to-cash projects fall short

CHAPTERS00:00 — Cold open + intro01:47 — When the throwaway MVP became the product05:15 — The environment: colliding sales-led and product-led motions07:09 — The gotchas of doing quotes in spreadsheets or out-of-the-box tools11:05 — Model your top reps: discovery, conversation intelligence, rip-and-replace14:39 — How he approached the build: mapping the full tech stack20:19 — The three hardest problems: co-termed expansions, churn, early renewals26:27 — The four-step build and the 50–70 property payload32:26 — Building it with Claude Code as a HubSpot extension UI35:05 — From MVP to production-grade: hardening and battle testing38:06 — Build vs. buy: when custom isn't enough42:27 — The maintenance tax: the HubSpot serverless scare50:28 — The last mile: invoicing, billing, and reconciliation55:13 — Why this isn't nice-to-have — it puts deals and reputation at risk

ABOUT THE GUESTDerek Mogar is an architect at LeanScale, where he leads quote-to-cash and CPQ transformations for B2B SaaS companies. With a background in sales — and a father who spent his whole career in enterprise sales — Derek lives in the machinery of how modern companies configure, quote, bill, and recognize revenue. He specializes in colliding product-led and sales-led motions, co-termed expansions, ramp deals, and rip-and-replace contracts. On the project featured in this episode, he built a production-grade CPQ inside HubSpot using Claude Code — replacing a $60K tool the customer had spent two months evaluating.

ABOUT THE LEANSCALE PODCASTThe LeanScale Podcast is the show for GTM operators building the next generation of revenue infrastructure. Hosted by Anthony Enrico, co-founder of LeanScale.

▶ Learn more: https://www.leanscale.team▶ Follow Anthony on LinkedIn▶ Follow Derek on LinkedIn

#CPQ #QuoteToCash #RevOps #GTM #HubSpot #AI #Billing #B2BSaaS #ClaudeCode #BuildVsBuy #LeanScale

Most founders can't wait to get out of the demo. Andy Guttormsen ran more than 1,500 of them himself — and the revenue was never the point.

Andy was the seventh employee at Teachable, where he helped scale the company from roughly $10K in monthly revenue to a quarter-billion-dollar exit. In 2020 he co-founded Circle, now home to 15M+ members and creators like Jay Shetty, Mel Robbins, and Ali Abdal — a profitable, venture-backed company he grew by personally running eight to ten demos a day for 18 months before ever hiring a sales team.

In this conversation with LeanScale co-founder Anthony Enrico, Andy breaks down why founder-led sales became Circle's unfair advantage, why you hire the sales leader before the reps, the real difference between an audience and a community, and why Circle renamed its RevOps team the "internal AI" team — the most valuable seat in the company.

WHAT YOU'LL LEARNWhy Andy ran 1,500 demos for product feedback and brand — not first-customer revenueHow founder-led sales built its own top-of-funnel flywheel on socialWhy you hire the sales leader before the reps — and how doing it backwards backfiresThe "unfair advantage" hire: bringing on people who have lived your customer's problemThe real difference between an audience and a community — and why community is the moatWhy a big following doesn't convert into a community without a real offer and real ritualsHow Circle drives roughly 30% of new customers through its own customer communityWhy Circle renamed RevOps the "internal AI" team — and what changed on their plateHow accurate data turns meetings into decisions instead of data-integrity debatesThe GTM tools Circle can't live without — and the AI category they can't make work

CHAPTERS00:00 — Cold open + intro02:10 — 1,500 demos: why the goal was feedback and brand, not revenue04:45 — Staying close to your first 100 customers06:43 — The closet, the full calendar, and knowing when to hand off08:36 — Hiring a coach who became VP of Sales (the Charlie story)10:00 — Hire the leader, not the reps — why founder win rates mislead11:52 — The unfair-advantage hire: empathy from lived experience13:26 — Content vs. community in the age of AI17:30 — A community is just a business — nail the offer20:34 — A B2B example: how GrowthX builds community23:10 — Audience vs. community: 600K followers vs. 1,000 members26:32 — Circle's 30% referral loop from eating its own dog food30:21 — The Teachable RevOps regret and when to bring RevOps in36:36 — Renaming RevOps the "internal AI" team42:12 — What accurate data unlocks — and the tools they can't live without

ABOUT THE GUESTAndy Guttormsen is the co-founder and Chief Revenue Officer of Circle, the all-in-one platform where creators and brands build their communities, courses, and digital businesses — now home to 15M+ members and creators like Jay Shetty, Mel Robbins, and Ali Abdal. Before Circle, Andy was the seventh employee at Teachable, where as VP of Growth & Marketing he helped scale the company from roughly $10K in monthly revenue to a quarter-billion-dollar exit. He co-founded Circle in 2020 alongside Sid Yadav and Rudy Santino, and personally ran more than 1,500 sales demos in the company's first 18 months before building out a sales team. Today Circle is a profitable, venture-backed business with 280+ team members.

ABOUT THE LEANSCALE PODCASTThe LeanScale Podcast is the show for GTM operators building the next generation of revenue infrastructure. Hosted by Anthony Enrico, co-founder of LeanScale, we go deep with the operators, founders, and executives shaping how modern go-to-market teams are designed, scaled, and transformed.

▶ Learn more: https://www.leanscale.team▶ Follow Anthony on LinkedIn▶ Follow Andy on LinkedIn

#RevOps #GTM #GoToMarket #FounderLedSales #CommunityLedGrowth #CreatorEconomy #AI #Circle #Teachable #B2BSaaS #LeanScale #LeanScalePodcast

A RevOps leader asked her co-founder for a $20,000 consultant budget. He handed her a $200 Cursor license instead — and accidentally turned her into one of the sharpest AI builders in go-to-market.

Sarah Madden — known across RevOps as Smadds — started as employee #64 at Braze, cold-calling accounts as a BDR until a single waterfall chart in an all-hands convinced her the data behind revenue was where she belonged. Today she is Head of Revenue Operations & Strategy at FERMÀT, and she runs almost her entire job out of the terminal.

In this conversation with LeanScale co-founder Anthony Enrico, Smadds opens up her greatest hits: the exact skills, agents, and workflows her team uses every single day. The three buckets every skill falls into, the rule of three that tells you when to build one, the Pipeline Ops plugin that surfaces evidence instead of autofilling your CRM, and the infrastructure discipline underneath it all. If you have ever wondered what RevOps actually looks like once AI does the grunt work — this one is the playbook.

WHAT YOU'LL LEARNWhy a single waterfall chart in an all-hands can turn a BDR into a lifelong ops obsessiveHow a $200 Cursor license replaced a $20K consultant budget — and rewired what "non-technical" meansThe three buckets every RevOps skill falls into: surfacing context, process, and infrastructureThe rules of three: the exact test for when a workflow should become a skillWhy the Pipeline Ops plugin surfaces the evidence for every field instead of autofilling itHow the import-lead-list skill collapses a full day of CSV cleanup into 40 minutesWhy "no MCP, no CLI" is now a dealbreaker for adopting any GTM toolThe infrastructure skills that keep a terminal-run job healthy: wrap, pick up, and a core-tools trackerHow the RevOps org is bifurcating — and why heads of RevOps keep becoming COOs

CHAPTERS00:00 — Cold open + intro03:06 — The waterfall chart that hooked her on ops07:18 — Why every ops person builds their own spreadsheets08:29 — The $200 Cursor license that replaced a $20K consultant13:34 — Reevaluating "non-technical" + the infinite RevOps backlog16:09 — The three buckets: surfacing context, process, infrastructure18:30 — The rules of three: when a workflow becomes a skill24:00 — Slack as a data lake + Anthony's customer-health agent27:43 — The data-enrichment eval that became a tool-eval skill36:02 — The Pipeline Ops plugin: evidence, not autofill42:00 — The import-lead-list skill: a full day down to 40 minutes47:08 — The FERMÀT tech stack + "no MCP, no relationship"49:58 — Conversational intelligence hot take: do you need video?53:10 — Building a RevOps team when the roles are changing56:57 — Heads of RevOps becoming COOs + GTM is the messiest data59:26 — Demos: CMUX, the context bar, wrap + pick up01:07:13 — The Skill Factory + core-tools tracker01:10:34 — Spend tracking, the RevOps OS, and managing blast radius

ABOUT THE GUESTSarah Madden — known across RevOps as Smadds — is Head of Revenue Operations & Strategy at FERMÀT, the AI-native commerce platform. She started as employee #64 at Braze, cold-calling accounts as a BDR until a single waterfall chart in an all-hands convinced her that the data behind revenue was where she belonged. From there she built pricing and media-planning teams at BuzzFeed, survived a fire-sale startup exit, and became the first RevOps hire at FERMÀT. Today she runs almost her entire job from the terminal, and her team ships skills and agents that collapse multi-hour RevOps workflows into minutes.

ABOUT THE LEANSCALE PODCASTThe LeanScale Podcast is the show for GTM operators building the next generation of revenue infrastructure. Hosted by Anthony Enrico, co-founder of LeanScale.

▶ Learn more: https://www.leanscale.team▶ Follow Anthony on LinkedIn▶ Follow Sarah (Smadds) on LinkedIn

#RevOps #GTM #AI #GTMEngineering #PipelineOps #ClaudeCode #MCP #Salesforce #B2BSaaS #LeanScale

Building an AI agent that works is the easy part now. Any RevOps person can open Claude Code, dump in a Salesforce export, a few Gong transcripts, and a Notion doc, and have something genuinely useful running by end of day. Then they try to get 300 people to actually use it — and it hits a wall.

Christopher O'Donnell spent a decade as HubSpot's Chief Product Officer, where he built the Marketing, Sales, Service, and Data Hubs from scratch and turned HubSpot into the platform hundreds of thousands of companies run on. Now he's the founder and CEO of Day AI, building the agentic GTM stack — with customer memory, governance, and permissioning — backed by Sequoia.

In this conversation with LeanScale co-founder Anthony Enrico, Christopher breaks down the single biggest topic in go-to-market right now: the gap between single-player AI (brilliant, easy, everywhere) and multiplayer mode (governance, permissioning, personalization at scale — barely working). They get into the brain folder every RevOps team is building, what it really takes to run agents for a whole team, the virtual-employee model, and where GTM roles, pay, and even our brains are headed.

WHAT YOU'LL LEARNWhy the single-player AI experience is incredible — and the multiplayer experience barely worksThe one folder every RevOps team is quietly building, and what's actually in itWhy internal meeting capture — not just customer calls — is the real breakthroughHow documentation in plain English becomes a compounding enterprise asset ("if I get hit by a bus...")Why your Claude account is the new Excel spreadsheet — and what SaaS taught us about fixing itWhere single-player agents fall over: MCPs, central graphs, and the Gmail problemWhy governance and permissioning are the unsexy things that actually let you scaleThe virtual-employee model: rolling out agents like a new hire class with names, job descriptions, and tiersHow to change the behavior of 1,000 reps as a single change-management actionWhere GTM is going: OTEs doubling, managers going from 7 to 14 reports, sellers becoming marketersThe atrophy question: are we mathematicians who just got handed calculators?

CHAPTERS00:00 — Cold open + intro01:26 — The one folder every RevOps team is quietly building05:23 — Internal meeting capture: the breakthrough hiding in your Zooms07:42 — "If I get hit by a bus": documentation as a compounding asset11:53 — Your Claude account is the new Excel spreadsheet13:06 — Where single-player AI falls over (and why MCPs get abandoned)17:30 — Governance and permissioning: the unsexy thing that lets you scale22:45 — The schoolyard fence: how boundaries expand what reps do27:07 — The deploy button: pushing skills into personal harnesses30:02 — The virtual employee: rolling out agents like a new hire class35:02 — Changing the behavior of 1,000 reps as one change41:31 — The coming "AI Operations" team46:36 — Where GTM is going: OTEs double, sellers become marketers01:00:15 — Mathematicians with calculators: the atrophy question01:08:21 — The 12th draft: writing the blank page yourself

ABOUT THE GUESTChristopher O'Donnell is the founder and CEO of Day AI, where he's building an AI-native, agentic go-to-market stack with customer memory, governance, and permissioning — backed by Sequoia. Before Day AI, Christopher spent a decade as Chief Product Officer at HubSpot, where he built the Marketing, Sales, Service, and Data Hubs from scratch and shipped the products that turned HubSpot into the platform hundreds of thousands of companies run on.

ABOUT THE LEANSCALE PODCASTThe LeanScale Podcast is the show for GTM operators building the next generation of revenue infrastructure. Hosted by Anthony Enrico, co-founder of LeanScale.

▶ Learn more: https://www.leanscale.team▶ Follow Anthony on LinkedIn▶ Follow Christopher on LinkedIn

#RevOps #GTM #AI #AIAgents #AgenticAI #GTMEngineering #B2BSaaS #HubSpot #DayAI #LeanScale

Every state-of-the-stack report you have read is a survey. Somebody filled out a form describing the stack they wish they had. This one is not. LeanScale runs go-to-market operations inside 50+ B2B software companies, so we read the live systems instead — the delivery data, the projects in flight, hundreds of strategy calls, and the customer Slack channels where the real conversations happen. All anonymized, no names attached.

176 tools across 27 categories, every one checked for provenance so we could separate what each company runs itself from what we run on their behalf. That separation is boring, and it is the entire reason these numbers do not match anybody else's.

The finding: the big stack decisions are not decisions. Your headcount picks your CRM. Your pricing model creates your gaps. Almost every company lives in one of five shapes — and the expensive systems that touch revenue are the ones nobody builds.

WHAT YOU'LL LEARNWhy the Salesforce vs HubSpot debate is really a headcount question, with the numbers at every company sizeThe HubSpot correction nobody else makes: 77% have it wired in, about one in five run it as the CRMThe metering gap — 24 companies price on usage, five run a real metering engine, and what the other nineteen do insteadWhy a $8M usage-revenue business ends up invoicing off a hand-updated Google SheetHow Clay went from not existing to the number three tool in four years, past ZoomInfo and ApolloThe CPQ hole: why the layer where deals actually close is among the most consistently missingThe five stack archetypes, and how to tell which one you are inThe three tiers to buy in if you are building from scratch — and the one tier the market is visibly under-tooled onWhy the cheap composable tools spread fast while the expensive systems that touch money quietly go unbuiltWhat an operator should actually do with all of it this quarter

CHAPTERS00:00 — What we did, and why it is not a survey--:-- — Who is actually in the study--:-- — The whole board: every tool, ranked--:-- — Conversation intelligence, and why Gong is the category--:-- — The thesis: your stack is gravity, not strategy--:-- — Salesforce vs HubSpot is a headcount question--:-- — HubSpot's two different jobs--:-- — The metering gap: 24 price on usage, 5 meter it--:-- — What usage billing looked like at Emailage--:-- — Clay: from nothing to number three in four years--:-- — The CPQ gap--:-- — The five stack archetypes--:-- — What an operator should actually do--:-- — Three tiers: table stakes, motion-driven, frontier--:-- — Caveats and the through-line

ABOUT THE GUESTAnthony Enrico is the co-founder and CEO of LeanScale, a go-to-market operations firm that runs RevOps embedded inside fast-growing B2B software companies. Before LeanScale he led revenue operations at three VC-backed companies, including one through a $500M exit, and ran RevOps at Emailage — a usage-based business that closed customers like JP Morgan on pure consumption contracts, which is where his views on metering infrastructure come from.

ABOUT LEANSCALELeanScale runs go-to-market operations for fast-growing B2B software companies — the RevOps team embedded inside your revenue engine. This channel goes under the hood on how modern go-to-market is actually built and operated across a portfolio of live B2B SaaS companies — no hype, just the systems, the data, and what the operators inside these companies are actually doing every day.

Read the full interactive field study: https://leanscale-gtm-stack-public.netlify.app/More on LeanScale: https://www.leanscale.teamSubscribe for more field research and GTM operating breakdowns delivered weekly.

#RevOps #GTM #GoToMarket #RevenueOperations #SalesOps #MarketingOps #B2BSaaS #Salesforce #HubSpot #Clay #Gong #CPQ #UsageBasedPricing #QuoteToCash #TechStack #AI #GTMEngineering #LeanScale #FieldStudy #SaaS

No rep has ever said their favorite part of the day is opening Salesforce to log meeting notes. So Justin Lee is building the version where they never have to.

Justin rode a single company from Series C to IPO in FP&A — and then did something almost no one does: he walked away from the post-IPO finance track to grind 100 cold calls a day as an outbound SDR. That rare mix of financial discipline and frontline empathy carried him through RevOps roles at Aircall and Reonomy, and today he leads GTM Strategy & Operations at Superblocks, where he has put an AI-powered app layer on top of a headless Salesforce so his reps live in a tool built for them, not for the org chart.

In this conversation with LeanScale co-founder Anthony Enrico, Justin gets into why the sharpest operators think like financial analysts, how to make bets when you have no data, the messy mechanics of consumption pricing (quotas, comp, and ARR), how to build AI tooling your team will actually adopt, and why go-to-market engineers are not going to replace RevOps.

WHAT YOU'LL LEARNWhy an FP&A background makes you a sharper RevOps operator — and what carrying a bag teaches you that a model never willThe empathy gap that quietly wrecks tool rollouts: if the reps do not adopt it, nothing else mattersHow to communicate up to the C-suite without the mental block (the blueberries story)How to make go-to-market bets when you have zero historical data to model fromThe first-principles method for turning 50 competing ideas into the 3 that actually matterWhy "the one big deal pays for it all" is the most dangerous line in enterprise GTMHow consumption pricing breaks quotas, comp plans, and ARR — and how Justin is rebuilding all threeThe Palantir model: using forward-deployed engineers and deployment strategists to drive activationWhat it takes to move a vibe-coded app from a local hack to production the whole team trustsWhy go-to-market engineers cannot replace RevOps — and the strategic + technical pairing that wins

CHAPTERS00:00 — Cold open + intro01:41 — Leaving the post-IPO finance track to cold call03:29 — Culture shock: FP&A discipline meets 100 dials a day05:06 — The path from FP&A to SDR to head of RevOps06:09 — The empathy you only build by carrying a quota09:03 — Two kinds of RevOps: policy-setters vs. in the trenches12:12 — Communicating up to the C-suite — the blueberries story19:40 — Making go-to-market bets when you have no data25:39 — First principles: turning 50 ideas into 329:25 — Hypothesis discipline: did it work, or was it dumb luck?33:10 — The new efficiency era: what good looks like now39:40 — Consumption pricing: quotas, comp, and defining ARR42:02 — The Palantir model and time-gated spiffs47:43 — Going headless: building the GTM Center on Superblocks55:57 — The last mile: taking vibe-coded apps to production safely01:02:21 — The strategic + technical pairing that wins

ABOUT THE GUESTJustin Lee is Head of GTM Strategy & Operations at Superblocks, the enterprise platform where teams build production-grade internal apps with AI. He started his career in FP&A, riding a single company from Series C to IPO, before leaving the finance track to become an outbound SDR — 100 dials a day, learning the frontline the hard way. That combination carried him into sales ops and RevOps roles at Aircall and Reonomy (acquired by Altus Group). Today he is building go-to-market software that puts an AI-powered app layer on top of a headless Salesforce, so his reps never have to open a CRM again.

ABOUT THE LEANSCALE PODCASTThe LeanScale Podcast is the show for GTM operators building the next generation of revenue infrastructure. Hosted by Anthony Enrico, co-founder of LeanScale.

▶ Learn more: https://www.leanscale.team▶ Follow Anthony on LinkedIn▶ Follow Justin on LinkedIn

#RevOps #GTM #AI #GTMEngineering #VibeCoding #HeadlessCRM #ConsumptionPricing #B2BSaaS #Superblocks #LeanScale

Noah Marks has spent the last decade building the go-to-market engine inside some of the most recognizable names in B2B software — Salesforce, Okta, WalkMe, Udemy, and Diligent — and he's doing it again at ECI Software Solutions. He's also the co-founder of GTM Council, which started ten years ago as a dozen ops leaders comparing notes because nobody else would tell them the truth about the tools they were being forced to implement.

What makes Noah unique is that he sits on both sides of the table: the operator who is always a step ahead of what the software can actually do, and the executive who signs the checks. And he has landed on a conclusion that should make every vendor nervous. He doesn't want to buy products anymore. He wants to buy expertise.

In this conversation with LeanScale co-founder Anthony Enrico, Noah makes the case that the software industry is quickly becoming a services industry — that the technology moat is gone, that the next moat is thought leadership you can actually learn from, and that any product a CRO can vibe code over a weekend was never a product in the first place. Along the way: build versus buy, the margin math behind services-as-SaaS, the three weaknesses on every sales team he's ever audited, and how to become the pipeline czar at your company.

WHAT YOU'LL LEARNWhy Noah won't buy another vendor — and what he'll pay a premium for insteadThe compensation story: a six-person team, a seven-figure budget, and a problem that still landed back on his deskWhy so many GTM vendors stalled — great CEOs who never sat in the operator's seatThe build-versus-buy answer GTM Council keeps landing on: buy the infrastructure, build the intelligenceWhether services revenue is still SaaS — and what that does to the multipleThe margin math: what happens when 90% software margins meet real AI costsWhy the favorite product beats the best product every time"If you have a product that can get vibe coded by a CRO, you do not have a product"The three weaknesses Noah says he'll find on any sales team in the worldHow to become the pipeline czar — and why it's worth tens of millions at exit

CHAPTERS00:00 — Cold open + intro01:51 — "I don't ever want to buy a vendor again"04:31 — The $1M comp team that still handed the problem back07:26 — Why GTM vendors stalled: CEOs who never sat in the seat10:12 — Build vs. buy inside GTM Council12:55 — Is services revenue still SaaS?16:30 — The margin math: 90% software meets the AI bill18:38 — Favorite product beats best product20:50 — Full accountability: buy the outcome, not the tool25:18 — "If a CRO can vibe code it, you don't have a product"29:56 — Have a point of view or lose mind share31:50 — Buy the infrastructure, build the intelligence34:12 — The three weaknesses on every sales team40:41 — A CRO is an architect, not a VP of Sales with a new title44:34 — How to become the pipeline czar50:58 — The origin of GTM Council

ABOUT THE GUESTNoah Marks is SVP of Customer Success & Operations at ECI Software Solutions and the co-founder of GTM Council, a private community of roughly 150 senior go-to-market operators. He has spent the last decade building go-to-market engines inside some of the most recognizable names in B2B software — Salesforce, Okta, WalkMe, Udemy, and Diligent. GTM Council also produces Stacked GTM, the podcast Noah co-hosts with Andy Mowat.

ABOUT THE LEANSCALE PODCASTThe LeanScale Podcast is the show for GTM operators building the next generation of revenue infrastructure. Hosted by Anthony Enrico, co-founder of LeanScale.

▶ Learn more: https://www.leanscale.team▶ Follow Anthony on LinkedIn▶ Follow Noah on LinkedIn▶ Learn more about GTM Council and the Stacked GTM podcast

#RevOps #GTM #GoToMarket #AI #B2BSaaS #BuildVsBuy #VibeCoding #GTMCouncil #Salesforce #Okta #CRO #LeanScale #LeanScalePodcast

Most companies believe they can bolt a self-serve motion onto their sales-led engine whenever they're ready. Bryce Winkelman has run both — and he's convinced it almost never works in that direction.

Bryce is the Chief Revenue Officer at Typeform, where he's turning a 140,000-customer forms business into a full workflow platform, with roughly half his organization operating out of Europe. Before that he was an early leader at Qualtrics through its $8B acquisition by SAP and subsequent IPO, tripled revenue from $35M to $100M as Chief Strategy Officer at Quantum Metric, and ran the GTM org at SeekOut.

In this conversation with LeanScale co-founder Anthony Enrico, Bryce breaks down why you can PLG your way into sales but never sell your way into PLG, why the growth-at-all-costs premium is dead, how to fight for brand budget when the ROI is nearly impossible to prove, and the industry-expert hire most GTM teams are sleeping on.

WHAT YOU'LL LEARNWhy you can PLG your way into sales but almost never sell your way into PLGHow owning the "front door" justifies owning the entire downstream workflow — enrichment, routing, segmentation, paymentsWhy qualitative research was the hardest problem AI could unlock, and how Typeform is rebuilding it end to endHow to shift a brand from "forms" to "workflows" without abandoning the core that made youThe packaging problem no one has cracked: what to give away in self-serve vs. reserve for enterpriseWhy churn will look terrifying in a healthy PLG motion, and how to keep finance and the board from pulling the plug too earlyHow to fight for brand investment when the ROI is nearly impossible to proveWhy bringing the team into the "why" beats one more enablement session on the "what"The industry-expert hire that becomes so valuable you need an intake process to ration itHow "nail it, then scale it" replaced "hire 50 AEs" as the growth model

CHAPTERS00:00 — Cold open + intro01:50 — Owning the front door: forms to a workflow platform04:20 — Entering qualitative research — the problem AI unlocked06:46 — Shifting the brand from forms to flows: paid, events, influencers10:47 — The messy middle: running PLG and sales-led at once11:17 — You can PLG into sales, but never sell your way into PLG14:24 — Why sales-led companies can't become product-led18:20 — Fighting for brand investment when the ROI is invisible25:28 — AI search: why brand and content matter more than ever26:25 — Enablement: bringing the team into the "why"32:56 — The roles that make it work: RevOps, PMM, and ops36:27 — The industry-expert hire most teams miss43:12 — Growth at all costs is dead — making bets under scrutiny48:29 — "Nail it, then scale it" and staying close to the signal51:09 — Wrap

ABOUT THE GUESTBryce Winkelman is the Chief Revenue Officer at Typeform, where he leads global go-to-market — marketing, sales, partnerships, RevOps, and customer success — as the company evolves from a 140,000-customer forms business into a full workflow platform. Over two decades in tech, Bryce was an early leader at Qualtrics, holding roles from EMEA Head of Sales to Global Head of Revenue and Solution Strategy through its $8B acquisition by SAP and subsequent IPO. He later served as Chief Strategy Officer at Quantum Metric — where revenue tripled from $35M to $100M in two years — and as Chief Business and Revenue Officer at SeekOut. He has also advised Warburg Pincus.

ABOUT THE LEANSCALE PODCASTThe LeanScale Podcast is the show for GTM operators building the next generation of revenue infrastructure. Hosted by Anthony Enrico, co-founder of LeanScale.

▶ Learn more: https://www.leanscale.team▶ Follow Anthony on LinkedIn▶ Follow Bryce on LinkedIn

#RevOps #GTM #PLG #ProductLedGrowth #SalesLedGrowth #AI #BrandMarketing #B2BSaaS #Typeform #Qualtrics #CRO #LeanScale