The LeanScale Podcast · Episode 89

Why He Left the CEO Seat to Become a CRO

Alex Wakefield on scaling AcuityMD from $2M to $50M ARR, when to bring in RevOps, the overhiring trap, and breaking the 'AI-first' mental wall

Alex Wakefield · Chief Revenue Officer, AcuityMD · AcuityMD Hosted by Anthony Enrico
Published Updated 00:53:52 48 min read 9,551 words
Executive Summary

The one-paragraph brief, extended

Why this conversation matters — and who should spend the hour.

Most operators spend a career 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 the 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. What makes his perspective unusual is the path behind it: he started in the Navy's supply corps, ran global supply-chain and logistics operations at IBM, got pulled into enterprise technology on an early SAP R/3 rollout, discovered selling through SPIN, and then led commercial teams at Model N, JDA, and Longbow Advantage before the CEO chair and the deliberate return to CRO.

Alex is candid about the reasoning. Before he leapt he talked to no fewer than 25 mentors, advisors, and CEOs asking whether going 'backwards' was crazy. What tipped him was product-market fit in a hard-to-crack vertical, a founding team with complementary skills, an investment thesis he believed in around vertical SaaS, and the plain math of build mode: in a high-growth company with a great culture, the compensation, equity, and how-you-feel-about-yourself math simply makes sense. He wanted to build something at rapid scale, and he trusted his own edge on the commercial side.

The heart of the conversation is an operator's clinic on how go-to-market has to be re-architected at every stage. Early on he ran a process-heavy motion and hired med-tech insiders who generated pipeline through sheer industry knowledge and hustle — good enough to go from ~20 to 100 customers and $2M to $10M ARR. Then the motion had to pivot: bigger, six-figure enterprise deals, software-selling talent, and process rigor. His biggest regret is being late to RevOps — roughly two-and-a-half to three years, and one failed data-completeness OKR, before he brought it in. His rules: start measuring once you hit critical mass (six to ten reps); gate rep hiring on ramp and attainment, not optimism; and treat overhiring as a genuine threat, because diluting territory and top-of-funnel is how you lose the A-players you can least afford to lose. In a specialized vertical, the common denominator he hires for isn't pedigree — it's work ethic and alignment to an altruistic mission.

On AI, Alex's contrarian claim is that the biggest barrier to adoption isn't skill — it's a mental model. AI makes software easier, not harder; it 'brings it backwards' to plain language, so the job of leadership is to demystify it ('I sell knees — how can you help me do that?') and knock down the AI-first mental wall. AcuityMD moved from broad internal experimentation to hardening its use and making its ~80–90-person customer-facing team experts in its own AI, betting that proprietary data plus deep industry context beats horizontal players. Anthony and Alex agree on the operating pattern: let people experiment to kill the fear, then centralize the valuable skills and data pipelines through RevOps before it becomes a bowl of spaghetti.

The episode closes on pipeline and career. Curated, researched outreach beats blasting — AcuityMD sees ~20% dial pickup and double-digit email response — and in-person events remain one of the highest-ROI plays when wrapped in pre-plan/execute/follow-up rigor. The through-line for Alex's career is that an operations background is a superpower in sales: once you see that managing a deal is like managing a project, it takes on a whole new meaning. His advice to RevOps people chasing the CRO seat is to go do a customer-facing or AE role for a couple of years. Who should listen: founders and CROs designing go-to-market at each stage, RevOps leaders deciding when to build and how to own AI, and sales leaders wrestling with hiring, enablement, and the AI transition.

Key Takeaways

12 things worth stealing

The load-bearing ideas, each with the business implication and who should care.

01

A CEO can rationally choose to go back to CRO — the build-mode math

Alex left the CEO seat for a CRO role at AcuityMD after pressure-testing the move with 25+ mentors and CEOs. What tipped him: real product-market fit in a hard vertical, a complementary founding team, a vertical-SaaS investment thesis he believed in, and the plain math that in a high-growth build with great culture, compensation, equity, and personal fulfillment line up.

Why it matters: Title is not the same as leverage. If you're strong on the commercial side, joining a high-growth build as CRO can beat running a slower company as CEO — evaluate the move on product-market fit, team, thesis, and equity math, not org-chart prestige.

Revenue ExecutivesFounders
02

Go-to-market has to be re-architected at every stage

The motion that took AcuityMD from ~20 to 100 customers (med-tech insiders generating pipeline through industry knowledge and hustle) is not the motion for six-figure enterprise deals. Later stages needed software-selling talent, process rigor, and analytics; early med-tech sellers were redeployed into enablement, customer success, and events where they excelled.

Why it matters: Don't cling to the playbook that got you here. Expect to re-tool talent, process, and metrics at each ARR band ($2M → $10M → $50M → $100M+), and consciously move people into the roles where their strengths now fit.

FoundersRevenue ExecutivesSales Leaders
03

Bring in RevOps earlier than feels necessary — data is the foundation

Alex's stated regret is waiting roughly 2.5–3 years to hire RevOps. The OKR he promoted but never delivered himself was data completeness and accuracy in CRM; without it, at 16–18 reps he could measure pipeline and bookings but almost nothing about sales efficiency, pipeline quality, or qualification.

Why it matters: Once you have a critical mass of reps (six to ten), stand up RevOps to build the data foundation. Measuring earlier means fewer downstream mistakes in hiring, enablement, and process — and you can't build analytics on dirty data.

RevOps LeadersFoundersRevenue Executives
04

Hire more reps on a formula — ramp and attainment, not optimism

Have a headcount plan and stick to it, but gate it on how well people ramp and what percent of quota they attain. If reps come in short of ~75–80% of quota or ~90%+ of ramped capacity, pull the hiring plan back rather than pressing forward on hope.

Why it matters: Define your onboarding/ramp model and attainment thresholds up front. Adjusting the plan down when leading indicators soften keeps you from over-hiring — and from the layoffs that follow over-hiring.

Sales LeadersRevOps LeadersFounders
05

The hidden second-order cost of overhiring: your A-players leave

Overhiring sales isn't just paying reps who miss quota. It dilutes territories and top-of-funnel demand across people who won't stick, starves your best reps of the pipeline they need, and when strong reps start leaving, that's noticeable to the outside world — the worst thing that can happen to a sales org.

Why it matters: Be precise about when you add heads. Protect top performers' territory and pipeline explicitly; there's no better ROI than your best salespeople, so don't manufacture their departure with aggressive hiring.

Sales LeadersRevenue ExecutivesRevOps Leaders
06

Don't hire vs. lay off — stay ahead by adjusting the plan down

AcuityMD runs a financially conservative, streamlined headcount plan and prefers not-hiring to letting people go. When they got aggressive earlier in the year — thinning territories to go deeper on strategic accounts — and saw attainment lag, they quickly pulled back, re-widened territories, and talked to top performers instead of cutting.

Why it matters: Build a conservative plan and lean in only where the metrics justify it. Staying ahead of the curve lets you avoid layoffs entirely, which protects both morale and your employer brand.

FoundersRevenue ExecutivesSales Leaders
07

In a vertical, hire for work ethic and mission — not resume pedigree

Alex went back and forth on whether industry background or software background matters more, and landed on a simpler common denominator: does this person want to put in the work to understand the customer and buy into the mission? Med-tech sellers work brutal hours for surgeons and hospitals; mission alignment to improving patient outcomes is hard to teach and predicts success.

Why it matters: Mirror and emulate your customer base when hiring. Screen for altruistic mission-fit and willingness to become an expert; you can teach sales process and product, but not work ethic and belief.

Sales LeadersRevOps LeadersFounders
08

AI makes software easier, not harder — the barrier is a mental model

Alex argues the biggest wall in the AI transition is the 'AI-first' mindset. People onboarded in a pre-AI world cling to point-and-click UI notions and treat AI as the next, harder evolution of technology. In reality AI 'brings it backwards' to plain language — easier than search. The gating factor is whether people drop old notions, not their technical skill.

Why it matters: Lead the transition as a mindset shift, not a training program. Demystify it ('I sell knees — how can you help me do that?'), tell people not to overthink it, and remove the fear rather than chasing perfect prompts.

Revenue ExecutivesSales LeadersRevOps Leaders
09

Decentralize AI experimentation first, then centralize the value through RevOps

In the commercial org Alex encourages daily-efficiency use but wants less scattershot tool-building, because everyone spins up their own reports and skills that aren't efficient in aggregate. The plan: RevOps builds shared skills (e.g., 'assess your team's deals against stage-movement criteria') and ultimately gets a look at process and structure so it's applicable across the org.

Why it matters: The experimentation phase is essential to kill fear and prove ease of use. But once tools splinter into a bowl of spaghetti, centralize the ~10 valuable skills, agents, and data pipelines through RevOps for anything mission-critical.

RevOps LeadersRevenue Executives
10

Context is the moat — proprietary data plus industry knowledge beats horizontal AI

AcuityMD pairs an industry-leading proprietary data set with a large cohort of people who came from the med-tech industry and know the customer's use cases. That combination lets it Sherpa customers into using AI well — an edge horizontal AI or pure data players can't match.

Why it matters: In vertical SaaS, lean into your data and domain context. The value isn't generic AI capability; it's relevance — building and guiding solutions grounded in the customer's specific industry, problems, and pains.

FoundersRevenue ExecutivesMarketing Leaders
11

Curated outreach beats blasting — and dials, text, and video still win

Alex has never liked playing the numbers with mass sends; he forwards the worst inbound to his SDRs as examples of what not to do. AcuityMD leans into researched, use-case-specific messaging to a narrow vertical buyer and sees ~20% dial pickup, 12–13% email response, and strong results from 90-second Looms built inside its own software.

Why it matters: In a targeted vertical, curated beats volume. Invest in account research and channel fit (dials and text where buyers live on their phones, personalized video) instead of scaling a low-hit-rate blast.

Sales LeadersMarketing LeadersRevOps Leaders
12

An operations background is a superpower for sales — a deal is a project

Alex's ops-then-sales path (Navy supply corps, IBM logistics, SAP, project-management certification, then SPIN selling) is exactly what he now hunts for on resumes. When you realize managing a sale is like managing a project — art of the sale (psychology) plus science of the sale (methodical progression to signature) — selling takes on a different meaning. The best reps are unbelievably methodical.

Why it matters: For RevOps and ops people eyeing the CRO seat: your operational rigor is an asset, not a gap. Go do a customer-facing or AE role for a couple of years to learn the product and customer — it's the best on-ramp to sales leadership.

RevOps LeadersSales LeadersRevenue Executives
Frameworks Discussed

11 named models

Every framework Jimmy names, defined and time-stamped.

The CEO-to-CRO Build Math

02:35

A framework for evaluating a 'backwards' move from CEO to CRO: weigh product-market fit, founding-team fit, and investment thesis against the compensation, equity, and personal-fulfillment math of joining a high-growth build with strong culture.

Alex reframes the move not as a demotion but as an optimization. In exponential-growth mode, equity and comp can exceed what running a slower company pays, and the fulfillment of building at scale on real product-market fit outweighs the title. He validated the logic with 25+ mentors and CEOs before leaping.

Re-Architecting GTM at Every Stage

03:59

The idea that the go-to-market motion — talent profile, process weight, and metrics — must be rebuilt at each ARR band rather than scaled linearly. Different stages leverage different areas of the process.

Med-tech insiders and hustle carried AcuityMD from ~20 to 100 customers and $2M to $10M ARR; six-figure enterprise deals then required software-selling talent and heavier process; the next phase demands sophisticated pipeline and sales-efficiency analytics. Early talent gets redeployed (enablement, CS, events) where it now fits.

The Rep-Hiring Formula (Ramp × Attainment)

11:01

Gate sales hiring on two leading indicators: how well reps are ramping against a defined ramp curve, and what percent of quota (and ramped-quota capacity) they are attaining. Below threshold, pull the plan back.

Have a headcount plan and stick to it, but treat attainment (~75–80% of quota) and ramped capacity (~90%+) as the signal to keep hiring or pause. Adjusting down early avoids the layoffs that follow over-hiring — AcuityMD prefers not-hiring to letting people go.

The Overhiring Trap (Territory Dilution)

13:20

The second-order damage of over-hiring sales: diluting territories and top-of-funnel demand across reps who won't stick, which starves top performers and eventually drives your A-players out.

The obvious cost is reps who miss quota; the hidden cost is losing the best people. Thinning territories to go deeper backfired for AcuityMD until they re-widened them and protected top performers. Visible A-player departures are the worst signal a sales org can send.

Mirror Your Customer Base (Hiring in a Vertical)

16:21

A hiring heuristic for specialized verticals: emulate your customer base and screen for the common denominator of work ethic and mission alignment rather than a specific sales or industry pedigree.

Med-tech buyers work brutal hours for surgeons and hospitals; the reps who win share that work ethic and buy into an altruistic mission (accelerating adoption of medical technology to improve patient outcomes). Process and product can be taught; belief and effort cannot.

Decentralize, Then Centralize AI

25:08

An AI-adoption operating model: allow broad, decentralized experimentation to reduce fear and prove ease of use, then centralize the valuable skills, agents, and data pipelines — governed by RevOps — for anything mission-critical.

Free-for-all building splinters into a 'bowl of spaghetti' of one-off reports and tools. AcuityMD and LeanScale both moved to reel experiments in, keep the ~10 valuable things, and have RevOps ensure shared skills are applicable across the org with clean data pipelines and context graphs so AI isn't hallucinating.

Curated Outreach Over Volume

29:38

A pipeline philosophy that favors thoughtful, researched, use-case-specific outreach to a narrow buyer over high-volume, low-hit-rate blasting.

Alex forwards bad inbound to his team as examples of what not to do. Against a specific vertical buyer, curated messaging drives ~20% dial pickup, 12–13% email response, and strong engagement from personalized 90-second Looms built inside AcuityMD's own software.

Events as a Full-Lifecycle Operating Motion

34:04

Treating in-person events as an operational play with three phases — pre-plan (targeting, pre-set meetings), execute (on-site, ideally with stage presence), and post-plan (structured follow-up tracked through CRM) — not as a booth you show up to.

Events are among AcuityMD's highest-ROI channels because med-tech buying is interpersonal and vertical targeting is easy. But 'magic doesn't happen' on its own; the biggest benefit comes from tons of planning, pre-set meetings, disciplined follow-up, and accountability driven to closure.

The 'AI-First' Mental Wall

38:29

The primary barrier to AI adoption is a mental model, not a skill gap: people onboarded in a pre-AI world treat AI as the next, harder evolution of technology and cling to point-and-click UI notions.

Alex reframes AI as making technology easier — it 'brings it backwards' to plain language, easier than search. Leadership's job is to shift mindsets to AI-first, demystify it ('I sell knees — how can you help me do that?'), and tell people not to overthink it. Those who hold old notions are the ones who won't adopt.

The Art and Science of the Sale

45:50

A model of selling as two blended disciplines: the art (psychology and influence — moving many stakeholders in the same direction) and the science (methodically progressing a deal through a rigorous process to signature).

Rooted in SPIN selling (whose author was a psychology researcher), Alex frames great selling as psychology management plus a disciplined close plan. The insight that 'there's a process to selling' was a revelation that reframed sales as something learnable and repeatable.

A Deal Is a Project

47:01

The reframe that managing a sale is like managing a project — bringing operational and project-management rigor (sequencing, stakeholders, milestones) to progressing a deal to close.

This is the through-line of Alex's ops-to-sales career: an operations background is invaluable in sales because once you see a deal as a project, it takes on a different meaning. The best reps are unbelievably methodical, time-box their days, and are numbers-oriented — soft skills alone don't close.

Best Quotes

19 lines worth clipping

Pulled verbatim. Copy or share any of them.

“What makes Alex's perspective unique is his path. He didn't come up through the traditional sales track. He started operations, moved to VP of Sales, became CEO of his own company, and then chose to go back to being a CRO.”
Anthony Enrico 00:00
“Before I made the leap, I talked to no fewer than 25 people — fathers and mentors and advisors and CEOs — and said, 'Is this kind of crazy, to do this move from CEO to CRO?'”
Alex Wakefield 01:57
“The compensation, equity, and how-you-feel-about-yourself math just kind of makes sense when you're in a good build and a high-growth mode with a great culture.”
Alex Wakefield 02:35
“The consistent OKR that I had promoted to the organization that I did not deliver was data completeness and accuracy in CRM.”
Alex Wakefield 08:03
“The sooner you can start to measure those things, the better decisions you can make. And I think you'll make fewer mistakes down the line in hiring, enablement, process efficiency.”
Alex Wakefield 09:36
“I still think it's the biggest mistake I see with the customers that we're working with — overhiring in sales.”
Anthony Enrico 13:20
“If you have A-player sales reps start leaving, that's pretty noticeable to the outside world. That's not a great thing.”
Alex Wakefield 14:53
“I always like to try to mirror and emulate your customer base.”
Alex Wakefield 16:51
“Work ethic, passion for an altruistic mission, and believing in what we do is a really interesting common denominator. There's so many things you can teach — those are things that are hard to teach.”
Alex Wakefield 17:16
“So much of the value is in the context. If you have deep context of your customer, their industry, their problems and pains, then you can build things that are just so much more relevant.”
Anthony Enrico 24:03
“I definitely want RevOps ultimately to at least have a look at it and a say in it, to make sure it's applicable to multiple parts of the organization.”
Alex Wakefield 26:19
“It quickly turned into a bowl of spaghetti and chaos, and we had to reel those experiments in and say, okay, here are the 10 valuable things that we need for our business.”
Anthony Enrico 26:56
“We have pickup rates on dials of like 20%. It's absurd, because folks in the industry are so dialed into using their phone.”
Alex Wakefield 30:52
“There's not just going to the event, because magic doesn't happen. There's tons of planning, prep, preset meetings, tons of follow-up and holding folks accountable.”
Alex Wakefield 34:15
“I actually think the biggest wall people are going to run into is the mental wall of AI first.”
Alex Wakefield 38:29
“It's not that AI is the next wave of technology. AI actually makes it a ton easier to interact with technology — it actually brings it backwards.”
Alex Wakefield 39:40
“Folks come up with these amazing prompts that yield amazing results — that's fantastic. But you should also be able to say, 'I sell knees. How can you help me do that?' You should completely demystify it.”
Alex Wakefield 40:33
“When you realize that managing a sale is like a project, man, it just takes on a whole different meaning.”
Alex Wakefield 47:01
“I would not discourage anyone from being an AE for a couple years. I think it's super valuable and probably the best way to get into sales leadership.”
Alex Wakefield 51:50
Practical Advice

What should you actually do?

The playbook, split by the seat you sit in.

Founders

  • Evaluate senior GTM hires on product-market fit, founding-team fit, thesis, and equity math — not title. A strong commercial leader will join a high-growth build as CRO if the build math works.
  • Re-architect go-to-market at every ARR band; the talent and process that get you to $10M won't get you to $50M. Plan to redeploy early hires into the roles their strengths now fit (enablement, CS, events).
  • Run a financially conservative, streamlined headcount plan and prefer not-hiring to layoffs. Lean in only where ramp and attainment metrics justify it.

RevOps Leaders

  • Push for RevOps and a data-completeness/accuracy foundation once you hit six to ten reps — don't kick the can. You can't build sales-efficiency analytics on dirty CRM data.
  • Let AI experimentation run to kill fear and prove ease of use, then centralize the ~10 valuable skills, agents, and data pipelines so tools don't splinter into a bowl of spaghetti.
  • Own the process and structure layer of AI: build shared skills (deal stage-movement checks, team assessments) and make sure they're applicable across the whole org, with context graphs so AI isn't hallucinating.

Sales Leaders

  • Gate rep hiring on ramp and attainment (~75–80% of quota, ~90%+ of ramped capacity). Below threshold, pull the plan back before you over-hire.
  • Protect top performers' territory and pipeline explicitly — overhiring dilutes top-of-funnel and drives your best reps out, the worst signal a sales org can send.
  • In a vertical, hire for work ethic and mission alignment over pedigree; mirror your customer base and screen for people who'll put in the work to become experts.

Marketing Leaders

  • Favor curated, researched, use-case-specific outreach over volume blasting — in a targeted vertical it drives far higher pickup and response rates.
  • Treat in-person events as a full-lifecycle motion: pre-plan targeting and pre-set meetings, on-site execution (ideally with stage presence off proprietary data), and disciplined CRM-tracked follow-up.
  • Lean into proprietary data and domain context to build genuinely relevant campaigns and assets, rather than generic AI-generated content.

Revenue Executives

  • Lead the AI transition as a mindset shift, not a training program — knock down the 'AI-first' mental wall and demystify the tools ('I sell knees — how can you help me?').
  • Make your customer-facing team experts in your own AI so they can Sherpa customers; in vertical SaaS, proprietary data plus industry knowledge is the moat against horizontal players.
  • If you're coaching operators toward the CRO seat, send them to do a customer-facing or AE role for a couple of years — operational rigor plus real selling reps is the best on-ramp.
AI Takeaways

How AI actually changes GTM

LeanScale's signature read on the AI-in-GTM question this episode wrestles with.

The thesis

The biggest barrier to AI adoption isn't skill — it's a mental model. AI makes software easier, not harder, by bringing interaction back to plain language. The winning move is to demystify it, let people experiment to kill the fear, then centralize the valuable patterns through RevOps — and, in vertical SaaS, win on proprietary data and industry context rather than horizontal capability.

AI-first is a mindset, not a skillset

People onboarded in a pre-AI world treat AI as the next, harder evolution and cling to point-and-click UI notions. The gating factor for adoption is whether they drop old habits — not their technical ability.

It makes software easier, not harder

AI 'brings it backwards' to plain language — easier than search. Leadership's job is to demystify it ('I sell knees — how can you help me do that?') and tell people not to overthink it.

Decentralize experimentation, then centralize the value

Free-for-all building splinters into a bowl of spaghetti. Keep the ~10 valuable skills and route mission-critical work through RevOps, with clean data pipelines and context graphs so AI isn't hallucinating.

Context is the moat

Proprietary data plus a cohort that knows the industry lets a vertical player Sherpa customers into good AI use — an edge horizontal AI and pure data players can't match.

GTM adopts faster than product/eng

A growth-equity partner (Radian Capital) sees higher AI adoption on the go-to-market side than in product and engineering across its portfolio — a pattern Anthony also sees inside LeanScale between GTM architects and engineers, tied to muscle memory and habits.

Agent & automation ideas

  • RevOps-built sales-leader skills: assess a team's deals against stage-movement criteria, flag what's missing, and surface the next meeting — served up rather than hand-built by each manager.
  • A curated-outreach agent that researches a specific vertical account, matches solvable use cases, and drafts a personalized email, dial script, text, or 90-second Loom built on the product's own data.
  • Customer-facing enablement: make the field expert in the product's own AI so reps can demystify it for buyers ('ask it whatever you want') and accelerate adoption.
Operations Takeaways

By function

The same conversation, filtered for RevOps, pipeline/marketing ops, and customer ops.

Revenue Operations

  • Don't be late to RevOps. Stand it up once you hit six to ten reps; the data-completeness-and-accuracy foundation is what everything else measures against.
  • Data before analytics. At 16–18 reps without clean CRM data you can only see pipeline and bookings — not efficiency, quality, or qualification. Build the foundation first.
  • Own the AI process layer. Let people experiment, then centralize the valuable skills, agents, and pipelines; RevOps ensures they're applicable across the org and grounded in accurate data.
  • Instrument the hiring decision. Give leaders ramp and attainment metrics so hiring is gated on evidence, not optimism — and so you can pull back before over-hiring.
  • Measure to hire better. The sooner you measure efficacy, the fewer downstream mistakes in hiring, enablement, and process.

Pipeline & Marketing Ops

  • Curated beats blasted. Researched, use-case-specific outreach to a narrow vertical buyer outperforms high-volume, low-hit-rate sends.
  • Channel fit matters. Dials (~20% pickup) and text work in med-tech because buyers live on their phones; personalized 90-second Looms drive engagement.
  • Reps own most of their pipe. Reps generate ~50% of pipeline; screen for willingness to prospect and create leads. Marketing ~20% and SDRs ~12%, plus a referral-partner network.
  • Events are high-ROI — with rigor. In interpersonal med-tech, targeted events are a top channel, but the return comes from pre-planning, pre-set meetings, and disciplined CRM-tracked follow-up.

Customer Operations

  • Redeploy talent as you scale. Early med-tech sellers who fade in enterprise deals can thrive in enablement, customer success, and event management — move people to where their strengths now fit.
  • Make the field expert in your AI. Turn the ~80–90-person customer-facing team into experts in the product's own AI so they can train and Sherpa customers through adoption.
  • Manage the AI-native transition. Migrating customers from a legacy point-and-click experience to an AI-native product is a deliberate change-management effort with senior-level engagement.
  • Tell the impact stories. In a mission-driven vertical, surface internal stories of positive patient impact to keep the team aligned to something bigger than the number.
Metrics Mentioned

The numbers, with context

$2M → $50M+
ARR growth

AcuityMD grew from roughly $2M ARR when Alex joined to past $50M in about four years.

<20 → 500+
Customer count

From fewer than 20 customers at Alex's start to more than 500 in the med-tech space today.

$80M at ~$1B valuation
Latest raise

AcuityMD's Series C, raised at a near-billion-dollar valuation.

~2.5–3 years (too late)
RevOps timing

How long after Alex joined before AcuityMD hired RevOps — his stated regret.

16–18 salespeople
Reps when measurement broke

The headcount at which it became very hard to measure anything beyond pipeline and bookings without RevOps.

6–10 reps
Critical mass to start measuring

The point at which you have enough reps to start collecting data and assessing efficacy, and should stand up RevOps.

~75–80% quota · ~90%+ ramped capacity
Hiring-gate thresholds

If reps come in below these attainment/ramp thresholds, pull back the hiring plan.

~20%
Dial pickup rate

Unusually high pickup rate on dials because med-tech buyers live on their phones serving physicians.

12–13%
Email response rate

High relative to norms, driven by curated, use-case-specific messaging.

Reps ~50% · Marketing ~20% · SDRs ~12%
Pipeline source mix

Approximate contribution split, with a referral-partner network on top; the strongest reps generate more of their own pipe.

~80–90 people
Customer-facing team

The org AcuityMD is making expert in its own AI so they can train and guide customers.

Entities

Companies, people & tools mentioned

Auto-extracted and linked into the knowledge graph.

Companies

AcuityMDHealthTech / MedTech

Alex's current company; he is CRO of AcuityMD, the commercial platform for the med-tech industry. He joined at <20 customers and ~$2M ARR; it now serves 500+ customers, has scaled past $50M ARR, and raised $80M at a near-billion-dollar valuation.

00:00 · 03:12 · 35:21Company →
Longbow AdvantageSupply Chain Software

Where Alex was Chief Commercial Officer and built out the commercial organization right before AcuityMD; he knew the founder and drove strong growth.

01:19Company →
Model NRevenue Management Software

Where Alex ran the Americas business — part of the mid-stage scaling experience the AcuityMD founding team valued in his background.

03:59Company →
JDA SoftwareSupply Chain Software

Supply-chain software company (now Blue Yonder) where Alex led a team; cited as part of his small-to-mid-stage growth experience.

03:59Company →
IBMEnterprise Technology

Where Alex did global supply-chain and logistics operations early in his career, built custom logistics/technology solutions for large contract manufacturers, and got pulled into an early SAP R/3 project (~1998) that started his pivot into software.

44:07Company →
SAPEnterprise Software

The enterprise software Alex worked on via an early SAP R/3 rollout around 1998 at IBM — the project that moved him into technology.

44:07Company →
GlobalMedHealthTech / Telemedicine

The med-tech company (telemedicine devices and software) where Anthony started his own career as a product trainer before moving into sales — the basis for his firsthand read on how unique med-tech selling is.

15:29Company →
Radian CapitalGrowth Equity

Growth-equity firm LeanScale partners with (transcribed as 'Radium Capital'); it shared a cross-portfolio observation that go-to-market teams have adopted AI faster than product and engineering — which Anthony says he also sees internally at LeanScale.

41:31Company →
RevOps Co-opRevOps Community

The RevOps community whose London event Anthony attended, where the big conversation was moving past AI experimentation into professionalizing and centralizing it.

24:36Company →
SnowflakeData Cloud

Cited as an example of how fast AI market share can shift — its results 'earlier this month' popped it into the leader category of AI, illustrating low switching costs and a dynamic environment.

20:47Company →
AnthropicFrontier AI

One of the two AI labs AcuityMD evaluated ('between OpenAI and Anthropic') before settling into Claude Code / Cowork for internal AI adoption.

19:41Company →
OpenAIFrontier AI

Named alongside Anthropic as the two providers AcuityMD weighed before settling on Claude tooling for internal use.

19:41Company →

People

Tools & software

Claude CodeAI Dev Tool

AcuityMD gave the team access to Claude Code (referred to as 'cloud code' and 'Claude Cowork'); LeanScale gave everyone a Claude Code max license in November 2025, sparking an explosion of building before it was reined in and centralized.

FableAI Model

Anthony references Fable being pulled down and a reluctance to release, as an example of how fast the AI landscape shifts as of the June 17, 2026 recording.

LoomVideo Messaging

Reps send curated, ~90-second personalized Loom videos — built inside AcuityMD's own software — as a high-response outreach play.

ChatGPTAI Assistant

Used as the everyday example of how easy AI adoption really is — migrating from Google search to ChatGPT is easier than search, not harder; you just touch the microphone and say what you want.

Methodologies referenced SPIN SellingMEDDICRange (David Epstein)
Frequently Asked Questions

Straight answers

Generated from the conversation, marked up for search and AI extraction.

Why would a CEO go back to being a CRO?

Alex Wakefield left the CEO seat to become CRO of AcuityMD because the fundamentals lined up: real product-market fit in a hard-to-crack vertical, a founding team with complementary skills, an investment thesis he believed in around vertical SaaS, and the plain math that in a high-growth build with strong culture, compensation, equity, and personal fulfillment can exceed running a slower company as CEO. He validated the move with more than 25 mentors and CEOs before making it.

How should go-to-market change as a company scales from $2M to $50M ARR?

It has to be re-architected at every stage, not scaled linearly. Early on, med-tech insiders generating pipeline through industry knowledge and hustle took AcuityMD from ~20 to 100 customers and $2M to $10M ARR. Moving up to six-figure enterprise deals required software-selling talent, heavier process, and analytics, while early sellers were redeployed into enablement, customer success, and events. Each ARR band leverages different talent, process weight, and metrics.

When should a startup hire its first RevOps person?

Once you reach a critical mass of roughly six to ten reps and need to start collecting data and assessing what's working. Alex's stated regret was waiting about 2.5–3 years; without a data-completeness-and-accuracy foundation in CRM, at 16–18 reps he could measure pipeline and bookings but almost nothing about sales efficiency, pipeline quality, or qualification. Measuring earlier means fewer downstream mistakes in hiring, enablement, and process.

How do you know when to hire more sales reps — and when to stop?

Gate hiring on two leading indicators: how well reps are ramping against a defined ramp curve, and what percent of quota (and ramped-quota capacity) they attain. Have a plan and stick to it, but if reps come in short of about 75–80% of quota or 90%+ of ramped capacity, pull the plan back. Adjusting down early lets you avoid layoffs — AcuityMD prefers not-hiring to letting people go.

What's the hidden cost of overhiring your sales team?

Beyond paying reps who miss quota, overhiring dilutes territories and top-of-funnel demand across people who won't stick, which starves your best reps of pipeline. The worst second-order effect is that strong A-players start leaving — a departure that's visible to the outside world and signals trouble. There's no better ROI than your top salespeople, so protect their territory and pipeline explicitly.

What should you look for when hiring in a specialized vertical like med tech?

Mirror and emulate your customer base and screen for a simple common denominator: work ethic and mission alignment rather than a specific pedigree. Med-tech buyers work brutal hours for surgeons and hospitals, and the reps who win share that work ethic and buy into an altruistic mission. You can teach sales process and product; you can't teach belief and effort.

Is AI making go-to-market harder or easier?

Easier, according to Alex Wakefield. The biggest barrier to adoption is a mental model, not a skill gap: people onboarded in a pre-AI world treat AI as the next, harder evolution of technology. In reality AI 'brings it backwards' to plain language and is easier than search. Leadership's job is to knock down the 'AI-first' mental wall, demystify the tools ('I sell knees — how can you help me do that?'), and tell people not to overthink it.

What's the best way to break from RevOps into a sales leadership or CRO role?

Go do a customer-facing or AE role for a couple of years. Alex — whose own path ran from Navy supply corps and IBM logistics through SAP and project management into SPIN selling — argues an operations background is a superpower in sales once you see that managing a deal is like managing a project. A stint carrying a bag teaches the product and customer and is, in his view, the best on-ramp to sales leadership, even though it isn't strictly required to become a CRO.

Full Transcript

The whole conversation

Broken into chapters, searchable, verbatim from the audio. Speakers inferred (not diarized).

00:00Cold open + intro

0:00 Today I'm talking with Alex Wakefield, the chief revenue officer at Acuity MD, a commercial platform for the med-tech industry that just raised $80 million at an almost $1 billion valuation. Alex was there at the beginning when they were just shy of 20 customers, and in just four short years, they're now serving over 500 customers in the med-tech space. But what makes Alex's perspective unique is his path. He didn't come up through the traditional sales track. He started operations, moved to VP of Sales, became CEO of his own company, and then chose to go back to being a CRO.

0:41 We're going to dig into why he made that choice, what CEO experience teaches you about being a better CRO, and how he thinks about building teams, especially his approach to hiring unconventional people who don't have the typical sales resume. Alex, you were CEO before coming to Acuity to be the chief revenue officer. Very few people go in that direction, and often they're searching to go the other way. I'd love for you to unpack that story. Yeah, sure, of course. Appreciate the time today, Anthony, and thanks a lot for the intro. So I did.

1:19 I joined Longbow Advantage as chief commercial officer and built out the commercial organization, which is a little bit tighter in my background. I'd known the founder for a little bit of the organization. So when I took the organization over and we experienced some great growth, it was a really good experience. I enjoyed it. Fantastic. People love the solution, but what really attracted me to Acuity MD was when I started digging in and looked at product market fit of the particular offering that they had, which is really challenging to come by, as you probably know. I will tell you before I made the leap, I talked to no fewer than 25 people.

01:45Why a CEO chose to go back to CRO

1:57 You know, father and mentors and advisors and CEOs and said, "Is this kind of crazy to do this move from CEO to CRO?" And, you know, the general consensus is if you're running a commercial organization and you think you have a great product and a great team, and I really wanted to go build something at a really rapid scale, those were a lot of the factors that played into the decision. I did dig into, you know, I thought I could partner with the founding team really, really well. Three amazing guys that have super complementary skills and know the space and technology really well. So I thought I could work with them real well to build things.

2:35 And I did love the investment thesis. I dug into the venture thesis on why they were investing, particularly in vertical SaaS. So a lot of those things came together, and then I just, I kind of, you know, reconciled myself to the fact that I think I'm great on the commercial side. I did like running a company, but when you're just kind of building and you can drive exponential growth, a lot of the, you know, honestly, like compensation, equity and how you feel about yourself, math, just kind of makes sense when you're in a good build and a high growth mode with a great culture.

3:12 So this was really a build based on some product market fit assessment, and I added like the commercial aspect to the organization. So it's been great, you know, just based on some of the growth you mentioned in the introduction. Well, and the growth that QT's gone on is absolutely no joke. Going from around 2 million ARR when you started skyrocketing up to 50 million ARR, that is a tremendous run already. And I know you guys are just getting started. I would love to hear how you approach. We get this question so much, and I think your ops background will probably help you here. But what does go to market look like at each of these stages?

3:53 There's when you're building it, but then as you're going through all of these new phases of the company, what are the biggest things you run into as you're scaling? I've done it. I've done a few different stages, which I think is one of the things that sort of attracted the founding team to my background is the idea was, hey, let's at least invest in a person that's seen a lot of these stages, you know, long, both small growth and then some mid stage stuff based on the team I ran at JDA and a very larger running in America's business and model. And so the different stages definitely carry challenges.

03:59Scaling go-to-market from $2M to $50M ARR

4:28 One of the things that I did when I first joined was I implemented pretty rigorous sales process, which I'd done a few companies before, perhaps a little process heavy, you know, for that stage. So I think that was sort of difficult to digest for the team that I was hiring. So I think I was kind of heavy on process at the beginning, but I heard some folks from the space that were like the med tech selling space. So a real expert and they were amazing at generating pipeline, getting excitement in the industry. They understood like the game changing technology we had.

5:01 So it was an interesting stage because I think a lot of that, like, you know, in the in the mud fighting and just growing like your pipeline and winning deals for excitement was really great and took us from, you know, I don't know, 20 customers to 100 or something like that. You know, 22 to 10 million in ARR, but then you you do have to pivot and as as the organization grows and kind of gets out of that hand to hand combat and you're really in process orientation. What was super interesting was I thought we had pretty good process in infrastructure, a little light on metrics like we were late on hiring RevOps.

5:39 I thought a little light on metrics, but trying to migrate some of those super early successful folks into larger enterprise deals. You grow into six figure deals, you go up market, you get into bigger organizations. That's kind of a different motion. So that's where process became a little bit more important. We started to bring in some folks that had kind of legacy software selling background, sort of move some of these med tech legacy folks into other areas of the organization. Like enablement, customer success, kind of, you know, event management, like super successful in those areas.

6:15 So it's interesting to see the backgrounds that were a little bit more successful later in stages. And now as we're getting bigger, process becomes much more important. RevOps is a significant contributor to how we're doing analysis and optimizing the team. And what's really interesting is we do have an awesome blend of people that have been selling software in the past and people that have been selling med tech in the past and have sort of cross-pollinated and learned the others industry. But yeah, the different stages have definitely leveraged different areas of the process.

6:52 And, you know, as we kind of like pivoted to the next phase of getting up to 100 million, 200 million, whatever it is, it becomes a lot more sophisticated in analyzing pipeline metrics and sales efficiencies and all those things we can talk about in RevOps. But yeah, it was super interesting to see the different stages and how we try to construct those and, you know, the mistakes we made and some things we did well. A lot of that stuff can be glazed over with a really, really good product, which we have. But yeah, it's been interesting. Absolutely. I want to go back to one of the things you said.

7:23 You said maybe you were a little too late in bringing RevOps into Acuity. I'm curious, specific to you when, in hindsight, do you wish you would have brought RevOps in? And then as a litmus test for others, when is it time? Is it a certain headcount threshold, a revenue threshold? Is there a certain complexity formula you have that says now is the time to bring RevOps in? Yeah, I don't know if there's a formula. I can tell you that the consistent OKR that I had promoted to the organization that I did not deliver was data completeness and accuracy in CRM.

8:03 So basically, like the underlying data to collect it and make sure it's clean so that you can actually have sort of a basis for how do you measure your organization. I continued to kind of kick the can. I thought I could do it on my own. I didn't really have enough time to do those things. So it got to a point where it was very difficult to measure anything. We might have had 16 or 18 salespeople, and it was really difficult to measure anything aside from the sales stages I defined, the pipeline and what people were booking.

08:06When to bring RevOps in (and why he waited too long)

8:33 So a close loss ratio. But there was very little sales efficiency and process efficiency is how well are we doing? How much? How well are we generating pipeline? What is the quality of the pipeline? How are we qualifying deals in? What are we closing? So we didn't bring RevOps on until three years, two and a half years after I joined or something like that. And it was a lot of catch up. It was a lot of catch up. We brought a person in at the beginning who I think was just it was really difficult to get their arms around what we were doing.

9:11 And so we brought a newer person in, you know, about a year ago, and he's just got a really strong analytical background. And it's got it. It's take somebody that wants to really build, get into the details, get their hands dirty. I actually learned in recruiting and said, hey, look, I know RevOps sounds super exciting, but I hope you want to get your hands dirty and like data cleanliness because we have to build that foundation in order to build from there.

9:36 So my sense was we were a little bit late. I think that as soon as you have some sort of critical mass where you've got enough reps, whatever you want to call it, like six, eight, ten, whatever the number is where you need to start collecting data and assessing the efficacy of what is working that they're doing. What are what are they pitching? Who's doing well? Who's not? The sooner you can start to measure those things, the better decisions you can make. And I think you'll make fewer mistakes down the line in hiring, enablement, process efficiency, things like that.

10:10 Yeah, I'm seeing a lot of philosophy recently. I think, you know, I grew up in the growth at all cost SAS era. That's when I entered and it was a lot of fun, but that doesn't fly as much anymore. So a lot of teams are thinking, OK, slower to hire reps than before. Earlier to bring in process and earlier to bring in things like RevOps. I'm curious, what is your threshold or your method to know that you need to bring on more reps? What does that formula look like to say, OK, now's the time to add X amount to the team? Yeah, I think like you should have a plan for what you think you're going to hire and stick to plan as best you can.

11:01The formula for when to hire more reps

11:05 But you should set a threshold of how well are folks ramping and what percent of their quarter are they achieving. So we had we had found a little bit earlier on that we were we were doing pretty well in the metrics. We had pretty good attainment and we continue to hire. And then as startups and high growth companies do, you kind of stub your toe or have a couple of hiccups here and there. And when you like the way we've done it, I think our our our founding and finance team has done a really good job. I would say we're very financially conservative. We maintain a really strong headcount plan, but we want to try to make it streamlined.

11:46 So we do a good job, I think, of not hiring rather than letting people go. So as soon as you see those indicators that, oh, man, I want to achieve 75 or 80 percent of my quota or I want to be at 90 plus percent ramp quota capacity, whatever threshold you pick. If you're coming in short of those, it's a good idea to pull back on the hiring plan. That way, we're not really laying people off. We haven't done that. I haven't really done that in my past.

12:16 You're not really laying people off because you've gone too fast and made mistakes. You kind of stay ahead of it and look at your sales productivity metrics and you adjust the hiring plan down, which we've definitely done. And we've tried to lean in and hire more where appropriate. But I think that's the best thing to do is figure out what your onboarding and ramp definition is, how well you're achieving quota compared to what you're assigned, and then how well you're achieving versus your ramped quota capacity.

12:49 Those are the things that we look at. So we didn't really get ahead of ourselves, but we've definitely pared back some hiring when we thought we were a little shy on where we wanted to be. Yeah, and I still think it's the biggest mistake that I see the customers that we're working with is overhiring in sales because all the time and it's not just there's more effects to it. So it's not just you hire people that might not hit their quota. It's also your good reps that you have on the team that are performing really well for you.

13:20 You're diluting the territory, you're diluting the top of funnel demand that's coming in and getting assigned to the team to people that just aren't going to hang there and you don't have enough to feed that machine. And then you see your good reps leave too. So I think it's unbelievably dangerous to overhire and you have to be really precise about when you bring people on. That last piece is one of the worst pieces there is. If you have a player reps that start to leave, people notice that. That is about the worst thing that can happen.

13:50The hidden cost of overhiring sales

13:51 We did a little bit of that because in a vertical asset organization, we try to narrow down your account list so that we can grow our largest customers as much as we can. We should be really large strategic partners with these companies. So the account list, as lots of times it does, I'm a big fan of this historically, but you want to shrink your account list because you want to go deeper and deeper and deeper and be more strategic and ultimately you end up selling more and being a more important partner.

14:20 So we leaned into that a little bit earlier this year and I thought we got a little bit aggressive on hiring, we restructured the territories, made them a little bit thinner. But we pretty quickly pulled that back when we saw there was some lack of attainment in what we wanted to do and we grew the territories a little bit, talked to our top performers and you have to make sure you're protecting everyone but you're really looking at your top performers and saying look, we got to make sure we're not diluting your pool as much as possible.

14:53 So, we've definitely had folks leave, we've definitely moved out of the organization, but I think we've done a pretty decent job of not really losing who we don't want to lose but that last bit you mentioned is like super important if you have a players, a player sales reps start leaving. That's pretty noticeable to the outside world. That's not a great thing. Yeah, no matter how much commission you're paying them, there's no better ROI than your top sales people. So, you don't want them to go. Yeah, if you're if you're perhaps in the top five paid people in your company you're in a good spot.

15:29 100% on hiring. You're in a very unique space, and I actually, I started my career in med tech I worked at a company called global med. So, telemedicine devices and software. That was a product trainer and then I moved into sales. It's a very very unique selling environment, if you're in the healthcare med tech space. How are you finding the right people you said you have a mix of some traditional SAS, plus some med tech sellers. What's the common denominator you're looking for that lets you know if this is a good profile for acuity.

16:08 Yeah, it's an interesting one because I've gone back and forth so much on is it the background is the experience and coming from the space, I will tell you about med tech sellers. They work really hard, and they really focus on their customers whether it's surgeons or hospitals I mean they work really hard around the clock is an exaggeration but odd hours is not. And so, I think what works for us is, I always like to try to mirror emulate your customer base. And so I think just a very simple common denominator is if we can start to suss out.

16:21Hiring in med tech: the real common denominator

16:51 Does someone really want to like put the time in to understand their customer whether they have to learn how to sell software a little bit better or they have to understand, or they have to learn the med tech space a little bit better. Does someone really want to put in the effort to become an expert and support customers that work really hard, and actually have a really great altruistic mission of, you know, helping patient outcomes and patient outcomes.

17:16 These are folks that that love what they do and they're passionate about healthcare. So it's an interesting common denominator for us, because I do think that like work ethic passion for like an altruistic mission and believing in what we do is a really interesting common denominator I know it's not you know quantifiable or sales process oriented or things like that there's so many things you can teach. Those are things that are that are hard to teach and I think that we've seen a lot of success for people that buy into what we're doing, really want to support their customers mission.

17:49 And it's kind of a unique position, I think for us to have an altruistic mission as a software organization for instance like our mission is to accelerate adoption of medical technology want to help our customers, like, get their technology into the hands of the physicians and hospitals that can get them into the lives of the patients that improve their outcomes as quickly as possible that's our whole goal is like to create visibility into your technology, so that the healthcare system can get them into the patient's lives as quickly as possible.

18:20 I think it makes a big difference when you have people who are mission aligned, and that when you know you're working for something bigger than yourself. That's what helps you put in that extra mile, being in the healthcare industry is, I think, easier to do because you're so close to the impact that you're making, and you can see the tangible difference you're making. And if you run it to the end it's like I know hey in some way, it might be a couple steps removed I probably saved a life or two by getting these people set up with what they need

18:54 to deliver care. Absolutely. Absolutely. Yeah, we try to tell those stories internally as much as we can where we have positive effect in folks lives. It wouldn't be a go to market B2B SAS podcast, if I didn't go down the AI path. I'm always curious because everything is changing every day today as of June 17 2026 you know fable got pulled down they're reluctant to release meet those. Everything feels like it's just in flux, and I think go to market in general has some of those interesting applications. I'm curious, how are you and your team leveraging AI, either internally, or how are you leveraging externally for your customers.

19:41 Actually, I think we did a really good job just from from our CEO Mike, on the way down like as soon as tools were released we didn't we didn't settle, you know between open air and thropic right away but but quickly settled into, you know, Claude co work, whatever but there was a pretty big push for internal testing utilization sharing of AI stories. So we did get pretty good feedback from the board that we were, we were doing a great job of adopting AI internally for efficiency and a lot of that stuff right out of the gate is like testing

19:59Why AI makes software easier, not harder

20:16 is it going to stick probably not. So as we get further down the path. How do we, how do we make sure that people aren't, you know, I wouldn't want to, I wouldn't say wasting their time I think smaller tasks can be, you know, easily done with with AI but how do we, how do we help folks in in automation and CRM and get visibility into what they need, without a lot of the point and click just like serve things up to them so that's kind of what we're working on right now so I were doing relatively well on the commercial side there.

20:47 And that's what we've done recently to pivot because my view is the AI space moves like super fast I just did an internal meeting yesterday. And, you know, the leaders like market share can shift quickly. I mean, snowflake came out with their results what earlier this month and all of a sudden popped into the popped into the leader category of AI with, with, with kind of pop q1 results so super interesting that the perspective shifts I think switching costs are pretty low.

21:21 So I think it's a really dynamic environment about what people can use. We see a lot of customers want to write internal agents. We've, we have sort of an industry leading data set. That we do sell and provide to our customers is one of our offerings. They want to ingest our data right agents on top of them, great like that's that's great you can do some of those things, but when you look externally at what we do with AI, we are now ensuring that our team our customer facing team, which is about, I don't know, 80 or 90 people but our customer

21:54 facing team is an expert in our own AI solution so that, you know, ask our solution whatever you want it to do we help, for the most part medical device sales reps, be more efficient in understanding their market their territory, how to sell better into hospital systems or surgeons. So we want our team to be experts in using our own AI inside our application so that they can train their, their customers or at least show them how simple it is, as one thing that I has done for us is it's made

22:30 tech more usable and easy to adopt you kind of don't need training or don't need to know anything you just have to not be afraid and ask it whatever you want so we've now pivoted hard into internal experts on our own AI so that we can help train our customers and show them how best to use it. So that's what we're doing right now and then, and then the reason, you know, we think that's important and why we think we can help our customers a little bit better than some of the horizontal

22:59 players or the data players is that, like I said, we do think we have an industry leading data set but we also have a pretty large cohort of folks that know our customers industry and our use cases that came from the industry. So between having proprietary data set folks that know the industry and can sit with our customers and show them the best way to use AI that's why we think we have a pretty good advantage so we went from testing internally to kind of what I would just say is

23:31 hardening our use of AI so that it can be broadly adopted to pivoting into using our own solutions and becoming experts there, so we can you know as kind of Sherpa our customers into the proper use of the ad that we provide to them. I think that's great because so much of the value is in the context. So, if you have deep context of your customer their industry their problems or pains, then you can build things that are just so much more relevant than somebody building

24:03 generic things for them. I was just at an event last week in London, rev ops, they have events put on by rev ops co op, and one of the biggest conversations was, okay we're past this experimentation phase, where, hey, everybody gets Claude code max license and go build whatever you want and connect it to any MCP you want. And we're moving into this okay it's time to like, professionalize it. And it feels like there's a couple different camps of how people are doing that.

24:36 One is rev ops is really taking a leadership role in this. Another is there's this centralized committee that's working across engineering and product. How are you thinking about who holds the keys to how acuity leverages AI internally. And for us, for us, and I, and I definitely can't speak to product or engineering I can say that we're, I'm gonna leave that and I'm not gonna speak to that I don't run that business I'll let answer that question.

25:08 But I can tell you in the in the commercial world. And the way our organization has pushed forward is it's kind of decentralization of AI. So, in the commercial world what I've done is I'm trying, I'm not. I encourage folks to do less testing because then I think you get all sorts of different reports and tools out of Claude code that are really cool, but everybody's got their own particular thing that they've built which isn't like super efficient at the end of the day. So we don't necessarily want to completely dissuade that I think there's huge efficiencies to be used on a daily basis in the tools for sure, of course.

25:54 But I'm trying to move it more into rev ops centralized to say hey look like here's a skill you can use sales leaders, here's a skill you can use to assess your team real quick. Look at a deal where is in stage. How are you doing against stage movement criteria. What are you missing, you know, where's your next meeting like things like that that we can build for folks rather than they build it on their own.

26:04Who holds the keys? Decentralized AI vs. RevOps control

26:19 So, from an organizational standpoint, there's definitely not a centralized command and control, but from a commercial standpoint, I do like people being efficient in the day to day, but when you're talking about overall process and structure. I definitely want rev ops, ultimately to at least have a look at it in a say in it to make sure it's, it's applicable to mobile, multiple parts of the organization but we're, you know, early on in that journey that's just like my kind of hypothesis right now is we're sort of building out the team and solidifying some of these things.

26:56 Yeah, I know it's early days and we're having our own, I'd say it was about six seven months ago. November of 25 is when everybody started getting their hands on cloud code here. And it was just like a massive explosion of creativity and building things. And then it quickly turned into a bowl of spaghetti and chaos, and we had to reel those experiments in and say okay. Here are the 10 valuable things that we need for our business and everybody needs to use these plugins and skills and agents and using this way and they have the connectors.

27:35 You can experiment and do your own personal stuff but like if you're doing something serious for the business. These are the things that you need to use and serving it up to them. And we've been wrangling that in for our customers. It's been one of our quickest growing practices we have revenue operations marketing operations and AI operations. Yep, and, you know, building in, making sure you have the data pipelines the context graphs, when you're asking cloud about data it's pulling accurate data it's not hallucinating.

28:02 All of those things are super important if you're going to do it at scale, especially like where your team is marching towards right now. Yeah, absolutely. I mean I think the beginning early experimenting phase is really important because in it, and then it, it reduces the kind of the fear and uncertainty of folks that might not be as technical, that it is really easy to use and I think that's an important

28:25 learning for when you project it out to your customers so the testing and experimenting phase is really really important. It's just as you said, so they splinter and proliferate and create a bowl of spaghetti like yeah, you want to tighten those things up. And then pivot into the next stage which is like really becoming efficient and how do you actually use it across your organization. Yeah, well, I'm sure more learning to come I don't know maybe they'll launch the model that just does everything for us and we won't have to worry about it too much but we'll see.

28:54 Yeah, we'll see. Another big topic, especially since AI is kind of gotten ingrained into how go to market teams are approaching building pipeline giving their messaging out is a lot of the older pipeline building tactics really aren't working. The outbound is having a lot of teams are having a real tough time with outbound things like paid ads things that used to feel like you can throw money behind it and it would scale. What are you seeing work to build pipeline get opportunities and get in front of the people that you're trying to sell to.

29:38 There's a few things I've never been a huge fan of like blasting lots of things out and playing the numbers whether it's a 2% hit rate or whatever like I'm, you know, 2% here let's like double our, our blasted out but I've always been more of a fan of really thoughtful curated messaging. We actually tend to send a lot of the inbounds you can imagine we all get like a lot of the inbounds that I find particularly ineffective to our SDR team and our sales team as examples of what not to do. Just catchy phrases at the end you know you're you're quintessential like how do I get somebody to respond.

30:23 We find that curated messaging and we're, we have the advantage of being in a vertical sass company where we're selling to a pretty specific buyer. So we really lean into curated messaging as far as specific research into the org and specific use cases that we can think we can solve, and it's very much a specific email or call or even in our industry like text work so.

30:27What's actually building pipeline now

30:52 Believe it or not, we have response rates, we have pickup rates on dials of like 20%. It's absurd because folks in the industry are so dialed into using their phone and serving their physicians that they're sensitive to those types of communication so we have pretty good hit rates on text, on dials, response rates on emails are very high, 12%, 13%, something like that, but I've seen a lot of folks in our organization get really creative quick loom, you know quick videos, 90 seconds specific to our customer built in our software, sent to them in a video.

31:31 Hey respond if you'd like to learn a little bit more specifically how we can help you in this territory. So we tend to lean into very curated messages where we have a pretty pretty good response rate. That I think is the number one thing for us that gets that gets folks to engage and respond. And are you building this with a classic SDR team that's focused on building the pipeline or your reps doing some of this themselves do you have a different approach. I mean I always think that I always think that you can cut the numbers however you want. I think reps are going to generate 50% of their pipeline, whatever, give or take.

32:10 So it's another criteria when you hire folks is, is you want to assess someone's ability to generate pipe or not be afraid to call call and not be afraid to create their own leads. So the, so the, I don't know if I want to say the majority but like the plurality like most the biggest contributor of their pipe is going to be the reps themselves and more successful reps definitely create more of their own pipe, but we contribute.

32:36 I don't know what the number is 12% from SDRs and 20% from marketing or something like that but the majority is going to come from the other bits are marketing SDRs, we have a pretty good referral partnership network, and then the reps themselves. Okay, last question on pipeline building any. I've seen a little bit of a resurgence with events for in person, are you seeing a similar trend or seem about the same or maybe less event events are actually very big for us.

33:09 Some folks have come in, you know, some just coming out of COVID I think and coming from some software companies considered events to you know, kind of be just boondoggles and waste of time, not for us. I mean events are very, very productive for us. It's a combination of the space, very interpersonal selling very interpersonal folks in the medical technology community community so it's very interpersonal so I think that plays into it. I also think that people like getting out to events and it's always better in person, no matter what, but we get a big percentage of our pipeline from events, we go to a lot.

33:51 I think it's, there's just so much noise in our inboxes or LinkedIn that, and especially if you're in a vertical SaaS where you know you can be pretty targeted about the events you go to and you know your buyers are going to be there. And it sounds like you have proprietary research and data that can probably get you some on stage presence and those type of things I think if you play them right and if it's a good fit.

34:04Are in-person events back?

34:15 It's a productive thing. And you still I would add I mean you still have to do tons of pre planning prep meeting set up in advance structure who you want to see go execute against it and then follow up measure the follow up that was a piece we put in over the past year but so I think there's not just going to the event because magic doesn't happen. There's tons of planning preps preset meetings, tons of follow up and holding folks accountable to communications and tracking that through CRM to make sure things are coming to closure.

34:44 And when you can do that, all the way beginning pre plan execute the event post plan follow up and drive pipeline. That's where we've seen the biggest benefit. Amazing. I'm sensing a lot of that ops background in the way you answer a lot of these questions and I really appreciate it. Post series see raised a fresh $80 million in capital. You know there's a directive to keep the growth going. What's going to be the biggest challenge for you, your team to continue that acceleration as you go.

35:21 What an interesting time because we like everyone else we are we are going to like move into a native like that's going to be the expert what is the experience of software look like it could be completely unique to each individual experiencing it like your traditional UI of point and click and hit tabs and you know dropdowns completely go away. I mean probably will see your experience could completely change. So we're in this interesting time where we are pivoting completely into, you know, a native thinking product and

35:55 figure out what what comes along in the platform. So as we're doing this, there is like a little bit of understanding that your, your, your growth might. I don't know, pick up a little bit as you make this transition like like you have to make a decision you're going to do this like right away and get killed in revenue, or are you going to slow burn it a little bit and continue like a really nice healthy growth,

36:07The biggest challenge after an $80M raise

36:21 but I would say we have a really thoughtful board that that gives us really good guidance and like things to think about in that in that journey. So what we've seen and what we're doing is looks like we're still maintaining pretty solid growth is as we move along and then we're in the process right now of trying to move folks into the QD AI solution. And that's a lot of what I talked about earlier in the commercial team being experts in our own solution so we can help sure bar customers in that direction.

36:55 So, it's kind of like a roundabout answer. We can't really stay on that same path because that legacy platform is going to change a lot or a little or whatever it is. So we're in this like interesting transition period I will tell you like, I feel pretty confident about the direction we're going and we're having great conversations and like our engagement at senior levels of our customers is phenomenal. So I think the direction we're going is really good.

37:25 I'm not, I haven't seen like major hiccups in growth, which is nice, but it's always it's always hard to predict so right now we're kind of maintaining plan I think we're doing, you know, pretty well against it, having an understanding board and a really transparent conversation helps those things because it's an interesting transition I mean like the companies haven't done this before, for the most part so, so far I think we're I think we're okay, I don't think I answered that question awesome, but it's a tough one to answer.

37:55 I'll take I'll take honest over awesome any day, and I think everybody's struggling with the same thing in acuity will have its own unique challenges going through that transition, but in general, most software companies are going to have to do this. Where do you think the biggest challenges in general are going to be is it going to be on enabling your team migrating customers. Do you need to change the profiles of your hiring change your culture in any way, what do you think the biggest walls people are going to run

38:29 into while going through this transition. I actually think the biggest wall people are going to run into is the mental wall of AI first. And so here's what I mean by that. Everybody has been kind of hired and onboarded in this pre pre AI world. So one of the things that I've been leading into for the past six weeks or whatever, and just didn't like I said an internal meeting yesterday is trying to shift the mindset of everyone to AI first like the world is going to change like your experience

39:05 with software is going to change the world is going to change is, is probably an overstatement but but your experience with software is going to change. If you maintain this legacy mindset of here is a user interface right term. The term is going to be relevant like here's a user interface. Here's how you think about these things. And if you think about AI as the next evolution in technology. I think that's a limiting way to think about it. So we're talking to our team about is forget about that. It's not that AI is the next wave of technology. AI actually makes it a ton easier to interact with technology actually like brings it backwards.

39:40 Don't overthink it. Ask whatever you want. Ask whatever you want. You know, I got my I got, I don't want to name any names but one of the things I tried to get you know whether it's your parents or your spouse or whatever, as you're as you're migrating from Google search into chat GPT is a lot of want to learn something new. Don't want to learn something new. It's easier than search like it's easier. You don't have to think at all touch the microphone and say what you want.

39:58The mental wall of "AI first"

40:06 It's that simple. I think the gating factor is going to be if folks cannot drop their past notions of how software works and what that experience is like. That's going to be the limiting factor. So it's really up to individuals and it shouldn't be that difficult to move into the new world. So that's really what I'm focused on. I'm focused on leading into the sales team and the professional services and customer success team to say,

40:33 this makes everyone's lives easy. It's easier to use. It's not hard. It's easy to use. Ask whatever you want. Do not overthink it. Don't overthink it. Well, folks, you know, come up with like these amazing prompts that yield amazing results. That's fantastic. But you should also say, I sell knees. How can you help me do that? I mean, that's it. You know what I mean? Like, you should completely demystify it. And I think if we can do that successfully, then most people will be okay.

41:02 But I think the limiting factor is people that hold on to old notions and think AI is this next evolution and more difficult. They're not going to learn it. I mean, nothing could be further from the truth. It makes the world so much easier. It's so interesting. One of the growth equity firms that we partner with really closely, Radium Capital, they shared, they've noticed across their portfolio, there has been much higher adoption on the go-to-market side of AI in general than on the product and in general.

41:31 Than on the product and engineering side. Yeah. And I will share, I noticed that internally at LeanScale too. We have go-to-market engineers, mostly heads down, coding and developing for our customers. And we have go-to-market architects that are more customer facing, half technical, but, and they've adopted AI a little bit more than our engineering team did. Yeah.

41:56 And I guess the big core of it that you brought up is, hey, you have these habits, you have this muscle memory of how you're used to working and you kind of have to go back and re-engineer those where some people that maybe didn't have any habits at all, it's easier for them to adopt because they weren't doing anything before. Exactly. Yeah, exactly. So that's like the biggest thing that I'm trying to attack right now. Alex, I could tell you have a deep operations background just based on how you're approaching a lot of these questions and problems or challenges that you're getting in your role.

42:30 I would love to hear, and I'll make it even more relevant. A lot of people listening to this podcast are in a RevOps role. They're thinking about, hey, how do I transition into that CRO role? Because that's kind of at the pinnacle of your career on the go-to-market side. So lots of people are interested in, how do I parlay this operational experience I have into that type of executive position? I would love to hear your story and how you went from operations into sales and then ultimately into the leadership position you're in today.

43:03 Yeah, happy to. This forms my thinking of sales, and I think it's a really big advantage, and I tend to try to pick this out. It's rare, but if you can pick it out on paper and suss it out in interviews, it's like magic if you can find someone with a background like this. We have a lady on our team today that I think just exemplifies this background, so I looked at her on paper and I loved it. So I started in supply corps in the Navy, hardcore operations, and a lot of folks, military officers come out, and they'll go into whatever corporate job they want to go into.

43:40 And a lot of these specialized recruiters will try to get folks into whatever specialty they think, and folks are trying to push me into sales, which I'll take as a compliment. It's fine. Like, okay, cool. You got a good personality, I guess. But that was not my dream. I was taking the GMATs and I wanted to go out of Wall Street. My dad was in finance, and so that's what I wanted to do. And like a lot of folks are, you think you know what you want to do and you have to learn over time.

44:07 So I ended up in like global supply chain operations, logistics operations at IBM. It was cool. Great. You can't go wrong. Go to IBM. It was fun. But what I ultimately ended up doing was I started getting close. I was very fortunate to jump into like an SAP R3 project, like in 1998. So I very quickly got into technology, which is ultimately like I made the pivot into software. But as I went through roles, I got closer and closer to the customer. So I was building like custom logistics solutions, technology solutions for our like large contract manufacturers.

44:08Operator to CRO: the career through-line

44:42 And then I partnered with the field sales engineering team on product managing, like a global visibility solution for semiconductor production for some of the ASICs and foundry customers like Nvidia and Xilinx and Qualcomm back in the day. And so what I found was I really enjoyed working directly with customers. And that just kind of like backed my way into it. Also happened to take project management certification courses. And that's where I think became really, really relevant because all of a sudden I popped up and I said, you know, I think I want to be in sales.

45:15 And so I kind of made a hard cut into a pretty non-technical product because I was given some advice that it might be a little bit more up my alley for selling in that like, you know, if you're selling semiconductors. Hey, you're an econ guy. They like tend to buy from double E's and you know, electrical engineers and masters and PhDs. Fine. I was very fortunate. I think if you put yourself in the position to recognize me, you get really lucky. That's great. So I had some project management training. And so I joined an organization where they were rolling out spin selling from, you know, Huthwaite back in the day in 2003 or whatever.

45:50 And I actually thought it was gold. I thought it was magic. I was like, wait a minute. There's a process to selling? Like there's things you can do, like you can actually move through a process. And so what I started to digest and like rolled out to organizations was this combination of spin selling, which is really like psychology management. You know, the author of spin selling was a psychology research. I love it. But it's like psychology management. The art of the sale. How do you influence people and then the science of the sale, which my teams I think would probably go, oh my gosh, not another clothes plan.

46:27 But the science of the sale is how do you methodically move through these sales so that you can ultimately get customers to agree to what we want to do together. But you're moving through a rigorous process to get through a sale and get to signature. So it's like this blending of how do you how do you master the art of psychology and working with lots of different folks to get everybody in the same moving in the same direction, which I think is a big like attribute of leadership and then methodically managing your way through sales.

47:01 And it was only after the fact that, you know, you heard about John McMahon and medic and medic and all those things. And I was like, oh, yeah, that sounds good. That sounds like kind of what I'm doing. But that I believe that operational background bringing into sales, you'd be successful in sales is it is absolutely invaluable because when it when you realize that managing a sale is like a project. Man, it just like takes on a whole different meaning. And then if you like, I could recommend something. I just I mean, I love the book range. It's just this, you know, people with varying backgrounds that culminate in one sort of successful move.

47:38 It's a very cool book for anybody with a varied background. And I read and I was like, oh, that's cool. That sounds like me. It makes me feel really good about making these like wild jumps and seemingly disconnected moves that I now, you know, connect together. But yeah, I love I love sales folks with non-traditional backgrounds. I think it brings a completely different perspective in like, how do you methodically move through the sale?

48:05 I've definitely, in my experience, the best reps have been unbelievably methodical. They time box their day in certain ways. They're very, very numbers oriented. Of course, they do have the soft skills and some of the qualitative abilities to move the sale along and have the right conversations at the right time. But they they have a process and I've seen plenty of people who have like all the soft skills, gift to gab presentation, very, very, you know, exciting people to be around that don't close anything because they're not moving the deal along as they need to.

48:46 So I've 100 percent seen that. I'm curious. Sounds like people pointed that out to you earlier in your career. They recommended you go into sales. So you clearly had some of those qualitative attributes, someone in a rev ops role. They're in. And usually rev ops, you get an eclectic bag of people, too. I kind of did a little bit of sales and marketing before doing rev ops, but then I fell in love with the science of it and had a great passion for it.

49:13 But a lot of people in it who maybe have not had that type of experience, what do you recommend they do? Do you do? Do you go hop out and get an eight year old? Do you look for some type of leadership role? Do you kind of get the next best opportunity? That's close. How do you and I know it's not linear, but how do you kind of work your way towards a zero position? Yeah, I think I think I've actually done both. When I left IBM, I actually took a sales leader role at that company, which was interesting because I've never been in sales before. Can I hang on there for a second?

49:48 How I would anticipate the biggest challenge would be gaining the respect of the sales team and being able to coach them with experience. How did you do that? How did you lead a team of sellers without selling before? Yeah, it was well, you know, I knew the executive team pretty well. This is where I think the fortunate timing came in. First of all, I've never been afraid of getting my hands dirty, so I would go manage accounts individually on my own.

50:14 I've been customer facing in the past, but having spin selling almost exactly at the same time when I joined and just having the eyes open, I was able to actually sink my teeth into something where I could help the team immediately. So a little bit of luck on the timing there, but I think if you're always from a leadership standpoint, if you're always willing to get your hands dirty and do anything you ask your team to do and just commit yourself to helping them, those things go a long way.

50:43 People can see those things. Those things go a long way. And those are things that I've always been willing to do. And you just have to understand that. Like when I joined IBM, you know, you had a lot of people that have been there for a long time working for a younger person. So those are not environments that I was not familiar with. I just think like basic leadership traits help you do that. And then back to your original question, I did, I was at a logistics organization, I was running the sales group in North America and like the IT solutions group, but it wasn't in software.

51:13How to break from RevOps into sales leadership

51:14 So I did take and it was a strategic account manager role in a software organization for like 21 months. And I kind of went in and I said, look, I want to do this to learn the product, learn the customer base and then get back into leadership. They were great about it. You know, got back into leadership, but I'm actually talking to a guy right now who was an executive. And I just think that if you go do the role, first of all, it's pretty fun. Second of all, you can make a lot of money and it is the best way to learn the customer base and the product. So a couple ways to do it. I would not discourage anyone from being an A for a couple years.

51:50 I think it's like super valuable and probably the best way to get into sales leadership. I don't think you have to be an A to ultimately be a CRO, but I never dissuade it. I would highly recommend it. I would too. And I was so fortunate. Mine was all over the place too. My early career, super eclectic. And then I found RevOps, which felt like it rewarded having range and was there. But I think even if you don't take that and move into a CRO role, let's say you're in RevOps, you go do an AE role, you go to a customer success role. There's just anything customer facing.

52:31 I think when you come back, you'll have more empathy, better recommendations. You'll be thinking about your customer better. So I think if anyone has an opportunity to do that, they should. Absolutely. Yeah. I hired a rep early on who's doing okay. Did amazing. Helped us stand up enablement. Amazing. Now he's one of our sales leaders and he is just leaning in and just doing an amazing job from a process standpoint, but has total like context of almost the entire commercial operation in our organization.

53:03 So it's just, it's a great purview to have. Well, Alex, I can't thank you enough for everything you shared unbelievably eloquent and structured. And I think you shared so many nuggets of information and insight that are going to help anybody in their career. And I am pumped for what you and Acuity are doing. I can't wait to see that conversion into AI native as well as the acceleration of growth post a series C congratulations. I know the job's probably feeling like it's just getting started, but you've already come so far. So excited to watch and follow and thank you so much for being on the lean scale podcast today.

53:42 Yeah, of course. Thanks a lot for having me Anthony. Appreciate it. Appreciate all the kind words and yeah, we're on to the next phase. So thanks a lot.