The LeanScale Podcast · Episode 60

The Hidden Mistakes of Scaling RevOps and Enablement

Andy Mowat on where scaling companies neglect the fundamentals — enablement, data foundations, GTM tooling, and the RevOps career

Andy Mowat · Founder & CEO, Whispered · Whispered Hosted by Anthony Enrico
Published Updated 00:34:29 33 min read 6,507 words
Revenue Operations Sales Enablement AI in GTM GTM Strategy Sales Leadership
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Executive Summary

The one-paragraph brief, extended

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

Scaling a company isn't just about hiring more reps — it's about building the right systems, data foundation, and enablement at the right time, in the right order. In this episode, LeanScale co-founder Anthony Enrico sits down with Andy Mowat, founder and CEO of Whispered and a former go-to-market and RevOps operator at Upwork, Culture Amp, Carta, and Fox. Andy has lived the scale-up phase from the inside at two unicorns, advises a stack of fast-growing companies, and now runs a network that helps VP- and C-level GTM leaders find the roles that never make it to a job board. The conversation is a fast, unhedged tour of where companies quietly break as they grow.

The heart of the episode is a catalog of the mistakes scaling companies make: they don't get the data foundation right, so they hand clunky, un-enrichable tooling to their reps and can't layer AI on top later; they don't know the right metrics to track; they build processes inefficiently; and — most consistently — they neglect enablement until it's too late. Andy, who has run enablement at two unicorns, argues that enablement is a stage-fit decision: with one manager and fewer than ten reps the manager does it, but the moment you start cloning teams, adding products, and multiplying complexity, formal enablement has to exist or your reps just cycle on the same problems. He's blunt about the talent bar too — enablement leaders (whether ex-reps or ex-teachers) have to act as the sales team's prioritization function and hold an opinion, not take orders — and about coaching, where the best managers review lots of calls rather than one here and there.

The middle turns to tooling and the near future of the RevOps stack. Andy tells the 'seven-to-eight email systems' horror story that greets every incoming RevOps leader, makes the case for a true data-warehouse-first architecture (his test: if we deleted your CRM instance, how exposed are you?), and predicts the entire GTM tech foundation will turn over in three to five years as next-gen, AI-native CRMs — 'imagine Clay, Gong, and HubSpot had a baby that actually worked' — come for Salesforce and Marketo. His view on AI is pragmatic: SQL gets easy, GTM engineering becomes central (as long as it sits under RevOps and solves root problems, not surface ones), and RevOps as a function survives — but operators who stay stuck in legacy platforms are genuinely at risk.

The final act is about careers. Andy's own path is the classic accidental-operator story — he cold-called his way into tech, got asked to run systems in month three, and 'fell into the function' like most RevOps people do. From that he draws Whispered's thesis: at the VP/C-level, roles aren't posted, they're whispered; everyone eventually gets 'punched in the face' and has to search proactively; and the way to build a durable RevOps career is to do tours of duty across the six functions (sales ops, marketing ops, CS ops, GTM systems, strategy, enablement), find a mentor, and get moved around by a leader who wants to grow you. He even makes the tongue-in-cheek-but-serious case that the best RevOps people come out of marketing ops.

Who should listen: RevOps and GTM leaders trying to future-proof both their systems and their careers, founders and revenue executives deciding when to invest in enablement and how to write a RevOps role that a real human can actually fill, and anyone weighing how AI will reshape the go-to-market stack over the next few years. The throughline is that scaling is a sequencing problem — get the data foundation, tooling, enablement, and talent right at the right stage, and everything downstream gets easier.

Key Takeaways

14 things worth stealing

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

01

Get the data foundation and GTM tooling right first — everything downstream inherits the mess

Andy's number-one scale-up mistake: companies don't build the data foundation the right way, so they hand clunky tooling to reps, can't stand up a data-enrichment layer, can't target the right accounts, and can't put AI on top later. Poor foundations compound into bad metrics and inefficient processes.

Why it matters: Sequence the foundation before the fancy layers. If the data and enrichment layer are wrong, no CRM, AI agent, or enablement program on top of it will perform — and rolling it back later means blowing it all up.

RevOps LeadersFoundersRevenue Executives
02

Enablement is the most neglected function — and 'crappy enablement' is a real career risk

Andy says companies routinely don't invest in enablement until it's too late, and without it teams just cycle and redo the same work over and over. He frames it starkly: being a revenue leader at a company with crappy enablement is a big bet against yourself.

Why it matters: Treat enablement as a first-class part of the scaling plan, not an afterthought. If you're evaluating a revenue-leadership role, diligence the enablement function the way you'd diligence the pipeline.

Sales LeadersRevOps LeadersFounders
03

Enablement is a stage-fit decision — the manager does it until you clone the team

With one sales manager and fewer than ~10 reps, that manager covers enablement (and rep ops). The trigger to build formal enablement is when you start cloning teams, adding products, and multiplying complexity — the point where the manager gets pulled in too many directions to do it well.

Why it matters: Don't hire enablement too early or too late; tie the decision to team-cloning and product complexity. Ask whether your frontline managers still have the bandwidth to enable, or whether they're already underwater.

Sales LeadersFounders
04

Hire enablement leaders with an opinion — order-takers fail

There are two profiles that work: the former rep you train up, and the teacher-type with an ops mind. Either can succeed or fail on one variable — whether they partner with sales leaders as the prioritization function and hold a point of view ('we should train on this, not this'). The 'wilting flowers' who just take orders can't enable anyone.

Why it matters: Screen enablement candidates for opinionated prioritization and alignment with sales leadership, not just content-building or facilitation skills. The best hires empathize with the field and have a teacher-and-ops mind.

RevOps LeadersSales Leaders
05

Coach with call review at volume — restructure how managers use Gong and Chorus

Andy has walked into companies where managers 'listen to a call here and there' and calls that the wrong answer. He relays Chorus founder Roy Raanani's line — you can listen to 100% of one call or 1% of 100 calls — and the best managers review lots of calls. Coaching, new-release training, and getting the corporate pitch right are core enablement, not extras.

Why it matters: Buy conversation-intelligence tools and then actually rebuild the manager's operating rhythm around them. Make call review, running better sales-team meetings, and rep-led training a standing part of the cadence.

Sales LeadersRevOps Leaders
06

The email-systems mess is the canonical martech trap — get the event stream right early

Andy has shown up to unicorns running seven to eight email systems — Marketo or HubSpot for top of funnel, Iterable or Braze for late-stage, a product-triggered tool, and a fourth someone bought because the others didn't work. The fix is sending intelligent, data-rich emails off the product event stream (e.g., what Inflection.io does for Clay's week-in-review), but if you get it wrong early it's nearly impossible to unwind without blowing it up.

Why it matters: Design the messaging/martech architecture around a clean event stream before the tools proliferate. One bad early decision here is one of roughly 20 similar landmines — the pattern, not just the tool, is the lesson.

Marketing LeadersRevOps Leaders
07

Most RevOps people fall into the function — build the career by getting moved around

Andy cold-called his way into tech, was asked in month three to run SMB sales and 'figure out the systems,' and, like most RevOps people, just fell into the function. Anthony's version: a new CRO told him 'you're not CS anymore, you're Ops.' Nobody went to college for this; you find out what you're good at and repeat it.

Why it matters: Career growth in RevOps comes from rotating across functions, not defending a title. Work for a leader who will move you around and challenge you so you become a full-funnel operator.

RevOps LeadersRevenue Executives
08

Everyone eventually gets 'punched in the face' — build the network before you need it

There's a comfortable phase where you always have something lined up, a mentor to follow, recruiters chasing you. Then you get laid off, clash with a boss, or the company runs out of money and you have to search proactively. Andy stresses this is jarring precisely because it isn't only 'shitty people' who end up searching.

Why it matters: Invest in networking and job-search skill while you're employed and comfortable, not when you're desperate. Proactive relationship-building is the insurance policy for the inevitable forced search.

RevOps LeadersRevenue ExecutivesSales Leaders
09

Executive GTM roles aren't posted — they're whispered

At the VP/C-level, the odds of the role you want being publicly posted are low; it's whispered to you through the network. Whispered's insight is that execs learn a ton interviewing at a company and then throw it away — so capturing those confidential company insights over years builds a real edge, and a bad job choice sticks to your resume forever.

Why it matters: For senior GTM roles, work the network and confidential intel rather than job boards, and diligence a company hard before you join — the wrong choice is on your resume for the rest of your career.

Revenue ExecutivesRevOps Leaders
10

The 'impossible RevOps JD' is a red flag — and the reason LeanScale exists

Andy and Anthony both laugh at the job description that asks one IC to build the GTM systems, the metrics cadence, CPQ, enablement, and commissions — plus board reporting and fundraising help — for around $200–225k. No single person has all those skill sets, and if they do, they won't work for that price.

Why it matters: If you've written that JD, you won't fill it; unbundle the role or bring in fractional/pod support. The mismatch between the ask and what one hire can deliver is exactly the gap fractional RevOps was built to close.

FoundersRevenue ExecutivesRevOps Leaders
11

Be data-warehouse-first — pass the 'delete your CRM' test

Andy asks companies whether their source of truth is Salesforce or a warehouse like Snowflake or Redshift, and notes the share saying 'warehouse' has moved from 5–10% to 20–30%. His resilience test: if we deleted your CRM instance, how exposed are you? Truly strong teams could bolt on a new front end and be fine.

Why it matters: Own your data in a real warehouse so the CRM is a replaceable front end, not the system of record. Learn SQL — with AI it's easy — and keep the RevOps mindset of 'configure, not customize.'

RevOps LeadersFounders
12

The whole GTM stack turns over in 3–5 years — but RevOps as a function survives

Andy tracks ~20 next-gen AI-native CRMs and believes they'll come for Salesforce, Marketo, and even HubSpot: 'imagine Clay, Gong, and HubSpot had a baby that actually worked,' with product data, call data, and enrichment built in. He's confident the tech foundation flips in three to five years while RevOps as a function keeps existing — but operators stuck in legacy platforms are in danger.

Why it matters: Upskill toward data, next-gen tooling, and AI now. Betting your career on deep Salesforce/Marketo specialization alone is risky over the next couple of years.

RevOps LeadersFounders
13

GTM engineering belongs under RevOps — data foundation first, agents on top

Andy likes the GTM engineer role when it's aligned with RevOps: build the data foundation, then build AI agents on top of it (he's a fan of Scale Stack as an enterprise Clay for exactly this). The failure mode is unaligned biz-ops people who ship the thing in front of them, solve the surface problem, and cause more chaos by never fixing the root.

Why it matters: Put GTM engineering inside the RevOps org with a data-foundation-first mandate so automation solves root problems. Separately, the unsolved frontier is a better rep-facing UX layer over the CRM.

RevOps LeadersRevenue Executives
14

The best RevOps leaders come from marketing ops — do tours of duty across the six functions

Andy names six functions within RevOps — sales ops, marketing ops, CS ops, GTM systems, strategy, and enablement — and argues you're unlikely to be great at all of them, so the way up is rotating across them. He half-jokingly says the best RevOps people come out of marketing ops, because it's more technical, more data-heavy, and forces working in the gray. Anthony's one regret is not spending more time in marketing ops.

Why it matters: Deliberately rotate through unfamiliar ops functions (especially marketing ops) to become a full-funnel operator, and as a leader, move your people around so they become full-function experts.

RevOps LeadersRevenue Executives
Frameworks Discussed

9 named models

Every framework Jimmy names, defined and time-stamped.

The Series A GTM Checklist

02:34

Andy's written checklist of the go-to-market foundations fast-growing (roughly Series A) companies forget: the data foundation, GTM tooling, the right metrics to track, efficient processes, CPQ, and enablement.

He wrote it for founder friends who were 'growing fast and forgot a lot of stuff.' It reframes scaling as a sequencing problem — getting a specific set of foundational systems and functions right in the right order rather than just adding reps.

Enablement Timing: The Clone-the-Team Trigger

03:54

Build formal enablement when you start cloning sales teams and multiplying products and complexity. Below that — one manager, fewer than ~10 reps — the manager owns enablement and rep ops themselves.

Early on the manager covers enablement by default; the moment you scale to multiple teams and products, that manager gets pulled in too many directions, and you need a repeatable way to do it 'the same way' across clones.

The Two Enablement Talent Profiles (Prioritization Function, Not Order-Taker)

07:14

Enablement hires come in two shapes — the former rep you train up, and the teacher-type with an ops mind. Either succeeds only if they partner with sales leaders as the prioritization function and hold an opinion on what to train.

Both profiles can win or fail on the same variable: alignment with the sales leader and a point of view. 'Wilting flower' order-takers who just ask what to train on are toast; the best hires empathize with the field and think like a teacher and an operator.

Getting Punched in the Face (Proactive vs. Passive Job Search)

13:29

You're a passive job-seeker — always with a role lined up or recruiters chasing you — until you get 'punched in the face': laid off, in conflict with a boss, or at a company that ran out of money, forcing a proactive, jarring search.

The point is that a forced proactive search happens to almost everyone at some point and isn't a signal of a weak operator. It's why you build networking and job-search muscle before you need it.

Roles Aren't Posted, They're Whispered

14:55

At the VP/C-level, the odds of a role being publicly posted are low; it's whispered to you through the network. Whispered captures the confidential company insight execs gather while interviewing (and then normally throw away) into a durable edge.

Over three years of execs sharing what they learned, the network accumulates confidential intel on companies — because a bad job choice sticks to your resume forever, the platform helps people both open doors and avoid the wrong ones, without doing the search for them.

The 'Delete Your CRM' Data-Warehouse Test

24:24

A resilience test for data architecture: if we deleted your CRM instance today, how exposed are you? Teams with a true data warehouse as source of truth could bolt on a new front end and be fine.

Andy uses it to separate CRM-as-system-of-record teams from warehouse-first teams (Snowflake/Redshift). The share answering 'warehouse' has climbed from 5–10% to 20–30%, and warehouse-first is the strong posture.

RevOps Is 'Configure, Not Customize'

25:36

The core RevOps mindset: configure systems to fit the business rather than deeply customizing them into brittle, un-maintainable states. Paired with a data skill set (SQL, which AI now makes easy).

Andy says he'd never hire someone who didn't understand SQL, but with AI the mechanics are easy — what endures is the configure-not-customize mindset that keeps the stack flexible as tooling turns over.

GTM Engineering Under RevOps (Foundation First, Agents on Top)

25:36

Put the GTM engineer role inside the RevOps org: first build the data foundation, then build AI agents on top of it. Keep it aligned so automation solves root problems, not just the surface problem in front of it.

Unaligned biz-ops people 'ship the thing' and cause chaos by fixing symptoms; aligned GTM engineering (Andy cites Scale Stack as an enterprise Clay running enrichment agents) compounds. The unsolved frontier is a better rep-facing UX layer over the CRM.

Tours of Duty Across the Six Functions of RevOps

32:41

RevOps spans six functions — sales ops, marketing ops, CS ops, GTM systems, strategy, and enablement. You won't be great at all of them, so build a full-funnel operator by rotating across them, ideally under a leader who moves you around.

Andy grew his people by rotating them at Culture Amp and Carta; he half-jokingly argues the best RevOps leaders come from marketing ops because it's more technical, data-heavy, and ambiguous. Anthony's regret is not doing a marketing-ops tour himself.

Best Quotes

18 lines worth clipping

Pulled verbatim. Copy or share any of them.

“They don't get their data foundation right, they don't get their GTM tooling right, so then they're just ending up giving clunky tooling to their reps.”
Andy Mowat 01:16
“A lot of people don't invest in enablement until it's too late. If you're going to be a revenue leader at a company with crappy enablement, that's a pretty big risk.”
Andy Mowat 01:56
“If you have a team of less than 10 reps, you probably don't need enablement. But as you start to clone that team, have multiple products, throw a lot of complexity at these people — that's when you should really start to think about it.”
Andy Mowat 03:54
“If you show up and you're like, 'Cool, just tell me what we should train on,' you're kind of toast. You have to have an opinion — we should be training on this, not on this.”
Andy Mowat 07:14
“I can't tell you the number of unicorns I've shown up to that have seven to eight email systems. Everyone flocks to you like, 'God, can you fix that email shit show?'”
Andy Mowat 08:39
“Like most RevOps people, I just fell into the function.”
Andy Mowat 12:13
“He goes, 'You're not CS anymore. You're Ops.' And that was it. I didn't really ask for it, but I'm very, very happy it happened.”
Anthony Enrico 12:52
“At some point in your career, you will get punched in the face — by that I mean you'll have to go search proactively for a job, versus being able to say, 'Oh, I don't want to take that call right now.'”
Andy Mowat 13:29
“At that level, the odds of the role you find being posted are really low. Odds are it's whispered to you.”
Andy Mowat 14:55
“If you're an exec and you interview for a role, you learn a lot about that company and you throw it away. For the last three years, people have been giving that to us.”
Andy Mowat 15:33
“We're not here to do someone's search for them. We're here to give them the tools to do it better.”
Andy Mowat 17:48
“An individual operator needs to build the GTM systems, build the metrics cadence, get CPQ running, run enablement, run commissions — and it's an IC role for 200 grand. You just laugh at those roles.”
Andy Mowat 19:38
“I walked into those roles with really high expectations — plus go to the board meetings with us, plus help us do fundraising. What one person has all of those skill sets?”
Anthony Enrico 21:10
“Imagine Clay, Gong, and HubSpot all had a baby together — and that baby actually worked. That's what I think is coming.”
Andy Mowat 24:24
“If your CRM gets killed and we delete the instance, how fucked are you? The people that are really strong are the ones that have a true data warehouse.”
Andy Mowat 25:02
“RevOps people are configure, not customize people.”
Andy Mowat 25:36
“My belief is that the entire tech foundation is going to turn over in the next three to five years within RevOps — but RevOps as a function will continue to exist.”
Andy Mowat 26:41
“There are six functions within RevOps: ops, mops, CS ops, GTM systems, strategy, and enablement. You're probably not going to be good in all of them.”
Andy Mowat 32:41
Practical Advice

What should you actually do?

The playbook, split by the seat you sit in.

Founders

  • Sequence the scale-up: get the data foundation and GTM tooling right before layering AI, enrichment, or fancy automation — a bad foundation makes everything downstream clunky and nearly impossible to unwind later.
  • Invest in enablement before it's 'too late,' but tie the timing to team-cloning and product complexity, not a calendar. Below ~10 reps under one manager, the manager does it.
  • Don't write the 'impossible' RevOps JD (systems + metrics + CPQ + enablement + commissions + board reporting for ~$200–225k). Unbundle the role or bring in fractional/pod help — one hire can't do it, and if they could, they won't take that price.

RevOps Leaders

  • Be data-warehouse-first: own your data in Snowflake/Redshift so the CRM is a replaceable front end. Pass the 'delete the CRM instance' test.
  • Put GTM engineering inside your org with a data-foundation-first mandate, then build AI agents on top — so automation fixes root problems instead of shipping surface-level chaos.
  • Upskill toward data and next-gen, AI-native tooling now; the stack will turn over in 3–5 years and legacy-only Salesforce/Marketo specialists are exposed.
  • Do tours of duty across the six functions (especially marketing ops) to become a full-funnel operator, and move your own people around to make them full-function experts.

Sales Leaders

  • Hire enablement leaders who act as the prioritization function and hold an opinion on what to train — not order-takers. Both ex-reps and teacher-types work if they align tightly with sales leadership.
  • Rebuild your coaching cadence around call review at volume (Gong/Chorus) — the best managers review many calls, not one here and there — plus new-release training and getting the corporate pitch right.
  • Run sales-team meetings as learning forums, bringing reps in to help evaluate and train, rather than only asking 'where's pipeline?'

Marketing Leaders

  • Design the martech/messaging architecture around a clean product event stream early — before you accumulate seven to eight overlapping email systems that are almost impossible to unwind.
  • Send intelligent, data-rich lifecycle emails triggered by real product behavior (the Inflection.io-style model) instead of 'let's send an email today' blasts.

Revenue Executives

  • Build your network and job-search muscle while you're comfortable — everyone eventually gets 'punched in the face' and has to search proactively.
  • For senior GTM roles, work the network and confidential intel over job boards (roles are whispered, not posted), and diligence a company hard before joining — a bad choice stays on your resume forever.
  • Find a mentor and, if you're early, consider being a strong number two at a well-run company over chasing the 'head of RevOps' title.
AI Takeaways

How AI actually changes GTM

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

The thesis

AI won't erase RevOps — it will turn over the stack and raise the bar for operators. The winners get the data foundation right first, put GTM engineering and AI agents under RevOps, and upskill toward data and next-gen tooling; the losers stay stuck in legacy Salesforce/Marketo specialization.

The stack turns over, the function survives

Andy tracks ~20 AI-native CRMs and expects the RevOps tech foundation to flip in 3–5 years ('Clay + Gong + HubSpot with a baby that works'), while RevOps as a function keeps existing. Operators who don't upskill are genuinely at risk.

Data foundation before agents

AI only pays off on a clean foundation. Build the data layer first, then run agents on top (he uses Scale Stack for enrichment). You can't put AI on tooling that never had a proper data-enrichment layer.

SQL gets easy, mindset stays hard

With AI, SQL is 'insanely easy,' so the durable edge is the RevOps mindset — configure, not customize — not the raw mechanics. Andy still won't hire operators without a data skill set.

Keep GTM engineering aligned

AI-empowered GTM engineers are great under RevOps but dangerous when unaligned — biz-ops folks who 'ship the thing' solve the surface problem and cause chaos by never fixing the root.

The rep UX layer is still unsolved

The open frontier is a better rep-facing experience over the CRM — Andy invested in Scratchpad and wants someone to lift teams out of Salesforce with a cheaper, better UX; the winner hasn't emerged.

Agent & automation ideas

  • Enrichment agents (Scale Stack / Clay-style) that continuously research accounts, bring back the data, and do the grunt work so RevOps operators run faster on a clean foundation.
  • Product-event-stream email agents that trigger intelligent, data-rich lifecycle messages (Inflection.io-style) off real usage instead of blast campaigns — collapsing the seven-to-eight-tool email mess.
  • A rep-facing UX/agent layer over the CRM (a better, cheaper Scratchpad) that lets sellers update pipeline, notes, and forecasts without living in Salesforce.
Operations Takeaways

By function

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

Revenue Operations

  • Foundation first. Data foundation and GTM tooling before everything else — bad foundations mean clunky rep tooling, no enrichment layer, and no place to add AI later.
  • Warehouse-first architecture. Own your data in Snowflake/Redshift so the CRM is a replaceable front end; pass the 'delete the CRM instance' resilience test.
  • Enablement is a stage-fit call. Manager owns enablement under ~10 reps; build the formal function when you clone teams and multiply product complexity.
  • GTM engineering under RevOps. Keep it aligned and foundation-first so agents solve root problems, not surface ones; unaligned biz-ops causes chaos.
  • Configure, not customize. The enduring RevOps mindset as tooling turns over; AI makes SQL easy, so the mindset and data skill set are the moat.
  • Grow via tours of duty. Rotate across the six functions — sales ops, marketing ops, CS ops, GTM systems, strategy, enablement — to become a full-funnel operator; the best often come from marketing ops.
Metrics Mentioned

The numbers, with context

< 10 reps per manager
Enablement trigger

Below roughly ten reps under one manager, you probably don't need formal enablement — the manager covers it; you invest once you start cloning teams and adding product complexity.

7–8 tools
Email systems at scale

The number of overlapping email/messaging systems Andy has found running at unicorns when he arrives as the incoming RevOps leader.

800,000 recipients
Automated email blast

Early in his career at Upwork, Andy automated an email to 800,000 people that 'got us in a little bit of trouble' — his accidental entry into RevOps.

~100 playbooks
Whispered free playbooks

The library of free career playbooks (from working with talent partners to sharpening your niche) that thousands of people a month use.

$200K–$225K IC
Impossible RevOps role comp

The pay attached to job descriptions asking one individual contributor to build systems, metrics, CPQ, enablement, and commissions — a mismatch you 'laugh at.'

~20
Next-gen AI CRMs tracked

The number of next-gen AI-powered CRMs Andy keeps in a Google doc, which he believes will come for Salesforce over the next 3–5 years.

5–10% → 20–30%
Data-warehouse as source of truth

The share of companies naming a data warehouse (not the CRM) as their source of truth has roughly tripled, a sign of the shift to warehouse-first architecture.

3–5 years
GTM tech turnover horizon

Andy's estimate for how long until the entire RevOps tech foundation turns over — even as RevOps the function persists.

Entities

Companies, people & tools mentioned

Auto-extracted and linked into the knowledge graph.

Companies

WhisperedTalent & Recruiting

Andy's company; a network that connects VP/C-level go-to-market leaders with executive roles that are rarely posted, using confidential company insights, ~100 free playbooks, an application-gated Pro tier, and a plugged-together operator network. Free for companies.

00:00 · 14:55 · 16:42 · 21:41Company →
UpworkFreelance Marketplace

Where Andy got his start after cold-calling the CEOs of oDesk and Elance (which merged to form Upwork); hired for BD, then asked in month three to run SMB sales and the systems.

00:00 · 11:27Company →
Culture AmpHR Software

A unicorn where Andy ran RevOps/GTM ops (his first time running sales ops, since they had no commissions) and moved his people across functions to grow full-function experts.

00:00 · 30:19 · 32:41Company →
CartaFintech

Where Andy took on commissions (which sat under finance) and continued rotating his team across functions.

00:00 · 32:41Company →
FoxMedia & Entertainment

One of the big-name companies where Andy held an operations role before his RevOps unicorn run.

00:00Company →
SnowflakeData Cloud

Cited as an example of a real data-warehouse source of truth (vs. Salesforce or Redshift); warehouse-first teams pass the 'delete the CRM' resilience test.

24:24Company →
New RelicObservability / DevOps

A former New Relic CMO is one of the function leads Andy has working with companies through Whispered on the marketing side.

17:48Company →
RevOps Co-opRevOps Community

Recommended as a good RevOps learning community, built by Matt Vollm, where Andy now spends more of his community time.

28:28Company →

People

Andy Mowatguest

Founder & CEO of Whispered and former GTM/RevOps leader at Upwork, Culture Amp, Carta, and Fox.

Founder & CEO, WhisperedProfile →
Anthony Enricohost

Co-founder of LeanScale and host of The LeanScale Podcast.

Co-FounderProfile →

Tools & software

GongRevenue Intelligence

Cited as the call-recording/conversation-intelligence category Andy wished for before it existed at Upwork; managers must restructure how they coach with it.

Website ↗
ChorusConversation Intelligence

Referred to (transcribed as 'Kors') alongside Gong; Andy relays founder Roy Raanani's line that you can listen to 100% of one call or 1% of 100 calls.

Website ↗
MarketoMarketing Automation

Named as the legacy top-of-funnel marketing-automation system (with Salesforce) that next-gen AI CRMs are coming for.

Website ↗
HubSpotCRM

Cited as a top-of-funnel email/CRM tool and as one ingredient in the 'Clay + Gong + HubSpot baby' vision of a next-gen AI CRM.

Website ↗
IterableMarketing Automation

Named as a late-stage-funnel email tool that shows up in the sprawling seven-to-eight-system email mess.

Website ↗
BrazeCustomer Engagement

Named alongside Iterable as a late-stage lifecycle-messaging tool contributing to email-system sprawl.

Website ↗
Inflection.ioMarketing Automation

Product-led email tool Andy pointed to as the fix for email sprawl — sending intelligent, data-rich emails off the product event stream; powers Clay's week-in-review. He nearly bought it before leaving a company.

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ClayGTM Data / Enrichment

Referenced as the enrichment/GTM-data tool whose week-in-review is powered by Inflection, and as an ingredient in the next-gen AI CRM vision; Scale Stack is framed as an enterprise Clay.

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SalesforceCRM

The legacy CRM Andy expects next-gen AI-native CRMs to come for; also the front end teams should be able to delete if they're truly data-warehouse-first.

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Scale StackGTM Data Automation

Andy's favored enterprise-grade Clay alternative; his team runs Scale Stack AI agents to enrich data and do work automatically as the 'agents on top of the data foundation' layer.

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ScratchpadSales Productivity

A rep-UX layer over Salesforce Andy invested in; he loves the concept but balked when the price jumped ~$50k — an example of the still-unsolved rep UX problem.

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Amazon RedshiftData Warehouse

Named alongside Snowflake as a real data-warehouse source of truth that separates strong, warehouse-first teams from CRM-dependent ones.

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Related LeanScale Services

Where this shows up in the work

Fractional RevOps

Embedded, field-facing RevOps leadership and execution — the operator model Jimmy describes, delivered as a service.

The 'impossible RevOps JD' — one IC expected to build systems, metrics, CPQ, enablement, and commissions — is precisely the gap fractional/pod RevOps was built to close.

Sales Enablement Build

Stand up a zero-based, sales-academy enablement motion sized to your span of control and sales complexity.

The episode is a clinic on when and how to stand up enablement (stage-fit, the two talent profiles, coaching via call review) — core to how LeanScale builds enablement motions.

AI for GTM

Agents and workflows that multiply operator throughput — the 'make humans superhuman' thesis, operationalized.

Andy's data-foundation-first, GTM-engineering-under-RevOps, next-gen-AI-CRM thesis maps directly to LeanScale's AI-for-GTM operating leverage.

Frequently Asked Questions

Straight answers

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

What mistakes do companies make when scaling RevOps?

The most common ones, per Andy Mowat, are not building the data foundation the right way (so reps get clunky tooling and there's no enrichment layer to target accounts or add AI later), not tracking the right metrics, building processes inefficiently, forgetting things like CPQ as they mature, and — most consistently — neglecting enablement until it's too late. Foundations are the theme: get them wrong early and it's nearly impossible to unwind without blowing it all up.

When should a startup invest in sales enablement?

It's a stage-fit decision. With one sales manager and fewer than about ten reps, that manager can cover enablement (and rep ops) themselves. You should build a formal enablement function once you start cloning sales teams, adding multiple products, and multiplying complexity — the point where the manager gets pulled in too many directions to do it well.

What makes a good sales enablement leader?

There are two profiles that work: a former rep who carried a bag and can empathize with the field, and a teacher-type with an ops mind. Either succeeds only if they partner with sales leaders as the prioritization function and hold an opinion on what to train ('we should train on this, not this'). Order-takers who just ask what to train on fail regardless of background.

Will AI replace RevOps roles?

No — but it will reshape them. Andy Mowat believes the entire RevOps tech foundation will turn over in three to five years as AI-native CRMs come for Salesforce and Marketo, while RevOps as a function keeps existing. The risk is to operators who stay stuck in legacy platforms; those who upskill toward data, next-gen tooling, and AI agents (kept under RevOps, on a clean data foundation) are well positioned.

What is Whispered and how does executive GTM hiring work through it?

Whispered is a network founded by Andy Mowat that connects VP- and C-level go-to-market leaders (RevOps, sales, marketing, CS) with executive roles that are rarely posted publicly. It offers ~100 free career playbooks used by thousands of people a month, an application-gated 'Pro' tier with confidential company insights and unposted role flow, and a plugged-together operator network. It's free for companies, who increasingly call directly for hard-to-fill VP-level roles.

What does it mean to be 'data-warehouse-first' in RevOps?

It means your source of truth is a real data warehouse (like Snowflake or Redshift), not the CRM. Andy's test: if we deleted your CRM instance today, how exposed are you? Strong, warehouse-first teams could attach a new front end and be fine, because the CRM is a replaceable interface rather than the system of record. The share of companies naming a warehouse as source of truth has moved from 5–10% to 20–30%.

Why do the best RevOps leaders often come from marketing ops?

Andy argues (half tongue-in-cheek) that marketing ops is more technical, more data-heavy, and forces working in the gray — defining ROI is harder than in sales, where the funnel is more visible. That ambiguity builds a stronger, more transferable data skill set. The broader point is to do 'tours of duty' across the six functions of RevOps to become a full-funnel operator.

What are the six functions of RevOps?

Andy Mowat lists them as sales ops, marketing ops, CS ops, GTM systems, strategy, and enablement. You're unlikely to be great at all six, so the path to a strong RevOps career is rotating across them — ideally under a leader who deliberately moves you around so you become a full-function expert.

Timeline

Jump through the conversation

Click any chapter to open it in the transcript.

00:00Intro: Andy Mowat and Whispered 00:39Where scaling companies neglect the fundamentals 02:34Enablement: the most neglected area 03:54Stage-fit: when to invest in enablement 04:32Coaching with call review (Gong / Chorus) 05:54Hiring the right enablement leader 07:50Tech-stack missteps: the email-system mess 10:43Andy's path into tech and RevOps 13:29Getting 'punched in the face' in the job search 14:55What Whispered does: the unposted role flow 16:42Inside the Whispered process: playbooks and Pro 19:38The impossible RevOps job description 21:41Coverage across GTM leadership roles 23:01AI and the next-gen GTM tech stack 25:36GTM engineering, Scale Stack, and the rep UX layer 26:41Will RevOps survive? Upskill or fall behind 28:28Where RevOps people should learn + get a mentor 30:19Tours of duty across GTM ops functions 31:29Why the best RevOps comes from marketing ops 32:41The six functions of RevOps 33:14Close
Full Transcript

The whole conversation

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

Transcript as markdown ↓ Whole episode as markdown ↓
00:00Intro: Andy Mowat and Whispered

0:00 Today we have Andy Moet, founder CEO of Whispered and previous head of operations for some of the biggest names in tech like Upwork, Fox, Culture Amp, and Carta. He thrives in environments where it's time to amp up the acceleration, begin scaling, and bring breakout companies to their full potential. With Whispered, he's helping execs find the hidden roles because when companies are looking for a new C-suite member, they're not posting on LinkedIn and sifting their resumes. Andy, so stoked to have you here. Thanks for being on LeanScale Podcast. Thanks Anthony. Great to be here man. Yeah, you bet.

00:39Where scaling companies neglect the fundamentals

0:39 Well, I think one thing to kick off, I think, especially for us at LeanScale, we're all about GTM ops, RevOps, helping these companies scale to that next level of growth, and you've had such an impressive background and have advised so many startups as well. I think one thing that would be interesting for us is, as these companies are growing and scaling, where do you see them neglecting things during their scale-up phase, underestimating the complexity? What are just some of those things that they're missing as they're going through that phase? God, yeah, I wrote an article on it and I'll have to see if I can dig it up.

1:16 We should dig it as an asset after. Yeah, there's so many mistakes people make, right? They don't get their data foundation right, they don't get their GTM tooling right, so then they're just ending up giving clunky tooling to their reps. They're not building the data foundation the right way, so they can't put in AI, they don't have a data enrichment layer that can really make sure that they're targeting the right things. Then as they scale, you'll see mistakes. The other one is they just don't know the right metrics to track. They are building processes really inefficiently.

1:56 Then you'll see things like, "Oops, they forgot CPQ," or they don't know how to mature the system side of things as they need to start to do that. A lot of people don't invest in enablement until it's too late. I always say if you're going to be a revenue leader at a company with crappy enablement, that's a pretty big risk as well too. There's lots of mistakes people make for sure. I think people are starting to maybe get their idea wrapped around hand, you'd have the data infrastructure done well, maybe earlier than we thought. Some of those foundations, maybe people are a little bit more aware.

02:34Enablement: the most neglected area

2:34 I'd love to actually double click on enablement because I think that is an area of the business, especially on the ops side, that is just unbelievably neglected. I found, by the way, the article I was thinking about, I called it the Series A GTM checklist. I wrote it for a couple of friends that are just growing fast and forgot a lot of stuff, but yes, enablement, it's critical. If you don't have it or you don't do it well, your teams just end up cycling and doing a lot of the same things over and over and over again. I'm happy to go as deep down that rabbit hole as we want.

3:12 I've run it at two unicorns and really know what good enablement looks or great enablement looks like and what bad enablement looks like, and are able to understand where to focus in on to be able to make it better. I think actually it's something that would be really cool, is understanding stage fit investment and enablement and what it might look like. If you're like Series A, Series B, Series C, pre-IPO kind of stage, when's the right time to invest in? What does that early investment look like? I think about it this way, as you're building out the number of sales teams, when you have

03:54Stage-fit: when to invest in enablement

3:54 one sales manager and a bunch of reps, it's that manager's job to do enablement. If you have a team of less than 10 reps, you probably don't need enablement, but as you're going to start to clone that team, you're going to start to have multiple products, you're going to start to have a lot of complexity thrown out these people. That's when you should start to really think about it. Early on, the manager is oftentimes covering for rep ops and they're covering for enablement, but at some point that manager just gets pulled in too many directions. Then you start to figure out how can you clone it, how can you do it the same way.

04:32Coaching with call review (Gong / Chorus)

4:32 I think it's also like you have to have leadership believe and understand the value of this. I remember I wrote an article in my 2015, I'm like, "How could you ever manage a team without analyzing voice?" That was before Kors and Gong ever existed and I got to become friends with those guys. To me, I won't name the company, but at one company I was looking at, I asked all the managers, "How do you coach with Gong or Kors?" They're like, "I guess I listen to a call here and there." I'm like, "Okay, that's the wrong answer." We had to restructure like, "How do you use these tools to be a good manager?"

5:08 I remember another company talking to people, a lot of them just didn't like the best managers were reviewing lots and lots of calls. I remember somebody, actually I think it was Roy, the founder of Kors who said, "You can listen to 100% of one call or 1% of 100 calls and if you can focus in and listen in, that's good." I think also, it's not all like on enablement, like you've got to create the right frameworks and dynamics. How did sales team meetings work? Most of them are like, "Hey, where we at? Where's pipeline?" In a dream scenario, you're saying to your sales team, "Hey, let's bring in discussions around this topic."

05:54Hiring the right enablement leader

5:54 You're getting the reps to help you kind of learn and evaluate and understand and be a part of their own training as well too. I could talk for a long time, but call review is a core part of enablement. Also new releases and new trainings, getting the corporate pitch right, those are all things that are critical on enablement too. Maybe you could help me understand a little bit about the talent profile. When you're looking for someone to lead enablement or be an enablement practitioner, I think before starting Lean Steel, I ran RevOps for three companies. I had a really strong enablement team at one of them.

6:36 For me, and I have, this is a data point of one, so it might be an anecdote, but he was a rep before, he carried a bag before, he kind of knew what it meant to be in the field, and I think he was really able to empathize, but he had a kind of teacher and ops mind as well. I felt like that worked well, but sometimes it's tough to find those perfect unicorns. What have you found be successful in getting the right enablement leader? There's two obvious profiles. There's the former rep that I like to train, and then there's the school teacher, teacher type of thing. I think they both work in different scenarios.

7:14 You have to be able to be partnered with the sales managers and leaders to be able to be their prioritization function. So either profile could fail or either profile could succeed, depending upon that. But if you show up and you're like, "Cool, just tell me what we should train on," you're kind of toast. You have to have an opinion on, "We should be training on this, not on this," and you should be able to really get aligned with that sales leader. I think either profile can, but what you'll find is the wilting flowers that are just order takers aren't going to be very effective at enabling that.

07:50Tech-stack missteps: the email-system mess

7:50 Yeah, I find order taking isn't really effective in most things, but I could definitely see where the aid is. It never is, yeah. Except at restaurants. Except at restaurants. And even then, maybe like, "Hey, have an opinion of what the experience is at each table." But I think that makes a ton of sense. So for those scaling companies, making sure you have the right enablement set up, stage fit level of investment in it. Maybe on the tech stack side, are there any big categories of tools you see teams not implementing, implement poorly, taking too long to bring on, maybe bring on too early? What do those missteps look like? Yeah, lots.

8:39 It's a broad question, so I can tell you in any direction. Maybe also get in the direction of a company that I really am passionate about. People make shitty designs in their email systems continuously. I can't tell you the number of unicorns I've showed up that, that they've got seven to eight email systems. And when you show up as a leading RevOps person there, everyone flocks to you like, "God, can you fix that email shit show? I should be able to see all my emails in one," or anything like that. Honestly up until this company called Inflection.io, I presumed that was an unsolvable task and I just didn't touch it.

9:23 But I think what they did was they brought, so in theory what you should have, and I'm again talking about companies that have enough trajectory and data within their product that you can use it. But you should be understanding that event stream and being able to send intelligent emails with data in them to people at the right times versus just like, "Hey, we should send an email today." So Clay's week in review is powered by Inflection. But every company I've been at, you've got Marketo or HubSpot for top of funnel, and then you've got something else like Iterable or Braze for late stage funnel, and then you've

10:04 got a product triggered notification one, and then somebody else has been like, "None of those work, so let me get another one." It always exists. If you're not getting that stuff right early, it's almost impossible to roll it back later unless you're willing to blow it all up. We got pretty close to buying Inflection a card before I left. I think they probably will soon. A number of my companies that I advise and help also take a look at that. That's one example of how you can get one thing wrong, but there's probably 20 of those types of examples. Yeah. No, it makes sense. It makes sense.

10:43Andy's path into tech and RevOps

10:43 I'm interested a little bit about going through maybe your career trajectory. I mean, a really impressive lineup of logos, going into a newer-- I'll say a newer. Probably this type of work was being done in the past, but newer titles on it being in RevOps and GTM. Maybe just walk through the story. How did you end up getting into tech? How did you end up finding yourself in these roles? What were you passionate about? How did it lead to what you've done so far? I joined a wealthy family that owned the third largest movie theater chain, and I basically helped them build a chain of athletic clubs. It was fun. I got paid well.

11:27 I didn't fly around on their jet, but I realized it wasn't tech. I read 4-Hour Work Week and basically said I wanted to go work at Odesker E-Lance, which ended up merging to become Upwork. I just cold called the CEO of both of them, ended up meeting them, just networked like crazy to get in, and had an offer to work for each of them, and ended up taking the one at E-Lance and worked directly for the CEO of what became Upwork. I was hired to start doing BD, but in month 3, he said, "Can you run my SMB sales team? Can you figure out my systems?" That was when I first realized we needed something like Gong, because I couldn't hear what these

12:13 people were talking about, and that was before Gong existed. Then I started sending emails, and I think I automated an email to 800,000 people that got us in a little bit of trouble. Like most RevOps people, I just fell into the function. Yeah, yeah, same story on my side too, ended up a collective background of GTM roles at tech companies. We had a new CRO come in. He asked, he said, "Hey, who runs Ops around here?" I was like, "Oh, we don't have anyone." He's like, "Well, who manages the systems?" I was like, "Well, I run customer success, and we have the most going on, so I tend to just lean in." He's like, "Well, who runs the forecast?"

12:52 He's like, "Well, most of the revenue is existing, so I run most of the forecast." He goes, "You're not CS anymore. You're Ops." Then that was it. That's cool. I was like, "Okay." I didn't really ask for it, but I'm very, very happy it happened. I think his name is Tom Miller. I thank him all the time for getting me in. I feel like nobody went to college to be RevOps, but we figured out what we were good at. Then from there, I just would do it again and again and again, but periodically I'd go start something in between. I got really good at navigating that job search between things.

13:29Getting 'punched in the face' in the job search

13:29 Because I'd been punched in the face early and I knew what it took to network and to get to a job, I think I got really comfortable at when I need to define the next role, how would I go do that? That's what sponsored eventually. I think some of the most successful professionals, they're not doing a bunch of applications, they already have jobs lined up, or they're networking and getting recruited into new roles and they always have some other option. I would say you are until you get punched in the face and you aren't. I see plenty of really impressive people and there's this mind of cool, I have something

14:14 lined up, I'm following my mentor, people are recruiting me out. But the day when you're at a company that you get laid off, you don't get along with your boss, the company runs out of money or you for some other reason leave and you have to proactively search. It's not like just shitty people are proactively searching. At some point in your career, you will get punched in the face and by that I mean you will have to go search proactively for a job versus being able to be like, "Oh no, I don't want to take that call right now." That is a very jarring moment for lots of people. Yeah, I agree though. I think you need to be really proactive.

14:55What Whispered does: the unposted role flow

14:55 What have you seen work really well and maybe this would be really good to tie into the type of work you're doing at Whispered as well. Yeah, Whispered kind of believes that we work with VP and C-level people in for go-to-market roles. We know that at that level, the odds of that role that you find being posted are really low. Odds are it's Whispered to you, right? And so what we've done is built the network, the insights on companies and just the flow of roles and the community to support people looking for those things. And so if you think about it, if you're an exec and you go out and you interview for

15:33 a role, you learn a lot about that company and you throw it away. And so for the last three years, people have been giving that to us. So we know confidential insights on lots of companies. It's brutal if you take a job and you go to that company and either they've been a little bit untruthful to you or your boss is a little bit of a crazy person. I was just on with a gentleman this morning who's like, "Yeah, I was there for ... He was at a five-year run at a really great company running RevOps. And then he was at four or five months at a place and he's like, "I'm really struggling."

16:06 He's an incredible operator, but that's on him now, which is he made any choice at a company. Even if the company sucked, lied, whatever, it's on his resume for the rest of his career. And so how do we help people make the right choices on those things? And then how do we help people open those doors? And so that's really what we've built. And so when I was searching for my last job, I just called all my friends running RevOps and I'm like, "Hey, when a recruiter hits you up, send me to roll and send me any insights on any hot companies." And that's what kind of became and we got whispered. Amazing. Amazing.

16:42Inside the Whispered process: playbooks and Pro

16:42 So if I'm, let's say, a head of RevOps, PPS sales, I come to Whispered, what does the process look like? There's a bunch of stuff for free on the playbook side. So we have like 100 playbooks on everything from how to work with a talent partner. That is something that if you've never been at that level before, you don't know how to meet those people, talk to them, what you can ask them, what you can't, how to show up prepared and all that. And so we've got 100 playbooks on everything from how to work with talent partners to like how to get your niche and be really clear how to show up right to a recruiter. And so that's all free.

17:16 And so thousands of people a month are coming and using that. On the platform side, if you want to explore that, you just apply for Pro. We still talk to every single person before we admit them to Pro. But effectively, if you join Pro, you get access to all the insights on all the companies, all the unposted role flow, you get access to this network where you can basically get plugged into pretty much any company you can imagine. It's like every Whispered member, we've plugged all of their networks in together. So they're working together. And then we've got this community that supports them.

17:48 And so that I think as a RevOps person, you'd appreciate that, right? But it's the how do you help people open doors? And we always say we're not here to do someone's search for them. We're here to give them the tools to do it better. And so yeah, we've helped a lot of people. And the coolest part now is companies are just finding us directly, right? Like this week, I talked to three companies about like VP level RevOps. I have a version of me, a former like CMO at New Relic, a person that so she's like on the marketing side. We've got a person on the CS side and a person on the sales side that are also working with companies there.

18:26 And so what we're starting to see is companies just call us directly because we're free for companies. Nice. So they're tapping into your network of talent, and then you're making sure you're getting the right matches. Are you doing skill matching, culture matching, or just kind of like exchanging that marketplace between the two parties? We do a little bit of everything, right? So like I was helping a CRO at a billion dollar company yesterday and talking about a role they had and they actually had four roles because they were just onboarding somebody new and they needed to backfill a couple of them quickly.

19:03 And his comment was like whisper to sense as higher quality talent that we can move faster on than our internal recruiting or external recruiting, right? And so I think when you call a recruiter and recruiters are you absolutely in some cases need to call them, but you generally will try and fail on your own first, right? Like let's put it up. Let's work through our network. Let's do all this. We're getting the calls at the, oh crap, I just need to start seeing candidates right now. I don't have a job description. I'm still thinking it through. I was talking to a public company last week about their role, how to craft it, how to get it right.

19:38The impossible RevOps job description

19:38 And I really appreciate that. I mean, you've been a RevOps person too. Like how many times do you look at that role and you're like, oh God, nobody's going to touch that one with a 10 foot pole, right? We see all those at the time. It's like an individual operator needs to be able to like build the GTM systems, build the metrics cadence, get CBQ running, um, run enablement, run commissions and two other things. And it's an IC role for 200 grand and you're just like, you laugh at those rules, right? And so with that company, I talked to him and I was like, Hey, here's how you think about it. Here's what you do. Here's what you're missing.

20:08 And they were like, amazing. Can you help us? And then I had another company recently where I talked to a COO and I was like, you got one of these rules. It's not that attractive. But anyway, your CRO and your VP of sales are also not there and you're looking for those two. This thing's kind of a mess and then you're willing to pay 225 for this thing. You're not going to get a legit rev ops person, um, for that price. And so they didn't like what I said and I was like, cool, like no problem. We won't help you then. And so I think what we get to do is be on the side. We're on kind of an interesting role.

20:39 Like we're not a recruiter, um, recruiters definitely can help more than like, we aren't going to keep searching and keep searching for companies. Um, we're going to be like, wait, here's a group of candidates and it's good. And if not, we'll make recommendations on the right recruiters. But we help like give feedback on that stuff, um, all the time. And so it's kind of fun, right? Because it's like all the train wrecks and mistakes that you and I have seen on rev ops rules before we get to kind of call out and try to help a little bit on that side. I love that. 100%.

21:10 I love the genesis of, of lean scale because I walked into those roles with really high expectations and like, yeah, we need you to do all everything you said, Oh, plus go to the board meetings with us and report on all of our data. Oh, and help us do fundraising. And it's like, I, well, one, what one person has all of those skillsets in one thing. And then two, like you said, if they are, then they're going to be demanding, um, a pretty high salary that most of these companies aren't prepared to pay with. So you mentioned it's mostly go to market executives, is it focused on rev ops or are

21:41Coverage across GTM leadership roles

21:41 you opening to the VP of sales roles, the CRO roles, uh, marketing, where, where is the like breath and then level of depth? You mentioned VP and up, but VP plus go to market leadership roles. So that would be CMO and VP of marketing, CRO, VP of sales, CCO, VP of CS, and then rev ops. Um, I would say just given my background, I'm personally very deep there. I think we see 90 to 95% of all roles, um, in rev ops, you know, either we see them from the companies or just an executive whispers that role to us. Uh, and so sometimes we have deep relationships with them there.

22:21 I'd say we're getting to that point in sales and marketing and CS, but it's broader, right? Like you may have one VP level role in rev ops, but you may have four or five in marketing or sales, um, and in CS as well too. And so it's taking us, you know, we're, we're going to get to the place where we see every role in those functions as well too. You can go to apt dot whisper.com and see every single role we see. We just don't share the names of the companies on that side. So we're very, very open with what we have and how we work. Very cool. Very cool. I'm curious, since you're in the space and thinking about talent, um, what do you see

23:01AI and the next-gen GTM tech stack

23:01 in the next one to five years, especially with better implementations of AI, um, the type of roles that you would expect to see in tech companies? Um, yeah. And then maybe a little bit focused on rev ops, if like the role of rev ops will change a little bit. Will we see new roles, less roles? What do you think the talent landscape is going to look like in the next couple of years? I see it changing a lot. Like I've got a, we have a group of like 50 VP plus rev ops people separate from whispered that we all kind of slack back and forth with each other on like the future of GTM tech.

23:38 I think we all recognize that it's still the legacy Marketo Salesforce, even HubSpot there, but you're seeing this next gen build, right? I talked about inflection on the marketing side. I've got a Google doc of like 20 next gen AI powered CRMs. I don't think they're ready to replace Salesforce yet, but I think they're coming for it. Right. And so when all of a sudden you have data built in, you have product data feeds built in, you have call data built in, and you have like enrichment data built in, right? So it's kind of like, imagine Clay Gong, HubSpot, and it all had a baby and they had it together and that baby like actually worked.

24:24 And like, that's what I think is going to come. And so I'm helping out a couple of those companies. I get really excited about that change. I think data, data architecture is really important, right? So like, if you ask a company, you say, what is your source of truth? Is it Salesforce or is it Snowflake or is it Redshift or something like that? And I'd say that, that needle started to change. It used to be like five or 10% now it's more like 20 or 30%. But then I ask, okay, if people are like, oh, it's a data warehouse, I'm like, cool. If your CRM gets like killed and we delete the instance, how fucked are you, right?

25:02 And the people that are really strong are the people that have a true data warehouse. So like, I'd be fine, like just turn me on with a different front end and I'd be fine. And so I really respect those people that are true data warehouse first. I think data skillset is a really important one, right? Like I would never hire, if people didn't understand SQL now, I think with AI, SQL becomes insanely easy, right? You just need to have like the mind, it's the mindset of RevOps, right? Which is, I always say RevOps people are configure, not customize people. And so I feel like that mindset keeps going.

25:36GTM engineering, Scale Stack, and the rep UX layer

25:36 You're seeing this GMTM engineer role evolve, which I think is a cool role as long as it's aligned with RevOps. If it's a bunch of biz ops people running around being like, dude, I ship this thing. It's awesome. I just observed biz ops people too many times solving the problem in front of them, but not solving the root problem and just causing more havoc and chaos. And so I'm big on, you got to make sure GTM engineering is part of your org. So in my mind, it's data foundation for RevOps. It's then building AI agents on top of it. So I'm a big fan of like scale stack, which is kind of like an enterprise version of clay.

26:12 But there's lots of those tools, but scale stack has been amazing for us. We've been using it on everything for like, you name it, like agents are going out there enriching stuff, bringing it back to us and doing the work for us. And so you should be able to have that. I think the thing that people haven't figured out yet is the UX layer for reps, right? Like I invested in scratch pad. I love the concept, but the second they charged me like 50 grand more, I was like, ah, Jesus. And so like my vision is that somebody shows up and is like, Hey, we'll take this team out of Salesforce for you.

26:41Will RevOps survive? Upskill or fall behind

26:41 We're going to save you money and we're going to give you a better UX for like, that's what I really want at some point. And when that starts happening, and I see a couple companies starting to do that, um, that I'm helping and kind of trying to do is there. So I guess my belief is that the entire tech foundation is going to turn over in the next three to five years within RevOps, but RevOps as a function continue to continue to exist for sure. Yeah. So I'm, I'm bullshittled continue to exist. I think there are a few, um, if you don't upscale, it's going to be an interesting situation.

27:12 Um, cause I think there's a good population of the RevOps community that is very focused on Salesforce and Marketo, like you said, and like, if you're kind of stuck in those platforms and have a tough time transitioning out or getting more holistic and broad, um, you know, I do think your position is in danger at least in the next couple of years. Yeah. Couldn't agree more. It's a, it's a very, like there are so many great solutions for GTM. I mean, you probably see it too, but there's so many places where people have said like, oh, I'll use AI and I'll use the same two or three data sets to do the same stuff. And so there's a lot of these me twos.

27:52 I think it's going to be a lot of mess, but it's going to end up being a much better overall setup for executive, like for GTM overtime. Yeah. I'm enjoying working. I help out a couple companies that are like in the new AI empowered that are growing really fast that are, I mean, I, spending time with a company, it's a hundred million in revenue, has no enterprise sales, starting to think that through, right? Those are really fun for me because it's like you get this start from ground zero for the B2B side. Yeah. Yeah. And we also have this amazing base of a hundred million dollars in revenue where you have

28:28Where RevOps people should learn + get a mentor

28:28 a lot of probably decent brand at that point in time too, that I'll build that out. For anyone who's in RevOps now, we have a lot of people who are in RevOps obviously who listen to this and the companies we work with all in the B2B SaaS and AI space, where should they be going to learn, get their information and then what tips would you have for anyone who's in RevOps right now? Wow. That's an interesting question. I mean, I'm a big fan of what Matt Vollms built with RevOps co-op, it's a good community. I used to be a fan of the WizOps and what Brad Metz had built, the Brad left Sonar and Sonar changed its name.

29:11 So I think that one's kind of gone, that one's been a lot quieter lately. So I spend more time with Matt. If your VP of bluffs of RevOps has dropped me a note, we've got a fun community like VP plus level folks that are there. I think the questions are, I mean, if I was somebody, I would go get a mentor. I'd never mind. I mean, I've had a lot of these chats recently with people that are like, "Hey, I'm a director level." I actually mentor two or three people that are at director levels and they can call me anytime about their career, how to think about it, how to get to that next level.

29:43 And so I don't ever mind helping out really great people at great companies as well too. There's a lot of people that are like, "I want to be head of RevOps." And it's more about the title, but I'm like, sometimes it's maybe better to go be like a number two at a really well-run company and a well-run team. And so I've done a lot of growing the people that have worked for me. I think a lot of people would be like, "Cool, I'd come up in CSOps or I've come up in mops or I've come up in sops." But I don't know the other functions. And you even said, I think what you were talking about is like cross GTM ops rather than just

30:19Tours of duty across GTM ops functions

30:19 sales ops or mops or something like that. And so I think people can learn a lot. And so I was a big fan of that at culture ramp and at Carta, which is, I move my people around so they become full function experts as well too. And so that I think has been really supportive and I try to do a lot of that. Yeah. And I think that's really smart. Go do a tour of duty in a few different areas on GTM and really use that context to better whatever role you end up being. Obviously if you do want to be holistic, you had a rev ops at one point in your career, it's unbelievably helpful to spend some time.

30:54 The one time I wish I would have spent a little bit more time in is marketing ops. Because I spent a lot of time in sales ops, I ran customer success, so I knew the ops of CS really, really well. And marketing was always just kind of like tangential and I didn't get that level of depth in the weeds with it. And I think that would have been really, really amazing to have. So obviously at LeanScale, I supplement with really great thought partners and marketing ops here, but I think doing a tour of duty and a few other functions just makes you so much more well-rounded and will give you the context and help you be a better thought partner

31:29Why the best RevOps comes from marketing ops

31:29 in the future too. Couldn't agree more. I wrote a phone article on like the best rev ops people come out of mops. It was a little tongue in cheek, but I agree. Not to speak against myself, but I agree because it's more technical, there's more data, there's more working in the gray, I'd say, and ambiguity. It's just, I think it's trying to define ROI in a little bit more difficult way versus sales where it's just very much like a funnel, whereas marketing, how do you do that? And some people can go down the wrong rabbit holes and yeah, you're right. It's a data skill set that's really valuable. Yeah.

32:03 I think you have more difficult challenges to solve in marketing ops. Sales ops gets a lot of visibility because everybody wants to know when the deals are coming in, the forecast and everything, but I agree. I think some of the best rev ops people I know came from marketing ops as well. Yeah. I mean, to me, there's like six functions within rev ops. I'll just lift them off the top of my head, but if I miss one, let me know. But it's like there's ops, mops, CS ops, GTM systems, strategy, and enablement, right? And it's like, you're probably not going to be good in all of them, but I think it's hard to add them and go to a new place.

32:41The six functions of RevOps

32:41 Sometimes you can do that, but you're like, Oh, we'll take a flyer on this person. I guess I got lucky. Like I had never run SOPS before I went to culture ramp and they didn't have any commissions. And so I was like, great, like no commissions, like I can do this. And so I was able to like transition to full funnel GTM ops. And then when I went to Carta, they were like, Hey, commissions is under financed. And I was like, cool, great. Like not the area that I gravitate towards. And so I feel like if I was somebody trying to build a career in rev ops, I would try to go work for a great PP and really like somebody that was wanting to move me around

33:14Close

33:14 and challenge me and push them. I like that. I like that a ton. Andy, this has been absolutely awesome. Thank you so much. I appreciate you spending time with us. I feel like I've learned a ton. I know people listening will learn a ton. I really, really like the insights that you have from your career and kind of how you felt in to rev ops. And then the advice that you have of doing some tours of duty in different areas, finding that mentor, finding a good VP to follow along. And I think what you're doing at Whisperd is just really, really exciting to match people who are serious about their GTM career, getting them in front of opportunities that would

33:53 be really, really difficult to find democratizing that access to these roles. And then for these companies, getting access to better talent and doing it in a way that really matches those really well. So I'm just really, really excited about what you're building, your vision for rev ops in the future. And I can't wait to follow what you're building and what you're doing. Thanks, man. I enjoy it. It's fun talking and I enjoy our conversations as well, too. Amazing. Well, thank you, Andy, so much for being on the podcast and hope to have you again in the future. You got it. Have a great day, Andy. Thank you.