Every software company is hiring a forward deployed engineer right now. Aimee Menne thinks most of them are just hiring professional services and calling it something else.

She would know. Aimee is Chief Revenue Officer at Sourcegraph — a company founded by two former Palantir forward deployed engineers, where she now owns sales, customer success, support, and field engineering under one roof. She studied computer science, started as a developer at IBM, and built services practices at Switchfly, Segment, and Sourcegraph before taking the revenue seat.

In this conversation with LeanScale co-founder Anthony Enrico, Aimee gives away the whole build manual: the two-question test for a real FDE, the signal that it's time to stand up professional services, the sequence from first hire to playbook to packaging to P&L, how Sourcegraph prices it, and when to own delivery versus lean on partners.

WHAT YOU'LL LEARN

Why the forward deployed engineer craze is professional services with a new name — and the two questions that separate the real thing from a rebrand

The maturity curve: first hire → repeatable playbook → packaging → P&L, in that order

Exactly how Sourcegraph packages and prices services, from a $10K mandatory attach to outcome-based projects

Whether services should run as a profit center or an adoption lever — and why outsourcing to partners costs more than the margin it protects

CHAPTERS

00:00 — Cold open + intro

02:05 — Computer science to IBM — and the Navy project that bored her

04:24 — Switchfly and Segment: building services practices from scratch

07:15 — The flip: internal work vs. work a customer sees

10:26 — The FDE craze: "professional services with lipstick on"

13:08 — The two-question test for a real forward deployed engineer

14:43 — When a software company actually needs professional services

18:58 — Product problem or service opportunity? How to tell

22:03 — The maturity curve: first hire → playbook → packaging → P&L

27:16 — Pricing and packaging: $10K attach, hour buckets, outcome-based projects

31:05 — Utilization, fully loaded cost, and running a company inside the company

34:20 — Profit center or adoption lever?

36:07 — In-house vs. partner-led — what outsourcing really costs

40:53 — The RevOps blind spot: nobody supports professional services

45:18 — Staying sharp as a new CRO

48:59 — Why software companies now look like services companies

ABOUT THE GUEST

Aimee Menne is Chief Revenue Officer at Sourcegraph, the code intelligence platform for the world's largest engineering organizations. She studied computer science, started as a developer at IBM, then built professional services practices at Switchfly and Segment — where she stayed through the Twilio acquisition. She joined Sourcegraph over five years ago on a six-person technical success team and climbed to CRO. Today she owns sales, customer success, support, and field engineering.

ABOUT THE LEANSCALE PODCAST

The 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.

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▶ Learn more about LeanScale: https://www.leanscale.team

▶ Follow Anthony on LinkedIn

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KEYWORDS / TAGS

Forward Deployed Engineer, FDE, Professional Services, Solutions Architecture, Field Engineering, Customer Success, Services Attach Rate, Gross Margin, Services P&L, Pricing and Packaging, RevOps, GTM, Outcome Based Pricing, CRO, Sourcegraph, Segment, Palantir, IBM, B2B SaaS, Developer Tools, Code Search, LeanScale, Anthony Enrico, Aimee Menne

HASHTAGS

#RevOps #GTM #ForwardDeployedEngineer #ProfessionalServices #SolutionsArchitecture #CustomerSuccess #B2BSaaS #EnterpriseSaaS #DeveloperTools #Sourcegraph #Palantir #Segment #CRO #LeanScale #LeanScalePodcast

Most companies hire enablement to fix a problem enablement cannot fix. Cheyenne Griffith has watched it happen from the inside — and she has three hard gates a company has to clear before the hire works at all: founder-led sales has to be over, product marketing has to have a real point of view, and the leader has to be genuinely ready to hand over the reins.

Cheyenne is building the go-to-market enablement function from the ground up at Deepgram, the voice AI company behind the speech-to-text, text-to-speech and voice agent APIs that over 200,000 developers build on. Her path there is unusual: she started as a fourth and fifth grade math teacher, got pulled into SaaS by the learning platform she used in her own classroom, and has since built enablement from scratch at a CRM company and an AI company.

Her thesis is deceptively simple. Enabling a seller to sell is not that different from teaching a fourth grader how to divide — the hard part was never the teaching, it was the system around it. In this conversation we get into why enablement is the most misunderstood function in go-to-market, how to prove its impact, why she thinks the function belongs under the CRO and not RevOps, and the AI problem that keeps her up at night — which is not slop, it is maintenance.

WHAT YOU'LL LEARNWhy an ARR number is the wrong trigger for hiring enablement — and the three readiness gates that actually matterHow launching MEDDIC at a sales kickoff is roughly 5% of the work, and what the other 95% looks like operationallyThe classroom "exit slip" and why call recording scorecards are the same instrument in a different roomHow to build the ROI case for an enablement program before you run it — conservative, medium, and blow-it-outWhy Cheyenne thinks enablement reporting into RevOps quietly turns into a helper functionThe leading indicators she pulls from call intelligence to know whether a talk track is landingWhy AI slop is the wrong thing to worry about, and who owns the pricing calculator when pricing changesThe build-versus-buy test she uses — and why she refused to vibe-code an LMS

CHAPTERS00:00 — Cold open and intro01:47 — From fourth-grade math teacher to GTM enablement04:55 — Teaching a seller to sell is teaching a kid to divide06:54 — What's actually under the iceberg08:45 — Exit slips became call recording scorecards12:54 — What actually changes by role, and what doesn't16:04 — Measuring a product launch across four teams18:47 — When the launch is over: how to find the cracks20:50 — What a QBR looks like for a technical buyer23:30 — Building the ROI case for an enablement program25:51 — Where enablement should report, and where it shouldn't30:17 — When is a company actually ready for enablement32:00 — The product marketing prerequisite36:01 — AI in enablement: what's working and what's risky39:39 — Who owns the tool when the pricing changes43:20 — Build vs. buy: why she refused to vibe-code an LMS46:50 — Cost of maintenance as the deciding test50:01 — Advice for anyone considering enablement

ABOUT THE GUESTCheyenne Griffith leads go-to-market enablement at Deepgram, the voice AI company whose speech-to-text, text-to-speech and voice agent APIs are used by more than 200,000 developers and 1,300 organizations. She started her career teaching fourth and fifth grade math, was recruited into SaaS by the learning management system she used in her own classroom, and has since built enablement from the ground up at a CRM company and an AI company.

ABOUT THE LEANSCALE PODCASTThe LeanScale Podcast is where go-to-market operators talk about how revenue actually gets built — the systems, the data, and the decisions underneath the number. Hosted by Anthony Enrico, co-founder of LeanScale.

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

#RevOps #GTM #SalesEnablement #GTMEnablement #AI #VoiceAI #Deepgram #MEDDIC #B2BSaaS #LeanScale

A senior executive at a fintech started vibe-coding a capacity model. The agent had access to the HR system. It began forecasting which women in the company were going to get pregnant.

That is a real story, told on this episode by Mark van Oppen, Chief Revenue Officer at SecureAuth — and it is not even the most alarming one. Mark has spent his career selling the least optional technology on earth: the critical-path infrastructure companies literally cannot run without. Primary seller at Blue Box Group before it sold to IBM. First go-to-market hire at Heptio, the startup founded by the creators of Kubernetes. Then a global sales team at VMware after the acquisition. Today he is leading SecureAuth into the newest and thorniest problem in identity: securing the AI agents we are all handing our access and our judgment over to.

In this conversation with LeanScale co-founder Anthony Enrico, Mark explains why identity used to be a red light, green light decision and what broke the day agents started acting on our behalf. They get into the three vectors that actually cause breaches, why the CISO became the department of no, and how you turn them into the department of yes. Then the second half turns to go-to-market: the spam cannon now sitting on every employee's desktop, whether cold email is dead, and what a $30 prospecting list says about who your best rep will be six months from now.

WHAT YOU'LL LEARNWhy one-time authentication broke the moment agents started acting on your behalfThe three vectors that actually cause AI incidents: credential theft, prompt injection, and rogue behaviorWhat continuous authority means, and why it will show up in SOC and ISO standardsHow an identity broker gives every agent its own downscoped, time-bound, attributable identityWhy the CISO became the department of no — and the specific controls that make them the department of yesThe vibe-coding C-suite problem: what happens when senior execs click through consent screensTwo real incidents: an agent inferring pregnancy from HR data, and one exposing a CEO's exit packageWhy every employee now has a spam cannon, and how over-personalized outbound became a tellHow to build pipeline in 2026 when cold outreach stopped working: anchoring everything to trust

CHAPTERS00:00 — Cold open + intro02:03 — Identity used to be red light, green light03:44 — What your employees are already doing without telling you07:05 — Three vectors: credential theft, prompt injection, rogue behavior08:36 — The CISO squeeze: becoming the department of no13:28 — Continuous authority — and who feels it first17:03 — The vibe-coding C-suite and the pregnancy forecast20:23 — The agent that exposed a CEO's exit package25:00 — Every employee now has a spam cannon28:26 — Is cold email dead? Building pipeline on trust31:10 — AEO, indexed content, and scaling the warm intro38:21 — Does AI raise the floor or 10x your best reps?40:59 — The $30 prospecting list43:13 — You can't teach give a shit

ABOUT THE GUESTMark van Oppen is Chief Revenue Officer at SecureAuth, where he leads global sales and marketing as the company takes on agentic identity — securing the AI agents now acting on behalf of employees, customers, and applications inside the world's largest enterprises. He has spent his career on critical-path infrastructure: primary seller at Blue Box Group (acquired by IBM); first go-to-market hire at Heptio, the startup founded by the creators of Kubernetes; and a global sales leader at VMware following the Heptio acquisition.

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 Mark on LinkedIn

#AI #AIAgents #AgenticAI #IdentitySecurity #CISO #Cybersecurity #RevOps #GTM #B2BSaaS #SecureAuth #LeanScale

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