The LeanScale Podcast with Anthony Enrico

Anthony Enrico
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We talk about all things RevOps, GTM, and AI.

  1. 14h ago

    The Agent Was Never the Hard Part | Kushal Sharma on the Data Layer Underneath AI

    A vendor called Kushal Sharma to tell him his $18,000 contract was now a $28,000 contract. That is normally the part of the story where the ops leader begrudgingly signs. He didn't have to — and the reason why had nothing to do with negotiation. Kushal leads the internal AI organization at Circle, a function he got to build because he had already spent two years merging Circle's data and revenue operations teams under one mandate: turn the ops people into product owners, turn the analysts into engineers, and put real architecture underneath the go-to-market motion. Medallion layers. A dbt semantic layer. Orchestration he controlled. Lineage on everything. Before Circle, he spent eight and a half years at Hootsuite, where he led the company's data organization. Then AI actually arrived — skills and agents shipped — and he was one of the very few operators in the market with something for them to operate on. Because this one goes deeper than usual, LeanScale CTO Jake Toepel joins Anthony Enrico to go layer by layer: what a semantic layer actually is, what a context graph actually does, when a vector database is worth buying, and why almost none of this is an LLM. WHAT YOU'LL LEARN How owning your orchestration layer quietly removes a vendor's pricing leverage before they ever call What a context graph does, why RAG existed before it, and why an LLM is not a store of knowledge How Circle built an AI SDR that generated close to seven figures, and what actually made it work CHAPTERS 00:00 — Cold open + intro 02:11 — The vendor call: an $18K contract becomes $28K 05:07 — Owning the data layer means owning your leverage 06:50 — What a semantic layer actually is 12:48 — The litmus test — if a human can't read it, neither can your AI 19:47 — Medallion architecture: bronze, silver, gold 26:17 — Context graphs from first principles 35:19 — "None of this is an LLM" — the software underneath 40:12 — The maturity ladder: when to actually buy a vector database 49:09 — Stop throwing your best model at a simple problem 51:33 — What it unlocks: a Slack bot in 10 minutes, and an AI SDR 1:04:27 — Relevance or support center: the choice facing RevOps 1:07:09 — Wrap ABOUT THE GUEST Kushal Sharma leads the internal AI organization at Circle, the community platform used by more than 15,000 communities. He joined Circle in 2024 to run a combined data and revenue operations function and spent two years putting real architecture underneath the go-to-market motion: medallion layers, a dbt semantic layer, orchestration the team controls outright, and lineage on everything. That foundation is what let Circle stand up an AI function when agents and skills actually shipped. Before Circle, Kushal spent eight and a half years at Hootsuite, where he led the company's data organization. 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. ▶ Subscribe for new episodes ▶ Learn more about LeanScale: https://www.leanscale.team ▶ Follow Anthony on LinkedIn ▶ Follow Jake Toepel on LinkedIn ▶ Follow Kushal on LinkedIn KEYWORDS / TAGS RevOps, Revenue Operations, GTM, GTM Engineering, AI in RevOps, AI Agents, AI Infrastructure, Semantic Layer, Context Graph, Vector Database, RAG, Medallion Architecture, Data Lineage, Data Warehouse, dbt, Analytics Engineering, Data Orchestration, LLM, Model Selection, AI SDR, Sales Operations, Salesforce, Snowflake, Circle, Hootsuite, B2B SaaS, RevOps Leadership, Data Org, LeanScale, Anthony Enrico, Jake Toepel, Kushal Sharma HASHTAGS #RevOps #GTM #AI #AIAgents #RevenueOperations #DataEngineering #AnalyticsEngineering #SemanticLayer #ContextGraph #VectorDatabase #dbt #B2BSaaS #AITransformation #LeanScale #LeanScalePodcast

  2. 1d ago

    Convert Your Entire CRM to Apex | Steve Dinner on Why the Two-Week Sprint Is Dead

    Steve Dinner came back on the show to argue against himself. The two-week sprint he once swore by is finished, and he's pulling the wires back out. Then he makes a claim most Salesforce practitioners would call heresy: you should consider converting your entire CRM to Apex. Steve is VP of Revenue Operations at Owner.com, where he runs the function with zero in-house Salesforce admins and zero developers. He came up as a BDR director who got handed RevOps, so he never built the deep technical foundation most operators lean on — which is exactly why he says agentic tooling made him a thousand times more dangerous. Over the last six months he's rebuilt how his team works: his own MCP servers, a shared context repo that syncs to every operator's machine overnight, an agent sitting at intake. In this conversation with LeanScale co-founder Anthony Enrico, Steve makes the case that when the cost of building collapses, the sprint stops serving the business, planning and testing become the expensive work, and the real job of RevOps becomes deciding what risk a change carries — not what week it ships in. Plus: the RevOps ratio he right-sized after it hit 29 to 1, how to ask a CFO for budget without being another hand out, and what's left for Salesforce once nobody wants to click through Flow Builder. WHAT YOU'LL LEARN Why the two-week sprint stopped serving RevOps — and the three-track model replacing it The case for converting your CRM to Apex, and the objections Steve calls uninspired CHAPTERS 00:00 — Cold open + intro 01:57 — Why the two-week sprint is finished 04:16 — The build got cheap. Planning and testing got expensive. 06:30 — What's left of agile, and what gets thrown away 08:00 — Walking the floor: a BDR director shipping his own Claude artifact 09:52 — Rigid business logic, democratized experience layer 12:01 — The new model: two gates and one custom app per role 14:54 — Three tracks: skin, metadata, project 20:58 — Does AI shrink the RevOps team? 24:27 — What becomes possible when three months turns into a day 25:54 — The RevOps ratio: 15:1, 25:1, and the 29:1 problem 30:37 — How to pitch a CFO for budget 33:43 — The Apex heresy 38:15 — Handing an LLM the gnarliest flow — and it finds two bugs 41:34 — A year out: does anyone still log into Salesforce? 46:17 — What is Salesforce actually worth now? 50:18 — The most AI-friendly CRM there is 54:55 — Wrap ABOUT THE GUEST Steve Dinner is the VP of Revenue Operations at Owner.com, the restaurant technology company that raised a $120M Series C at a $1B valuation and now serves more than 10,000 restaurants. He came up through sales development — a BDR director who got handed RevOps — and runs the function today with no in-house Salesforce admins and no developers, betting instead on strong process, senior generalists, and agentic tooling. This is his second appearance on The LeanScale Podcast. 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. ▶ Subscribe for new episodes ▶ Learn more about LeanScale: https://www.leanscale.team ▶ Follow Anthony on LinkedIn ▶ Follow Steve on LinkedIn KEYWORDS / TAGS RevOps, Revenue Operations, GTM, GTM Engineering, Salesforce, Salesforce Apex, Apex, Flow Builder, Salesforce MCP, MCP Server, Model Context Protocol, Claude, Claude Code, AI Agents, Agentic AI, AI in RevOps, Agile, Two Week Sprint, Change Management, Sales Operations, Sales Enablement, MEDDIC, CRM, CRM Strategy, RevOps Ratio, RevOps Budget, CFO, CRO, B2B SaaS, Owner.com, LeanScale, Anthony Enrico, Steve Dinner HASHTAGS #RevOps #GTM #AI #Salesforce #Apex #RevenueOperations #AIAgents #MCP #Agile #B2BSaaS #CRM #AITransformation #LeanScale #LeanScalePodcast

  3. 2d ago

    You Can't Get Promoted Until You Replace Yourself | Cole Gillespie, CRO at Branch

    Cole Gillespie's boss told him he could have the sales leadership job — right after he replaced himself. So he sat down and tried to write out what he actually did all day. He expected to find charisma. He found a recipe. Cole is the Chief Revenue Officer at Branch, the workforce payments platform. He started out selling commercial loans to dentists, opened a Texas territory from zero, and was running the sales team by 27. He spent more than a decade leading sales and BD for Bank of America's small business unit, ran BD at LendingClub as it went public, and took Beam Benefits from under $10M to $120M in revenue as CRO. He has guest lectured at MIT Sloan and still teaches Ohio State sales majors, because he thinks every college should have a sales program. In this conversation with LeanScale co-founder Anthony Enrico, Cole makes the case that sales is a teachable craft — and gets specific about what that means for the people you manage. The three-hour callback SLA. The career obituary. Why the leader who has to be asked for the raise already lost. And the lesson he wishes someone had told him at 30: once your basic needs are met, every promotion stops being a step and starts being a trade. WHAT YOU'LL LEARN How to replace yourself on paper — the exercise that turns a top rep into a repeatable playbook CHAPTERS 00:00 — Cold open + intro 01:52 — "You can't leave this job until you replace yourself" 03:12 — Writing the recipe for a sales rep 05:16 — How much of sales is process versus personality 05:44 — Capitulation: when a rep stops copying and starts owning 08:08 — The trap of hiring for personality 14:33 — The career obituary 18:00 — Turning "responsive" into a three-hour SLA 21:36 — The four things you should expect off the elevator 25:01 — OKRs at the VP level, activity at the rep level 29:36 — Paying fairly when your best rep joined at the bottom of the band 36:39 — The raise nobody asked for 42:10 — Resourcing the job — the fourth thing, and the one leaders skip 49:30 — Respect, friction, and the "no assholes policy" problem 57:18 — Dad Wisdom 1:00:09 — When a career stops being survival and becomes a choice 1:04:00 — The cocktail: comp, title, industry, people, impact 1:12:00 — "Why do you want to be a CRO?" 1:13:39 — Wrap ABOUT THE GUEST Cole Gillespie is the Chief Revenue Officer at Branch, the workforce payments platform powering fast, flexible pay for W-2 and 1099 workforces. He started out selling commercial loans to dentists, opened a Texas territory from zero, and was running the sales team by 27. He spent more than a decade at Bank of America leading sales and BD for its small business unit, then ran BD at LendingClub as it went public. He later served as CRO at Beam Benefits, helping take it from under $10M to $120M in revenue. He has guest lectured at MIT Sloan and still teaches sales majors at Ohio State, because he believes every college should have a sales program. 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 led. ▶ Subscribe for new episodes ▶ Learn more about LeanScale: https://www.leanscale.team ▶ Follow Anthony on LinkedIn ▶ Follow Cole on LinkedIn KEYWORDS / TAGS Sales Leadership, Sales Management, Chief Revenue Officer, CRO, RevOps, GTM, Sales Enablement, Sales Playbook, Sales Coaching, Sales Hiring, Sales Compensation, People Management, B2B SaaS, Fintech, Workforce Payments, Branch, Beam Benefits, MIT Sloan, Ohio State, LeanScale, Anthony Enrico, Cole Gillespie HASHTAGS #SalesLeadership #RevOps #GTM #CRO #SalesManagement #SalesEnablement #SalesCompensation #B2BSaaS #Fintech #Leadership #PeopleManagement #SalesCoaching #CareerAdvice #LeanScale #LeanScalePodcast

  4. 5d ago

    Balance Is the Wrong Goal: Fixing Burnout in RevOps | Joe Mosely, Coactive AI

    Every time someone told Joe Mosely to find work-life balance, he was already underwater. His reaction was always the same: easier said than done. In this episode, the VP of GTM Strategy and Operations at Coactive AI makes a quietly contrarian case — that balance is the wrong goal, because it sounds like a destination and gives you nothing to do on Monday. What actually changed for him was realizing he'd spent years trying to solve an energy problem with his calendar. Joe has spent more than a decade in go-to-market — marketing for Peter Diamandis, GTM strategy and demand gen at Okera up to the Databricks acquisition, and RevOps at Krisp. Here he walks LeanScale co-founder Anthony Enrico through the day it broke, the three tactics that actually stuck, why RevOps people fail by over-indexing on the wrong things rather than by working too little, and what he's changing now with his first child due in November. WHAT YOU'LL LEARN Why "work-life balance" fails as advice — and the question that replaces it How to tell an energy problem from a calendar problem before it costs you a year Ruthless prioritization, the two work streams every RevOps board needs, and why RevOps are "undefendable truth tellers" CHAPTERS 00:00 — Cold open and intro 01:24 — Why "balance" is the wrong goal 02:22 — An energy problem he'd been solving with a calendar 04:53 — The day it broke: caffeine, weekends, and a bad day on the couch 07:08 — "I don't know that you will" — his wife calls the pattern 09:15 — Tactic 1: Google's 20% rule, rewired for RevOps 11:02 — Why RevOps people fail: over-indexing on the wrong things 12:45 — Tactic 2: sleep and exercise as non-negotiables 14:05 — Tactic 3: therapy before you need it 15:16 — Is this a luxury you earn through the grind? 17:52 — The mentor's advice: poise, presence, accountability 19:16 — Marathons, not sprints — and the beast mode button 21:01 — Seasonality: when being unbalanced is the right call 23:52 — The to-do list that would take ten years 25:06 — He never learned to say no — he learned to prioritize 25:21 — The two work streams: ad hoc vs. roadmap 27:52 — "In RevOps we are undefendable truth tellers" 29:40 — A baby girl in November, a half marathon in October 31:25 — His boss's framing on parental leave 33:33 — Covering the seat while RevOps is out on leave 35:45 — Wrap ABOUT THE GUEST Joe Mosely is the VP of GTM Strategy and Operations at Coactive AI, the multimodal AI platform that turns enterprise video and image libraries into searchable, monetizable intelligence. Over more than a decade in go-to-market, he has built the engines behind Krisp and Okera — where he led GTM strategy and demand generation up to the company's acquisition by Databricks, generating eight-figure inbound pipeline along the way. Earlier he ran marketing strategy directly for Peter Diamandis, who called him a future CMO. He contributes to the RevOps Co-op community and holds a B.B.A. in Marketing from San Francisco State University. 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. ▶ Subscribe for new episodes ▶ Learn more about LeanScale: https://www.leanscale.team ▶ Follow Anthony on LinkedIn ▶ Follow Joe on LinkedIn: https://www.linkedin.com/in/joe-mosely/ KEYWORDS / TAGS RevOps, Revenue Operations, GTM, RevOps Burnout, Work Life Balance, Career Sustainability, Ruthless Prioritization, Google 20% Rule, RevOps Leadership, Parental Leave, Mental Health in Tech, Coactive AI, Krisp, Okera, Databricks, RevOps Co-op, B2B SaaS, LeanScale, Joe Mosely HASHTAGS #RevOps #GTM #RevenueOperations #Burnout #WorkLifeBalance #Prioritization #RevOpsLeadership #RevOpsCareer #MentalHealth #B2BSaaS #StartupOperations #CoactiveAI #LeanScale #LeanScalePodcast

  5. 6d ago

    What RevOps Should Look Like at Every Stage | Hassan Irshad, Head of RevOps at Unify

    "If you have RevOps that just agrees with everything a CRO says and executes — you're a ticketing center. You're not strategic." Hassan Irshad has spent nearly a decade in RevOps — about as long as anyone can honestly claim, because that's roughly when the function was born. He's Head of Revenue Operations at Unify, the AI-native GTM company backed by Battery Ventures and the OpenAI Startup Fund. Before that he ran RevOps at Fundraise Up, where he migrated a CRM from HubSpot to Salesforce in under three months and passed an external audit with the highest score in his category. In this conversation with LeanScale co-founder Anthony Enrico, Hassan gets tactical: exactly what a RevOps team should look like at Series A, Series B–D, and after IPO — who you hire, in what order, and why the impressive resume from an IPO company is usually the wrong first hire. Then the AI half: why the context layer is the real moat, how a confidently wrong churn rate spreads through a company in three days, and the agents he's running to take grunt work off his reps' plates. WHAT YOU'LL LEARN What a RevOps org should actually look like at Series A, Series B–D, and post-IPO — and the exact hiring order How AI made RevOps more relevant, not less, and where AI without governance spreads bad data faster than insight CHAPTERS 00:00 — Cold open + intro 02:07 — Building the car while it's already going 100 miles an hour 04:20 — The small boat vs. the cruise ship 06:45 — Why every new VP of Sales rewrites the sales stages 09:56 — "If RevOps just executes, you're a ticketing center" 12:27 — The comp model for a company with no contracts 16:06 — How usage-based pricing breaks quotas, territories, and comp 19:04 — Timestamping account moves so comp survives mid-month 22:55 — Predicting ARR from 60 days of usage data 26:54 — Top-down vs. bottoms-up quota setting 30:03 — The RevOps unicorn problem 30:56 — Series A: hire the generalist, not the admin 34:28 — Twenty Salesforce admins and the case for structured chaos 35:32 — Series B to D: board meetings and data you can trust 38:07 — The two hires that make a RevOps leader strategic 40:02 — Post-IPO: specialization, signed comp plans, and the sandbox debate 46:20 — Should RevOps hold its own budget? 47:40 — The thankless job — your best day is a boring day 49:40 — The $120k call-prep agent 53:20 — The Formula One pit crew — and who designs the car 56:59 — Stop asking what the ROI of the agent is 1:00:43 — Is AI making RevOps irrelevant or essential? 1:03:19 — Confidently wrong: how AI spreads bad data faster 1:07:19 — Flip the question: what's the cost of NOT having RevOps? 1:09:13 — Wrap ABOUT THE GUEST Hassan Irshad is Head of Revenue Operations at Unify, the AI-native go-to-market platform backed by Battery Ventures and the OpenAI Startup Fund. He has spent nearly a decade in RevOps — from analyst to head of function — building revenue operations from zero to one at VC- and PE-backed startups and scaling through to IPO stage. Before Unify he led RevOps at Fundraise Up, where he migrated the company off HubSpot to Salesforce in under three months and passed an external RevOps audit with the highest score in its category. He is also the founder of RevInfinity, where he advises companies on building revenue engines that function cross-functionally. 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. ▶ Subscribe for new episodes ▶ Learn more about LeanScale: https://www.leanscale.team ▶ Follow Anthony on LinkedIn ▶ Follow Hassan on LinkedIn KEYWORDS / TAGS RevOps, Revenue Operations, GTM, AI in RevOps, AI Agents, Sales Compensation, Salesforce, Series A, IPO, Unify, LeanScale, Hassan Irshad

  6. Sep 9

    Outbound Isn't Dying. Yours Is. | Joey Gilkey on Why 8,000 Dials Beat 200,000

    Two teams ran the same outbound motion. One made 200,000 dials over eleven months; the other made 8,000. The 8,000-dial team generated 25% more meetings — and when Joey Gilkey pulled the call logs apart to show why, people got fired. Joey is the founder and CEO of TitanX. In 2023 he bought a piece of obscure intellectual property to build a moat around Apex Revenue, his $6.5M services business. Six months later he realized the moat was worth more than the castle it was protecting — so he turned the castle off and started a software company at zero. That bet became TitanX, bootstrapped until this January's $27 million Series A led by Updata Partners, followed by the eight-figure acquisition of the dialer FrontSpin. In this conversation with LeanScale co-founder Anthony Enrico, Joey breaks down the reach rate almost nobody measures, the four pillars that decide whether outbound works, the MDR role he invented — an SDR who isn't allowed to book meetings — and the clearest framework we've heard all year for where AI belongs in a sales motion and where it does not. WHAT YOU'LL LEARN Why 8,000 single-line dials beat 200,000 parallel dials by 30x — the full case study, with the numbers Why you shouldn't trust your data provider, and what AI dossiers get wrong that conversations get right CHAPTERS 00:00 — Cold open + intro 01:58 — Turning off a $6.5M business to start over at zero 04:18 — The moat is worth more than the castle it's protecting 06:47 — Why he bet the house on the phone 09:41 — The only outbound channel that talks back 11:24 — The four pillars: list, messaging, rep, follow-up 14:59 — Anatomy of a cold call script 18:54 — Don't be memorable until it's time to be memorable 20:37 — The list is the strategy — don't trust your data provider 23:42 — AI dossiers vs. what people actually tell you 25:54 — Infantry to special forces: rebuilding the SDR org 30:40 — The MDR: an SDR who isn't allowed to book meetings 35:07 — The reach rate: why you'll only ever reach 200 of 1,000 39:47 — Voicemail, AI screeners, and burning your shot 43:55 — Outbound is not dying — but yours is 46:06 — Where AI belongs: the restaurant analogy 52:27 — What can't be automated out of the front of house 55:58 — The two camps: volume vs. precision 57:05 — The 30x case study: 200,000 dials vs. 8,000 01:00:42 — Why parallel dialing breaks: the bridge and the carriers 01:05:15 — Preparation is the real edge 01:08:49 — Where to find Joey and TitanX ABOUT THE GUEST Joey Gilkey is the founder and CEO of TitanX, the phone intent intelligence platform that tells sales teams who will actually pick up before they hit dial. His career ran from capital raising into enterprise tech sales, up through two VP of Sales seats and into the CRO chair, before he went out on his own in 2017 and began stacking companies. In 2023 he built a moat around Apex Revenue, his $6.5M fractional VP of Sales firm, then shut it down to build software at zero. TitanX was bootstrapped until January 2026's $27 million Series A led by Updata Partners, alongside the eight-figure acquisition of dialer FrontSpin. Joey lives on a 70-acre ranch in Tennessee. 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. ▶ Subscribe for new episodes ▶ Learn more about LeanScale: https://www.leanscale.team ▶ Follow Anthony on LinkedIn ▶ Follow Joey on LinkedIn: https://www.linkedin.com/in/joeygilkey/ ▶ TitanX: https://titanx.io KEYWORDS / TAGS Outbound Sales, Cold Calling, Phone Intent, Precision Outbound, Parallel Dialing, Reach Rate, Sales Dialer, SDR, MDR, RevOps, GTM, AI in Sales, AI SDR, TitanX, FrontSpin, B2B SaaS, Enterprise SaaS, CRO, LeanScale, Anthony Enrico, Joey Gilkey

  7. Sep 8

    Forward Deployed Engineers Are Just Professional Services | Aimee Menne, CRO at Sourcegraph

    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. ▶ Subscribe for new episodes ▶ Learn more about LeanScale: https://www.leanscale.team ▶ Follow Anthony on LinkedIn ▶ Follow Aimee on LinkedIn 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

  8. Sep 7

    Why Enablement Fails Before It Starts | Cheyenne Griffith, Deepgram

    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

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