Before you replace them

A couple of weeks ago, I was talking to an operating partner at another PE firm about the transition to AI-era GTM. We got into a discussion about why some SaaS companies were finding it harder than others.

His biggest concern was the leadership. Across the portfolio, he felt most leaders were still operating with old ways of thinking. They didn’t really understand what it meant to operate as an AI-era GTM leader.

So I asked how they were solving that.

They’d started taking some operators out of their roles and hiring people they believed had more of an AI GTM mindset.

I could understand why. If you don’t think someone can take the business where it needs to go, finding someone who can seems like an obvious response.

But how were they assessing the next person? Were they looking for experience of the transition? Were they testing how candidates thought about changing GTM?

They were mostly asking how people used AI and which use cases they’d tried.

That’s the part I struggled with. They were making a decision about someone’s ability to lead the business through a transition, but the interview was mostly about using the tools.

The AI-GTM capability gap

How do you hire someone with that mindset shift anyway? It’s new to all of us.

You might find someone who understands AI better. They might have useful experience and be a good hire. But even if all of that is true, the company still needs to work through what the transition means.

The rest of the leadership team still needs the context. They need to understand what changes for the business, what changes for them and how they’re going to make it happen together.

That work doesn’t go away when the new person arrives.

If you’re the CEO, this is currently an existential threat. You’re probably already talking with your chair and investors about flat pipeline, how to make GTM more effective and how to improve the operating model.

You need answers to those questions. And if you don’t adapt, you risk falling behind your category, your competitors and new people coming into the market.

A list of AI use cases won’t give you those answers. Neither will a change of leader unless the organisation changes how it operates.

Here’s how I would think about it instead

First, I’d look at the capabilities of the leadership team already there. With the right support, insights and knowledge, can these people make the transition?

Some won’t be able to. Some won’t be willing. You may need to make changes. But I’d want to understand that properly before deciding the capability has to come from somewhere else.

I’m seeing this challenge across investor portfolios, with leaders in sales, marketing and customer success. We promoted people for running bigger teams. Now we’re asking them to improve output per human. Someone who has always solved a capacity problem by hiring needs to learn a different way of working.

That’s a real development need. I’d start succession and development reviews on that basis in 2026, while there’s time to help people, rather than waiting for the gap to show up in a miss.

Then I’d get the whole leadership team contextually aware of what being an AI GTM leader means. I’d work through it in three ways.

Externally, what has changed for your buyers? How do they discover, evaluate and purchase? What do they already know when they speak to sales? Where do they need more help? What does that mean for how your company goes to market?

Internally, what needs to change in the operating model? How should pipeline generation, qualification, forecasting and customer expansion work? Which roles and handoffs need to change? Where are you simply making an existing process faster, and where should you rethink the process itself?

Personally, how does each leader develop their own AI-driven GTM leadership mindset? What does self-governance look like? Where do they rely on AI, where do they challenge it, and how do they remain accountable for their decisions?

That last question matters. HBR warned in August 2026 that AI can weaken leaders’ capacity for original judgement. HBR The research it cited found that written explanations increased people’s willingness to follow AI recommendations without improving decisions over unaided evaluation. Study

I’d want to know how a leader questions an answer, what they would investigate and what would make them change their mind.

You can work on that through coaching around the decisions the business is already facing. Then build the roadmap together: what changes now, what changes over time and what the impact should be for the business.

The key is to not rely on individual heroics of learning AI. You’re trying to get the organisation to make the transition together.

The one thing to get right

The concern that operating partner raised was a fair one. Some leaders will struggle with this, and hiring different people will sometimes be the right decision.

But I’d want to give the people who already understand the business a serious opportunity to develop the understanding they’re missing.

They may need more context than you expected. They may need coaching to work through what it means for their role. That doesn’t necessarily mean they can’t get there.

You may have people who understand AI less well than the candidates you’re interviewing, but understand your business considerably better.

Before trading one for the other, work out whether you can develop the combination.

Because that combination is what you were trying to hire in the first place.

This Week’s Tangible Prompt

At your next leadership review, ask:

“What would a leadership team capable of running AI-era GTM be doing in this business that our team isn’t doing today?”

Write the answers as specific decisions and changes. Then work through which require better context, which require coaching and which require capability you don’t currently have.

That becomes the brief for developing the team and the basis for assessing anyone you might bring in.

Cheers,
Edwin & Josh

Demand Karma works with boards, investors and GTM leaders dealing with this now. If you have cut the GTM team, added AI and the number has not moved, the answer may not be another tool.

The AI GTM Leadership Kickstart is a short, structured programme for leadership teams to work through what changed, what still works and what no longer does, applied to their live GTM challenges. Leadership Development sustains it. Both are for the people who carry the number.

demandkarma.com