Most people spend their careers climbing toward the CEO seat. Alex Wakefield sat in it — and then chose to go back to being a Chief Revenue Officer. On purpose.He made that move to AcuityMD, the commercial platform for the med tech industry, when it had fewer than 20 customers and roughly $2M in ARR. Four years later, the company serves more than 500 customers, has scaled past $50M in ARR, and just raised $80M at a near-billion-dollar valuation.

In this conversation with LeanScale co-founder Anthony Enrico, Alex breaks down what go-to-market actually looks like at every stage of that climb — when to bring in RevOps (and why he waited too long), how to avoid the overhiring trap that quietly kills sales teams, what’s really building pipeline now, and why he believes the biggest barrier to AI adoption isn’t skill — it’s a mental model. Two operators who came up through the details, going deep on how modern go-to-market gets built.

WHAT YOU’LL LEARNWhy a CEO would choose to go back to a CRO seat — and the math that makes it smartHow go-to-market has to evolve at every stage from $2M to $50M ARRWhen to bring RevOps into your org — and the data foundation most teams skipThe productivity formula for knowing when to hire more reps (and when to stop)The hidden second-order cost of overhiring your sales teamHow to hire in a specialized vertical — and the one common denominator that predicts successWhy AI makes software easier, not harder — and how to break the “AI-first” mental wallWhat’s actually generating pipeline now: curated outreach, dial pickup rates, and videoWhy in-person events are still one of the highest-ROI plays in go-to-marketHow to break from operations or RevOps into sales leadership and the CRO seat

CHAPTERS00:00 — Cold open + intro01:45 — Why a CEO chose to go back to CRO03:59 — Scaling go-to-market from $2M to $50M ARR08:06 — When to bring RevOps in (and why he waited too long)11:01 — The formula for when to hire more reps13:50 — The hidden cost of overhiring sales16:21 — Hiring in med tech: the real common denominator19:59 — Why AI makes software easier, not harder26:04 — Who holds the keys? Decentralized AI vs. RevOps control30:27 — What’s actually building pipeline now34:04 — Are in-person events back?36:07 — The biggest challenge after an $80M raise39:58 — The mental wall of “AI first”44:08 — Operator to CRO: the career through-line51:13 — How to break from RevOps into sales leadership

ABOUT THE GUESTAlex Wakefield is the Chief Revenue Officer of AcuityMD, the commercial platform for the med tech industry, which recently raised $80 million at a near-billion-dollar valuation. Alex joined when the company had fewer than 20 customers and roughly $2M in ARR; today AcuityMD serves more than 500 customers and has scaled past $50M in ARR. His path to CRO is anything but typical: he began in the Navy’s supply corps, moved into global supply chain and logistics operations at IBM, got pulled into enterprise technology on an early SAP rollout, and discovered sales through SPIN selling — eventually running the Americas business at Model N and leading commercial teams at JDA and Longbow Advantage before stepping into the CEO seat and, ultimately, choosing to return to a CRO role. He’s one of the rare leaders who went from CEO back to CRO on purpose.

ABOUT THE LEANSCALE PODCASTThe LeanScale Podcast is the show for GTM operators building the next generation of revenue infrastructure. Hosted by Anthony Enrico, co-founder of LeanScale.▶ Subscribe for new episodes▶ Learn more about LeanScale: https://www.leanscale.team▶ Follow Anthony on LinkedIn▶ Follow Alex on LinkedInHASHTAGS#RevOps #GTM #GoToMarket #AI #ArtificialIntelligence #RevenueOperations #SalesOperations #B2BSaaS #EnterpriseSaaS #VerticalSaaS #MedTech #SalesLeadership #CRO #SalesEnablement #PipelineGeneration #AITransformation #ScalingSales #LeanScale #LeanScalePodcas

Why He Left the CEO Seat to Become a CRO | Alex Wakefield, AcuityMD

The LeanScale Podcast with Anthony Enrico

Why He Left the CEO Seat to Become a CRO | Alex Wakefield, AcuityMD