The LeanScale Podcast · Episode 142

How to Sell Against Claude: Differentiation Is a System

Simon Kirk on why selling against Claude is the Lattice problem again, teaching buyers what to notice, bringing lawyers into the sales process, SE ratios and win-rate lift, why no playbook survives a copy-paste, and how to interview AEs and sales leaders now that every candidate has Claude

Simon Kirk · Interim Chief Revenue Officer, Orbital · Orbital Hosted by Anthony Enrico
Published Updated 00:49:16 42 min read 8348 words
Sales Enablement Brand & Positioning Enterprise & Public-Sector Sales Sales Leadership AI in GTM GTM Strategy
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Executive Summary

The one-paragraph brief, extended

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

Simon Kirk is the interim Chief Revenue Officer at Orbital, the legal AI company for commercial real estate. Before going independent about two years ago, he spent five years at Culture Amp as the first hire for the CRO, building sales development, revenue enablement and solutions consulting across Australia, the US, the UK and Europe, and before that worked alongside the CRO at InVision. Since then he has done fractional and interim go-to-market leadership for companies ranging from a technical founder learning outbound from scratch to later-stage scale-ups.

The episode starts with the objection every sales team now hears: why can't I just use Claude for this? Simon's answer is that the sales mechanics are familiar. At Culture Amp, Lattice played the same role: a competitor whose arrival in deals made the team anxious even though he believed Culture Amp was the stronger product. The lesson he took is that reacting emotionally to a competitor's latest announcement is less useful than asking whether your team can explain why a buyer should choose you. He illustrates it with Culture Amp's top revenue producer, who would tell prospects during demos that what he was about to show was really unique, and watch distracted buyers snap back to attention. Differentiation, Simon argues, means teaching the buyer what to notice, and teaching the AE how to do that, which takes a system: product marketing keeps positioning current, enablement turns it into something sellers use, leadership buys in, and frontline managers reinforce it so it doesn't die after one training session.

On build versus buy, Simon has watched internally built Claude Code tools launch to fanfare and then get abandoned for the previous product, in one case HubSpot, because nobody owned maintenance once the builder moved on. He favors shared Claude skills for work like account research, rolled out centrally, and buying specialist software where the workflow is specific to an industry or depends on proprietary data. Anthony Enrico adds governance, permissions and the opportunity cost of pulling engineers off the core product.

The middle of the conversation covers people. At a legal AI company Simon put lawyers, sometimes very senior ones, into deals as domain experts, and says the credibility is enormous as long as they are also coached on how to operate in a SaaS sales environment. He runs solutions consultants at roughly 80 percent deal work and 20 percent projects, sees SE-to-AE ratios fall as contract values rise, and has seen up to a 10 percent win-rate lift on SE-covered deals. Anthony puts that in plan terms: on a $20 million plan converting 20 percent of pipeline, one point of conversion is another million dollars in bookings.

The final third covers playbooks and hiring. Simon is skeptical of any universal sales playbook: too much process kills an SMB motion, too little kills an enterprise deal, and the work is deciding which principles transfer. What he does treat as non-controversial everywhere is a disciplined interview process and some form of performance management. For AEs he uses the coachability test he credits to Mark Roberge: give one piece of feedback and judge the second attempt. For sales leaders he hands over data, encourages them to use any AI, and asks them to defend their analysis. He most wants leaders who have used Claude to make a whole team faster, which is still rare enough that he calls it gold dust.

Key Takeaways

15 things worth stealing

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

01

Selling against Claude is the Lattice problem again

When prospects at a company Simon works with started asking why they couldn't just use Claude, the internal reaction was trepidation, because Claude is a very good product. Simon recognized the pattern from Culture Amp, where Lattice's arrival in deals made a team that had enjoyed open market space anxious, even though he believed Culture Amp was the stronger product.

Why it matters: The risk is the emotional reaction and the distraction it causes, not the competitor's announcement itself. The useful response is to check whether your team can actually explain why a buyer should choose you.

Sales LeadersRevenue ExecutivesFounders
02

Teach the buyer what to notice

Reviewing call recordings of Culture Amp's top revenue producer ever, Simon noticed he would say during demos that what he was about to show was really unique, or that the prospect should pay attention to this. Prospects who had drifted off snapped back to attention.

Why it matters: It sounds stylistic, but it shows that differentiation is not a battle card sitting in a drive. The AE has to direct the buyer's attention to what is different, and the AE has to be taught how to do that.

Sales LeadersMarketing Leaders
03

Differentiation is a system, not a battle card

Simon's system has four owners. Product marketing keeps positioning and competitive materials current. Enablement translates them into something sellers can use. Leadership buys in. Frontline managers reinforce it, because otherwise everything dies at the one training session you held.

Why it matters: The test is whether AEs have internalized the differentiators: can they explain them naturally, tailor them to the buyer in front of them, and weave them through from the first conversation to the demo, rather than waiting for the buyer to ask how you are different.

Sales LeadersMarketing LeadersRevenue Executives
04

Differentiation has to run through the whole sales process

It can't first appear on slide 17 or at minute 55 of a 60-minute demo. It should shape how a BDR opens, what the AE asks in discovery, what gets emphasized in the demo, how objections are handled, and arguably how the customer is onboarded after signing.

Why it matters: Buyers often see products as similar and want help understanding why this one differs from the three other demos they saw that day. Making that easy is part of making it easy to buy.

Sales LeadersMarketing LeadersCustomer Success
05

Specialist products win on specific workflows and proprietary data

Simon separates the two questions an AI competitor raises: a sales-execution question (are we sharp about our differentiation?) and a company-strategy question (where can a specialist product create value a general-purpose product is less designed to deliver?). His answer to the second is industry-specific workflows and proprietary data. Products that stay in a generalist lane, such as plain document review, are under threat.

Why it matters: If your product's value can be described without reference to a specific workflow or data set, expect the 'why not just use Claude' objection to land, and expect it to be a strategy problem as well as a sales one.

FoundersRevenue ExecutivesMarketing Leaders
06

Internally built tools fail on maintenance

Simon has seen someone build a tool with Claude Code, launch it to great fanfare, and the team use it for a while before going back to the previous product, in one case HubSpot. The question nobody answered was who maintains custom code, and what happens to it when the builder leaves. He also warns that well-meaning teams without data-privacy experience can leave sensitive internal information a link away from public discovery.

Why it matters: Even with the capability in-house, his preference as a buyer is specialist software, with Claude skills used to optimize workflows within existing tools. Anthony adds governance, permissions at scale and the opportunity cost of pulling engineers off the core product.

RevOps LeadersRevenue ExecutivesFounders
07

Lay traps in discovery for generic AI

Asked how to sell against the idea that AI could do the job, Simon admits he has no hard proof points yet, but points to a channel where his team sees prospects who tried certain AI products that didn't work. Great discovery uncovers the root problem, what else the buyer is using and who else they are talking to, which lets the AE proactively lay traps around where a generalized tool won't deliver the value.

Why it matters: Handling the AI objection is a discovery skill, not a rebuttal script. The traps are set before the objection comes up.

Sales Leaders
08

Put domain experts in deals, then coach them to sell

At a legal AI company Simon used lawyers, sometimes very senior ones, as domain experts in the sales process, and says the credibility with prospects is incredible when someone has sat in their shoes. People hired straight from industry, though, don't know how to turn that credibility into conversion.

Why it matters: The effective combination is domain expertise plus a management structure or coaching on how to show up commercially. 'I worked in your industry' can't be where it starts and ends. Anthony adds that vendors should be opinionated about the process they build for, rather than handing domain expertise back to the customer.

Sales LeadersFoundersRevenue Executives
09

AI's pull makes domain experts easier to hire

Many people in industries outside AI feel AI converging on their field and want direct experience in it, so they are more willing to leave practice for an AI company. Once in, their day is mostly deals: demos, pilots, rehearsals and prepping with the AE on what makes this conversation unique.

Why it matters: They also serve as a bridge back to product and as public figures for the company through webinars and white papers, so the company gets content and leads through the lens of their credibility.

Sales LeadersFoundersMarketing Leaders
10

SE ratios tighten as deal size grows, and the lift can be large

From asking candidates about their companies' ratios, Simon's impression is that the higher the average contract value, the lower the ratio: around one-to-one for seven-figure deals, two, three or four to one for six figures, and pooled below that. He has seen up to a 10 percent win-rate improvement on SE-covered deals, while warning that the better deals tend to get SEs, which distorts the comparison.

Why it matters: In a new motion, overinvest in the function while you find the right ratio, and check it against average contract value and the fully loaded cost of every persona on a deal. Anthony's math: on a $20 million plan converting 20 percent of pipeline, one point of conversion adds about $1 million in bookings.

Sales LeadersRevenue ExecutivesRevOps Leaders
11

No sales playbook survives a copy-paste

Good discovery is good discovery in SMB or enterprise, and the diagnostic questions are the same: where is the funnel breaking, are we hiring correctly, are we creating enough demand, are reps converting as expected. What changes is how much orchestration the salesperson does and how much process to impose. Too much process can kill an SMB motion. Too little can kill an enterprise deal.

Why it matters: Simon avoids arriving with 'my Culture Amp playbook'. The work is deciding which principles transfer and which assumptions to throw away. Anthony calls the alternative, a new CRO imposing a playbook and hiring 100 reps, a meme that keeps hitting a brick wall.

Revenue ExecutivesSales LeadersFounders
12

Two non-controversial fixes: interview discipline and performance management

In loose hiring processes, interviewers aren't told what to ask or what to evaluate against, candidates answer the same question repeatedly, and each interviewer passes a merely adequate candidate to let the next person make the hard call. Companies hiring at volume end up hiring many people nobody stood their ground on. Simon also treats some form of performance management as non-negotiable, with the criteria tailored to the culture.

Why it matters: Clear criteria protect good reps too: an AE who has hit nine quarters out of ten shouldn't be left wondering whether a miss in the tenth gets them fired. Managers usually need training, coaching and accountability to hold performance conversations at all.

Sales LeadersRevenue Executives
13

The coachability test: judge the second attempt

Simon credits Mark Roberge for the technique. Ask the candidate for a pitch or demo, ask for their self-evaluation, give one piece of feedback rather than an essay, watch their body language as they receive it, and have them do it again. If the second attempt is essentially the same as the first, he doesn't see how to assume they'll be coachable once hired.

Why it matters: He also checks that recruiters, especially those not hiring AEs consistently, actually ask for attainment over the last couple of years and how it compared with the rest of the team.

Sales LeadersFounders
14

Hiring leaders: let them use Claude, then make them defend it

For sales manager roles Simon now hands candidates a data set, encourages them to use any AI they want, and asks them to explain and defend their analysis. If they can't explain why they did what they did, he gets suspicious about who did the thinking. He also gives a recorded sales call to analyze and asks how they would coach the theme over time to a measurable outcome.

Why it matters: He distinguishes between leaders who use Claude to help themselves and leaders who think about making a whole team faster with it structurally, such as a Claude skill that turns a company name into a multi-page account brief. Candidates who have done the second with results are still rare.

Sales LeadersRevenue ExecutivesRevOps Leaders
15

One piece of feedback per quarter, not 30 Gong comments

A first-time manager Simon worked with was covering reps' Gong calls with 30 comments each. Simon told him that 30 pieces of feedback means zero remembered, and to pick one. The manager fed transcripts into ChatGPT with an evaluation framework and showed the rep a weekly chart on that one metric until they had held the target for about a month, then moved to the next.

Why it matters: AI makes it easy to generate feedback at volume. The coaching discipline is in narrowing it to one measurable theme and staying on it until it sticks.

Sales LeadersRevOps Leaders
Frameworks Discussed

10 named models

Every framework Jimmy names, defined and time-stamped.

Differentiation Is a System

05:45

Competitive differentiation sustained by four owners rather than a battle card: product marketing keeps positioning and competitive material current, enablement turns it into something sellers can use, leadership buys in, and frontline managers reinforce it.

Simon's test of whether the system works is whether AEs have internalized the differentiators. Can they explain them naturally, tailor them to the buyer, and weave them through from the first conversation to the demo, or are they waiting for the buyer to ask how they differ? Without manager reinforcement, he says, everything dies at the training session held once.

Teach the Buyer What to Notice

04:47

An AE's job in a demo includes directing the buyer's attention to what is genuinely different, explicitly, and an enablement team's job includes teaching AEs how to do that.

Taken from Culture Amp's top revenue producer, who would say during demos that what he was about to show was really unique or that the prospect should pay attention, and watch distracted prospects re-engage. Simon extends it across the funnel: differentiation should shape the BDR opener, discovery questions, demo emphasis, objection handling and even onboarding, not first appear on slide 17.

Two Questions When AI Is the Competitor

07:14

Split the 'why not just use Claude' problem into a sales-execution question (are we sharp about our differentiation and consistently teaching the buyer what to notice?) and a company-strategy question (where can a specialist product create value a general-purpose product is less designed to deliver?).

Simon's answer to the strategy question is industry-specific workflows and proprietary data, with generalist lanes such as plain document review most exposed. His broader point is that AI is not like every other competitor, but the underlying sales mechanics are more familiar than people think.

Domain Expert Plus Commercial Coaching

14:56

Bring practitioners from the buyer's industry, such as lawyers for a legal AI product, into the sales process for credibility, and pair them with a management structure or coaching that teaches them how to operate in a SaaS sales environment.

Credibility from having sat in the buyer's shoes is very high, but people hired directly from industry don't know how to turn it into conversion. Simon targets these roles about 80 percent on deals with a revenue target and 20 percent on projects such as content. They also feed market insight back to product and act as public faces of the company on webinars and white papers.

SE Ratio Scales With Contract Value

18:58

The higher the average contract value, the lower the SE-to-AE ratio: roughly one-to-one at seven figures, two-to-four AEs per SE at six figures, and pooled SE coverage below that.

Simon built the view by asking hiring candidates about their companies' ratios. In a new motion he would overinvest while finding the right ratio, measure win rates on SE-covered versus AE-only deals (up to a 10 percent lift in his experience, with selection bias to watch for), and check against average contract value and fully loaded cost per persona.

Principles Transfer, Assumptions Don't

26:51

Rather than importing a playbook from a previous company, identify which selling principles transfer to the new motion and which assumptions to throw away.

The diagnostic questions are the same in SMB and enterprise: where the funnel breaks, whether hiring is right, whether there is enough demand, whether reps convert as expected. The amount of process is what changes. Too much kills an SMB motion, too little kills an enterprise deal. Simon balances using his experience with listening to what already works inside the company.

The Coachability Test

34:16

In an AE interview, have the candidate pitch or demo, ask for a self-evaluation, give one piece of feedback, observe how they receive it, and have them do it again. The second attempt matters more than the first.

Simon credits the approach to Mark Roberge's book on sales acceleration. Body language while receiving feedback (leaning in versus crossing arms) and the size of the improvement on the second attempt are the signals. If the two attempts are essentially the same, coachability after hire is hard to assume.

Use Claude, Then Defend It

38:45

For sales-leader interviews, hand over a data set, encourage the candidate to use any AI they like, and then have them explain and defend each choice in their analysis.

Simon would rather see how candidates use Claude than ban it, since they will use it in the job. Weak rationale under questioning reveals who did the critical thinking. He pairs it with a recorded call to analyze and a plan for coaching one theme over time to a measurable outcome.

One Metric Until It Sticks

40:16

Coach a rep on one theme at a time, measured weekly against a defined framework, until they hold the target consistently, then move to the next.

Simon's example: a first-time manager who left 30 Gong comments per call switched to one focus area, scored transcripts in ChatGPT against a framework, showed the rep a weekly chart, and closed the theme after the rep held the target for about a month.

Three Reasons to Bring in Interim GTM Leadership

46:28

Interim or fractional go-to-market leadership fits three situations: a leadership gap during a search, leave or transition; a founder or first-time CRO who needs a senior pair of hands; and an important project with no obvious owner that doesn't yet warrant a permanent executive hire.

The common thread is a company that wants to do more, faster than current management bandwidth allows. Simon works from company strategy down to individual Gong calls, often starting with one problem and expanding, with the goal of leaving something that keeps working without him.

Best Quotes

20 lines worth clipping

Pulled verbatim. Copy or share any of them.

“My conclusion wasn't, Claude is the better product, how do we survive? My thinking is there are real areas where specialist products are better suited to a particular use case or workflow.”
Simon Kirk 02:34
“It's less helpful to react emotionally to whatever competitor has just announced something amazing. And it's much more interesting to say and think about, are we actually good at explaining why somebody should choose us?”
Simon Kirk 03:57
“Differentiation isn't just about having a battle card somewhere. You actually have to teach the buyer what to notice, and you have to teach the AE how to teach the buyer what to notice.”
Simon Kirk 05:33
“Frontline managers have to actually reinforce it, because otherwise everything dies at the training session that you held once.”
Simon Kirk 06:01
“The lesson here isn't that AI is just like every other competitor you've ever seen before. It's that some of the underlying sales mechanics are more familiar than people think.”
Simon Kirk 07:37
“If you start to build something in custom code, who is maintaining that? And if that person leaves, what happens to it?”
Simon Kirk 09:31
“That same engineering power has a huge opportunity cost of just building your core product.”
Anthony Enrico 10:53
“You should have people on your team that are opinionated about how you should do pricing and quoting and what that process should look like, not just build a platform and pass off the domain expertise to the customer to figure out.”
Anthony Enrico 14:12
“You get incredible amounts of credibility with the prospects when you have someone who's sat in their shoes and can really understand what's going on for them.”
Simon Kirk 14:56
“We would sometimes see up to a 10% win rate improvement on SC-covered deals, and that is worth the money many times over.”
Simon Kirk 20:09
“If you improve your conversion rate by just one point, you can add another million dollars into your bookings for the year.”
Anthony Enrico 20:53
“Too much process can kill an SMB motion. Too little process can kill an enterprise deal.”
Simon Kirk 26:51
“I've become pretty skeptical about the idea of a universal sales playbook.”
Simon Kirk 27:03
“The interesting work is about understanding which principles transfer and which assumptions we need to throw away.”
Simon Kirk 27:34
“I feel like that's almost become the CRO meme of showing up with your playbook and then go hire 100 reps and hope for the best.”
Anthony Enrico 27:41
“I find that the second go is more consequential to me than the first go.”
Simon Kirk 35:21
“I don't want to hire someone who doesn't use Claude in their job. I'd rather see how they use it and then test their thinking.”
Simon Kirk 38:31
“If you give someone 30 pieces of feedback, they're going to remember zero pieces of feedback.”
Simon Kirk 40:16
“It's kind of gold dust, to me at least, to find people who've successfully implemented and seen an outcome from that.”
Simon Kirk 44:34
“The goal is to sort of come in, own the problem with them for a period of time, and ideally leave it behind in a way that something keeps working without me.”
Simon Kirk 48:00
Practical Advice

What should you actually do?

The playbook, split by the seat you sit in.

Sales Leaders

  • Audit whether AEs can explain your differentiators naturally and tailor them to the buyer, not just whether a battle card exists.
  • Coach reps to tell buyers explicitly when something in the demo is unique and worth their attention.
  • Build differentiation into the BDR opener, discovery questions, demo emphasis and objection handling, not a late slide.
  • Use discovery to find where a generic AI tool would fall short for this buyer, and lay those traps before the objection comes up.
  • In AE interviews, give one piece of feedback after a pitch and judge the second attempt and how the feedback was received.
  • Coach one theme at a time against a measurable target until it holds, rather than leaving dozens of call comments.

Revenue Executives

  • Treat a new AI competitor as a test of your team's ability to explain why buyers should choose you, and keep the emotional reaction out of deal reviews.
  • Track win rates on SE-covered versus AE-only deals, correcting for the fact that better deals tend to get SEs.
  • Size SE coverage to average contract value and fully loaded cost per persona, and overinvest while a new motion finds its ratio.
  • Run a fast diagnosis before importing any playbook, and decide explicitly which principles transfer and which assumptions to drop.
  • Put transparent performance-management criteria in place so consistent performers know where they stand after a miss.
  • When hiring sales leaders, look for people who have used AI to make a whole team faster, not just themselves.

Founders

  • Decide where your product beats a general-purpose model: an industry-specific workflow or proprietary data. Generalist lanes are exposed.
  • Have opinions on the process your product serves and staff people who hold them, rather than leaving domain expertise to the customer.
  • Recruit practitioners from your buyers' industry as domain experts, and budget for coaching them on how to sell.
  • Consider interim go-to-market leadership for a leadership gap, a first-time CRO who needs support, or a cross-functional project with no owner.

Marketing Leaders

  • Keep positioning and competitive materials current as AI competitors move, and work with enablement so sellers can use them.
  • Use domain experts on the sales team as public voices for webinars and white papers to generate content and leads through their credibility.

RevOps Leaders

  • Before building an internal tool with Claude Code, decide who maintains it and what happens when the builder leaves.
  • Prefer centrally managed Claude skills, such as account research, that work inside existing tools over custom-built replacements.
  • Build reporting that separates SE-covered from AE-only win rates and shows the bookings value of one point of conversion.
  • Give recruiters and interviewers defined questions and evaluation criteria, including attainment history relative to the team.
AI Takeaways

How AI actually changes GTM

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

The thesis

General-purpose AI like Claude is now a competitor in many deals, but the sales mechanics of beating it are familiar: a team that can explain and demonstrate differentiation, a product anchored in specific workflows and proprietary data, and leaders who use AI to make the whole team faster rather than only themselves.

Agent & automation ideas

  • An account-research skill that takes a company name and returns key stakeholders, a suggested outreach sequence and the value proposition, run across each rep's full book.
  • A coaching agent that scores every call transcript against one chosen framework and charts a rep's weekly progress on that single metric.
  • A competitive-objection agent that pulls examples of prospects who tried a general-purpose AI tool and found it didn't fit, so AEs can use them in discovery.
  • A win-rate analysis agent that compares SE-covered and AE-only deals, flags the selection bias, and estimates the bookings value of conversion changes.
Operations Takeaways

By function

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

Revenue Operations

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Pipeline & Marketing Ops

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Metrics Mentioned

The numbers, with context

Up to 10%
Win-rate lift on SE-covered deals

What Simon has sometimes seen when managing solutions-consulting teams, which he says is worth the investment many times over. He cautions that better deals tend to get SEs, which inflates the comparison.

About 1:1
SE-to-AE ratio at seven-figure deals

Simon's impression from surveying hiring candidates: ratios tighten as average contract value rises.

1:2 to 1:4
SE-to-AE ratio at six-figure deals

Two, three or four AEs per SE, with pooled coverage for smaller deals.

About $1M in bookings
Value of one point of conversion

Anthony's example: a $20 million plan converting 20 percent of pipeline, which he calls a decent enterprise SaaS conversion rate, gains about $1 million from a one-point improvement.

80% deals / 20% projects
Domain-expert time split

How Simon structured solutions consultants' time, with a revenue target on the deal work.

5
Years at Culture Amp

Simon's tenure as the first hire for the CRO, building enablement, sales development and solutions consulting.

30 comments, 0 remembered
Feedback overload

Simon's warning to a first-time manager who was leaving 30 Gong comments per call. The fix was one metric at a time, closed once the rep held the target for about a month.

About two years
Time working independently

How long Simon has done fractional and interim go-to-market leadership.

Entities

Companies, people & tools mentioned

Auto-extracted and linked into the knowledge graph.

Companies

OrbitalLegal AI

Simon's current company, where he is interim Chief Revenue Officer. Orbital is a legal AI company for commercial real estate. In the episode he describes using lawyers, sometimes very senior ones, as domain experts in the sales process at a recent legal-domain company.

14:56Company →
Culture AmpHR Software

Where Simon spent five years as the first hire for the CRO, building enablement, sales development and solutions consulting. Lattice was its main competitor, and its top revenue producer's habit of telling buyers what to notice shaped Simon's view of differentiation.

03:05 · 04:47 · 23:19 · 27:21Company →
LatticeHR Software

Culture Amp's competitor. Simon's analogy for selling against Claude: when Lattice appeared in deals it caused anxiety in a sales team used to selling alone, even though he believed Culture Amp was stronger.

01:57 · 03:05Company →
InVisionDesign Software

Where Simon worked for the CRO before Culture Amp, starting with specific projects such as approaching large agencies with multinational subsidiaries.

23:41 · 27:21Company →
OpenAIFrontier AI

Named by Anthony alongside Claude as a general-purpose AI provider that purpose-built products have to compete against.

08:33 · 12:32Company →
LeanScaleGTM Operations

Anthony's company. Host of the show.

01:48Company →

People

Simon Kirkguest

Interim Chief Revenue Officer, OrbitalProfile →
Anthony Enricohost

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

Co-FounderProfile →
Mark Robergementioned

Author, The Sales Acceleration FormulaProfile →

Tools & software

ClaudeAI Assistant

The general-purpose AI prospects now cite as an alternative ('why can't I just use Claude for this?'). Simon uses it all day, favors centrally rolled-out Claude skills for sales work such as a company-name-to-account-brief skill, and expects sales-leader candidates to use it and defend their work.

Website ↗
Claude CodeAI Dev Tool

Named (transcribed as 'Cloud Code') as the tool teams use to build internal software. Simon has seen such builds launched and then abandoned because nobody owned maintenance.

Website ↗
HubSpotCRM

The product one of Simon's teams went back to after an internally built tool was abandoned, and where he hopes Claude-generated account outreach will eventually be sent from.

Website ↗
GongRevenue Intelligence

Where a first-time manager left 30 comments per call before Simon coached him to focus on one theme. Simon also offers to listen to Gong calls with reps during engagements.

Website ↗
ChatGPTAI Assistant

The first-time manager fed call transcripts into ChatGPT with an evaluation framework to score a rep weekly on one coaching metric.

Website ↗
Methodologies referenced Four-owner differentiation systemDiscovery traps for generic AI80/20 domain-expert role designSE-covered versus AE-only win-rate comparisonStructured interview loopCoachability exerciseAI-allowed analysis plus defenseClaude skill for account research
Related LeanScale Services

Where this shows up in the work

Sales Enablement Build

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

Simon's differentiation system is an enablement build: positioning kept current, translated for sellers, reinforced by frontline managers, plus interview loops, coachability tests and one-metric coaching.

Fractional RevOps

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

Measuring SE-covered versus AE-only win rates, sizing SE ratios to contract value, and structuring recruiter screens and performance criteria are RevOps foundations.

AI for GTM

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

The episode covers selling against general-purpose AI, when to build with Claude Code versus buy, and centrally managed Claude skills for account research and coaching.

Frequently Asked Questions

Straight answers

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

How do you sell against Claude or other general-purpose AI?

Simon Kirk, interim CRO at Orbital, treats it as a familiar competitive problem, like Culture Amp selling against Lattice. Avoid reacting emotionally to the competitor's latest announcement and check whether your team can explain why a buyer should choose you. AEs need to have internalized your differentiators, tailor them to the buyer, and weave them through the whole process, from the BDR opener and discovery to the demo and objection handling. In discovery, learn the buyer's root problem and alternatives so you can show early where a general-purpose tool would fall short. At the strategy level, specialist products hold up where workflows are industry-specific or data is proprietary.

Why is differentiation a system rather than a battle card?

Because a battle card in a shared drive doesn't change what happens on calls. Simon Kirk describes a system with four owners: product marketing keeps positioning and competitive material current, enablement turns it into something sellers can use, leadership buys in, and frontline managers reinforce it. Without manager reinforcement, everything dies after the one training session. The goal is AEs who teach buyers what to notice, for example by saying in a demo that what they're about to show is unique, which Simon saw Culture Amp's top revenue producer do.

Should a company build internal tools with Claude Code or buy specialist software?

Simon Kirk generally prefers buying specialist software and using shared Claude skills to optimize workflows within existing tools. He has seen internally built tools launch to fanfare and then be abandoned, with the team returning to the previous product, because nobody owned maintenance once the builder left. Anthony Enrico adds that tools used by thousands of employees need governance, data security and permissions, and that engineering time spent on internal tools has a large opportunity cost against the core product. Simon also warns that teams without data-privacy experience can expose sensitive internal data.

What is a good SE-to-AE ratio?

In Simon Kirk's experience, the higher the average contract value, the lower the ratio. Seven-figure deals can justify roughly one SE per AE, six-figure deals two to four AEs per SE, and smaller deals pooled SE coverage. In a new motion he suggests overinvesting while you find the right ratio, measuring win rates on SE-covered versus AE-only deals (he has seen up to a 10 percent lift), and checking the result against average contract value and the fully loaded cost of everyone on the deal. Better deals tend to get SEs, so the raw comparison overstates the lift.

How should you use domain experts in the sales process?

Hire practitioners from the buyer's industry, such as lawyers for a legal AI product, for the credibility of having sat in the buyer's shoes, and coach them on how to operate in a SaaS sales environment. Simon Kirk targets such roles about 80 percent on deals with a revenue target and 20 percent on projects such as content. Their work includes demos, pilots and prepping with the AE, feeding market insight to product, and acting as a public voice on webinars and white papers. He finds AI companies can recruit them more easily now, because many professionals want direct experience in AI.

How do you test a sales candidate's coachability in an interview?

Simon Kirk uses a technique he credits to Mark Roberge. Ask for a pitch or demo, ask the candidate to evaluate themselves, give one piece of feedback, watch their body language as they receive it, and have them do it again. The second attempt matters more than the first. If it is essentially unchanged, it's hard to assume they will be coachable once hired. He also makes sure recruiters ask for attainment over the last couple of years and how it compared with the rest of the team.

How should you interview sales leaders now that candidates can use AI?

Simon Kirk lets them use it. For sales manager roles he hands over a data set, encourages candidates to use any AI they want, and then asks them to explain and defend each choice. If they can't, he questions who did the critical thinking. He also has candidates analyze a recorded sales call and describe how they would coach the theme over time to a measurable outcome. He looks for leaders who have used tools like Claude to make a whole team faster, not just themselves.

When should a company bring in an interim or fractional CRO?

Simon Kirk sees three situations: a leadership gap during a search, leave or transition; a founder or first-time CRO with too much on their plate who needs a senior pair of hands; and an important project, such as US or European market entry, that has no obvious owner and doesn't yet justify a permanent executive hire. The common thread is a company that wants to move faster than its management bandwidth allows. The goal is to own the problem for a period and leave behind something that keeps working without the interim leader.

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00:00Cold open + intro 01:48Selling against Claude is the Lattice problem all over again 07:51Build vs. buy when anyone can build with Claude Code 12:07Laying traps for the 'couldn't AI do this?' objection 14:29Bringing domain experts (and lawyers) into the sales process 18:41SE ratios, win-rate lift and what one point of conversion is worth 21:47From Culture Amp and InVision to interim leadership 24:41Why no sales playbook survives a copy-paste 29:45Non-controversial fixes: hiring process and performance management 33:22How to interview AEs: the coachability test 37:29Hiring sales leaders: use Claude, then defend it 42:41Making the whole team faster with Claude skills 45:30Why companies bring Simon in: three buckets 48:19Wrap
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00:00Cold open + intro

0:00 It's kind of gold dust, to me at least, to find people who've successfully implemented and seen an outcome from that.

0:30 I do think one thing businesses are being challenged to do is the pressure to be on companies to lean in here.

0:39 And I think it's very important to know that you have a very specific workload that someone does in the industry that makes a difference.

0:48 You have very specific data that you need, that proprietary, that can be a wedge.

0:54 I do think one thing businesses are being challenged to do, the pressure to be on companies to lean in here,

1:00 is to have an opinion on the process and the subject matter that they are helping build a solution for.

1:06 One more recent company, in the legal domain, we actually use lawyers with the prospects when you have somebody sat in their shoes.

1:15 I feel like that's almost become the CRO meme of showing up with your playbook and then go hire 100 reps and hope for the best.

1:23 Too much process can kill an SMB motion. I've become pretty skeptical about the idea of a universal sales playbook.

1:30 I would say at this point in time, we're talking in October 2026. By now, you should be leveraging Claude and OpenAI.

01:48Selling against Claude is the Lattice problem all over again

1:48 Diamond, you said something on our prep call that I've not heard anyone say out loud yet.

1:53 Everybody's panicking about selling against Claude.

1:57 And your take is that this is basically the same problem as selling against Lattice five years ago.

2:03 How did you mentally get there?

2:06 Yeah, sure thing. So I don't want to say that I figured out every component of this, but it's come up with one of the companies I'm working with and where customers are starting to ask or prospects are starting to ask.

2:18 Why can't I just use Claude for this?

2:20 And I think the reaction internally is understandable in that there's some trepidation because Claude is a really good product.

2:26 I use it all day long when you're selling into a market where buyers already have access to an enterprise wide tool that's doing very powerful things.

2:34 It can be daunting. So my my conclusion wasn't Claude is the better product.

2:40 How do we survive? I think what my what my thinking is is there are real areas where specialist products are better suited to a particular use case or workflow.

2:51 And the challenge is actually making the customer understand and experience that differentiation.

2:58 So one of the things I realized after I started to process what was happening in the deals is that I've seen this before.

3:05 Actually, maybe at least one or two companies. So in my last company, Culture Amp, we had a competitor named Lattice.

3:12 And you could swap in and out Lattice specifically for another competitor that was there at one time or another.

3:17 But internally, when they start to come up in deals, particularly if you've had a lot of space in the market to sell by yourself, it can cause anxiety amongst the sales team.

3:27 And you can start to feel like there's this big scary monster coming for you that you don't know what to do about.

3:33 Even if you internally believe that your company and your product is stronger, which which I did, I thought Culture Amp was the winner.

3:40 And so I would say one of the lessons is that you can really internally still think that you are the better product and get very distracted by what a competitor is doing.

3:54 And I think that Claude is very distracting with all the headlines we're reading.

3:57 And what I began to think about over time is that it's less helpful to react emotionally to whatever competitor has just announced something amazing.

4:10 And it's much more interesting to say and think about, are we actually good at explaining why somebody should choose us? So that means things like, do our AEs really understand and internalize differentiators?

4:25 Or do they just know that there's a battle card somewhere in some drive with those differentiators?

4:31 Can they explain them naturally?

4:33 Can they tailor them to a customer in front of them?

4:36 Are they weaving them through from the first conversation through to the demo?

4:41 Or are they waiting for somebody to say, wait a minute, how are you actually different from this other company?

4:46 In this case, Claude.

4:47 Something that really struck me when I was watching as just a small anecdote, when I was watching one of our AEs at Culture Amp, I think I mentioned to you before, is I was going through cool recordings.

4:57 And this guy was the top person globally, top revenue producer ever.

5:02 And I was trying to figure out, what is he doing that's special in his calls that's really standing out?

5:08 And one of the things I flagged amongst a few is that he would say in his demos, what I'm about to show you is really unique.

5:17 Or he'd say, hey, you should pay attention to this.

5:22 And if someone was like gently daydreaming away a prospect, you suddenly notice them snap back into attention.

5:28 And on one level, it sounds really trivial. It's like a sort of stylistic thing. Why does that matter?

5:33 But it made me realize that differentiation isn't just about having a battle card somewhere.

5:38 You actually have to teach the buyer what to notice, and you have to teach the AE how to teach the buyer what to notice.

5:45 And to do that, you kind of need a system.

5:49 So product marketing needs to keep the positioning and competitive materials current.

5:55 Enablement has to translate that into something sellers can actually use.

5:59 Leadership has to buy into it.

6:01 And then frontline managers have to actually reinforce it because otherwise everything dies at the training session that you held once.

6:08 And the other thing I think about is the differentiation has to show up throughout the sales process.

6:15 So it can't suddenly appear on slide 17 or a minute 55 or a 60-minute demo.

6:21 It needs to affect how a BDR opens, what the AE asks in discovery, what they emphasize in the demo, how they handle objections,

6:30 and probably even, you might argue, like how you onboard the customer once they're actually signed.

6:35 And none of that is me saying like there's nothing special happening with AI.

6:40 Obviously, there's a ton going on that's very unusual.

6:42 But what I'm trying to say is on a human level, a lot of the sales dynamics are actually very familiar

6:49 and have been around for a while with SaaS.

6:51 And products often look similar to buyers to other products.

6:55 And what they want are things that make it easy for them to understand why this product is different from the other three demos they had earlier in the day.

7:03 And they need for it to be easy for them to buy.

7:05 And if a human is selling to a human, then part of your job is helping that person on the other side understand what's actually special.

7:14 So I think maybe kind of getting towards the end that there are maybe two questions.

7:19 One is a sales execution question.

7:21 So are we sharp enough about our differentiation?

7:23 Are we consistently teaching the buyer what to notice?

7:26 And the second is a company strategy question.

7:29 Where can a specialist product create value that a general purpose product is naturally less designed to deliver?

7:37 And for me, the lesson here isn't that AI is just like every other competitor you've ever seen before.

7:45 It's that some of the underlying sales mechanics are more familiar than people think.

07:51Build vs. buy when anyone can build with Claude Code

7:51 Well, and I think this is unbelievably relevant.

7:54 So many teams are really taking seriously the build versus buy of a given product.

8:03 And before, I think a lot of times it would just be disqualified.

8:06 It's like, okay, well, I'm not going to hire a team of engineers to do this.

8:09 But now it feels very achievable to build anything you want.

8:14 I know that's not the case.

8:16 I know there's still a massive market for purpose-built, point-built solutions or specific platforms.

8:24 From your perspective, what are the categories of functionality that remain very, very competitive for a specific solution?

8:33 That something like Cloud, OpenAI, no matter how powerful their models get, will have a difficult time replicating.

8:41 I think when you have very specific workflows that someone does in an industry, that makes a difference.

8:47 If you have very specific data that you need that's proprietary, that can be a wedge.

8:54 If you're sticking to a generalist lane where maybe it's a document review or something like that, you come under threat.

9:05 My personal experience working with some of our companies is there have been times where people have wanted to build stuff internally rather than us buying something.

9:16 And someone goes off, and they use Cloud Code, and they build a thing, and they spend a while on it, and they're very proud.

9:22 We're all very excited, we're proud of them, and we launch it.

9:25 And then the reality is that these things often, unless it's like a cloud skill, which I think is great, and you can use widely,

9:31 but if you start to build something in custom code, who is maintaining that?

9:35 And if that person leaves, what happens to it?

9:38 And so we've actually had a couple of times where, to great fanfare, we've rolled out a thing, and we used it for a while.

9:46 And then actually you go back to the previous thing, so in our case HubSpot, for example.

9:51 So I think there are workflows you can optimize, there are things you can do in Cloud.

9:56 I'm a big believer in using Cloud skills across the sales team to help, for example, with account research or something like that,

10:02 that you can set up centrally and then roll out.

10:04 But even in my own experience, I don't think that having everybody in the company go off and use Cloud Code to build whatever they want for the company

10:12 and then expect everyone to adopt that in perpetuity is a feasible solution right now.

10:18 And we even, despite having all those capabilities internally, would prefer to go and buy our specialist software.

10:26 It makes a ton of sense. I always think of things that are regulated, you need governance, especially as things get in multiplayer mode.

10:36 Like it's one thing for you to build an app for yourself to just use, but if you need thousands of people in your organization to use it

10:41 and you need the data security and permissions and all of those things, that's very, very difficult to do.

10:47 And even if you could do it, let's assume you could, and I'm talking to a lot of tech companies that have excellent engineering teams,

10:53 that same engineering power towards that has a huge opportunity cost of just building your core product.

10:59 So I don't think the build versus buy equation is too far off outside of maybe a few solutions that probably weren't adding that much value anyway.

11:10 The security thing is real because there's a temptation, you know, imagine you're in a department that handles internal sensitive information

11:19 and you're following the mantra, do more AI, build more yourself, be more forward thinking, be more progressive.

11:25 So you go and do the thing and you release it and then you don't have any background in thinking about data privacy for internal employees.

11:33 And then suddenly you might put very sensitive stuff that's just sort of a link away from someone discovering publicly

11:41 and then you're really endangering the company in certain ways.

11:44 So yes, I think it's impractical along many dimensions for people to do this right now.

11:50 Perhaps this will change in a number of years, but for the time being, even my preferences as a buyer is buy specialist software where you can optimize workflows

12:00 elsewhere internally using things within existing tools.

12:03 I think it's a recipe for success if you can do that.

12:07Laying traps for the 'couldn't AI do this?' objection

12:07 Going back to the sales process and the positioning when you're in a sales process where they're bringing up things like,

12:18 "Oh, couldn't I do this with cloud or couldn't I do this with AI or couldn't I build it myself?"

12:23 I really like the insight that you shared earlier of like, "Hey, let the prospect lean in. This thing in particular is very unique.

12:30 You're going to want to hear this."

12:32 And I think when you say that, you are directly saying this is unique, something maybe cloud or open AI can't do as well.

12:38 What other sales processes can be applied when you're selling against the idea that AI could do what you're doing?

12:49 I don't have proof points.

12:53 We have a channel where we can see people who've used certain AI products and then found it not to be working.

13:00 And I think there's ways to lay traps.

13:02 If you're familiar with the sales sort of traps and blocks, you can lay traps of AI being used for generalized purposes that then don't translate to value for the customer and putting those in proactively.

13:14 Generally, you need to do great discovery.

13:19 This is very cliche, but people often talk about great discovery in sales.

13:23 But if you're doing great discovery, you're going to understand what's really at the root of the issue for the customer or the prospect, what are their pains, what else are they using, who else are they talking to, et cetera.

13:32 And that's going to allow you to be proactive about laying traps around what the edges are that won't actually fulfill the value they need

13:41 and where you can then, as we talked about earlier, differentiate.

13:45 Another thing you mentioned in the prep call, and I think this is really important, too.

13:50 I do think one thing businesses are being challenged to do, which I think is healthy, I think it's actually good for the pressure to be on companies to lean in here, is to have an opinion on the process and the subject matter that they are helping build a solution for.

14:07 So if you're building a, I'll use a RevOps example.

14:12 If you're building a CPQ, configure price quoting solution, you should have people on your team that are opinionated about how you should do pricing and quoting and what that process should look like, not just build a platform and pass off the domain intelligence or domain expertise to the customer to figure out.

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

14:29 Have you had a good experience with bringing in domain experts into the sales process and using that as a differentiator?

14:38 Yeah, I tried this a few different ways.

14:41 In a couple of companies I've been involved in either being adjacent to or running sales engineering.

14:48 Sometimes it's domain expert and then also involved in hiring the AEs and thinking about the kinds of backgrounds they should come from.

14:56 One more recent company, Illegal Domain, we actually used lawyers, sometimes very senior lawyers, as the domain experts and you get incredible amounts of credibility with the prospects when you have someone who's sat in their shoes and can really understand what's going on for them.

15:16 The way you have to supplement that though is if you hire people directly from industry is they haven't had the background in the sales environment to know how to take their incredible credibility in industry and make that weaponized into something that's commercially going to get you the best conversion rates.

15:36 So what I think is a very effective combination is taking people who have domain expertise and credibility and then providing them with the resources in either a management structure or additional coaching that tells them how do you show up in a commercial situation that you can be successful.

15:52 So we talked about differentiation, for example, how do you highlight certain things, how do you introduce yourself in the right way so that I don't think it can start and end with I worked in the same industry as you, we're all good.

16:06 It has to be that plus how do you operate in a SaaS sales environment and if you put the two together I think it's incredibly powerful.

16:15 There absolutely needs to be a little bit of polish that's tailored to what you're doing. I'm curious, how do you find these people? How do you convince them to leave what they're doing to be a subject matter expert and then what does their day to day look like?

16:31 Structurally, are they just hopping on calls all day? Are you putting them in charge of content creation as well? What's everything that lands on their plate?

16:40 Yes, I think it can depend by company. At a previous company, there were people who came from other companies in similar roles like solution consulting roles so they weren't directly coming from industry.

16:52 And in terms of how they structured their day, I tended to give them 80% working on deals and I would target them on a revenue target related to how much they brought in and then they'd have a 20% time to work on projects to do the kinds of stuff you're talking about, content, etc.

17:08 More recently, I think if you're working in an AI company, thankfully many people in industries that are not AI are feeling the pressure of AI converging on them and they are interested in looking for ways to get out into an AI industry and get direct experience.

17:25 So then I think it's a matter, they may actually just by virtue of the incredible hype we're in at this moment be willing to take that leap, which is great if you're in AI space, which has been the case with one of the companies I work with.

17:39 And so therefore they're interested and it's a matter of helping them get adjusted to the environment. And in terms of the day, if they're a sort of solution consultant equivalent, typically most of their day is working on deals.

17:52 So it should be getting on demo calls, getting on pilots, rehearsing for those, getting the demo ready, thinking about tailoring.

18:00 When done well, they're prepping with the AE ahead of time, so they're thinking about what's the unique conversation we're having with these prospects right now.

18:08 And then also they may do other things. So they can be a very good bridge back to product in a way that they can kind of take what they're seeing in the market and then help product understand how they should continue to evolve the product.

18:20 And then sometimes they can also be public figures for you. So they can be on webinars, they can be writing white papers, and they can put stuff out in their name that the company can benefit from.

18:31 So the company is getting the content and the leads, but they're through the lens of this person's credibility in the market that they represent.

18:41SE ratios, win-rate lift and what one point of conversion is worth

18:41 Do you have a good ratio of SMEs to reps? I know it'll probably depend on what the company is and what their go-to-market is, but in general, do you have a rough idea of how many people you should be staffing in your org?

18:58 I've heard many different – when I would hire people, I'd ask them, "What does the ratio look like at your company today?" So I kind of got a survey. My impression is the bigger you go, the higher the average contract value, the lower the ratio.

19:13 So if you're dealing in seven figure, you may even have like a one-to-one. Six figures might be two, three, four-to-one. And then as you go down, it could be higher, maybe into a pooled system.

19:29 It's interesting when you're kind of doing a newer system, you may want to overinvest in this function while you figure out the right ratio, particularly if you're seeing the value pay off in your win rate.

19:39 It's a little hard to distinguish very scientifically the lift you get on an SC-led company deal versus an A-only deal, but I used to look roughly at what's my win rates with non-SC deals versus SC deals.

19:57 The thing you have to be aware of is deals that need SCs tend to – the sort of self-reinforcing moment here in the better deals might go to SC, so they might get a higher win rate, so it kind of distorts the numbers there a little bit.

20:09 But when I was managing this kind of team in the past, we would sometimes see up to a 10% win rate improvement on SC-covered deals, and that is worth the money many times over investing in that resource.

20:25 So it can really depend, but you probably need to keep an eye on A, your average contract values, and if you want to be more sophisticated, your fully loaded costs across all the different personas on the deal to make sure it makes sense for you from a cost perspective.

20:40 Well, I think some people significantly underestimate the magnitude of impact, a few points increase of a conversion rate can have on your overall go-to-market plan.

20:53 I always give the example, if you're on a $20 million plan, let's say you're converting 20% of the pipeline, which would be a decent conversion rate for an enterprise SaaS, if you improve your conversion rate by just one point, you can add another million dollars into your bookings for the year.

21:10 So by bringing on these types of roles, these types of resources, if you can increase that conversion rate, like you mentioned, it pays for itself very quickly.

21:22 Yeah, in most companies, I work with you're staring at the conversion rates, staring at the deal velocities, and you're looking at what can I do to move this by 1%, 2%, 3%.

21:34 And if you're talking in double-digit movement, that's obviously amazing, and most people would do whatever they can to do that, but yes, every single digit and conversion rate makes sense.

21:47From Culture Amp and InVision to interim leadership

21:47 I would love to get into a little bit around your approach to go-to-market and the role you've carved out for yourself of doing this as a fractional service, fractional offering.

21:59 What's the story and career arc that got you into coming into these companies and helping to get that go-to-market foundation running?

22:07 I started out working in retail on the corporate side, then various different startups, and to be honest, I've done a variety of different roles.

22:17 I don't really have a clear, replicable arc that I could say, do this, then this, then this.

22:25 It's been everything from product management to marketing to selling myself to special projects and so on.

22:34 I'd say the consistent theme has been that CROs and CEOs often have more to do than they have time for or they have senior management bandwidth for.

22:47 And if you can be someone that can come in and help them in a flexible way and listening to their needs and then take ambiguous problems and make them concrete and cut them up so that they can be moved forward, you can be someone of value.

23:03 So generally speaking, my goal is to listen, figure out what the highest challenge problems are, so pipeline, win rates, conversion rates, as we just talked about, and then see how can I help with that.

23:19 And so at Culture Amp, I was the first hire for the then CRO Rich, and we worked together for five years. And for him, he was struggling. Well, he just started and he didn't have enough time.

23:34 He knew enablement needed work on. He eventually realized sales development needed work on, and then solutions consulting, et cetera.

23:41 And so he sort of just added one thing at a time for me to help him with. And so before that, I was working for the CRO of Envision, who subsequently became the CRO air table and places like that.

23:56 And similar, many, they have many ideas. It's very hard to execute them, incredibly creative people. How can you trust someone to take these on and move things forward for you? And it might start with a specific thing like how to approach the large agencies with multinationals where they have subsidiaries.

24:16 And then you sort of work on that and you expand from there. So that sort of been the non-traditional path to where I've ended up now.

24:23 And then a couple of years ago, I ended up going out solo and companies have invited me in for various different things from training on how to get next steps through to how do we increase our sales into our back book?

24:38 And you just kind of start somewhere and then continue from there.

24:41Why no sales playbook survives a copy-paste

24:41 From your perspective, especially doing this across a few companies, what seemed to be some common things that go-to-market teams are challenged with that they really have a tough time overcoming?

24:57 So despite the fact that I've worked at companies that have high velocity SMB motions or slower mid-market enterprise motions, there are often things that translate across both of them. Good discovery is good discovery. Bad discovery is bad discovery.

25:13 Doesn't really matter if you're SMB or your enterprise. You still need to understand where an individual rep is strong or weak and coach them accordingly. You need to have enough pipeline. You need to track your conversion rates.

25:25 You still need good differentiation. I think that the numbers can be different, but the diagnostic questions are very similar. So where is the funnel breaking? Are we hiring correctly? Are we creating enough demand? Are reps converting at the rate we would expect?

25:37 The thing that probably changes is how much orchestration the salesperson has to do. So in a high velocity SMB or product-led motion, the product is doing a lot of the work.

25:48 One company I worked with just got a ton of inbound leads. Those are great leads. Everyone wants that. It's interesting when you take a company like that and you give them outbound, the work you have to do to uncover pain and budget and outbound is different and maybe need new muscle.

26:06 But when you probably have fewer stakeholders at SMB and you need less multi-threading and shorter sales cycles, if you were to take an elaborate enterprise playbook and dump it onto a high velocity PLG or SMB motion, you're probably going to be inserting friction where there wasn't any before or less before.

26:28 So obviously you want to tailor that. Conversely, if you took an enterprise sale, the AE becomes the orchestrator or the quarterback. And so you probably have multiple different stakeholders. I mean, there's a lot of committee buying in the moment.

26:43 There's different priorities. You need to build consensus. You need to build value. Different ways you've got to navigate procurement.

26:51 So one of the things that doesn't really transfer is the amount of process you impose. Too much process can kill an SMB motion. Too little process can kill an enterprise deal.

27:03 Because I worked across a few of these different types of companies, I've become pretty skeptical about the idea of a universal sales playbook. You can start by having the underlying principles of selling from the habits that happen to work at one particular company.

27:21 You've just got to be careful how you adapt that across. So I guess when I think about being useful when I go into company, I try not to say who is my playbook at X company like culture amp or Envision, and therefore you should use it too.

27:34 For me, I think the interesting work is about understanding which principles transfer and which assumptions we need to throw away.

27:41 I feel like that's almost become the CRO meme of showing up with your playbook. This is what we're doing, not listening, just kind of like shoving it down the throats of everybody working there and then go hire 100 reps and hope for the best.

27:55 That play has been lived out so many times and then just run straight into a brick wall, but it still keeps happening.

28:06 I'm sure there are some times where it works. You'd have to have incredible organization to do that. Sorry, you'd have to have incredible organizational buy-in to do that.

28:17 I think if you're in an organization, if you've ever worked on yourself and a new leader comes in and they appear to be taking zero interest in anything that's happened before they came in and they throw it all away, and you're meant to still work there under this person.

28:33 Unless the person is amazing at explaining the why and leading you through the change, you're going to have incredible organizational resistance to that because you're just going to feel like this person does not understand me.

28:44 They don't understand our company. They're just bringing in their people. They're bringing in what they've done before, and it's not going to work.

28:51 There should be some balance. Obviously, if you're hired for your experience and you don't use any of that experience, the person that hired you is probably thinking, "Why do they hire you?" You've got to have some of that, but I think there's a balance between using your experience with also making sure that you use what's there in the company and do a lot of listening.

29:13 Yeah, and I think absolutely go in, make your diagnosis phase as quick as possible, but then tailor everything you have. Just as you mentioned, take what you have that's worked well, tailor it to the business for the context, the specific problems that they have, and then you can run implementation.

29:31 I think if you don't stop and take that time to do the diagnostic, which sometimes, I don't know, maybe some CROs feel under pressure to drive change faster and just try to skip that phase or they're just overly confident in the playbook that they're coming in with, but I think it's crucial.

29:45Non-controversial fixes: hiring process and performance management

29:45 Yeah, there are some things that I feel pretty confident in that when I go company to company, I think they're fairly noncontroversial and repeatable. For example, it's very easy to have a lackadaisical hiring process where you don't really prep the people in the hiring process who are also doing interviews.

30:05 You don't tell them what questions to ask, you don't tell them what to evaluate against, and then one candidate goes from one person to the next and to the next. They're asked the same question over and over again when you go back and listen to the interviews, you see them answering the same question over and over again.

30:19 The criteria which they're being evaluated is completely loose, and the scoring then therefore becomes very easy for one interviewer to say, "You know what? This person was good enough. I don't think they were bad. I don't think they were amazing.

30:40 I'll say yes, and I'll kind of let the next person make the difficult decision." And what I noticed is you get a lot of, "Yeah, I can see this," and the person goes through and through and through, you get to the end of the process, and you hire people, and then if you're hiring a lot, you hire a lot of people like that because no one in the process really stood their ground.

31:01 And so that's the kind of thing where I think, "Okay, it's not too controversial when you go to a new company to say, 'Hey, do you have a really great hiring process?'" And some of them really do, and so that's great.

31:14 But if you don't, this is the thing that we all believe that people are really important in companies. We're not yet all AI, so hiring great people is really important, and to hire great people, unless you're incredibly lucky over and over again, you're going to need to have a solid process.

31:30 Yeah, and I wouldn't count too much on that luck, and it's one of the most expensive mistakes you can make by bringing on the person that's not the right fit, and often there's really easy ways to sift through that by having the right process in place, too.

31:49 Yeah, and there are other areas that I think are probably fairly non-controversial. Having performance management of some sort is fairly non-controversial, I think. I think work that's controversial is the criteria, so you might argue, "Do we give someone this amount of time or that amount of time, or this amount of revenue, or that amount of revenue, or are we more harsh, or are we more lenient?"

32:13 But I assume most people would agree when you go to a new company if they have no performance management, and it's up to the managers that that's probably going to go awry.

32:24 Similarly, that most people find having performance conversations with another human to be really yucky and horrible, and something to avoid because it doesn't make you feel good.

32:33 And so a lot of people need training and coaching and prodding and being held accountable to have those conversations. And so that's kind of another area I'd say, "This is pretty non-controversial, you'd want to bring this in. Let's talk about what's right for you and your culture as to how aggressive we want to be, but we should have something."

32:51 Because the other flip side of this is, for example, with AEs, you might get an amazing AE who's hit nine quarters out of ten. They get to their tenth. They don't know the grounds under which they might be let go.

33:03 And suddenly they're super anxious, like, "Is this the quarter that they don't love me anymore?" And they shouldn't have to go through that.

33:09 You should be able to say, "Hey, no, we've got this specific criteria. Don't worry. It's very transparent. It's this and this. It's predictable. Please try and hit your quarter, but this is where you're going to land."

33:22How to interview AEs: the coachability test

33:22 I would love your perspective on how to interview and hire AEs because I think this may be one of the most difficult roles to hire for because it's very, very difficult to validate their past experience or successes.

33:44 And also salespeople are pretty good at interviewing. So if you're not peeling back a few layers of the onion, I think it's difficult to get through.

33:55 How have you conducted AE interviews or what are the types of questions or process that you have them go through to make sure you're getting the right fit?

34:07 So of late, I spent more time hiring managers and VPs than I have with AEs, but some things I've thought about in the past.

34:16 Firstly, Mark Roberge, I really liked his book, I think, The Acceleration Formula. He had something in there that stuck with me in terms of hiring for a long time.

34:28 I've used across roles, which is when you ask someone to do... coachability, essentially. Ask someone to do a pitch or a demo for you.

34:39 When they end the pitch, ask them to let them know you're going to give them some feedback.

34:44 I'm probably not doing justice to the exact methodology, but bear with me.

34:50 When they end the pitch, give them some feedback. Ask them for their self-evaluation.

34:56 When you're giving them feedback, look at their body language.

34:59 Are they leaning back, crossing their arms, frowning, looking kind of annoyed or scared?

35:04 Are they leaning in and asking for their feedback?

35:07 Ask them to give them one thing to work on, maybe, not a whole essay. Ask them to redo it.

35:16 How good is the second attempt and how did they receive the feedback?

35:21 I found that very useful as an interviewing technique. I find that the second go is more consequential to me, as I think he said in his book, than the first go.

35:31 Because the second go, if you give them two tries and feedback and one is essentially the same as the other, then to me, I don't know how you're meant to assume that once you hire them, they're going to be highly coachable.

35:45 If you give them a bit of feedback, they lean in, they go for it, and the second one, they make a market improvement.

35:52 I think that's one indicator amongst others you should also look for that this person might be highly coachable.

35:57 For me, when I get someone highly coachable, I'm very excited to work with them.

36:00 They're the best kind of people to work with because you can do so much as they're ceiling.

36:04 That would be one thing I look for. The other thing I've noticed in interviewing recently is I've noticed at the recruiter stages, particularly if you have a recruiter that isn't hiring for the same role consistently, like an AE or an AE manager, they don't always ask for the numbers.

36:26 I find that head scratching. I want to know what has been someone's attainment over the last couple of years.

36:36 Past success, I know does not predict future success, but at the very least I want to know, has this person never hit their number? Do they sometimes hit their number?

36:45 If they sometimes hit their number, what were the factors? How are they relative to the team? If no one on the team hit, that's relevant versus they were the only one that didn't hit.

36:54 There's all kinds of things. I think one of the things in answering your question is I would go back to the recruiter interview and double check what questions they're asking, what are they looking out for in their answers, and making sure you're equipping them as a non-sales person to ask things that can help them distinguish between someone they should probably screen out immediately versus someone who may be in that "yes" bucket where they should probably say "no" to "awesome track record"

37:23 So very consistent hitting that's moving forward. So there would be a couple of ways I've been thinking about this recently.

37:29Hiring sales leaders: use Claude, then defend it

37:29 I think those two are very, very helpful. And since you mentioned in the beginning, I'm curious, do you have a different approach for sales managers or VPs?

37:39 Or even if somebody's trying to look for a CRO, are there certain things you're looking for in those roles or ways you would interview that would help you understand if they're the right fit?

37:50 I think there's lots of ways to do this and many people who are probably listening way better than me, but one search I did with a company where the company was leading and I was just in the process, I was super impressed by how data-driven they expected the VP role to be.

38:11 They handed this person a set of data about trends and asked them to analyze it. Obviously now you can put stuff into Claude, so there's a debate around how Claude comes into interviews.

38:22 I think people have different ways, different thinking. My current thinking is people are going to use Claude in their jobs.

38:31 I don't want to hire someone who doesn't use Claude in their job. I'd rather see how they use it and then test their thinking.

38:36 There's a debate as to whether you want to give someone a live thing where they just show up, you discuss something, and that's probably a valid way because then they can't use Claude.

38:45 I've recently been trying out with some sales manager roles. Here's a set of data. You are encouraged to use any AI you want, and then we're going to ask you to explain and defend it.

38:57 We've been trying that more recently. Why did you do this? Why did you do this? If it becomes apparent that the person doesn't really have a rationale behind what they picked, then I'd be more suspicious as to who's doing the critical thinking.

39:12 The data part is obviously important. It's obviously things about culture. I've been with sales managers more specifically. I've been interested in how they think about coaching.

39:27 I've been using a sales call torch and to ask them to analyze it, what was good/bad. I'm particularly interested in what their coaching approach is going to be, and then how does that maintain over time.

39:42 In my next one, we talk about this. I'm more interested in over this period of time, knowing that this is the theme I picked out from this call, assuming that more calls would say something similar. This is how I'm going to approach it until I get to this end result with these measurable outcomes.

40:01 Therefore, I'll know that the person has passed this gate on this, and we can move to the next one. A company I worked with, a great first-time manager, and he was giving reps feedback for the first time.

40:16 The first thing he was doing was to go into Gong, and he was lighting up Gong with 30 comments about where they could improve. What I said to him was if you give someone 30 pieces of feedback, they're going to remember 0 pieces of feedback.

40:37 Even though you're thinking 30 things need to improve, pick one. Focus on that thing for a period of time, like a quarter, until you believe it's better.

40:48 He picked something for this rep to improve on. He actually fed the transcripts into chatgbt before that was MCPs. He gave chatgbt a framework to evaluate it, and then each week he showed this rep how they were doing on that metric in a chart.

41:07 He gave one week the rating. Until this person gradually got better consistently, and when that person had been hitting the rating they wanted against that metric for, I think, a month, they were like, "Okay, we consider this done. You've done a great job. I will trust that you want to handle this. Let's move on to the next metric."

41:26 We like the push to have the manager or VP have that data-driven approach. Even in that case, like, "Hey, can you extract everything from Gong? Can you make sense of it?" A little related to, "I agree. I think we should have the expectation people will be using AI to do their jobs, and it should be a big concern if they can't."

41:48 I think that reveals itself very, very quickly if you start asking any follow-up questions, whether it's their own thoughts or not. I'm not overly concerned with that as a risk. If somebody knows how to find an answer through AI, but they also can defend it, great.

42:07 If they're blindly showing something, then maybe it's an issue. Or if they're blindly managing their team with Gong recommendations, that's an issue, too. You have to have some conviction behind what the recommendations are giving you, too.

42:20 Yeah. As far as I can tell, it's more table stakes for people to have an AI requirement on certain job descriptions. Certainly, it seems like it would be table stakes for RevOps and things like that. But I would imagine in sales leaders now, you'd probably want that to be a requirement.

42:41Making the whole team faster with Claude skills

42:41 I differentiate between an individual using Claude to help themselves and an individual who started to think about organizationally, how can I move my team forward using Claude structurally?

42:55 So for an example, at a company I'm involved in now, I'm really impressed by a couple of ICs and the enablement person who've created the Claude skill that allows a BDR or an AE to put in the company name, and it will spit out a multi-page document with everything from the key stakeholders, the sequence they should write, the value prop, etc.

43:24 We're going to add in different shaders, etc. And then where I want to get to is then you plug in the entire book of business for each rep, and rather than the AE and the BDR just showing up and they get their book and they're starting to do all the research online, we actually have done that work for them.

43:45 They get their account, they read through everything, they've got suggested language, maybe eventually that's even plugged through into HubSpot for it to be sent out, and they can really focus on the human part, which is the selling, the calling, the selling, etc.

44:00 Maybe obviously tweaking and checking everything for accuracy, but if I were hiring a leader now, I think I would probably want to engage them in organizationally how can you make your teamwork 10x faster using these types of skills, not just when did you last use Claude to help you complete the task.

44:23 Yeah, I think the expectations are getting exponentially higher for how people are leveraging and implementing AI, and I expect that to continue too.

44:34 The hard part on that is there hasn't been enough time elapsed to have many candidates who've done a lot of that. So it's actually most people are in experimental phase and can only tell you their experiments because, you know, we're not that far in. So it's kind of gold dust to me at least to find people who've successfully implemented and seen an outcome from that.

44:59 Yeah, true. True. Well, I think maybe in the next three, six months, I would say at this point in time, if we're talking in October 2026, by now you should be leveraging Claude, open AI, regularly making skills, some of your own workflows, your own artifacts, analyzing data with AI.

45:22 That should be part of your workflow now. So I'm hoping in the next three to six months, it just becomes table stakes with candidates.

45:30Why companies bring Simon in: three buckets

45:30 Yeah, I assume so. And then it will be a question of how we interview them and evaluate the work they've done about just somebody else and how effective it was. Simon, I'm curious, where do you tend to find go to market teams? And what are some of the things that maybe they're challenged with or working on that make it a really good time to bring you in?

45:52 Yeah, I mean, it can really vary. I've worked with, you know, a technical founder who was very early at a company that went really big. And, you know, he exited and, and he wanted to start something himself. And he'd never done outbound sales. And he literally did someone to tell him how to do outbound sales.

46:07 And that was like, very tiny company, all the way up to, you know, later states, 50 million, 80 million, etc. So their sales teams can vary from, they don't have that they have a first time CRO, they have found the lead sales, they have a specific problem with pipeline or conversion rates, etc.

46:28 I mean, in generally, most of the work I do tends to fall into three buckets. So one is a leadership gap. So somebody needs to own the commercial agenda during a search or a leave or a transition.

46:43 The second one is there's a leader who needs some kind of support. So maybe it's a founder, or a first time CRO, who has loads of stuff on their plate. And they want a senior pair of hands to help with the priorities or management or execution.

46:58 And then the third one is there's an important project they have in mind that doesn't have an obvious owner. So it could be something in sales or customer success or like market entry to the US or Europe, or some kind of go to market area that needs more senior cross functional attention,

47:16 but doesn't actually warrant quite yet a permanent executive hire. And so the common thread is usually the company wants to do more, they want to do it faster, and particularly faster than the current management bandwidth allows.

47:30 And so I think one thing that is slightly unusual about how I work is that I'm pretty comfortable getting all the way from like, let's talk about your company strategy all the way down to let me listen to this gong call for you and help this BDR or SDR or AE with their call and what theme they should think about.

47:50 So a lot of engagements have actually started with somebody saying, hey, can you help me with one thing, and then it kind of expands from that into, okay, you're inside the business, we'll go see this other constraint.

48:00 So the goal is to sort of come in, own the problem with them for a period of time, and ideally leave it behind in a way that something keeps working without me.

48:09 So basically, I'm sort of opening up the capacity for that kind of work internally. So I'd love to talk to sort of founders and CROs who are interested in things like that.

48:19Wrap

48:19 Amazing. Well, Simon, thank you so much for everything you shared today. I really love your perspective on how to position solutions when Claude is starting to seem like an alternative, and really how to handle that.

48:34 I also really appreciate how you laid out the type of roles to bring in like bringing in subject matter experts to help bring validity to the product and solution that you have. And then everything you shared on hiring and how to interview.

48:50 I think these are some of the most difficult roles to hire for, and especially all the complexities AI is bringing into it at this moment too, really making it even more difficult. So Simon, really appreciate everything you shared on the podcast.

49:04 And I can't wait to see what you and the next companies you work with do next.

49:10 Awesome. Thank you so much, Anthony.