---
title: "How to Sell Against Claude: Differentiation Is a System"
episode: 142
podcast: "The LeanScale Podcast"
publisher: "LeanScale"
guest: "Simon Kirk"
guest_title: "Interim Chief Revenue Officer, Orbital"
date_published: 2026-10-19
date_modified: 2026-10-21
duration: 00:49:16
word_count: 8348
topics: ["sales-enablement", "brand-positioning", "enterprise-sales", "sales-leadership", "ai-in-gtm", "gtm-strategy"]
canonical_url: https://www.leanscale.team/knowledge/podcast/simon-kirk-orbital-how-to-sell-against-claude/
source: "LeanScale Knowledge Hub — https://www.leanscale.team/knowledge"
license: "Free to quote and cite with attribution to The LeanScale Podcast."
---

# How to Sell Against Claude: Differentiation Is a System — Full Transcript

> Episode 142 of The LeanScale Podcast, with Simon Kirk.
> Published October 19, 2026 · 00:49:16 · 8348 words.
> Machine-transcribed and **not diarized** — speaker attribution is inferred, so verify
> attribution against the audio before quoting a specific person.
> Structured breakdown: https://www.leanscale.team/knowledge/podcast/simon-kirk-orbital-how-to-sell-against-claude/

## 00:00 — Cold 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.

## 01:48 — Selling 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.

## 07:51 — Build 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.

## 12:07 — Laying 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.

## 14:29 — Bringing 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.

## 18:41 — SE 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.

## 21:47 — From 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.

## 24:41 — Why 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.

## 29:45 — Non-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."

## 33:22 — How 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.

## 37:29 — Hiring 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.

## 42:41 — Making 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.

## 45:30 — Why 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.

## 48:19 — Wrap

**[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.