The LeanScale Podcast with Anthony Enrico

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

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

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

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

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

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

Every sales team is hearing the same objection right now: "Why can't I just use Claude for this?" Simon Kirk's take is that this isn't a brand-new problem. It's the Lattice problem from five years ago, and the answer is the same one: a team that can actually explain why a buyer should choose you.

Simon is the interim Chief Revenue Officer at Orbital, the legal AI company for commercial real estate. Before that he spent five years at Culture Amp as the first hire for the CRO, building sales development, revenue enablement and solutions consulting across Australia, the US, the UK and Europe, and was part of the go-to-market team at InVision before that.

In this conversation with LeanScale co-founder Anthony Enrico, Simon breaks down why differentiation has to be a system rather than a battle card, how to bring domain experts (like actual lawyers) into the sales process, what SE ratios and win-rate lifts really look like, why no sales playbook survives a copy-paste between companies, and how to interview AEs and sales leaders now that every candidate has Claude.

WHAT YOU'LL LEARN

Why selling against Claude is the same problem as selling against Lattice, and why the emotional reaction is the real risk

Where specialist products still beat general-purpose AI: workflows, proprietary data and maintenance

SE-to-AE ratios by deal size, and why Simon has seen up to a 10% win-rate lift on SE-covered deals

The coachability test for AE interviews: give one piece of feedback and watch the second attempt

CHAPTERS

00:00 — Intro: Simon Kirk, interim CRO at Orbital

02:29 — Selling against Claude is the Lattice problem all over again

08:15 — Build vs. buy when anyone can build with Claude Code

14:29 — Bringing domain experts (and lawyers) into the sales process

19:30 — SE ratios, win-rate lift and what one point of conversion is worth

35:27 — How to interview AEs: the coachability test

39:56 — Hiring sales leaders: use Claude, then defend it

49:19 — Why companies bring Simon in: three buckets

52:12 — Wrap

ABOUT THE GUEST

Simon Kirk is the interim Chief Revenue Officer at Orbital, the legal AI company automating commercial real estate legal work. He spent five years at Culture Amp as global go-to-market VP and the first hire for the company's CRO, building sales development, revenue enablement and solutions consulting into a roughly 70-person function across Australia, the US, the UK and Europe. Before that he worked alongside the CRO at InVision during its scale-up years. For the last two years he has done fractional and interim go-to-market leadership for companies from early-stage, founder-led teams to later-stage scale-ups, typically stepping in where there's a leadership gap, a leader who needs a senior pair of hands, or an important project without an obvious owner.

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 Simon on LinkedIn

KEYWORDS / TAGS

RevOps, GTM, GTM Strategy, AI, AI in Sales, Selling Against AI, Claude, Claude Code, Build vs Buy, Competitive Positioning, Differentiation, Product Marketing, Sales Enablement, Solutions Consulting, Sales Engineering, SE Ratio, Win Rate, Discovery, Objection Handling, Sales Hiring, Interviewing AEs, Coachability, Performance Management, Sales Coaching, Interim CRO, Fractional CRO, CRO, Legal AI, Commercial Real Estate, Orbital, Culture Amp, Lattice, Enterprise Sales, B2B SaaS, LeanScale, Anthony Enrico, Simon Kirk

HASHTAGS

#RevOps #GTM #AI #Claude #SalesLeadership #CRO #SalesEnablement #SalesEngineering #SalesHiring #SalesCoaching #LegalTech #B2BSaaS #FractionalCRO #LeanScale #LeanScalePodcast

Anyone can vibe code a polished website over a weekend now. The design, the copy, the deck — all of it can be generated. Matt Overman's argument is that this is exactly why the one thing you can't generate has quietly become the credibility badge: the address your brand lives at.

Matt is Chief Revenue Officer at Identity Digital, which runs the world's largest portfolio of top-level domains — 270 extensions sold through more than 500 partners, from GoDaddy and Namecheap to Vercel and the vibe-coding platforms. He has spent nearly two decades in the domain industry, built NameJet into the premier auction marketplace, ran Rightside's premium domain business, and was named a 2026 CRN Channel Chief.

In this conversation with LeanScale co-founder Anthony Enrico, Matt breaks down the trust recession, why publishing on someone else's platform builds their brand instead of yours, the bit.ly billboard at SeaTac, what the next round of TLDs (hello, .agent) means for 2028, how Identity Digital merchandises 270 products like the Procter & Gamble of domains, and why the team is spending more on in-person events than ever.

WHAT YOU'LL LEARN

Why AI-generated everything has created a trust recession — and where buyers are looking for proof instead

Why you can vibe code a business over a weekend but you can't fake a domain

Is .com still Park Avenue? How .ai, .team and industry TLDs became trust signals

Why AI made Identity Digital's team spend more on in-person events, not less

CHAPTERS

00:00 — Intro: Matt Overman, CRO of Identity Digital

04:02 — The trust recession

06:34 — You can vibe code a website. You can't fake a domain.

09:04 — Is .com still Park Avenue? .ai, .team and trust signals

14:44 — Shipping on Netlify and Vercel subdomains: the AEO cost

20:00 — The next wave: .agent and the 2028 TLD round

33:36 — The Procter & Gamble of domains: a channel-only GTM

39:20 — AI in the pricing engine — and why relationships matter more

42:49 — Two humans on either side: why in-person is back

46:26 — Wrap

ABOUT THE GUEST

Matt Overman is Chief Revenue Officer at Identity Digital, the company behind the world's largest portfolio of top-level domains, where he oversees sales and registry growth across a network of more than 500 partners — registrars, website builders, AI and vibe-coding platforms, and SaaS companies. Matt has spent nearly two decades in the domain industry: he was general manager of NameJet, which he built into the industry's premier auction marketplace, and led Rightside's monetization and premium domain sales business before it was acquired by Donuts, now Identity Digital. He started his career in advertising at McCann Erickson in Seattle and was named a 2026 CRN Channel Chief.

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 Matt on LinkedIn

▶ Learn more about Identity Digital: https://www.identity.digital

KEYWORDS / TAGS

Domain Names, Top-Level Domains, TLD, gTLD, .ai domain, .agent domain, .com, Identity Digital, NameJet, Rightside, Donuts, ICANN, New gTLD Program, Domain Registry, Domain Registrar, GoDaddy, Namecheap, Vercel, Netlify, Lovable, Vibe Coding, Brand Trust, Digital Identity, Trust Recession, AEO, Answer Engine Optimization, SEO, Channel Partnerships, Channel Sales, CRN Channel Chiefs, CRO, GTM, RevOps, AI, AI Agents, Agentic Commerce, Event Marketing, B2B SaaS, Startup Branding, LeanScale, Anthony Enrico, Matt Overman

HASHTAGS

#RevOps #GTM #GoToMarket #AI #LeanScale #LeanScalePodcast #Domains #DigitalIdentity #BrandTrust #AEO #SEO #VibeCoding #ChannelPartners #CRO #AIAgents #B2BSaaS #IdentityDigital

Most sellers walk into a discovery call with a thing they want to sell. Julie Mall thinks that's exactly why deals take longer than they should — and why the work piles up at the end of the cycle, right when it's hardest to do.

Julie is the Chief Revenue Officer at Zoovu, the AI product discovery platform behind ecommerce experiences for brands like Microsoft, Bosch, Canon, and Honeywell. She didn't come up through quota. She started at PwC running change management on Fortune 50 ERP transformations, deployed B2B ecommerce through the first dot-com boom, built and led global solutions teams, took on customer success, and now runs sales, customer success, and solutions as one organization.

In this conversation with LeanScale co-founder Anthony Enrico, Julie breaks down her one-word edit to the oldest line in software sales — not always be selling, but always be solutioning — and what it looks like in a discovery call, in a proof of concept, in a board meeting, and in a renewal you should never have to fight for.

WHAT YOU'LL LEARN

Why "always be solutioning" closes faster and bigger than "always be selling"

How a fire-safety deal closed fast with one demo — by starting with the customer's own ROI metrics

The best discovery question Julie has heard: what does this pain really mean to the business?

Where AI actually helps GTM leaders today: Gong deal patterns, a private AI workspace, and board prep

CHAPTERS

00:00 — Intro: Julie Mall, CRO at Zoovu

01:38 — Dot-com B2B ecommerce and the costliest 80% of customers

03:41 — Always be solutioning, not always be selling

08:50 — Discovery is for learning, not for scoping the demo

13:00 — The best discovery question: what does this pain really mean?

17:43 — The solutions-engineer edge in the CRO seat

25:29 — Making AEs solution-led; TAMs over CSMs

31:38 — AI in GTM: Gong deal patterns, Langdock, and board prep

41:00 — Solutioning after the sale: renewals that sell themselves

44:41 — Closing thoughts: the CRO role is solutioning at scale

ABOUT THE GUEST

Julie Mall is the Chief Revenue Officer at Zoovu, the AI product discovery platform powering ecommerce experiences for brands including Microsoft, Bosch, Canon, and Honeywell. She began her career at PwC leading change management for Fortune 50 ERP transformations, then spent the first dot-com boom deploying B2B ecommerce for large SAP customers including Occidental Chemical, Chevron Phillips Chemical, and Pennzoil-Quaker State. From implementation she moved into sales engineering, built and led global solutions teams, took on customer success — rebuilding it around technical account managers — and today runs sales, customer success, and solutions as a single commercial 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 Enrico on LinkedIn

▶ Learn more about Zoovu: https://zoovu.com

KEYWORDS / TAGS

RevOps, Revenue Operations, GTM, Go-to-Market, CRO, Chief Revenue Officer, Solutions Engineering, Sales Engineering, Solutions Consulting, Pre-Sales, Discovery Call, Sales Discovery, Value Selling, Solution Selling, Proof of Concept, ROI Modeling, Customer Success, Technical Account Manager, Net Revenue Retention, Renewals, Sales Enablement, Gong, Salesforce, AI in Sales, AI in GTM, Board Meeting Prep, Deal Velocity, B2B Ecommerce, AI Product Discovery, Zoovu, Microsoft, Bosch, PwC, SAP, B2B SaaS, Enterprise SaaS, Sales Leadership, LeanScale

HASHTAGS

#RevOps #GTM #GoToMarket #AI #CRO #SalesEngineering #PreSales #SalesDiscovery #SolutionSelling #CustomerSuccess #NetRevenueRetention #SalesLeadership #B2BSaaS #Ecommerce #Zoovu #LeanScale #LeanScalePodcast

Years of 6 a.m. laptops, full days in the office, back on the laptop after dinner, and a couple of hours every weekend. It worked — until the first panic attack of his life, when Miles Kirkpatrick genuinely thought he was dying.

Miles is the Chief Revenue Officer at SITE Technologies, the Chicago company using drones, satellites, and AI to tell commercial property owners what condition their roofs, pavement, and facades are actually in. Before SITE he was CRO at Productiv, ran Central US and Canada at Sprinklr from pre-IPO to public, and built revenue teams at Salesforce. Before any of it, he chased professional golf.

In this conversation with LeanScale co-founder Anthony Enrico, Miles breaks down what elite performance really costs, how he found the 45 minutes a day where he does his best work, why decision velocity beats waiting for data, why he promoted a former commercial roofer to run customer success, and how SITE builds pipeline now that the old volume plays have stopped working.

WHAT YOU'LL LEARN

Why being "in the zone" at work is the same state athletes describe — and how to get there on purpose

Decision velocity vs. flip-flopping: making calls with limited data and pivoting without drama

Why customer success is the most underrated revenue function — and why the best hire had never done the job

How SITE builds pipeline with points of view, handwritten notes, customer dinners, and real content instead of automated sequences

CHAPTERS

00:00 — Cold open + intro

01:34 — Seeing the shot before you hit it: being in the zone

05:28 — Hitting the wall: the first panic attack

09:02 — The 30-minute morning routine and the 5:30 a.m. peak window

17:19 — The warning signs before the crash

28:37 — Decision velocity vs. flip-flopping

32:37 — Bets that missed: comp plans and early PR

37:12 — The best decision: a commercial roofer runs CS

42:06 — Pipeline: points of view, handwritten notes, customer dinners

50:45 — RevOps is "me on a Sunday"

54:40 — Wrap

ABOUT THE GUEST

Miles Kirkpatrick is the Chief Revenue Officer at SITE Technologies, the Chicago-based asset intelligence company that uses drones, satellite imagery, and proprietary AI to assess the condition of commercial property portfolios before problems turn into capital expense. He joined SITE in 2024 and built its go-to-market function from the ground up. Previously, Miles was CRO at Productiv, VP of Central US and Canada at Sprinklr, where he joined pre-IPO, and held sales leadership roles at Salesforce. Before tech, he spent years playing competitive golf, including a run at it professionally. He is an outspoken advocate for mental health and daily breath work.

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 Miles on LinkedIn

▶ Learn more about SITE Technologies: https://sitetechnologies.io

KEYWORDS / TAGS

RevOps, Revenue Operations, GTM, Go-to-Market, CRO, Chief Revenue Officer, Sales Leadership, Peak Performance, Burnout, Mental Health, Breath Work, Flow State, Decision Velocity, Decision Making, Startup Leadership, Customer Success, Enterprise Sales, Value Selling, Sales Storytelling, Pipeline Generation, Point of View Selling, Sales Compensation, PR Strategy, AI, AI in Sales, Commercial Real Estate, PropTech, Drones, Asset Intelligence, SITE Technologies, Productiv, Sprinklr, Salesforce, B2B SaaS, LeanScale, Anthony Enrico, Miles Kirkpatrick

HASHTAGS

#RevOps #GTM #AI #LeanScale #LeanScalePodcast #CRO #SalesLeadership #PeakPerformance #Burnout #MentalHealth #DecisionMaking #CustomerSuccess #EnterpriseSales #PropTech #B2BSaaS