The LeanScale Podcast · Episode 82

How an Ops Guy Became CRO of a $3B Company

Joshua Trott on selling in heavy industries, RevOps as the operational backbone, and why delivery — not the deal — is the real contract

Joshua Trott · Chief Revenue Officer, Patch · Patch Hosted by Anthony Enrico
Published Updated 00:54:33 53 min read 10,689 words
Executive Summary

The one-paragraph brief, extended

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

Joshua Trott is a Chief Revenue Officer who opens by insisting he's 'not really a sales guy' — and means it. He has never held an individual-contributor sales title. His career started in strategy consulting at Booz & Co. (now Strategy&/PwC), inside the energy, chemicals, and utilities practice, where he spent years designing governance frameworks and operating models in rooms full of C-suite executives. Only much later, when a quota was thrust on him at the expert network GLG, did he realize that everything consulting taught him — how complex organizations think, decide, and manage risk, and how trust compounds over time — was the actual job of enterprise selling. He went on to become CRO at Workrise (the labor-marketplace-turned-enterprise-supply-chain-platform valued at nearly $3 billion) and now leads revenue at Patch, the platform helping companies navigate carbon markets and scale climate action.

The spine of the conversation with LeanScale co-founder Anthony Enrico is a contrarian thesis for operationally intensive industries — energy, utilities, oil & gas, sustainability, carbon markets, healthcare — where the standard SaaS playbook simply breaks. In these worlds, closing the deal isn't the finish line; it's the audition. The real contract is earned through delivery. Buyers make 20-year infrastructure decisions where a delivery mistake can mean a safety incident, destroyed equipment, or the company on the front page of a newspaper, so the bar to even get in is extraordinarily high and expansion is a trust problem, not a product problem. You don't win by selling more seats; you win by delivering at a consistent, high bar until they open the aperture and hand you bigger questions.

Because of that, Joshua treats RevOps as the first port of call at any company he joins — 'the language in which companies test, measure, learn, and drive rapid scalability' — and pushes hard against the reflex that 'RevOps equals Salesforce hygiene.' His build order is deliberate: systems first, then people, then process. The CRO's job, he argues, isn't just hitting the number; it's demonstrating control over the number — knowing when you're behind and what the corrective actions are — which is only possible with the operational backbone in place. He also makes the case that the services organization has to be a first-class citizen, not a margin-enhancement afterthought, and that the most underrated commercial talent pool is operators who become sellers: hire for learning agility and structured communication, teach the selling later.

The back half turns to AI, and Joshua lands somewhere refreshingly non-hype. He's less interested in AI-as-efficiency (the 'we can cut headcount' story he and Anthony both dismiss) than in AI-as-quality: at Patch, near-100% daily AI usage lets a small team sift thousands of carbon projects, collapse information asymmetry, and scale delivery quality that used to erode as teams grew. He describes Patch's 'embedded climate strategist' as its version of the forward-deployed engineer, and frames the durable advantage as product + expertise + data as a force multiplier. His prediction: over the next decade, operators — not growth-at-all-costs sales leaders — will increasingly win, because the questions shift to 'how are you doing this with less, and why are you still doing it that way?'

Who should listen: RevOps and GTM operators who want a path into revenue leadership, founders and CROs selling into complex or regulated industries, services and consulting leaders building AI-native delivery, and anyone weighing whether AI should shrink teams or make them more valuable. The throughline is that operational excellence, not sales charisma, is what earns the right to win — and that in an AI era, that edge only compounds.

Key Takeaways

15 things worth stealing

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

01

Consulting was a stealth crash course in enterprise sales

Years of governance-framework and operating-model work at Booz & Co. taught Joshua how complex organizations think, decide, and manage risk. When he later got a quota, he realized selling into these industries is the same job: deeply understand the problem, the people, and the internal decision process, then tell a story that makes your solution the obvious fit.

Why it matters: Backgrounds that look 'farthest from sales' — consulting, ops, strategy — can be the strongest foundation for complex enterprise selling, because the differentiator is navigating organizations and earning trust, not pitching product.

Revenue ExecutivesFoundersRevOps Leaders
02

Closing is the audition; delivery is the real contract

In operationally intensive industries, the SaaS assumption that 'the work is getting the deal closed' is backwards. The first contract is a limited-blast-radius audition. All the real work — and the real money — happens after signature, when you have to deliver at a high bar to earn the right to be asked bigger questions.

Why it matters: Design your GTM so delivery and post-sale execution are the growth engine. Treating the signature as the finish line is exactly how classically trained SaaS sellers fail when they move into complex industries.

Sales LeadersRevenue ExecutivesCustomer Success
03

RevOps is the first hire and the operational backbone — not Salesforce hygiene

Joshua's first port of call at any company is the RevOps backbone, because it's 'the language in which companies test, measure, learn, and drive rapid scalability.' The stereotype that 'RevOps equals Salesforce' badly undersells it — clean CRM is part of it, but the real value is setting targets, holding people accountable, and running data-driven experimentation.

Why it matters: Stand up RevOps before you layer in sellers. Smart CROs treat the head of RevOps as their chief of staff and number two; without that language in place, you're guessing, not deciding.

RevOps LeadersFoundersRevenue Executives
04

Build order: systems, then people, then process

Because he thinks like an operator, Joshua starts with systems, then people, then process. You need the system in place to run diagnostics, find what's working, and then go all-in where the signal is. Skip it and you get wasted effort and blown trust.

Why it matters: Sequence your build deliberately. The system is what lets you A/B test, understand stages, and gain real control over forecasting before you pour money into marketing or headcount.

RevOps LeadersRevenue ExecutivesFounders
05

The CRO's job is demonstrating control over the number, not just hitting it

Forecasting is a statistical exercise — probabilities, stages, corrective actions. The senior responsibility isn't only landing the number; it's knowing when you're behind, what to do about it, and whether the corrective actions are working. That requires measuring your actions and seeing the downstream impact.

Why it matters: Over-invest in the operational backbone or you operate without objectivity. A CRO who can't demonstrate control is 'flying behind' and will spin trying to find the path forward.

Revenue ExecutivesRevOps Leaders
06

In heavy industries, mistakes mean safety incidents and front-page risk

Unlike 'the software broke and it's annoying,' a delivery miss in energy, utilities, or oil & gas can hurt people, destroy expensive equipment, or land a company on the front page of a newspaper. The stakes make the entry bar extremely high and the cost of getting delivery wrong severe.

Why it matters: The services organization must be elevated to a first-class citizen alongside sales and account management — three legs of one stool — not treated as a margin-enhancement play.

Sales LeadersCustomer SuccessFounders
07

Expansion is a trust problem, not a product problem

In concentrated, capital-intensive, often duopolistic industries, expansion doesn't come from selling more seats or another module. It comes from delivering the first contained project so well that the customer opens the aperture and asks bigger questions — a self-fulfilling prophecy where doing well begets more winning.

Why it matters: Right-size the first engagement so its blast radius is limited, then let flawless delivery earn the larger ACV. The way you win is 'unsexy': do what you said and say what you do.

Sales LeadersCustomer SuccessRevenue Executives
08

In tight-TAM industries, referrals are the unbeatable growth engine

These communities are small and tightly knit — the same conferences, the same problems, often the same former employers. A referral to 'trust them' lets you skip the early work of winning the right to ask for the bigger thing, and word-of-mouth beats any outbound strategy, AI-enabled or otherwise.

Why it matters: There's no better CAC equation than referrals. Invest up front for slower early growth, then watch the growth rate turn as delivery-driven referrals compound and competitors find it harder to break in.

Sales LeadersFoundersRevOps Leaders
09

Hire operators who become sellers — teach the selling later

Joshua leans toward hiring people who've done the job or operated in the space and can speak with credibility about the challenges. He can teach the selling motion; it's far harder to ramp someone on a complex, technical industry they haven't lived. Operators build trust and instinctively tie what they're selling to real outcomes.

Why it matters: For complex industries, weight industry credibility and operational empathy over classic sales pedigree. Pure-play SaaS sellers often get the first meeting on a good demo but fail to discover the true outcomes tied to the buyer's KPIs.

Sales LeadersRevOps LeadersRevenue Executives
10

Recruit for learning agility and structured communication

The top trait Joshua screens for is voracious curiosity — because credibility in technical industries is tied to staying current, and it can't be faked. Second is structured communication: distilling highly complex, interrelated problems into digestible ideas for a diverse room of stakeholders, from finance to procurement to the sustainability function.

Why it matters: Interview for how people learn ('what's the last thing you taught yourself, and why?') and how they simplify complexity. Enablement gets a natural lift when your people genuinely love the space and love to learn.

Sales LeadersRevOps LeadersFounders
11

Lead with humility — you'll own things you've never done

Taking a sales funnel he'd never run, with experienced sellers reporting to him, Joshua won them over by owning his gaps: 'teach me how to run a pipeline review,' while offering what he was strong at — systems thinking, mathematical pricing, operational rigor. Pretending seniority equals expertise in everything is a 'failed thought experiment.'

Why it matters: As you rise you'll be accountable for functions you haven't done (Joshua later took over marketing at Workrise). Complement your capabilities with people strong where you're weak, and go on a fast learning journey so you know enough to be dangerous.

Revenue ExecutivesSales LeadersFounders
12

Your job is to be a resource, not to sell

Joshua coaches his teams that the job is to be the person a buyer picks up the phone to when they have a problem — sometimes recommending something other than your own product. Buyers staring at some archaic, disconnected spreadsheet don't want another tool; they want someone to take the problem off their plate, and there's real willingness to pay attached.

Why it matters: Move reps from vendor to trusted advisor by identifying where it genuinely makes sense to sell. It takes organizational confidence to absorb short-term pain, but the data shows it pays out in ACV growth and durable relationships.

Sales LeadersCustomer SuccessRevenue Executives
13

AI's real prize is quality, not headcount cuts

Both Joshua and Anthony reject the AI-as-layoffs narrative — if you can make someone 10x more productive, cutting people makes no sense; it should incent you to hire more and produce more. The bigger unlock, especially in services, is scaling quality: the passion and skill that erode as a team grows can now be captured and shared so quality holds across the board.

Why it matters: Frame AI as a quality and capacity multiplier. In AI-native services, near-100% daily AI usage lets a team pass on cost savings while the quality of every project improves as more learnings flow through the platform.

FoundersRevenue ExecutivesRevOps Leaders
14

Product + expertise + data is the force multiplier — the embedded strategist is the moat

In carbon markets there's no clearing house and heavy information asymmetry, so Patch's 'embedded climate strategists' (its forward-deployed engineers) guide buyers through complexity. The platform ingests market data, applies each customer's quality parameters, and instantly narrows thousands of projects to a short list — turning weeks of sifting into days.

Why it matters: Differentiation comes from combining software, human expertise, and proprietary data, not any one alone. AI-native services collapse information asymmetry and let experts spend their time on the highest-value judgment work.

FoundersRevenue ExecutivesSales Leaders
15

Operators will increasingly win the revenue seat

Joshua predicts that over the next decade operators — not growth-at-all-costs sales leaders — will have more voice, because the questions shift to 'how are you doing this with less, what are you using AI for, why are you still doing it that way?' None of that conversation is possible without an operational backbone to measure against.

Why it matters: For RevOps and ops-minded leaders, the AI era is a career tailwind. Invest in operational rigor now; it's what makes AI leverage measurable and what the next generation of revenue leadership will be judged on.

RevOps LeadersRevenue ExecutivesFounders
Frameworks Discussed

10 named models

Every framework Jimmy names, defined and time-stamped.

Systems → People → Process (Operator's Build Order)

10:14

When standing up or fixing a go-to-market org, sequence your build in a deliberate order: put the systems (RevOps backbone) in place first, then the people, then the process.

The system is what lets you run diagnostics, figure out what's working, and then go all-in where the signal is. Starting with people or process before the system produces wasted effort and blown trust — you can't tell what to double down on or pull back from.

The Audition vs. The Real Contract

07:20

In heavy industries the first contract is the audition, not the win. Delivering it at a high bar earns the right to the 'real contract' — the bigger, expansion opportunity that follows.

SaaS playbooks assume the work is closing the deal; here all the work happens after signature. The stakes are high and expansion is earned over time, so nailing the contained first project is what opens the aperture to bigger questions and larger ACVs.

RevOps as the Operational Backbone

08:47

RevOps is 'the language in which companies test, measure, learn, and drive rapid scalability' — the first port of call at any company — not just Salesforce hygiene.

Without this language in place you can't tell what's working, set targets, hold people accountable, or run data-driven experimentation. Clean CRM is only part of it; the backbone is what makes rapid, objective scaling possible and lets AI become a force multiplier on top.

Control Over the Number (Not Just Hitting It)

12:35

The senior CRO responsibility is demonstrating control over the number — knowing when you're behind, what the corrective actions are, and whether they're working — rather than merely landing the target.

Forecasting is a statistical exercise of probabilities and stages. Demonstrating ownership requires measuring your actions and seeing downstream impact, which is only possible if you've over-invested in the operational backbone; without it you operate without objectivity and 'fly behind.'

Expansion Is a Trust Problem, Not a Product Problem

15:50

In concentrated, capital-intensive industries, expansion doesn't come from more seats or another module — it comes from earning trust through delivery so the customer opens the aperture to bigger questions.

Deliver the first contained project with a limited blast radius at a high bar, and the customer considers you for larger scope — a self-fulfilling prophecy where doing well begets more winning. The way you win is unsexy: do what you said and say what you do.

Operators Who Become Sellers

22:26

A hiring thesis for complex industries: recruit people who've operated in the space and can speak with credibility, then teach them the selling motion — screening above all for learning agility and structured communication.

It's easier to teach selling than to ramp someone on a complex, technical industry they haven't lived. Operators build trust and tie the sale to real outcomes; curiosity keeps their credibility authentic, and consultant-style structured communication distills complexity for diverse stakeholder rooms.

The Services Org as a First-Class Citizen

14:47

Treat the service/delivery organization as a co-equal leg of the stool alongside sales and account management — not as a margin-enhancement play.

Because delivery is where trust and expansion are earned in high-stakes industries, the CRO must elevate the services org to the same level as sales. Getting delivery wrong can mean safety incidents, destroyed equipment, or reputational damage, so it is core to how the company wins the next, bigger opportunity.

The Embedded Climate Strategist (Forward-Deployed Engineer)

48:11

Patch's consulting arm embeds strategists directly with customers to navigate the complexity and information asymmetry of carbon markets — its version of the forward-deployed engineer.

With no clearing house and low market fidelity, buyers can't easily know what to buy or the risks. The embedded strategist, supercharged by a platform that ingests market data and applies customer quality parameters, narrows thousands of projects to a targeted short list in days instead of weeks.

Product + Expertise + Data as the Force Multiplier

51:57

Durable differentiation in complex industries comes from combining software, human expertise, and the proprietary data the product generates — not from any one of them alone.

AI-native services compound: the platform enables cost savings and speed, while every engagement pushes more learnings and insight through the system, improving quality daily in a way competitors can't match. The combination is what gets buyers to answers and takes problems off their desks.

Horizon 1/2/3 Growth Strategy in an AI World

45:32

The classic three-horizon framework (core business, adjacent bets, and future/experimental bets) becomes far more actionable when AI lets you experiment cheaply.

Because scenario analysis and experiments cost a fraction of what they used to, leaders get more latitude to test horizon-two and horizon-three ideas beyond the core — probing product-market fit, market opportunity, and required capabilities — while thinking two to three years out, not just about the quarter.

Best Quotes

18 lines worth clipping

Pulled verbatim. Copy or share any of them.

“You do what every smart person with an MBA does — you go and tell people what to do with their business, even though you don't know a lot.”
Joshua Trott 01:23
“The value was less in the things that they were buying, whether it was a product — it was actually in the trust that you earned over time to help them solve problems.”
Joshua Trott 02:52
“I've literally never held an individual contributor sales title. I went from leading CS to overseeing sales and CS simultaneously.”
Joshua Trott 05:39
“You're not selling them a platform. That's just a surface layer. The growth engine is actually the delivery.”
Joshua Trott 06:45
“A lot of the historical SaaS playbooks think the work is getting the deal closed. In these industries, all the work happens after the first deal is closed. The first contract is the audition — then you play for the real contract.”
Joshua Trott 07:20
“I've seen a lot of people think RevOps equals Salesforce. And I'm like, that's part of it — but there's so much more that can be done.”
Joshua Trott 09:42
“One of the key responsibilities once you're CRO is it's not just hitting the number — it's demonstrating control over that number.”
Joshua Trott 12:35
“Expansion in these industries isn't a product problem. It's actually a trust problem.”
Joshua Trott 15:50
“The way that you win is somewhat unsexy. It's just about delivering — doing what you said and saying what you do.”
Joshua Trott 16:20
“There's no better CAC equation than referrals.”
Anthony Enrico 18:31
“I can teach them the selling stuff, but it's harder to ramp someone up on an industry if they haven't done the job for a few years.”
Joshua Trott 22:26
“To pretend that as you get more senior it's because you are an expert in all of the things is a failed thought experiment.”
Joshua Trott 25:47
“For a long period of time I couldn't empathize with that stress in an authentic way. When something goes wrong — well, they just lost 15% of their earnings for the quarter. It's a different game when you carry that kind of weight.”
Joshua Trott 26:53
“Your job is not to sell. Your job is to be a resource. And then you identify the opportunities where it makes sense for us to sell.”
Joshua Trott 34:57
“Trust comes through consistent execution over time.”
Joshua Trott 39:21
“If you can make somebody 10 times more productive, why would you need to cut anyone? It should actually incent you to hire more people.”
Anthony Enrico 42:40
“The product plus the expertise, and the data that product enables, is really the force multiplier for how we differentiate in the market.”
Joshua Trott 51:57
“If you don't have that operational backbone, none of this conversation is possible.”
Joshua Trott 52:28
Practical Advice

What should you actually do?

The playbook, split by the seat you sit in.

Founders

  • Make RevOps one of your first hires, not your last — you need the language to measure, learn, and scale before you pour money into marketing or sellers.
  • If you sell into complex or regulated industries, elevate your services/delivery org to a first-class citizen; delivery, not the demo, is what earns expansion.
  • Frame AI as a quality-and-capacity multiplier. A 10x productivity gain is a reason to produce more and hire more, not to cut heads.

Revenue Executives

  • Sequence your build: systems first, then people, then process. The system is what lets you run diagnostics and go all-in where the signal is.
  • Redefine the CRO job as demonstrating control over the number — know when you're behind, what the corrective actions are, and whether they're working.
  • Lead with humility: you'll own functions you've never run. Complement your gaps with strong people and offer your operational strengths in return.
  • Bet on operators. Over the next decade the winning revenue leaders answer 'how are you doing this with less?' — which requires an operational backbone.

Sales Leaders

  • Treat the first contract as an audition with a limited blast radius; win the bigger 'real contract' by delivering flawlessly, not by pushing more seats.
  • Coach reps to be a resource, not a seller — sometimes recommend something else — and move them from vendor to trusted advisor.
  • In complex industries, hire operators who've lived the space and teach them selling, rather than dropping in classically trained SaaS reps.
  • Screen candidates for learning agility ('what's the last thing you taught yourself?') and structured communication that distills complexity for diverse rooms.

RevOps Leaders

  • Reject the 'RevOps equals Salesforce hygiene' framing — position yourself as the language of the business and the CRO's chief of staff / number two.
  • Get the go-to-market lifecycle and lead attribution tight first, so you can measure conversion, cycle, and CAC by channel and know where to double down or pull back.
  • Invest in the operational backbone before AI: it's what makes AI leverage measurable and turns your rigor into a career tailwind in the AI era.

Customer Success

  • In heavy industries, treat delivery as the real contract — a miss can mean safety incidents, destroyed equipment, or front-page reputational damage.
  • Keep selling customers in a good way after the close: speed-to-lead energy applied to delivery is what feeds LTV and referrals in tight-knit communities.
AI Takeaways

How AI actually changes GTM

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

The thesis

AI's real value in go-to-market isn't efficiency-as-layoffs — it's quality and capacity. In AI-native services, near-total AI usage lets a small team scale delivery quality, collapse information asymmetry, and free experts for the highest-value judgment work, which should grow teams, not shrink them.

Quality over headcount

The AI-as-layoffs narrative is 'silly.' If you can make someone 10x more productive you should produce more and hire more; companies doing layoffs 'probably needed to do them anyway and are using this as an excuse.'

Scaling the hard thing: quality

In services the biggest bottleneck is scaling quality — passion and skill that erode as teams grow. AI lets you capture and share what a great operator does so quality holds across the board.

Ops is the prerequisite

The best way to apply AI is to understand your processes, then decide what's automatable and what still needs a human. Without an operational backbone to measure against, 'none of this conversation is possible.'

Collapse information asymmetry

Patch ingests market data and applies customer quality parameters to instantly cut thousands of carbon projects to a short list, reducing operating cost and sharpening insight days faster.

Product + expertise + data

The durable moat is combining software, human expertise, and proprietary data — a force multiplier competitors can't match as more learnings flow through the platform and quality improves daily.

Cheaper experimentation

AI makes scenario analysis and horizon-2/3 experiments a fraction of the cost, giving leaders latitude to test beyond the core business and think two-to-three years out.

Agent & automation ideas

  • A customer-call-prep agent that pulls context from Salesforce and Gong plus historical purchase and live market data, so reps walk in with insight instead of doing manual research.
  • A project-screening agent that applies each customer's quality parameters across thousands of options (e.g., carbon projects) to produce a targeted short list in days, not weeks.
  • Real-time, dynamic account scoring that pulls live market signal against a strategic account list to prioritize outreach.
  • AI-native delivery tooling that captures a top operator's process and shares it so quality holds as a services team scales.
Operations Takeaways

By function

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

Revenue Operations

  • RevOps is the backbone, not hygiene. It's the language in which companies test, measure, learn, and scale — clean Salesforce is only part of it. Make it the first port of call.
  • Build order. Systems first, then people, then process — the system is what lets you diagnose and go all-in where the signal is.
  • Lifecycle + attribution first. Get go-to-market staging and lead attribution tight so you can measure conversion, cycle, and CAC by channel and know where to double down.
  • Chief of staff to the CRO. Smart CROs treat the head of RevOps as their number two; the CRO holds the bag first, then layers in AEs once the calendar is full.
  • Control over the number. Ownership means knowing when you're behind and whether corrective actions are working — impossible without the operational backbone.
  • Ops is a career tailwind in AI. Operators will increasingly win the revenue seat because the questions shift to doing more with less, which only measures against a solid backbone.

Customer Operations

  • Delivery is the real contract. The first deal is an audition; expansion is earned by delivering at a consistent high bar, not by selling more seats.
  • Elevate the services org. Make delivery a first-class citizen alongside sales and account management — a miss can mean safety, equipment, or reputational damage.
  • Be a resource, not a seller. Become the first phone call for a problem — sometimes recommend something else — to move from vendor to trusted advisor.
  • Referrals are the flywheel. In tight-knit industries, word-of-mouth beats any outbound strategy; delivery-driven referrals compound and lock competitors out.
  • Keep selling after the close. Apply speed-to-lead energy to delivery; treating customers like prospects in a good way is what drives LTV over five-year relationships.
Metrics Mentioned

The numbers, with context

~$3 billion
Workrise valuation

Workrise's valuation after transforming from an oil-field labor marketplace into an enterprise supply-chain platform, under Joshua as CRO.

~100% daily
AI usage at Patch

Patch's AI-forward founder pushed the team to near-100% daily AI usage across everything they do, compounding delivery quality and cost savings.

10x
Productivity multiple

Anthony's framing: if AI makes someone 10x more productive, it should incent hiring more people to produce more, not cutting headcount.

2021 · ~5 years
LeanScale founded / longest customers

LeanScale started in 2021 and still serves customers from the beginning — a nearly five-year partnership that feeds referrals and high LTV.

Few $B revenue · spreadsheets · to the penny
Fortune 1000 forecast example

A multi-billion-dollar company rolled up its forecast every Friday via EAs emailing spreadsheets — and forecast to the penny — Joshua's proof that the outcome, not the sophisticated tool, is what matters.

Thousands of projects → days quicker
Carbon projects sifted

Patch's platform applies customer quality parameters to narrow thousands of carbon projects to a targeted short list, turning weeks of sifting into days.

Entities

Companies, people & tools mentioned

Auto-extracted and linked into the knowledge graph.

Companies

PatchClimate Tech / Carbon Markets

Joshua's current company; he leads revenue as CRO. Patch helps companies navigate carbon markets and scale climate action, and runs an AI-forward, near-100%-daily-AI culture with 'embedded climate strategists' as its forward-deployed engineers.

00:00 · 40:00 · 48:11Company →
WorkriseEnergy / Supply Chain

Where Joshua was CRO, helping transform a labor marketplace for oil-field workers into an enterprise supply-chain platform now valued at almost $3 billion; also where he took over marketing for the first time.

00:00 · 27:49Company →
GLG (Gerson Lehrman Group)Expert Network / Research

Expert network where Joshua got his first quota — moving from leading customer success to a GM role owning the full P&L including sales — and where selling clicked as an extension of consulting.

03:24 · 04:31Company →
Booz & CompanyManagement Consulting

Strategy-consulting firm (now Strategy&/PwC) where Joshua worked in the energy, chemicals, and utilities practice on governance frameworks and operating-model design — his stealth crash course in enterprise sales.

01:23Company →
LeanScaleGTM Operations

Anthony's firm, described as an AI-native RevOps-as-a-service company that built its own agents and platforms to auto-push workflows to Salesforce and HubSpot; customers since 2021 illustrate the LTV/referral flywheel.

07:59 · 18:31 · 35:57Company →
Sequoia CapitalVenture Capital

Cited (with Y Combinator) as a signal that AI-native services are now vogue — noted for labeling the trend 'service as a software.'

19:44Company →
Y CombinatorAccelerator / Venture

Cited as looking for its cohorts to be services companies — evidence that the once-unsexy services model is now 'the hottest place to be.'

19:44Company →

People

Tools & software

SalesforceCRM

Stands in for the 'RevOps equals Salesforce' back-office trap Joshua pushes against; also the CRM LeanScale's agents auto-push workflows to, the system a Fortune 1000 forecast was moving onto, and a source of context for a call-prep agent.

HubSpotCRM

Named alongside Salesforce as a destination LeanScale's AI platform can auto-push workflows and designed processes to.

ClayGTM Data / Enrichment

Cited as the go-to for improving lead enrichment and highly customized, targeted automated outbound within a good go-to-market org.

GongRevenue Intelligence

Used to mine and review calls, run role-play workshops, and — with Salesforce — feed a call-prep agent with historical and market context before a meeting.

Claude CodeAI Dev Tool

Anthony references LeanScale being 'Claude code demons,' leveraging it across the business to build internal tooling.

Frequently Asked Questions

Straight answers

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

Can someone from an operations or consulting background become a successful CRO?

Yes. Joshua Trott became CRO of a ~$3B company (Workrise) and now leads revenue at Patch without ever holding an individual-contributor sales title. He came up through strategy consulting at Booz & Co. and operations roles, then got his first quota at GLG. His argument is that selling into complex industries is the same skill as consulting — understanding how organizations decide and earning trust over time — so an operational background can be a superpower, not a liability.

Why do standard SaaS sales playbooks break in heavy or operationally intensive industries?

Because in industries like energy, utilities, oil & gas, and carbon markets, closing the deal is only the audition — the real work happens after signature, in delivery. Buyers make 20-year infrastructure decisions where a delivery miss can cause safety incidents, destroy expensive equipment, or become front-page news, so the entry bar is very high. Classic SaaS sellers often win the first meeting on a good demo but fail because they haven't discovered the true outcomes tied to the buyer's KPIs.

Is RevOps the first hire or the last?

Joshua argues RevOps should be one of the first hires, not the last. He calls it the operational backbone and 'the language in which companies test, measure, learn, and drive rapid scalability.' Without it in place from the start, you can't tell what's working, so every downstream decision — marketing spend, hiring sellers — becomes guesswork. Smart CROs treat the head of RevOps as their chief of staff and number two.

What does 'RevOps equals Salesforce hygiene' get wrong?

Clean CRM is part of RevOps but badly undersells it. The real value is the language the business uses to set targets, hold people accountable, run data-driven experimentation, and control forecasting. Joshua's build order is systems first, then people, then process — the system is what lets you diagnose what's working and then go all-in where the signal is. Reducing RevOps to Salesforce upkeep caps its impact.

What should you look for when hiring operators into sales roles?

Two traits above all. First, learning agility and voracious curiosity — in technical industries your credibility is tied to staying current, and it can't be faked; Joshua interviews around 'what's the last thing you taught yourself, and why?' Second, structured communication — the ability to distill highly complex, interrelated problems into digestible ideas for a diverse room of stakeholders. He can teach the selling motion; industry credibility and communication are harder to build.

Does using AI in a services business mean cutting headcount?

Joshua and Anthony both reject that framing. If AI makes someone 10x more productive, cutting people makes no sense — it should incent you to hire more and produce more. In services the biggest bottleneck is scaling quality, which erodes as teams grow; AI lets you capture and share what a great operator does so quality holds across the board. The prize is quality and capacity, not layoffs.

What is an 'embedded climate strategist' and how does it relate to the forward-deployed engineer?

It's Patch's version of the forward-deployed engineer — a consultant embedded with customers to navigate the complexity and information asymmetry of carbon markets, where there's no clearing house for project price or quality. Supercharged by a platform that ingests market data and applies each customer's quality parameters, the strategist can narrow thousands of carbon projects to a targeted short list in days instead of weeks.

How does expansion work in trust-based, heavy industries?

Expansion is a trust problem, not a product problem. You don't grow by selling more seats or another module; you deliver the first, contained project with a limited blast radius so well that the customer opens the aperture and asks bigger questions. Because these communities are small and tightly knit, flawless delivery generates referrals that beat any outbound strategy — doing well begets more winning, and ACVs grow as you become the trusted first phone call.

Full Transcript

The whole conversation

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

00:00Intro: the strategy consultant who became a CRO

0:00 Today, I'm sitting down with Joshua Trott, who leads revenue at Patch. They help companies navigate carbon markets and scale climate action. Before that, Joshua's CRO at Workrise, where he helped transform them from a labor marketplace for oil field workers into an enterprise supply chain platform, now valued at almost $3 billion. What makes Josh different from most revenue leaders I talked to is that he's not really a sales guy. He's an operations and strategy person first who grew into sales leadership. And his whole career has been in operationally intensive industries where the typical Saas playbook just doesn't work. We're

0:48 going to dig into what's different about selling when your buyers make 20-year infrastructure decisions, when you need services and software to deliver the value, and how to build urgency in industries that move slowly by design. Joshua, you told me you're not really a sales guy, which is the most interesting thing to say as a chief revenue officer, that you're more of a ops and strategy person who ended up in sales leadership. And as a RevOps person myself and a lot of the RevOps community, I think that is a really interesting take. But walk me through how

1:23 that happened. Yeah, well, first of all, thank you for having me. And if RevOps is close to your heart, I have a feeling we're going to have a good conversation today. But yeah, my background actually starts more from the strategy consulting landscape. And so I kind of did the business school thing, didn't know what I wanted to do with my life. And so you do what every smart person with an MBA does, you go and you tell people what to do with their business, even though you don't know a lot. And so I ended up going to Booze and Co, who became strategy and who got acquired by PwC.

01:36How sitting with the C-suite was a crash course in enterprise sales

1:53 And I worked within their energy, chemicals and utility space. And I'd always been fascinated by the complexity of these like global, like really like technically proficient markets. And what I ended up doing a lot of in that space was working on governance frameworks and operating model design, which I don't think sounds very exciting and probably couldn't pick a farther away topic from sales than that. But like ultimately, what I did every single day for a few years was sit in rooms with the C-suite and help them think about how the organization should be structured. How do

2:23 they make decisions? What are the considerations when they're making those decisions? How do they manage risk? And time and again, what you were really being brought to do was process all this like complexity, organizational complexity, design issues, the risk management, and really help them drive towards their own internal decision making. And so like what I didn't realize was happening at the time, and it only dawned on me much later, was I was actually learning how these organizations thought and how they made decisions. And then if you think about what sales really is, it's like how

2:52 do you tell a story that will line up to that so that they can see that your solution perfectly matches the problem that they're trying to solve. And so like maybe just by complete coincidence, I'd gotten a crash course on really how to navigate complex large organizations in these complex industries. And maybe more importantly, understanding that the value was less in the things that they were buying, whether it was like a product, but it was actually in like the trust that you earned over time to help them solve problems. Like that was like the core thing that I really started to see that made good consultants good and great consultants great,

3:24 as the great ones were just trusted advisors. And so it wasn't until I was handed a quota many years later, when I was working at a company called GLG, that it kind of all clicked for me that like the way in which you sell, especially into these spaces, wasn't really all that different than like how you delivered this consulting services, which was like deeply understand the problem, understand the people and the processes internally to get to a decision and how do you tell a compelling story that doesn't just sell a point solution, but really makes you viewed as a problem solver.

3:54 And so that's really kind of like how I landed in the space and like really how I ended up being a salesperson was it was much more rooted and just like how organizations operate and how you think about moving them to get to decisions. So it was a great cast a crash course that I deeply enjoyed. I think there's so much to be learned just having a structured thinking process, structured problem solving process. Talk to me about when you got to GLG and you're getting in your first quota carrying role. One, how did that happen? And two, what exactly was the role? And how did you approach it?

04:25GLG, the first quota, and learning to win on execution

4:31 Yeah, so I had inherently been leading their kind of customer success function. But what the company did was it focused on connecting experts to large kind of like financial institutions, consulting firms, etc. to be able to like get smart quickly on topics. And so this was a highly competitive, highly dynamic space where every single opportunity was inherently a jump ball. And so the things that one new business in this space was a combination of like speed and quality. So you needed to like find the experts quickly. And they needed to be the exact kind of person that they were looking for.

5:06 And so the value proposition was ultimately one time and again, on the last thing that you did for them. And so by default, you had to be able to build like really strong execution prowess to be able to deliver like in with speed and quality at the same time. And so I would I happened to be relatively decent at it. And so I ended up going from leading kind of the service side and the customer success side of the function to then be moved to become a general manager. And so I was overseeing like the full P&L that included sales. And so like sales was sort of thrusted on me with

5:39 no previous kind of like sales experience. And that's where I say like when I'm saying I'm not a sales guy, like I've literally never held an individual contributor sales title. I went from leading CS to then like overseeing sales and CS simultaneously. And I think that journey really cemented to me the idea that like if you can connect the service delivery and execution to then being able to be in a room and help to like vouch for what you're actually selling, that really seemed to resonate. You won based off of the trust you were building in these like high

6:12 stakes environments for these very sophisticated clients. And the more you improve that execution, the more you saw the business grow. And so there was a very close linkage to like that kind of like operational excellence to then being able to drive the P&L in the right direction and ultimately win in the market. And so for me like GLG was really about how it inculcated this concept of like service kind of like focus into the go to market strategy long before I ever held like a CC title or you started to get all these other levers that you could pull. And it really cemented that idea

6:45 of like you get the execution right and then like you earn the right to win more business. You're not selling them a platform. That's just a surface layer. The growth engine is actually the delivery. And so like the product is the service that you are selling at the end of the day focused on the outcomes. And I think that's where as we'll delve into like the heavy industries, more complex industries, whether it's energy, whether it's sustainability, carbon markets, whether it's healthcare, you name it. These industries care so much about the outcomes and the quality of the delivery and the bar that you operate at because it's so

07:14Why SaaS playbooks break in heavy industries

7:20 just core to the cultures of how these companies operate. And so they want to see their partners operate with that same focus and rigor. And a lot of what I've seen from historical SAS playbooks is like they think the work is actually like getting the deal closed. Whereas like in these industries, all the work actually happens after the first deal is closed. It's all about like that's the audition is the first part, the first contract for then when you play for the real contract, because like the stakes tend to be a lot higher if you miss on the delivery. It resonates so much with me. Before founding LeanScale, I ran RevOps for three companies,

7:59 had a couple of exits and started this in 2021. And that's exactly what our process is. And we actually we have something we call the flywheel here at LeanScale where step one of that flywheel is doing work our customers can be proud of, because it's right. Selling the deal sometimes can be relatively straightforward, delivering on it, making sure LTV is as high as possible, and then getting referrals in a close industry. That's a bigger challenge. And you have to actually do what you say you do and keep the promises that you made in the sales process too.

8:33 100% agree. And I think that's where, as we then start to think about how that translates into how you build kind of like these go to market functions in these operationally intensive industries, really starting to think about like the kind of operational backbone of the business and how you can time and again, deliver at a high bar and at a consistent bar is really what drives expansion opportunities. And so like when we think about kind of leaning in at any organization that I go to, you're always kind of step one, looking at like what is the RevOps backbone of the company

08:47RevOps as the operational backbone (not just Salesforce hygiene)

9:09 as like a first port of call, which I do think is different from a lot of maybe more sales first sales leaders that I've seen that will start more on the what's the sales enablement and like how we think about pricing and packaging. And they jump straight to kind of the stuff that's going to directly lead to me going in front of a customer and talking. But for me, when I think about like building operational excellence within these organizations, RevOps is the language in which companies kind of test, measure, learn, and ultimately like drive rapid scalability. And if

9:42 you don't have that language in place right out of the gate, you can't actually figure out what's working and what's not. And so like the focus on really establishing not just like is Salesforce clean, which I've seen a lot of people, they think RevOps equals Salesforce. And I'm like, that's part of it. But there's so much more that can be done. And like, I've always seen that as like the kind of the right hand, it is again, like the language in which you set targets, hold people accountable, learn experiment. And now that you layer in what you can do with AI, and it becomes this force

10:14 multiplier that I don't think we fully even understand like the potential for. But if you don't have that foundation that RevOps provides, everything else is kind of dampened. And like your ability to scale rapidly, I think is quite constrained. And so I think that's where it probably comes out most in like how I think about these functions and like my operating background and not being sales is I start with like the kind of systems, then I think about the people, then I think about the process. And you want to like focus on a three of those concepts. But like

10:42 if you don't have the system in place to start, you can actually like tinker with the rest of it to figure out the right diagnostics to then go hard, right? When you figure out, then you go all in. And I think you just see a lot of wasted effort and a lot of blown trust, which is like I think one of the key components to this industry. 100%. And I think it starts with hey, let's get the go to market life cycle type to understand what staging means by channel by go to market motion, what it means to move something from lead to close to delivered and all the customer stages, and then getting your lead attribution

11:13 really tight as well. So you know where things are coming from. And then you can measure the conversion, the cycle, the CAC of each of your channels. And then just like you said, if you don't have that data, you have no idea where to double down, take risks, pull back. I've seen plenty of companies burn so much money and waste so many resources on bad marketing, or getting sellers in before there is an ability to ramp them and feed them pipeline. And I think the smart CROs are coming in, thinking of your head of rev ops almost as your chief of staff, your number two as well, I think it's really, really smart.

11:17The CRO build order: systems, people, process

11:56 And then you hold the bag first. And when your entire calendar is booked with meetings, then it's time to start layering in AEs. Yeah, no, I think that's exactly right. And like you said, if you don't have that in there, you're not really making decisions, you're guessing. And I think that's where I see a lot of challenge is if the if this is under invested in as a function, your ability to run data driven experimentation, which again, I'm speaking more like an operator than anything else. It becomes extremely hamstrung, right? You want to be able to truly A/B test or truly have definition or like in control over forecasting.

12:35 That's a that's a statistical exercise, right? You want probabilities and you want to understand stages and you want to be able to refine and continue to demonstrate ownership, which I think is like one of the key responsibilities once your CRO is it's not just hitting the number, but it's demonstrating control over that number and being able to know when you're behind and then what the corrective actions are and being able to say whether they're working or not. This all requires the ability to measure the actions that you're taking and then see the impact downstream. And if you don't take that first step of over investing in that operational

13:00When delivery mistakes mean safety incidents and front-page risk

13:06 backbone, which is revenue operations for the CRO, you are flying behind, right? You're just not operating with objectivity. And I think that's where you see a lot of spinning in terms of then figuring out the right path forward. And again, when you think about that in a world in which you're delivering SaaS, you can iterate on a product really quickly. But like if you are trying to think about how you align software and services to really like intensive industries, your ability to think about capabilities and how you build those to meet the needs of your customers and to build trust where they are, it is a lot harder. And so like you

13:41 have to be much more intentional and calculated with the bets that you take. And so it actually like magnifies the criticality of having that data. Because quite frankly, like your the mistakes that you make when you get the delivery wrong in these industries can be quite significant, have significant ramifications, right? Safety is a big thing. People get hurt in a lot of these industries. It could be really expensive equipment that gets destroyed. It could be public issues where the company ends up on the front pages of a newspaper because they're associated with like

14:12 a bad project. Like all of these things are risks that these companies think about. And so the bar to even get in is extremely high because the stakes are very high. It's not like, oh, I use this software and it like broke and this is annoying. But like I go on with my life. Like there's critical processes that you're trying to lean into to like say, hey, my solution can help you here. And if it doesn't work, it can cost very big amounts of money and they have very significant ramifications. And so again, I think that ownership as a CRO to recognize that your service organization, whatever that is, is a first-class citizen. It's not like a

14:47 margin enhancement play. It's like one of the other big pieces that like when I go into organizations, I look at and say like, how are we elevating this org to the same level as we manage like the sales function or the account management function? Because this is like kind of three legs of the stool. Like you need to make sure that like we've delivered on what we promised because that's how you're going to get access to the next bigger opportunity. It's earned over time. You don't just earn them right out of the gate. No one's given you the keys of the kingdom in these

15:14 industries on like the first contract. And often the type of industries you're talking about, the TAM is relatively tight in terms of number of logos and app bats. So if you mess up with one, it's very unlikely to keep growing with the other ones. And the opportunities are massive when you can expand with that customer too. I think that's spot on. And you think about some of these industries that tend to be kind of like duopolies or like highly concentrated at the top type industries, highly capital intensive. And so when you think about it from a pure SaaS lens

15:50 historically, like expansion usually comes through like, oh, I'm going to sell them more seats. Or maybe I'll add another module. Expansion in these industries isn't a product problem. It's actually like a trust problem, which is like, how do you earn in that kind of first phase of the contract and your audition the right to be asked bigger questions and the right for you to be able to ask bigger questions of them, because that's where you see expansion play out here where it's and it becomes this beautiful, self-fulfilling prophecy where if you can like

16:20 deliver the first time at a high bar, they will usually consider like, oh, okay, you solved that problem for me. That was very contained. The blast radius was like limited. Now I'm going to like open up the aperture a little bit and like the expansion on those ACVs because it is, there's lots of money in a lot of these industries. You can see like pretty rapid expansion of the contracts. But the way that you win that is like somewhat unsexy. It's just about delivering, doing what you said and saying what you do. But once you've done that and you've built operational excellence

16:50 in like the kind of background there and you have this amazing combination of a platform that can help to scale the service that you are delivering and like I'll bring up a term that I think is becoming quite vogue, but this idea now when you layer in AI, kind of like AI native services, it becomes this incredible mechanism where if they have a great experience and it is a small community and they all go to the same conferences and they are all dealing with the same problems and they probably have worked at some of the same companies, the word of mouth impact from a

17:20 referral to be like trust them means you get to skip some of that like early winning the right to ask for the bigger thing. And so the referral mechanism that comes from that can be far more impactful than any like outbounding strategy AI enabled or otherwise because of how tightly knit a lot of these communities are and then how similar and transferable a lot of the problems are and because it is trust-based, you win by doing well and then that begets more winning. And so a lot of the conversations I will have with folks is around the investment maybe up front,

17:56 you'll see a little bit slower growth, but then you'll see this kind of turn in the growth rate as like things start to pick up and as those services start to catch on because I think like the expansion opportunities, the retention opportunities if you're doing that, it's much harder for then others to break in because you become more and more indispensable in that space. Yeah, and there's no better CAC equation than referrals. So that's right. That's exactly right. Yeah, if you can get those ramped up and coming, it's incredible. And there is, I think people are

18:31 coming around to the idea like LeanScale, we're an AI native services company as well. So we deliver RevOps as a service, but we built our own AI agents and platforms to help deliver the work like platforms that can auto push workflows to Salesforce and HubSpot or design your entire processes at the click of a button rather than weeks of discovery. And it does become interesting when you have the combination of tech and services, but you still have to solve the problem. And I think the companies that are really focused on solving the problem, not necessarily caring

19:07 about the mechanism or the how, let's just solve it in the highest quality, highest efficient way possible. And I think to me, I'm like, oh my goodness, that's just like obvious business. That's every other anything, but SaaS isn't used to needing to roll up their sleeves and actually do work too. But I think it's finally coming to a point where people are not open to buying vaporware and just letting it sit on the shelf. Whether it's high risk or not, even a low risk, it's like, no, I need you to solve the actual problem. I think that's extremely poignant. And so when I, especially on this, I think with the concept of

19:44 AI native services, like very much, I think now coming into becoming very vogue, but the idea. Yeah, I mean, even Sephoya labeling it service as a software and YC is looking for their cohorts to be services companies. It's just so, it's interesting. Like, oh, this was like the not sexy thing two minutes ago. And now it's like the hottest place to be. And I would love to say that I had the foresight to see this coming, but that would be a lie.

20:14 Yeah, exactly. And so it's a funny thing as you look back and I think about the stages of my career that have enabled this kind of like moment to really make sense. And you're like, oh, this is always kind of what made sense on a business level, which is like, if you're not delivering outcomes, if you can't measure the value, a lot of what happens when you're on the inside of the company is doing the purchasing is the stuff ends up being put in the shelf. So like I can think when I left consulting and I went to work for a very large publicly traded utility where I was, I had like a relatively senior operations and strategy role. One of the

20:53 things I did was like build like a data analytics function there. And so we were building a lot of like it was early days for some of this stuff. There's like predictive mortality models that you would use for like assets. And if you couldn't directly tie it to a clear business outcome, the amount of like these companies public issue, especially large enterprises are built to like kill and squash inefficiency, right? Like it's like they don't want stuff unless it really adds value and like everyone is hammered on their budgets and what they're spending on

21:22 the justifications. And it was a great learning experience in that like, unless you can successfully integrate whatever it is that you're doing, it won't get legs and it won't expand. And at the time, it was like an internal experience for me where it was more of like watching again, like I kind of knew how decisions made or decisions were made within organizations. I've done that a lot in the consulting side. And you could maybe get past the first hurdle because you knew how to position all the things and say the right things about the metrics. But if you didn't deliver the metrics,

21:53 it became very clear. And I think it's important for like folks to remember, like again, like it's not about selling the product, like you have to be selling an outcome. And that shift is where I think, especially in the operational intensive industries and honestly, where I've seen when people hire pure play, classically trained SaaS sellers to go work in these industries, they really struggle to be successful because they'll get the first things potentially through the door because the demo may look good, but they haven't spent enough time discovering the true

22:00Owning a sales funnel for the first time

22:26 problems that are being solved. What are the outcomes that are truly needed that tie to the KPIs of that organization that you're selling to so that they can demonstrate that they've added value in their job. And that like shift away from like, oh, we've got like this many like monthly active users and like, I'm going to go back and push them to up the ante on how many seats to what did you get? Like, what did you need out of this thing? And did that actually materialize? Like did what we promise actually show up? What I've seen is like operators who then become sellers, which is how I think about hiring in these industries. I actually lean towards

22:58 people who have like done the thing or operated in the space and can speak with credibility about the challenges. And if like lived those challenges, I can teach them the selling stuff, but it's harder to like ramp someone up on an industry if they haven't like done the job for a few years. Is that like those people are much better at like building trust and understanding truly like, oh, we should like link the like the thing we're selling to these outcomes. And they'll get really excited about this. And we can feel confident about how we might even structure a contract

23:29 tied to outcomes based pricing, right, which is I think we're like, you see a lot of these native services heading towards where it's like, we'll put our money where our mouth is. But again, that's where this comes down to, which is like understanding the operational requirements of your customer. The technical complexity that might exist there is really where you see the difference of a company able to drive integration of what they've sold, which leads to expansion versus the like it goes on a shelf, which I think you again see a lot from folks that haven't come from these spaces and like dealt with those problems internally.

24:03 I think it makes a ton of sense and having that operational credibility just lends itself to the prospect or customer empathizing with the person, being able to really speak to their problem at a visceral level and then give examples. I'm curious when you when you stepped into the role, and I think there are so many advantages of coming from an operations background moving into the type of role you're in, but what were the gaps when you first took ownership and you're responsible for hitting a number now, what were some of the gaps that you had to quickly ramp up and how did you do it?

24:35 Yeah, I had never managed a sales funnel before, so there was a pretty extreme gap, which was your manage. I was blessed with having some extremely experienced and highly competent sellers as well as like really strong sales leaders in the organization. How did they take to you getting the job? Were they excited that you brought some operational excellence to it? Were they like hey, this guy's never sold before? What was the reaction? If I was being honest, it was probably mixed. I think what they had seen was demonstration of commercial acumen through the lens of running the other large organization,

25:07The gaps Joshua had to ramp on fast

25:16 like the customer success organization, and I'd been in the room with them side by side on like many of the renewals and like customer conversations that we were having. So they knew that I could show up in a room. I could demonstrate some level of executive presence. I could be commercial and think about how to drive that, and I'd worked very closely with the kind of like leadership of that organization prior to kind of like us moving to a GM model at the time, but I think they also recognized like what are the things I'm likely going to get out of this person versus what

25:47 are the things that I probably won't get a ton of help on because like I have more experience than he does, and I think for me the way I managed through that was owning it, right? This comes more into like leadership, but I think when you get to the CRO level, depending on how the org is structured, you could own anything from all the way from marketing all the way through to customer success and potentially likely rev ops and sales. And so to pretend like as you get more senior, that is because you are an expert in all of the things I think is like a failed thought

26:25 experiment. And so for me, it was really more about how you think about like if you go back to the kind of the people process systems, when you look at the people, it's do you have the people that complement your capabilities and ways in which like they're strong where you're weak and you're weak, you're strong where they're weak? And how do you then quickly ascertain how much space you can give people? And how do you then, you know, go on a learning journey for yourself so you know enough to be dangerous? But I'm always the first person to say like, yeah, I mean, I

26:53 carry, you know, quotas, and I'm responsible for numbers now. But you know, there's a large period of time where like I had very limited experience operating with that type of stress, where like I eat what I kill and like, this is how my whole mindset is set when something goes wrong in the org. Why is sales always so mad? It's like, well, you like just feel like you just got in trouble. But like, you know, it's a coaching conversation, like they just lost 15% of their earnings for the quarter. Like it's a different, it's a different game when you carry that kind of weight. And like

27:10The humility move that won over experienced sellers

27:21 I, you know, for a long period of time didn't understand, I couldn't emphasize like empathize with that in an authentic way. And for me, I think that was the key was just being really clear about here's how I'm going to help you. Here's how I'm going to develop you to make you more effective in your job because I see opportunities around all the things we're talking about now. How do you become more operational? How do you think more like a systems thinker so that you can more effectively position? How do you think about pricing more mathematically? Like how do we actually get

27:49 sharper and data driven and how we do pricing? Like these are skills that will become important for you as you become more senior in the role. But simultaneously, it's like, teach me how to run a pipeline review. And I think like just being very open and honest about that ultimately worked out. And I think it's aided my career because again, you get more and more as you get more senior. And you know, it's like I was never a marketer. And then at work rise, I oversaw marketing. And that was like new. And I think the same methodology applied. And it's great for you because you

28:20 develop and it's great for them because they learned something different. But yeah, I think the humility is important. That was the word that was coming to mind was humility. And yeah, anytime you move into those higher levels of leadership, like you mentioned, you're just going to be you're going to end up being responsible for something that you haven't done before. So having that humility leaning on your team, I'm curious on the ground floor. So bringing in operators into those selling roles. Yeah, I've seen it work really well. I've seen it be a complete disaster. So two part question, when you're recruiting, what things are you looking for

28:57 to say, hey, this person can translate their experience into a commercial prospect customer facing role? And then two, when you bring them in, what are the areas where you really need to give them support and training and and get them up to speed to perform really well? Yeah, first and foremost is, I guess it called learning agility and or the aptitude and desire for learning as a general statement. And why I say that, and I don't know if this is necessarily specific to these industries, but I think it absolutely in these industries is like mission critical, is that so much of your credibility when you are selling to them is tied to your ability

29:32Hiring operators into commercial roles: what to look for

29:39 to stay current, stay abreast on what are very complex, usually very technical industries. And so if someone is voracious in their desire to consume new information, to just be naturally inclined to be interested in what is going on in the space, your ability to build credibility authentically, where it's not a show, I think becomes such a differentiator when you're having these conversations. So like I look at my current company patch, like the people are obsessed with solving like the climate crisis, which is amazing to see their depth of understanding of sustainability

30:18 topics, ranging from like the core aspects of our business today in carbon, all the way through to kind of all of these like leading edge technologies that are being experimented with and like trying to be catalytic and like driving kind of like this big problem, huge problem that the world faces is where we then get invited into lots of rooms because they just are so knowledgeable in so many things. And it's not through any like structured enablement that we do to be like, oh, have you read like the newest white paper, are you following these newsletters? They are the ones posting in

30:49 channels being like, read this new thing. This is amazing. Like I went to this symposium over the weekend. This is what I heard. And so I think you just get such a natural lift in terms of your efficacy with enablement, generally speaking, by having people that just love the thing that they are doing and love to learn. And so that's like the number one thing I usually look for is that intellectual curiosity and that drive to want to learn and even how I do interviews, it's really focused on how do you learn? Like what is the last thing that you've taught yourself? How did you do

31:20 that? What motivated you to do that? Because I want to see how much of it's like I do it because I have to versus this is what I just love doing. And so I think that's one huge, huge element that we look for. I think the other piece is ultimately kind of like the structured communication skills. And this is probably a remnant or a vestigial organ of my time as a strategy consultant. We love structure. We love frameworks. We love two by twos and things and threes and sevens and all of the good stuff. And for better or for worse, that group of people is very effective at communicating complex ideas and distilling it down and very digestible

31:59 things. And as I said, a lot of the problems that we solve are highly complex, highly interrelated. There's lots of different stakeholders. It might be highly technical. And the people you're talking to in a room might be a very diverse set of stakeholders as you're trying to like multi-thread and ultimately get into and present to a group of people that might range everywhere from finance to procurement to today, like the actual sustainability function, their level of understanding on a lot of the things you're talking about is going to vary. And so like it is critical that you can articulate really complex things in very digestible ways.

32:31 And so that's really what I look for. Because ultimately, when I think about this, and what I learned being in those rooms, is that the job of that person is to ask smart questions, which can be helped and informed by learning constantly and bringing really interesting kind of ideas into the room, be able to then communicate that clearly and effectively, and then listen and synthesize and process information and communicate it back into the company, whether that's to influence or affect the services or product that we're delivering, whether it's to help to sharpen a deliverable that we're going to bring there.

33:01 And so you can teach through having the right operational backbone, which goes back to the RevOps piece, the sales stuff, because I know I'll be able to measure whether the activities are good, or like what's happening at each of the stages and are they qualifying appropriately. And now we have all this intelligence with Gong and like, I can mine calls and I can look at calls and I can run, you know, like the workshops and you can do the role playing and all the things that you can now do that technology makes far easier than it was two years ago, that part

33:30 you'll have if you've invested appropriately upfront. And so like the getting them to be able to do the repetition piece and run the playbook the right way is not as heavy as a lift as trying to be able to get someone to do a lot of those soft skills that ultimately I think drive trust. Again, it goes back to that trust and authenticity, because the beautiful thing as they start to build these relationships is they'll be invited into more and more rooms. And I think like the visual we always talk about, and I've always seen I think consistent across a lot of these industries is

34:02 like you'll have some executives staring at some terrible spreadsheet with all this complexity because these big companies tend to have a lot of archaic, not interconnected systems. And they're trying to make heads or tails out of this thing. And what they really want is not another system, not another tool that they log into. They want someone they can go to and say, how do you help take this off of my plate? I have so many important competing priorities to do. And if you can solve even just one of those things they really don't want to do, there's actually usually a pretty large

34:31 willingness to pay attached to it because it still will be tied to some critical process. But because these people wear so many hats and more and more people are pulled in more and more directions, if you can be that person that they pick up the phone to and say, I've got a problem, can you help me solve it? That's where you see the ACVs grow. And that's when you move from just being like a vendor to actually a trusted advisor. And that's what we're always coaching. And I'm always coaching my folks to move towards is like your job is not to sell. Your job is to be a

34:57 resource. And then you identify the opportunities where it makes sense for us to sell. And sometimes it might mean that you don't sell, that you recommend something else. But like that ability and demonstration will build trust where like when it's right, we will be there and it will pay out. And I think it takes some level of confidence and conviction and trust from your own organization to do it that way, because it might mean short term pain. And I think again, that's where having data can be like, but you got to, it's not just me saying it, like look at how the business is

35:26 moving. Look at what happens when we invest in what are very long sales cycles in the right way, it yields. And I think that's, you know, we've perhaps seen ACVs skyrocket over the past year. And I think a lot of that is tied to like how good our service organization has been and how good our sales organization has been and like trusting the process and really driving the value of those conversations tied to like solving a problem, not like selling a solution. Yeah, and I think it becomes very evident in the LTV. And, you know, we've had, we've had customers

35:57 with us, we started in 2021. And we have customers with us that have been here since the beginning, almost five years. And when you build partnerships and relationships like that, that are continually growing, they're feeding your referrals. It's a beautiful thing that comes from executing day in and day out and treating your customers like their prospects, always selling them in a good way, like always looking to delight them. I mean, people talk about speed to lead, speed to close, like being on top of every single little communication. And then after that, yeah,

36:29 we'll see how it goes. No, be on top of it the same way later in the process as well. And you can solve things in funny, archaic ways. I mean, you brought up, they don't want another tool to log in. It wasn't that long ago. It was 2019, 2020. I was working at a Fortune 1000 company. They did a few billion in revenue a year. And I was working on implementing Salesforce. But they rolled up their whole forecast with spreadsheets. They had EAs emailing each other spreadsheets. And then they would copy this spreadsheet and put it in this spreadsheet and just made sure the formats are the same. And then they would roll it up every single Friday. It was

37:11 like this whole thing. And I'm like, oh my goodness, you're probably, it sounds silly, but I'm like, you would actually probably spend more on Salesforce and analysts and all this stuff than your EAs emailing spreadsheets around. And you're getting the exact same outcome of they could forecast to the penny. It was like so impressive. Yeah. And so I guess, I mean, that's a great example, right? Of like, if you focus on the outcome, like what is, what do you get by driving through some massive software transformation project that would be wildly expensive? Salesforce has its own

37:46 complexities in and of itself. But I think it's a very poignant case where sometimes maybe even like the most sophisticated quote unquote answer isn't the right one. And I think it's a good example of like people that can recognize those moments and recognize that maybe that's not the thing you need, even though it's the thing I want you to need is where I see this kind of combination of like, when you have software and services combined, it gives you more ways to think about how you deliver value. And the services usually allow you to spend more time with a customer to

38:22 really understand the pain points and the problems that you're solving. And you can use that to continue to think about how you add more value and how you evolve your offering so that you continue in a durable long-term way to be a trusted advisor over time, right? And I think you said it's like five plus years of existing customers. The problems you were solving five years ago, I imagine, look extremely different than the ones you solved today for them, but they come to you because you just know how to solve problems. It's not that you're an expert in, I don't know, clay

38:51 integrations or whatever that you know it's going to be. You weren't five years ago because it didn't exist, but that's not the point. They just trust you to solve the problem. They're like, "This seems important. Anthony probably knows. Let me like talk to Anthony." And I think that's where in these industries, the more you build that relationship and you become that first phone call, it is not about the thing they're logging into. It is not even about the service you're delivering today. It's that you've built trust and trust comes through consistent execution over time.

39:21 And so if you don't have as a CRO focus on the operational excellence of your company, I don't think you're doing your job in these industries and you're setting yourself up for failure. And you might not feel it in the year, but you'll feel it if you're there for more than a year. Like it'll start to erode because you only get, as you said, kind of one shot. You get the audition and if it doesn't work out, it's hard to get back in. So, and I think that's where AI becomes really interesting for this space because up until now, this year was really the year I was

39:53 like, "Oh, I've like always kind of had to argue about why this matters." Like generally speaking, when I speak to people in the industry and I kind of say stuff like this, people will be like, "But your job is ultimately to like drive this number, like focus more on the sales side." And I'm like, "I don't know if I agree, like this is a good intellectual debate." But now with like the ability to scale that service organization in a way that is like margin of creative, all of a sudden all that differentiates you is your delivery. And like that's the thing that

40:00AI in carbon markets: turning information asymmetry into advantage

40:25 I think has been the big aha moment for me at Patch where like our founders extremely AI forward and has like pushed us all to be pretty much at like 100% like daily usage of AI and everything that we do, which is amazing, that we're starting to learn how to compound all of this value that we create. Because not only does it enable us to pass on savings to customers because we can do stuff at a fraction of the cost that it would have normally taken, but the quality of that project improves every single day because as you push more and more learnings and knowledge and insight

40:59 through the platform, it informs services in a way that like no one else can compete with. And so you see this not only like margin scaling, like profit machine that like the technology will provide, but it has this just massive multiplicative impact on the quality of the value that you can provide to the customer. And so it's just like this beautiful moment where I'm just like I definitely didn't see this coming, but man am I glad that I've thought a lot about ops because the best way for me to think about AI is understanding the processes and then being able

41:31 to see oh this is probably something you could do with this. This needs to be a human for now and you can make those calls in a way that effectively use it where you don't see kind of AI slot. It's just like empowering the org to spend their time on the highest value work. And so that's where I get, as you can't tell, really excited about what's coming because I think the next 10 years operators will more and more become successful in driving sales versus like probably the past 10 years. It was really about sales, like traditional sales leaders know how to drive like the kind of

42:05 growth at all costs model. I think the operators will start to have more of a skin in the game and more of a voice in the conversation because it's going to be well how are you doing this with less? What are you using this for? How are you improving your processes? Why are you still doing it that way? And the questions will be more and more on that and less and less on the other stuff. At least that's my my view. I am so happy that you brought up enhancing the quality because I think all of the noise on AI right now is so focused on efficiency. Oh we can cut head count.

42:40 And I just think that that's so silly. First of all, those companies that are doing layouts, they probably needed to do them anyway and they're just using this as an excuse because now it sounds okay. And if you can make somebody 10 times more productive, why would you need to cut anyone? Your company should just be able to do 10 times the productivity with the people and then it should actually incent you to hire more people because if you can produce more with a single person, why not continue to scale that? And what we've been focused on, we may end up spending the same

43:14 amount of time on something, but especially in a services organization, the biggest bottleneck is scaling the quality. Like typically when it starts, you have somebody really passionate, really skilled, and whatever it is you're doing, and then it starts to erode as you grow and scale the team. Now when somebody does something, it's easily shared. You can maintain the quality across the board and then you can actually scale. I think it's a tremendous time to be in services right now, whether it's tech component or not, but AI driven services, I think it's a phenomenal,

43:51 phenomenal time to be in. And one of the things we were a little concerned about and I think we've gotten over this fear, but some companies may be fearing this. So a lot of times it's tough to do a full outcome based service. It's the holy grail if you can get there, but sometimes there's not enough control over the end outcome to do it. So you end up needing to do time and materials as you're pricing your packaging. What we noticed is, oh wow, we're getting things done so much quicker. And our first worry was, well, we're spending half the time and we're not billing anymore for it,

44:27 so actually the losing revenue, the better we do, which is a weird incentive system, but then quickly, the more you do, the customer finds even more work for you to do. So that was our experience. You're like, oh wow, you can do this in an hour, though I have a whole laundry list of things I'd like you to do. And then two, it also just passes on that value to the customer and keeps your value super high and then keeps them from going to alternatives, hiring in-house, going with other firms, going with other providers. So I think we've gone through this whole like

45:01 curve of this and I feel like we're at a sober place on it right now. So for anybody else going through it, I feel like that end should feel right where you're just giving so much value to your customer. And I think, again, it creates really exciting space then, should you have it, and the demand is just not wildly outpacing your ability to address it. To think about how you start to solve, again, different problems. I think that's where it gets really fun when you start to think about kind of growth strategy. And it's like, what else could we be doing? And I think that the luxury

45:32 of being able to ask that question, have the space to truly think about that in a structured and deliberate way, and then be able to test and iterate to try to see where the actual opportunity is. Is there really product market fit? What is the market opportunity? What are the capabilities required to win to doing that thing? You can experiment with that stuff a lot easier at a much lower cost. And so I actually think like, as you think about like long term growth strategy, and you think kind of like horizon one, two, three, kind of growth strategy framework, your ability

46:04 to toy with and get signal on kind of like horizons two and three, like beyond the core business, just got a whole hell of a lot easier. And for someone who's hopefully trying to think not just about how I hit the quarter in the year, but thinking about the long term value of the company and where do we look and go, not next year, but two and three years. That's where like a lot of this becomes beautiful. It's like you can kind of run scenario analysis or do things so much cheaper. So you have more latitude to experiment where it's not such every experiment isn't so expensive.

46:34 And again, I think people lose sight of like the fact that when you give people more productivity, it creates the space to create more value, right? And you can maintain the quality of life of your employees so that they're not constantly in like a wood chipper, which is like, I think a nice thing when you think about retention and all of those other fun metrics that we could talk about from an operational perspective. Yeah, you've got to get your team out of the salt mines and do your work that they enjoy doing. That's right. One last thing, and I'm especially excited to ask you

47:05 because I feel like you have such a great background for this plus mixed with the go to market ownership. How are you leveraging AI and go to market? Is there anything specific like lean scale, we're Claude code demons and leveraging it all over the place. And we built some really cool stuff there. But how are you using it with your team? There are many, many ways. So there's probably the less interesting and I imagine folks listening to this would be like, yes, I understand this, which is like, how do you just do the improvement on lead enrichment? How do you

47:38 start to think about like, you know, things like clay? How do you think about automated outbound in a highly customized and targeted fashion? How we're doing really like much more dynamic and real time account scoring that's pulling like real time market signal tied to like, you know, a strategic account list and like all of these things that I would say are really like part and parcel with like running a good kind of go to market org. I think the things where I see a lot more interesting outcomes and opportunities for these more like AI native services is how we're

48:11 actually scaling the delivery, the outcomes. And so if I think about the teams that I have the privilege of helping to work with, we have like a consulting arm that inherently there we call them like embedded climate strategists. So you can think about them as is that your version of the forward deployed engineer is that all right, nailed it. And so the thesis here right is that in sustainability, the problems are really complex. There's very low fidelity into market data. And so the way it works is like you want to try to buy these carbon credits that are generated from

48:51 various projects that can be made all across the world. And so there's not like a clearing house where you can kind of know the price and the quality of these projects with like high degrees of certainty. And so if you're trying to build a strategy that helps to enable your sustainability goals and your climate goals, it can be quite daunting to know what should I buy and what are the risks and like how do I do that? And so how do I think about the strategy? What should my claim be? And so what we realized is that ultimately the ability to deliver services tied to navigating

49:23 the complexity of the sustainability market was actually one of the key things to enable these folks to actually move to purchasing and engaging in the market. And so like the lack of like transparency and the like kind of like information asymmetry that existed within the market created a space to need someone to help guide and help to supplement the information they already had because they also wear like a million different hats. And so as you can imagine, if this was being done at an early stage startup and you're trying to kind of deliver consulting service and like do it at a really high bar and you have to try to like sift through all the

49:34The 'embedded climate strategist' — Patch's forward-deployed engineer

49:58 complexity that I just articulated and all the various data sources and what's real and what's not. And it was a lot of work. And so the key things that we've really seen that started to supercharge the business is actually how our platform which ingests like all of this information can surface insights in a much faster way. So like we can apply for example customer parameters to like how they define quality for their programs and it'll look at like the totality of the market and be like this is like the first pass of projects you should not even consider because

50:30 they will not meet the bar. And so all of a sudden an exercise of sifting through you know thousands and thousands of projects becomes a much more targeted effort. And now you're starting to get to a much sharper view like days quicker than you would have like instant ability to like reduce our operating costs improve the insights that we're providing. We have different ways in which we are thinking about the sales process and like how they're actually like teed up with all of this contextual information on the market before they go into a call to have that like surfaced which

51:00 is like I think an interesting use case for our specific business that you see more broadly right where it's like you almost can have an agent that's like a customer call prep agent that will just be like you know give me all the context that's in sales force and gong and like I don't have to do the research anymore but this throws in more of like the historical context and like what have they bought and what's going on in the market and are there any insights that you can bring because again that's going to help provide value. We want to like constantly be in

51:13Product, expertise, and data as the new force multiplier

51:24 every engagement adding value whether it's through an actual paid process or through just like our normal interactions because we know that these people are trying to do great things and we want to be catalytic to their efforts and like to these companies efforts and so it's been really fascinating to see how we are able to make sense of the chaos that is this market and translate that into like direct and quick insight through the leveraging of AI levered through our expertise and I think that's where we see the power is like the product plus the expertise and that data that

51:57 that product enables is really the force multiplier for how we believe we differentiate in the market and get people to get to answers that they need so that they can do their job and take one problem off of their desks so they can focus on other problems and we've seen a lot of a lot of impact already and we know every day these models get better and so like it really just feels like we're scratching at the surface of like what's going to be able to be done but like yeah we could probably talk about this for hours on like what you can do and what is being done with it but it's incredible

52:28 to see just the focus and the impact and how immediately measurable again going back to the operational component of it you can measure it in the operational productivity of the teams you see it in their ability to like how long things have taken them and how they take how long it takes them now it informs my head count plans it informs quotas how we're thinking about target setting across these various teams what are the jobs to be done what are the quality bars if you don't have that operational backbone none of this conversation is possible um so i love it i love it well joshua thank you um it's always great to get on with a fellow operations

53:06 person and kind of take that lens to go to market sales marketing customer success i'm fully with you on the paradigm that we're moving into and it's going to all be about solving your customers problems through services through software through whatever it takes to solve their problem and being their go-to person and earning the business every single day not closing the deal and and then calling it a done job i love your trajectory going from operations and strategy into the CRO seat i think it's going to be really inspiring for a lot of rev ops people who i know

53:36Why operational backbone makes AI leverage even possible

53:45 listen to this podcast and i think it's a a good example of how you did that through humility of getting into the role knowing where your gaps are filling them quickly as you got there and then also leaning in on your strengths and then finding the industries and companies where that becomes a massive advantage and where you can lead so i am so excited to see what you do next to hear more about how you're leveraging ai to see what you and the team come up with and i just can't wait to see your future success i really appreciate it it's been a very enjoyable

54:22 conversation i always like sharing discussions with some like-minded operations people so it's been a it's been a real fun time so thank you for having me amazing thank you josh