The LeanScale Podcast with Anthony Enrico

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

  1. 1d ago

    The AI Hiring Echo Chamber Is Breaking Sales | Melissa McCann-Tilton, CRO at Criteria

    Melissa McCann-Tilton got into sales for a reason almost nobody says out loud: she needed a metric. A number was the one credential nobody could argue with — and it's how she stayed in every room she wanted to be in. Today she's President and Chief Revenue Officer at Criteria, the pre-employment assessment platform used by more than 4,000 organizations. Before that she ran revenue as CRO at Convoy and Chief Sales Officer at Payscale, and led go-to-market across automotive software at CDK Global, ADP, and Reynolds and Reynolds. In this conversation with LeanScale co-founder Anthony Enrico, Melissa breaks down the AI hiring echo chamber — candidates using AI to apply to every job, applicant tracking systems that only like resumes written by AI, and why nearly half of new hires now fail. Then she gets into what she does instead: redesigning the SDR job, testing candidates in the room, why your inbound lead is already an order, and why softness is not weak. WHAT YOU'LL LEARN Why a number is the one credential nobody can argue with — and why it cuts both ways How AI is industrializing old GTM processes instead of redesigning them What's actually keeping women out of CRO seats and sales roles The AI hiring echo chamber: AI-written applications, AI screening, and fake candidates Why nearly half of new hires fail between six and 18 months — and what it does to your number Why your inbound lead is already an order — and why the new motion breaks old sales-cycle math CHAPTERS 00:00 — Cold open + intro 01:48 — "Melissa's going to do it": the meeting that pushed her into sales 06:37 — The double-edged sword and the 18-month CRO 08:27 — What's keeping women out of the CRO seat 12:46 — AI SDR tools and redesigning the SDR job 19:32 — The AI hiring echo chamber 23:46 — The system of effort: why half of hires fail 26:35 — More talent signals — and homework done in the room 31:09 — The SaaS playbook isn't working anymore 32:59 — Your inbound lead is an order 36:07 — Showing up in the LLMs — and the Reddit strategy 42:08 — Has it gotten better for women in GTM? 46:17 — Fear and intimidation vs. strength and softness 54:28 — Wrap ABOUT THE GUEST Melissa McCann-Tilton is President and Chief Revenue Officer at Criteria, the talent signal platform more than 4,000 organizations use to hire beyond the resume. Over two decades running revenue at the top of the house, she has served as Chief Revenue Officer at Convoy and Chief Sales Officer at Payscale, and led go-to-market across automotive software at CDK Global, ADP, and Reynolds and Reynolds. She is a two-time published author and speaks regularly on hiring, leadership, and women in go-to-market. 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 Melissa on LinkedIn KEYWORDS / TAGS RevOps, Revenue Operations, GTM, Go-to-Market, GTM Strategy, AI, AI in Sales, AI in Hiring, AI Recruiting, AI SDR, AI Agents, Sales Operations, Sales Enablement, Sales Hiring, Sales Leadership, CRO, Chief Revenue Officer, Women in Sales, Women in GTM, Women in Tech, SDR, BDR, Outbound, Inbound Leads, ATS, Pre-Employment Assessments, Talent Signals, Hiring, Recruiting, Fake Candidates, Sales Interview, Thought Leadership, Reddit Marketing, LLM Visibility, AEO, B2B SaaS, SaaS Playbook, Criteria, Convoy, Payscale, CDK Global, ADP, Reynolds and Reynolds, Gong, Claude, LeanScale, Anthony Enrico, Melissa McCann-Tilton HASHTAGS #RevOps #GTM #AI #AIinHiring #AIinSales #SalesLeadership #CRO #WomenInSales #Hiring #SDR #B2BSaaS #SalesHiring #ThoughtLeadership #LeanScale #LeanScalePodcast

  2. 3d ago

    Confidence Is a Metric: The Enablement Survey That Ties Training to Revenue | Chad Trabucco

    Every enablement leader eventually gets the same question from a CFO: what is this team actually worth? Chad Trabucco has an answer, and it starts with a number most enablement teams never measure: how confident the reps feel. Chad leads enablement business partner strategy and activation at Boomi, where his team of enablement partners sits inside commercial, enterprise, solutions engineering and customer success. He was the founding enablement hire at Glint, helping take the company from roughly $1M in ARR to about $60M at its acquisition by LinkedIn, ran Glint's win-loss program for four straight years, then built enablement from zero at Dixa and at Guru. In this conversation with LeanScale co-founder Anthony Enrico, Chad breaks down the quarterly confidence survey he runs on reps and managers, why enablement should invest in frontline managers as much as reps, the leading metrics that tie training to conversion rate, ACV and win rate, what a fully ramped rep actually looks like, and why AI role play is the new warm-up before a live call. WHAT YOU'LL LEARN How to run a quarterly rep-confidence survey and turn it into a leading metric enablement can actually move Why the fundamentals slip, and the "seven times, seven ways" rule for making training stick How to enable frontline managers: a written process, deal "green lights," coach camps and always-on coaching alerts How AI mentions went from 20% to 60% of calls at Guru, and what happened to ACV over the same stretch CHAPTERS 00:00 — Cold open + intro 01:55 — The confidence survey: a leading metric enablement can control 06:01 — Surveying managers too, and what to do when the scores disagree 18:28 — Why enablement has to invest in managers 23:08 — Green lights, coach camps and always-on coaching 29:55 — AI mentions from 20% to 60% of calls, and ACV doubled 33:30 — One point of conversion = $1M 38:49 — The enablement data cockpit 54:23 — AI role play: stretching before the sprint 58:22 — Wrap ABOUT THE GUEST Chad Trabucco is Director of Enablement Business Partner Strategy and Activation at Boomi, where he leads a global team of enablement partners embedded in commercial, enterprise, solutions engineering and customer success. He got into enablement about 11 years ago by answering RFPs, which led to his role as the founding enablement hire at Glint. There he helped take the company from roughly $1M in ARR to about $60M at its acquisition by LinkedIn, and ran the win-loss program for four straight years. After seeing enablement at LinkedIn scale, he built the function from zero at Dixa and at Guru, where he was such a vocal customer that the team nicknamed him "the Chadvocate" before he ever joined. 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 Chad on LinkedIn ▶ Learn more about Boomi: https://boomi.com KEYWORDS / TAGS Sales Enablement, Revenue Enablement, Enablement Metrics, Enablement ROI, Rep Confidence, Confidence Survey, Win-Loss Analysis, Competitive Win Rate, Sales Onboarding, Ramp Time, Sales Coaching, Frontline Managers, Manager Enablement, Sales Methodology, Persona Training, AI Role Play, AI Sales Coaching, Conversation Intelligence, Gong, Leading Indicators, Conversion Rate, Win Rate, ACV, Sales Kickoff, RevOps, GTM, AI, AI Agents, Sales Leadership, B2B SaaS, Boomi, Glint, LinkedIn, Guru, Dixa, LeanScale, Anthony Enrico, Chad Trabucco HASHTAGS #RevOps #GTM #AI #LeanScale #LeanScalePodcast #SalesEnablement #RevenueEnablement #SalesCoaching #SalesOnboarding #WinLoss #SalesLeadership #AIinSales #B2BSaaS #Boomi

  3. 6d ago

    What Needs to Be True? The Question That Changed How a CRO Leads | Nick Reyes, PushPress

    Most revenue leaders ask "how do we hit the number?" Nick Reyes asks "what needs to be true?" — and the difference between those two questions is the whole episode. Nick skipped college out of one of the top prep schools in the country to join the Marine Corps. He moved into enterprise sales at Caterpillar's rail division and grew an inherited ~$500K territory past $20M a year. Then he walked away for equity and almost no salary to become the first salesperson at PushPress, the gym management platform built by gym owners for gym owners. Nearly a decade later, he's the company's Chief Revenue Officer. In this conversation with LeanScale co-founder Anthony Enrico, Nick gets into the RevOps investment he wishes he'd made years earlier, the signal that tells you you're past due, how RevOps is shifting from building tools to building guardrails, why the modern CRO has to be both a builder and a seller, the 5 a.m. habit that made him fluent in his company's financial model, and the one question that's changed how his team solves problems. WHAT YOU'LL LEARN Why "what needs to be true?" opens up options that "how do we get there?" never will When to make your first RevOps hire — and the signal that you're already past due How RevOps is shifting from building the castle to building the guardrails around the sandbox The 5 a.m. habit that made a CRO fluent in LTV to CAC, CAC payback, and the financial model CHAPTERS 00:00 — Cold open + intro 01:08 — Skipping college for the Marine Corps 14:47 — Early days: selling software to a "we don't use software" market 25:06 — When to invest in RevOps — and the signal you're past due 27:46 — How RevOps is changing: guardrails, not castles 44:16 — "What needs to be true?" 54:59 — Wrap + Nick's ask: drop into a local gym ABOUT THE GUEST Nick Reyes is the Chief Revenue Officer at PushPress, the gym management platform built by gym owners for gym owners. A Marine Corps veteran who skipped college out of one of the top prep schools in the country, Nick started in sales at Sprint before moving into public-sector sales of in-car digital video systems for police departments, then moved into enterprise sales at Caterpillar's rail division, where he grew an inherited ~$500K territory past $20M a year in hardware and software sales. After helping rescue his local CrossFit gym, he met the PushPress founders and left Caterpillar for equity and almost no salary to become the company's first salesperson. Over nearly a decade he has owned sales, customer experience, and marketing on the way to CRO. He is based in Kansas City. 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 Nick on LinkedIn ▶ Learn more about PushPress: https://www.pushpress.com KEYWORDS / TAGS RevOps, Revenue Operations, GTM, Go-to-Market, GTM Engineering, AI, AI in RevOps, AI Agents, AI Voice Agents, Sales Operations, Marketing Operations, Sales Enablement, Pipeline Forecasting, First Principles Thinking, What Needs to Be True, CRO, Chief Revenue Officer, Financial Literacy, LTV to CAC, CAC Payback, Sales Compensation, SDR, Outbound, SDR to AE Career Path, Sales Hiring, Vertical SaaS, B2B SaaS, SMB SaaS, Gym Management Software, Fitness Software, PushPress, CrossFit, Mindbody, Caterpillar, Enterprise Sales, Marine Corps, Veterans in Sales, Leadership, Endurance, Founder Journey, LeanScale, Anthony Enrico, Nick Reyes HASHTAGS #RevOps #GTM #GoToMarket #AI #RevenueOperations #CRO #SalesLeadership #SalesOperations #VerticalSaaS #B2BSaaS #SDR #FirstPrinciples #Leadership #Veterans #PushPress #LeanScale #LeanScalePodcast

  4. Oct 28

    The CRO Who Wasn’t in the Board Meeting | Christian Miller, TechCXO

    In a private equity–backed board meeting, roughly 80% of the conversation is about sales. So why is the CRO so often not in the room? Christian Miller calls it the biggest red flag in the job. Christian has spent his career walking into revenue organizations when something isn't working. He led corporate payments sales at U.S. Bank, was part of the team that grew Electronic Funds Source from $27M to $89M in EBITDA ahead of a roughly $1.5B exit, and has been Chief Revenue Officer at Motus and Global CRO at HRS Group. Today he's a partner in TechCXO's Revenue Growth practice and the founder of Florian Growth Advisors. In this conversation with LeanScale co-founder Anthony Enrico, Christian breaks down how a CRO earns the trust of the CEO and the board: the data that has to sit underneath it, why pipeline coverage only means something by segment, the founder-led snapback that stalls companies after they raise, and how to use AI without letting your message turn into fifty versions of the same deck. WHAT YOU'LL LEARN Why a CRO who isn't in the board meeting is a red flag, and what it costs in follow-up afterward How Christian diagnosed a hidden payments business in 60 days and handed the CEO and CFO three options Why pipeline coverage has to be read by segment and by stage, not in aggregate The founder-led snapback: why companies drift back to founder-led sales after they raise CHAPTERS 00:00 — Intro 01:59 — Sixty days to diagnose a hidden payments business 19:38 — Why the CRO belongs in the board meeting 31:33 — The founder-led snapback 41:53 — Pipeline, AI tools and hiring in 2026 52:57 — Wrap ABOUT THE GUEST Christian Miller is a partner in TechCXO's Revenue Growth practice, where he works as a fractional CRO with private equity– and venture-backed companies, and the founder of Florian Growth Advisors. He started his career carrying a bag at GE Capital, led corporate payments sales at U.S. Bank, and was part of the team at Electronic Funds Source (EFS) that grew EBITDA from $27M to $89M ahead of a roughly $1.5B exit. He has since been Chief Revenue Officer at Motus and Global CRO at HRS Group, held senior leadership roles at Perforce Software and Tricentis, and co-founded companies including Dealer Teamwork and CAMP Digital, which Tonka Bay Equity Partners acquired in 2026. He holds an MBA from the University of Notre Dame. 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 Christian on LinkedIn: https://www.linkedin.com/in/christian-miller-092bb23/ ▶ Work with Christian at TechCXO: https://www.techcxo.com/partners/christian-miller/ KEYWORDS / TAGS RevOps, Revenue Operations, GTM, Go-to-Market, CRO, Chief Revenue Officer, CEO, Board of Directors, Board Meetings, Board Reporting, Private Equity, PE-Backed Companies, Venture Capital, Revenue Transformation, Fractional CRO, Fractional Executives, TechCXO, Florian Growth Advisors, Founder-Led Sales, Sales Leadership, Sales Operations, Sales Forecasting, Pipeline Coverage, Pipeline Generation, Conversion Rates, Sales Cycle, MEDDPICC, Sales Enablement, Discounting, Channel Partnerships, Strategic Partnerships, Payments, Fintech, Corporate Payments, Fleet Payments, Electronic Funds Source, U.S. Bank, American Express, Motus, HRS Group, Tricentis, AI, AI in Sales, AI Agents, B2B SaaS, Enterprise SaaS, LeanScale, Anthony Enrico, Christian Miller HASHTAGS #RevOps #GTM #GoToMarket #AI #LeanScale #LeanScalePodcast #CRO #ChiefRevenueOfficer #SalesLeadership #BoardOfDirectors #PrivateEquity #FractionalCRO #FounderLedSales #SalesForecasting #RevenueOperations #B2BSales #Fintech #TechCXO

  5. Oct 27

    Fall in Love With the Buyer, Not the Product | Triple Whale CRO Zach Rego

    Most sales careers chase the hottest product. Zach Rego picks the buyer first, and he thinks it's a big part of why his teams win. Four and a half years ago, Zach joined Triple Whale as its first head of sales. What he got was an Airtable of 2,000 waitlist names, no enrichment, no playbook, and one rep he brought with him from his last job. Between the two of them they ran roughly 250 demos in the opening sprint. Today he's Chief Revenue Officer of the AI operating system for commerce used by 60,000+ brands, leading roughly 40 reps across the US and international markets plus partnerships, SDRs and marketing. He's still on demos every week. In this conversation with LeanScale co-founder Anthony Enrico, Zach breaks down why a CRO should still sell every major launch (and how to do it without stepping on the AE's deal), what Triple Whale learned across several rounds of AI pricing, why credits quietly inhibited usage, how he hires reps who will bang their head against the wall for 90 days, and why personalization now has to go "to the craziest degree" to build pipeline. WHAT YOU'LL LEARN What to actually do on day one when you're handed 2,000 names and no data Why the CRO should still sell new products, and the division of labor that keeps the AE in the deal How Triple Whale moved from credits to good-better-best pricing for AI, and why credits inhibited usage Fall in love with the buyer, not the product: the career case for staying in one pond CHAPTERS 00:00 — Cold open + intro 01:26 — Day one: an Airtable of 2,000 names and one rep 06:14 — Why the CRO still takes demos 13:59 — How to price AI when the economics have changed 20:09 — Why they hired a head of pricing and packaging 23:14 — Fall in love with the buyer, not the product 27:57 — Chasing the hot product vs. staying in one pond 31:08 — Hiring: why the first reps came from his network 36:19 — Interview red flags: job hops, no progression, severance asks 44:04 — AI in GTM: top-down or bottoms-up? 46:47 — Personalization to the craziest degree 51:21 — Wrap ABOUT THE GUEST Zach Rego is the Chief Revenue Officer at Triple Whale, the AI operating system for commerce used by more than 60,000 brands, where he leads sales, partnerships and marketing. He joined four and a half years ago as the company's first head of sales, starting from an Airtable of 2,000 waitlist names, and has built the revenue org from two sellers to roughly 40 reps across SMB, mid-market, enterprise and international markets. Before Triple Whale, Zach spent seven years at WordStream, rising from individual rep to general manager of the global agency business, and then led sales and marketing at Unstack, later acquired by Elastic Path. He started his career in IT consulting services, selling to Fortune 500 CIOs. 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 Zach on LinkedIn KEYWORDS / TAGS RevOps, GTM, GTM Engineering, AI, AI Pricing, AI Pricing and Packaging, Pricing Strategy, Usage-Based Pricing, Credit-Based Pricing, Good Better Best Pricing, Token Pricing, AI Margins, AI Agents, Sales Operations, Sales Enablement, Sales Leadership, CRO, Chief Revenue Officer, Sales Hiring, Sales Coaching, Peer Coaching, Pipeline Generation, Outbound, Personalized Gifting, Data Enrichment, HubSpot, Airtable, Ecommerce, DTC, Shopify, Triple Whale, WordStream, Unstack, Elastic Path, B2B SaaS, LeanScale, Anthony Enrico, Zach Rego HASHTAGS #RevOps #GTM #AI #LeanScale #LeanScalePodcast #SalesLeadership #CRO #AIPricing #PricingStrategy #SalesHiring #SalesCoaching #Ecommerce #DTC #TripleWhale #B2BSaaS

  6. Oct 23

    No SDRs, Still Growing: How a CRO Builds Pipeline in 2026 | Xander Kotsatos, CRO at Aqfer

    In sales, the most important thing is hitting your number. Xander Kotsatos says the second most important thing is being right about whether you will — because a quarter you blow out without seeing it coming breaks the same feedback loop as a miss. Xander is Chief Revenue Officer at Aqfer, running sales, customer success and technical solutions at the same time for the first time in his career. He was the first East Coast trader at what became one of the largest demand-side platforms, lived through an IPO, an acquisition, a private-equity rollup and a bankruptcy inside a single company, and helped lead sales at Beeswax through its exit to Comcast. Today he sells data infrastructure with no SDRs on the team. In this conversation with LeanScale co-founder Anthony Enrico, Xander breaks down what changes when one leader owns the whole go-to-market org, why sales should narrow its focus while CS and solutions widen theirs, what replaced volume outbound, why AI slop is making curation more valuable, and where he draws the line on AI — including why his sales reps don't use it to write proposals. WHAT YOU'LL LEARN Why being right about your forecast matters almost as much as hitting it How Aqfer grew new business year over year with no SDRs Why AI slop is making trusted curators and good content more valuable, not less Where Xander lets AI in, where he keeps it out, and why AI can't be accountable CHAPTERS 00:00 — Intro: Xander Kotsatos, CRO at Aqfer 07:22 — Owning sales, CS and solutions for the first time 13:22 — Hit the number, then be right about whether you will 23:33 — Growing without SDRs: "I want to be your best SDR" 39:40 — AI can't be accountable: Waymo vs. LLMs 51:18 — Wrap ABOUT THE GUEST Xander Kotsatos is Chief Revenue Officer at Aqfer, a marketing data platform that helps enterprises unify, process and activate customer and marketing data inside their existing cloud, where he runs sales, customer success and technical solutions. Xander graduated into the 2009 recession, talked his way into an internship at an Omnicom-owned PR agency, and went on to become the first East Coast trader at what became one of the largest demand-side platforms. He has since lived through an IPO, an acquisition, a private-equity rollup and a bankruptcy inside a single company, helped lead sales at Beeswax through its 2021 acquisition by Comcast's FreeWheel, and held sales leadership roles at Comcast before joining Aqfer. 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 Xander on LinkedIn ▶ Learn more about Aqfer: https://aqfer.com KEYWORDS / TAGS RevOps, Revenue Operations, GTM, Go-to-Market, CRO, Chief Revenue Officer, Sales Leadership, Customer Success, Solutions Engineering, Sales Engineering, SDR, SDR Team, Outbound, Pipeline Generation, Sales Forecasting, Forecast Accuracy, Pipeline Forecasting, AI, AI in Sales, AI Agents, AI Slop, Sales Operations, Sales Enablement, Sales Proposals, Ad Tech, Martech, Programmatic Advertising, Demand-Side Platform, DSP, Data Infrastructure, Marketing Data Platform, Connected TV, Event-Led Growth, Conference Strategy, Content Curation, Streaming, Advertising Week, Aqfer, Comcast, FreeWheel, Beeswax, HubSpot, Grain, SalesIntel, Claude, Waymo, B2B SaaS, Enterprise SaaS, Series A, GTM Strategy, GTM Engineering, LeanScale, Anthony Enrico, Xander Kotsatos HASHTAGS #RevOps #GTM #GoToMarket #AI #LeanScale #LeanScalePodcast #ChiefRevenueOfficer #SalesLeadership #CustomerSuccess #SalesForecasting #Outbound #SDR #AdTech #MarTech #DataInfrastructure #B2BSaaS #AIinSales #Aqfer

  7. Oct 22

    BDRS Are Earned: Don’t Build GE at $10M | Ari Greenberg, CRO of Ascend Analytics

    A startup's biggest advantage over GE is that it can move at light speed: turn on a trial instantly, turn a contract around in a day, let the people closest to the customer make the call. Most companies give that advantage away years too early — with a deal desk at $10M, approval chains for trials, and a BDR for every rep on day one. Ari Greenberg is Chief Revenue Officer at Ascend Analytics, whose forecasts inform more than $50 billion in energy project financing and procurement evaluations. He started out as a systems specialist at Reuters and went on to lead sales at SNL Energy through its sale to S&P Global, then at S&P Global, AlphaSense and ZEMA Global. He has run go-to-market at almost every stage of growth. In this episode Ari and Anthony Enrico go stage by stage: what to leave out early, when the deal desk finally earns its keep, why BDRs should be earned, how a tiered commission plan keeps top reps and lets the rest leave on their own, why the trial that breaks can be the one you win, and what selling looks like when your buyer has the same AI you do. WHAT YOU'LL LEARN Why adding process too early gives away the one advantage a small company has: speed Why Ari argues you don't need a formal deal desk under roughly $20M ARR, and what a light version looks like at $50M How a tiered commission plan (2% on the first $100K up to 20% above quota) keeps top performers and lets the rest leave on their own How a proof of concept that crashed in the middle of the night won a long-term customer Why Ari leaves renewal price increases out of the contract, and what changes when buyers have AI too CHAPTERS 00:00 — Intro: Ari Greenberg, CRO of Ascend Analytics 01:57 — Don't engineer your company to be GE at $10M 04:30 — You don't need a deal desk under $20M ARR 07:53 — Playing business too early: marketing spend and BDRs 10:37 — BDRs are earned, not given 15:41 — Tiered commission: pay winners, let the rest self-select 27:37 — Fix the Frankenstein CRM at seven, not thirty-three 30:27 — AI and the data model pull ops investment earlier 32:27 — The proof of concept that crashed, and won the customer 36:14 — Let the cheap guy win 41:33 — How Ascend uses AI in go-to-market 43:07 — When the buyer has AI too 48:33 — Why Ari doesn't lock in renewal increases 54:00 — Recap and close ABOUT THE GUEST Ari Greenberg is Chief Revenue Officer at Ascend Analytics, the Boulder-based energy analytics and software company whose forecasts inform more than $50 billion in project financing and procurement evaluations. Ari has spent about 25 years in energy and market data. He began as an Open Systems Specialist at Reuters, moved into sales at LIM, GlobalView and SNL Energy, and from 2012 led sales teams at SNL Energy, S&P Global and AlphaSense before serving as VP of Global Sales at ZEMA Global and then joining Ascend. ABOUT THE LEANSCALE PODCAST The LeanScale Podcast — conversations with the operators building modern go-to-market teams. Hosted by Anthony Enrico, co-founder and CEO of LeanScale. LeanScale is RevOps as a service: we stand up the GTM infrastructure for some of the fastest-growing companies in tech. Subscribe for new episodes every week. Learn more → https://www.leanscale.team KEYWORDS / TAGS RevOps, GTM, Chief Revenue Officer, CRO, Sales Leadership, Scaling Sales, Startup Scaling, Deal Desk, BDR, SDR, BDR to AE, Sales Compensation, Tiered Commission, Quota Setting, Sales Hiring, Sales Enablement, Forecasting, Customer Success, Renewals, Usage-Based Pricing, Pricing Strategy, Proof of Concept, Competitive Pricing, Retention, Salesforce, CRM, CRM Migration, AI, AI in Sales, AEO, Claude, Energy Analytics, Ascend Analytics, S&P Global, SNL Energy, AlphaSense, Controlled Growth, B2B SaaS, Vertical SaaS, LeanScale, Anthony Enrico, Ari Greenberg HASHTAGS #RevOps #GTM #AI #LeanScale #LeanScalePodcast #CRO #SalesLeadership #SalesCompensation #BDR #DealDesk #CustomerSuccess #Pricing #B2BSaaS #EnergyTech #Scaling

  8. Oct 20

    A Decade in One CRO Seat: Make More Money Than You Spend | David Cady, Virtuous

    Every 18 months the venture world changes what "good" means. Rule of 40. Magic number. CAC payback. David Cady's CEO has one answer that never changes: make more money than we spend, and treat this like a real business. David has held the go-to-market seat at Virtuous for more than a decade — from six people and about $100,000 in revenue to 200 employees, 10,000+ nonprofit customers, and a $100M round from Susquehanna Growth Equity. The average CRO lasts about 18 months. He started in sales during the 2008 crash, after leaving a teaching job that couldn't cover his newborn's health insurance. In this conversation, he and host Anthony Enrico — who went to the same Phoenix high school seven years later — get into building a durable company outside the coasts, why the SaaS partner-program playbook missed in a mission-driven market, how category creation builds trust, and why the people who get promoted are the ones who just go solve the next problem. WHAT YOU'LL LEARN Why "make more money than you spend" beats chasing whatever metric investors love this cycle How go-to-market changed over a decade — and why spray-and-pray outbound stopped paying back Why no go-to-market trick can outsell a bad product — and why the CRO owns retained revenue too Why partners drive retention and expansion, not just new leads How Virtuous used category creation ("Responsive Fundraising") to build trust in a trust-driven market How to spot high-agency problem solvers — and why you promote them into the problem they just solved CHAPTERS 00:00 — Intro: two kids from Ahwatukee and Mountain Pointe 01:38 — What staying in Phoenix cost — and what it was worth 05:02 — "Make more money than we spend" 08:09 — From the classroom to cold calling in the 2008 crash 14:00 — The lunch that turned into Virtuous 17:56 — A decade in one CRO seat: how GTM changed 21:12 — Partnerships, community, and why product comes first 25:14 — What brand really is — and Responsive Fundraising 32:19 — Why the SaaS partner program missed 37:59 — Partners drive retention, not just leads 40:19 — The hardest season: 2021–2022 46:11 — High-agency problem solvers 51:46 — N of One and what's next with AI 56:06 — Closing ABOUT THE GUEST David Cady is Chief Revenue Officer at Virtuous, the Phoenix-based responsive fundraising platform used by more than 10,000 nonprofits. He joined when the company was six or seven people and has led go-to-market for more than a decade, through Virtuous's $100M round led by Susquehanna Growth Equity. Before software he taught high school English, then started his sales career cold calling for CDW right as the 2008 financial crisis hit. He spent the next decade selling enterprise transformation software before joining Virtuous founder Gabe Cooper. ABOUT THE LEANSCALE PODCAST The LeanScale Podcast — conversations with the operators building modern go-to-market teams. Hosted by Anthony Enrico, co-founder and CEO of LeanScale. LeanScale is RevOps as a service: we stand up the GTM infrastructure for some of the fastest-growing companies in tech. Subscribe for new episodes every week. Learn more → https://www.leanscale.team KEYWORDS / TAGS RevOps, Revenue Operations, GTM, Go-to-Market, Chief Revenue Officer, CRO, Sales Leadership, B2B SaaS, Vertical SaaS, Nonprofit Software, Fundraising Software, Responsive Fundraising, Virtuous, Gabe Cooper, Susquehanna Growth Equity, Capital Efficiency, CAC Payback, Rule of 40, Unit Economics, Profitable Growth, Partner Programs, Channel Partnerships, Category Creation, Brand Building, Outbound Sales, Sales Hiring, High Agency, Customer Retention, Net Revenue Retention, Phoenix Tech, AI, AI in Sales, Enterprise SaaS, LeanScale, LeanScale Podcast HASHTAGS #RevOps #GTM #AI #LeanScale #LeanScalePodcast #CRO #SalesLeadership #B2BSaaS #VerticalSaaS #Nonprofit #Fundraising #Partnerships #CategoryCreation #CapitalEfficiency #PhoenixTech

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