Why PE-Backed Go-to-Market Strategies Fail: Talent, CRM, AI and Execution

Dan Bernoske, Founder and CEO of Cortado Group, joins Alex Rawlings to explore how private equity firms and portfolio companies can strengthen go-to-market performance while effectively leveraging AI.

Dan explains why speed matters after an acquisition, particularly when assessing commercial talent, and why firms need to separate emotional attachment to legacy teams from objective performance data. He also explores the importance of treating CRM systems as strategic infrastructure rather than simply another piece of technology.

The conversation then turns to AI. Dan shares practical applications for using call transcripts to coach sales teams at scale, improve qualification, identify performance trends, and ultimately increase win rates. He explains why successful AI adoption starts with the business problem, not the technology, and why portfolio companies should build a strong proprietary context engine around their CRM data, call transcripts, buyer personas, and historical wins and losses.

Dan and Alex also discuss how AI is changing organizational design, allowing salespeople to spend more time building relationships with buyers while technology handles lower-value tasks. Crucially, Dan warns against viewing AI as a replacement for human salespeople: poorly deployed automation can damage relationships and even burn entire territories.

Key Takeaways

• Move quickly when evaluating commercial talent, but understand where founder-led strengths still create value.
• Build the sales process first and configure the CRM around it, not the other way around.
• CRM data integrity is essential for reliable pipeline visibility and forecasting.
• Use AI to analyze sales calls, improve qualification, and deliver coaching at scale.
• Create a proprietary context engine before becoming overly dependent on any single AI model.
• Redesign roles by identifying tasks AI can handle while allowing people to focus on empathy, listening, trust, and relationships.
• Don't automate bad processes. Strong sales fundamentals remain essential regardless of the technology.

Timestamps

00:00 - Introduction to Dan Bernoske and Cortado Group 00:57 - Where PE firms and portfolio companies move too slowly 02:54 - Warning signs that commercial talent needs replacing 04:37 - Three fundamentals of an effective CRM 06:34 - How AI can transform go-to-market strategy 08:21 - Using AI to analyze sales calls and coach teams 09:46 - Measuring qualification frameworks such as BANT 11:45 - ChatGPT, Claude and choosing AI technology 13:14 - The three foundations for successful AI implementation 13:40 - Building a proprietary AI context engine 15:03 - How AI is reshaping organizational design 16:34 - Why empathy and relationships remain human advantages 17:24 - The biggest mistakes companies make with AI 18:20 - Why replacing sales reps with AI can burn territories 19:18 - Freeing sales teams to spend more time with buyers 21:14 - Dan's recommended AI and professional-services resources 23:13 - Why portfolio companies may need an AI innovation advisor 23:42 - How to connect with Dan

00:00 Welcome back to the Raw Selection Private Equity Podcast. Joining us today is Dan Bernoske, Founder and CEO of the Cortado Group, a go-to-market consulting specialist firm. Today’s podcast is on exactly that: go-to-market, but leveraging AI. Dan, if you can share with us a brief insight into you.

Yeah, so Dan Bernoske. I’m...

00:27 Founder and CEO of the Cortado Group. I founded the firm in 2019 with a laser focus on go-to-market growth for companies that need to grow, mostly in private equity, but we also spend a good bit of time in non-PE-backed private firms. But I will say this: I’ve got a lot of very talented people behind me. I’ve got a very strong team, so now it’s way beyond just me.

00:57 What’s one mistake that you see private equity firms or portfolio companies making, and what would you suggest to correct them?

So, they don’t move quickly enough, which sounds crazy because they all want to move fast, but often they don’t move fast enough. Let me break it down for you into two main areas. We look at go-to-market through two lenses: talent and performance conditions. So, just looking at the talent...

01:27 Oftentimes, they’ll hang on to talent a little too long. If you think about the skills of the sales team or the go-to-market team that got the portco to where they are, it’s rarely the same skill set that gets them through the next five years of a hold period. Or they rip and replace the CEO, maybe a little too fast — the founder.

01:53 There’s a bit of a renegade nature to a lot of founders, and sometimes there’s some friction there. Often, we see that renegade nature is exactly the scrappiness you need to get to the next level. So making that decision can either be a little rash or a little bit drawn out, and that’s tough.

Then finally, on the performance conditions side, often the portco has a bad CRM. It might not have been well taken care of, if they even have one.

02:23 So the mistake that PE firms often make is they don’t treat Salesforce or HubSpot, for example, as strategic imperatives. And that is a big mistake. You need to take those platforms very seriously because, obviously, without good data, you’re pretty much flying blind.

So those are really two big areas — performance conditions and talent — where we see PE firms making mistakes.

02:54 What are the warning signs that you see, that you recommend private equity or portfolio executives look out for, when it comes to commercial sales talent that may need to be, or is likely to need to be, replaced?

03:13 Well, what often happens is we work with a lot of founder-led companies that recently got purchased by private equity. Let’s just say it’s Bain Capital or somebody like that who comes in, buys a founder-led company, and now the power dynamics have changed.

What often happens is the founder might have grown quite attached...

03:42 ...to the sales leadership, the sales team, et cetera. And if you really peel back their performance data, you’ll find that there are one or two people who are absolute heroes driving the number. So it might be one or two out of ten who are actually driving that number.

And often what happens is the comp structure is incentivizing the wrong behavior.

04:06 And so there are a lot of people who are underperforming, but it’s super comfortable. They can kind of stay there. So the mistake is not looking at that performance data quickly enough, not separating the emotional tie to whoever the folks are on your legacy team, and then really being able to make the quick decision to remove them, have them move on, and replace them with the high performers that you need.

That’s a real common challenge.

04:37 You also mentioned CRM. Everyone comes away either going, “We don’t use our CRM,” “We do use our CRM,” or “Our CRM is amazing,” but nobody really has anything to compare it to other than prior companies.

What are three things either private equity firms or portfolio executives should look at so they can measure the barometers? What should every good company have from a CRM to leverage their go-to-market strategy?

05:07 Well, first of all, you have to start with a very sound process that’s been defined before you even get to technology. So: process first, technology second.

A good CRM would reflect that. And let’s just take the opportunity management process. It’s going to be very outside-in. It’s going to be from the buyer’s perspective, with very clear stages and exit criteria. That solid guidance...

05:36 ...needs to be in the platform. So that’s number one. If you don’t have that, it’s all — I wouldn’t say useless — but it’s very much inhibited.

Number two for a good platform is data integrity. So if your sales reps are not entering data correctly and on a regular basis, what happens is the entire instance of the CRM just gets pretty stale and unreliable. So that’s the next one.

06:05 The sales reps are following the process. They’re entering their data correctly. And then, really, the final part is: does it provide visibility into the pipeline and forecast accurately?

So that means great reports, great dashboards that are drawn from that data. That is the core and backbone of a good CRM. And so if you don’t have that, then the whole thing kind of falls apart.

Okay, so your website references...

06:34 ...AI in the go-to-market space and leveraging that hot topic for everybody at the moment of ChatGPT and Claude, and all of the different platforms that AI specialists use.

What’s your take on how companies should be leveraging AI to implement that within their go-to-market strategy?

06:56 Well, one of the biggest opportunities we see is in the realm of coaching. A great example there is taking call recordings, which is becoming more and more prevalent. It’s much more acceptable to record every single call.

Every company now has this massively valuable store of call transcripts that are...

07:24 ...frankly, proprietary to the company. Where we’re seeing a lot of success is with companies that can harness all of those transcripts toward something productive, and in particular, coaching.

Let me give you a great example. Span of control is a big challenge for a manager managing a huge sales team. So imagine you’ve got...

07:52 ...50 sales reps, maybe you have two managers. How do you really effectively coach all of those reps?

A great way to do that is to be able to sift through all those call transcripts and start to spot trends, mistakes, and strengths that individual sales reps have. We can get into more detail about how we build that out, but that is a great example of how you could use AI to your advantage to improve things like win rate and average sales price, for example.

08:21 So I’m a big student of sales and have invested a lot of time in creating a strong commercial process. We believe that every touchpoint should be scripted. I know there are lots of companies that don’t like this, but my argument is that you can’t scale without it.

As much as you can, with regard to every process and every interaction, it creates standardization, a process, and obviously a quality metric. Now...

08:47 How should companies be using this specifically? If I go, “Right, okay, we’re going to listen back to some calls,” and we have a coach who comes in every week and helps support them, listens back to calls, gets through scripts, goes through processes, et cetera — what are you looking for in these automated calls?

Is it the number of “ums”? Is it the fact they’re following a script or process? Is it buying indicators? How powerful is this AI, and how much can it be leveraged...

09:16 ...based on your experience in using it?

You’re bringing up some great points about scripting. In particular, we look at, at a minimum, a call plan. So maybe it’s not down to the word-for-word script, but what is your objective? What is your general outline when you get on a call with someone?

So what we look for in the call recording — a great place to start is: are you qualifying?

09:46 That’s where we get to the script idea that you’re talking about. So depending upon your qualification method, maybe it’s BANT — budget, authority, need, timing — you have to establish one or all four of those on a call. Or there are other ones like MEDDIC. It goes on.

What you can get from the call is: did the seller establish...

10:16 ...these different qualification criteria? And you can actually listen for that. Did they ask the right question? Did they ask about budget in a creative way that got back from the client or buyer that they do, in fact, have a budget to buy this? They do have a need. They are talking to the right authority in order to make this purchase.

You can glean that from the call. You can see the Q&A, and not just within one call, but...

10:46 ...across a series of calls, to spot whether or not this individual really has a hard time asking one of those questions in particular.

So you can dial it in down to a script, like you said, or come out a little bit to just a broad methodology. Are they able to get those particular points on every call, or on particular calls?

Sorry to interrupt. Just a quick mention of a long-standing partnership with Grata.

11:16 As you all probably know, the private equity scene is constantly evolving, and deal flow is moving now to proprietary and data-driven processes.

Grata provides you with the data and information of over seven million private companies. So if you’re looking to improve your proprietary deal flow and improve data access, then reach out to Grata today.

Now back to the podcast.

And AI is always a difficult one because, even if I think about it, I’ve not quite moved over to the...

11:45 ...Claude preference, with everybody at the moment telling me that’s better. So I’ve got ChatGPT embedded, and it would be quite a pain to move across.

Are you recommending that companies are leveraging ChatGPT and creating a GPT structure around this? I know there are obviously companies out there that will specialize in this and give feedback, and some of the VoIP systems and other bits and pieces have these as add-ons.

What’s your take on, I suppose, what’s best for each individual company? But if you go for best-in-class...

12:15 ...what are the best companies you’re seeing doing? How are they actually building these systems into their processes?

It’s a great question because the AI landscape is just shifting constantly. When you made the ChatGPT decision, it was the leader. Then all of a sudden, overnight, we’ve got Claude as the leader. And right now, there’s a latest release...

12:44 ...from OpenAI that might put them back into the lead.

So I would say companies need to get used to the fact that this sort of instability, or constant change, is truly the new normal. It’s just going to be a constant fight over who’s number one.

But first and foremost, success — setting the technology aside — comes from...

13:14 ...first and foremost, is there a champion within the portfolio company? So it has to start from the CEO down. Do you have a couple of power users who are big champions of AI in the organization? You have to establish that human element first and foremost.

The second success factor is just understanding: what is the problem that we need to solve? As I’m sure you know, you don’t just start with the...

13:40 ...technology and say, “Right, now I’ve got to go and find what problem this thing needs to solve.”

So it’s about understanding that problem. And then the third part is going to be what we call a context engine. So, like I mentioned, the proprietary data from call transcripts — I would call that context. Context would be your entire CRM database...

14:07 ...your opportunity data, how you win, how you lose, what your ideal customer profile is, your buyer personas.

What you have to build is the central database that provides context to the language model so that it knows what the good answer is relative to you and your business.

So those three things you need before you even get to a large language model. And then, if you establish that context engine...

14:37 ...kind of outside of the language model, you’re in a good position where you can swap out the leader on top of that. You could pretty easily snap on OpenAI or switch over to Claude, kind of seamlessly.

That is a model that we are starting to see really emerge and be highly, highly effective.

Marvellous, marvellous.

15:03 Yeah, so I think we’ve looked into some of this stuff ourselves and are starting to work out how we’re going to leverage it and what we’re going to do. And we’ve tried some of the software that’s been plugged in, and it’s been a bit of a nightmare.

Well, I say nightmare — interesting. It’s been one of these add-on things that you think is going to be simple, and then you end up, like everything, having to invest more time around it.

So looking at the org design side of things, with us leveraging AI or making sure the org design is effective and efficient, talk to us about your experience there.

15:34 Well, what’s happening is that AI is forcing companies to re-examine roles within their organization, specifically go-to-market, sales, and marketing.

If you look at a particular role, it is broken down into essentially a bundle of tasks and responsibilities. That’s what a role is. And in the old world, you would have to...

16:04 ...follow certain processes that enable this particular bundle of tasks.

With AI, it gives us a way to completely rethink that model. So now what you do is take all those tasks, unbundle them, and figure out how to arrange them more efficiently so that we can offload some of the tasks to AI and let the talent do what they do best.

So, for example, a sales rep — their primary...

16:34 ...role is empathy. They need to be able to establish a strong relationship with the buyer, rapport and trust, and actively listen to what their problem is.

Once they establish that, then the buyer is going to be much more open to hearing about the solution. AI can’t accomplish that. What AI can do, though, is enable the seller to be smarter during the call and to ask smarter questions, for sure.

17:01 So when you think of just that alone, what does that do? It opens up an entirely new opportunity, a new role within the organization, to create these enablement tools for the sales reps — to be the AI engineer. That’s an entirely new role.

So that is just one example where...

17:24 ...the sales rep can be much more efficient at doing what they do best. And then you create these other roles to support them and utilize the tools in a super-effective way.

With artificial intelligence and the whole go-to-market strategy, when it comes to companies, what’s your take on the single biggest thing that they are getting wrong? Now, you mentioned the hiring of people and the utilization of the CRM. It may be that we repeat that conversation.

17:54 But what should they be doing? In fact, what are the best companies doing that means they’re getting it right and seeing organic growth?

I hate to repeat my previous point, but what they get wrong is that they think AI is going to solve everything.

18:20 These companies feel like, “I can take AI and replace the sales rep.”

And I don’t know about you, but I’ve gotten inundated with robocalls and these emails that are kind of ridiculous. You can just tell there’s no soul in it. That is not the right way to go.

A lot of companies are experimenting in those areas, and I would say the danger there is you can burn a territory. I mean, if I get a call from a company and it’s a robocall...

18:49 ...I’m going to put them into spam, and they’re never going to be able to reach me again. I mean, that is the quickest way to burn a territory.

So that’s something they get wrong. The ones that get it right, on the flip side, go back to enabling reps to do what they do best.

And the other aspect is just following the fundamentals. It boils down to executing the fundamentals, like running a good sales process...

19:18 ...and following it. Don’t speed through it. Listen to the buyer. Companies that don’t do that fail every time.

Yeah, I think the way we see it — and we were speaking about this this morning, actually, with the team — is that we were looking at constraints in the business, what we need to resolve, and how we scale quicker.

We spoke a lot about flipping the model around for the sales team, all the work they do to get on the phone call with...

19:48 ...what we regard as a prospect or see as a buyer, and trying to get as much of that removed from them as possible, so that when they’re actually working, we split that time so it’s like 80% of their time is spent speaking with potential customers.

And that’s where I think, for us, the leverage of AI, the leverage of offshore talent, the leverage of moving roles and responsibilities, and putting fuel on the fire in different areas is...

20:18 ...what’s worked for us. We’ve done a lot of leveraging around that and made progress.

And in addition, we’re starting to look at what our lead channels are and how we expand those. Rather than trying to expand ten, we’ve just gone, “Right, well, if you’ve got four main lead channels, let’s just add a fifth, and our goal is to get it to this number a month.”

So I think sometimes it can be overly complicated, especially when AI comes into it and you ask ChatGPT, and ChatGPT gives you what would be the old Danaher reference of an answer of, “Here’s what you guys should be doing. You’re going to need...

20:47 ...10,000 people to deploy this, but you won’t because I’ll help you, and I’ll tell you this list and ask you a thousand questions.”

And then you get to the end and you’re like, “You need more leads.” And you’re like, “Well, there are 17 ways of generating leads. Why don’t we implement all 17?” You go to your sales team, they don’t do any of it, and then you’re back down at the start again.

Yeah, it’s amazing you’re experiencing that. That is a pretty common evolution that’s happening with all of this — everything you just outlined. I think that...

21:14 ...a lot of portcos are going through that experience because they’re experimenting. Everybody sees the promise of the tool, so, “I’m going to go try it.”

But everything you just outlined is sort of the circle and epiphany that others arrive at as well. So it makes a lot of sense.

Dan, tell me, what do you read, watch, or listen to that you recommend others should check out?

Well, from an AI point of view, it’s not go-to-market specific, but I listen to...

21:44 ...the a16z Podcast, Andreessen Horowitz. Some of it is, frankly, a sales pitch on what’s in their portfolio. However, you’re hearing from the practitioners who are on the bleeding edge of AI, and I learn a ton from that.

Because whether we like it or not, my world — consulting and professional services — is getting disrupted by AI.

22:14 The other one is a gentleman by the name of Greg Alexander. He’s the founder of Collective 54. He was a founder of a company called SBI, and he is focused on professional services firms. You can find him on Substack.

He talks a lot about how professional services need to adjust to the new world of AI.

And then the last one I’ll tell you is...

22:43 ...David Russell, who is a Distinguished Innovation Fellow at Cortado Group. You can find him on Reddit, Medium, Substack.

And I get a lot of information from our three-hour innovation call each week, where he just has his finger on the pulse and brings it back to me.

I’m bringing that example up because I recommend that every CEO in a portco out there gets an innovation...

23:13 ...fellow of sorts on the team. That’s all they do — they focus on AI and go-to-market, and they can pull that knowledge into the company.

So you kind of have this advisor once a week giving you a debrief. Of all three of those, that’s probably my biggest source of knowledge at this point.

If anybody wishes to reach out to you, how best do they get in touch?

Yeah, connect with me on LinkedIn.

23:42 Dan Bernoske. You’ll see me as CEO of Cortado Group. Or shoot me an email at dan.bernaski@cortadogroup.com, or head to our website. But those are the best ways, and I’d be happy to hop on a call and talk through and brainstorm anything they want.

Marvellous. Well, thank you very much for coming on the Private Equity Podcast.

You’re welcome. Thanks for having me. I really appreciate it. I enjoyed it.

And as always, to all our listeners...

24:10 Thank you for joining us yet again on the Private Equity Podcast. Until next time, keep smashing it.