Friends,

I think we’ve probably all been there.

You’re working for a company that is growing, and looking for an exec that can take it to the next level in some relevant function.

Usually, they go to market with an external agency, and hire someone from a company at the size and stage they aspire to.

Your new exec joins the company, and quickly realises that the structure, team and processes that existed in a mature company, aren’t in place at your scrappy startup.

It becomes very apparent that while your new exec might have been working at the level of company yours aspires to, they didn’t actually get the company there.

Today’s edition tackles who you need to hire for, not just in that scenario, but the one we’re all living in now. The one where uncertainty and change are the new normal.

Enjoy this week’s edition ✌️

Matt

In case you’re new here (or just missed it) here’s the past three editions of the FNDN Series:

You’re building the people function inside a growing company.
You’re juggling ten ‘priority one’s’.
You’re doing it all on a shoestring.

Meanwhile, you’re wondering how others in similar roles are facing those same challenges.

You know you’re using AI but are you really using it?
You’re seeing the role of leaders change, and wondering how to adapt.
The skills gap everywhere keeps increasing.

Keeping up with the expectations of the role alone is a full time job.

That’s why we built Startup People Summit.

It’s all happening on the 3rd of September.

The entire speaker line up and the first release of tickets are available now.

Grab one now and I’ll see you there.

(and because you’re a FNDN Series reader, use code 2026*MATTM for 15% off 🤗 )

Interested in sponsoring the FNDN Series? Drop me a line!

Know a startup Head of People looking for answers 🙋 why not forward this to them for some instant karma? ✨

Can the executives you just hired solve a problem none of them have seen before? In a fast-scaling business under AI-driven change, that's the question that actually matters, and a polished CV won't answer it. During a packed session at last year’s Startup People Summit, Raechel Gavin shared the capability she rates above experience, and why a bench of generalists protects you when a role suddenly falls vacant. Here's how to hire for it.

Every scaling startup eventually hands its exec team a problem no one in the room has solved before.

It's always been part of the job. What's changed is AI, which keeps resetting how fast markets, products and teams move, so those moments have stopped being occasional. No blueprint, and no "here's how we handled it last time."

And the person you hired precisely because they'd done it all before is often the one who freezes.

Case in point: Leadership IQ tracked more than 20,000 new hires and found 46% failed inside 18 months. Only 11% of those failures were about a skills gap. The rest came down to attitude and adaptability, whether someone could take feedback and adjust as things shifted.

The instinct is to fix uncertainty with more experience. Hire whoever has seen the most and held the biggest title. Raechel Gavin, a seasoned tech CPO, thinks that instinct works against you. In a talk on getting the top team right, she argues that in a fast-scaling business, experience is the most overrated line on the CV.

If you lead the People function, it's your call more than most. You're often in the room before the rest of the exec bench exists, which makes the criteria for who comes next yours to enable. 

Get them wrong and you spend two years unwinding it.

So the shift here runs deeper than a hiring tactic. It's about what you treat as evidence that someone will succeed. Pedigree is a poor predictor when the ground keeps moving. Two things predict better, and the question is whether your hiring process is built to look for them.

Scaling teams solve first-time problems constantly, so the capability that matters most is whether someone can solve a problem they've never seen.

Think about the first time a company runs a redundancy after growth suddenly reverses (something many of us can relate to, of late). No one has done it here before, the stakes are high, and there's no precedent to copy. That's the kind of problem a scaling business hands its execs, and it's where a tidy track record from a stable company isn’t of much support.

She calls the answer agility, and more precisely learning agility. The people who have it tend to be strong across four areas. They're mentally agile, thinking critically and making fresh connections when things get complex. They're people-agile, self-aware and able to work with all kinds of people in hard situations. They're change-agile, happy to experiment and sit with the discomfort of constant change. And they get results while bringing people along with them.

So she makes a deliberate trade. Between a candidate with exactly the right experience who struggles to adapt outside it, and one who's demonstrably agile across contexts, she takes the agile one. Experience that transfers is useful. Experience that only works when conditions hold still becomes a liability the moment they don't.

It's also why she looks for people who genuinely enjoy problem-solving, not just tolerate it. At the exec level you're often working it out for the first time, so wanting to be in that spot tells you something.

None of this makes experience worthless. It just answers the wrong question. It tells you someone handled a known problem under known conditions, and in the biggest body of hiring research we have, years of experience is one of the weakest predictors of how someone actually performs. What it can't tell you is whether they'll handle the unknown problem heading your way. That's the one you're hiring to solve.

The second marker is favouring generalists over pure specialists.

Expertise helps, and Raechel isn't saying throw it away. She wants execs who bring real depth and can still work across the business, stepping into other areas when the situation calls for it.

You build a stronger team that way, because the capabilities you're hiring for belong to everyone rather than being locked inside one person's function.

You also build bench strength. Say a senior role falls vacant with no notice. If one of your execs has enough range, they can step across and hold it for a quarter until you backfill, keeping the strategy moving instead of stalling.

A team of narrow specialists can't do that. Every gap becomes a crisis, because no one else can hold the ground.

Specialist depth still earns its place, especially where the work is genuinely technical. The point is range as the default, and real depth where the work truly needs it.

If agility and range are the markers, your hiring process has to be built to find them, and most aren't.

Raechel pushes for more rigour in assessment, and the research backs her. Structured, evidence-based assessment predicts performance far better than the gut-feel interview most loops still run on. Gut feel has a place, particularly on whether you'll work well together, but it's a weak substitute for assessing capability against what the role actually needs.

Be honest about the role, too. Raechel will sometimes play black hat and walk a candidate through everything that's hard about the company and the job. The worst outcome is a strong hire arriving to surprises you could have named up front.

Then get people out of the interview room. A lunch, a walk, a session with the teams they'd work with. People relax, say what's actually on their mind, and self-select on culture before you've made an offer.

Lastly, hire for headroom. Raechel's rule of thumb is to hire someone who could handle the company you'll be in a few years, ahead of the one you're in today. That isn't a bigger CV in disguise. It's the agility point over time: can this person keep growing as the business changes, or top out the moment it does.

Your company will keep handing its exec team problems it can't predict, and AI is only shortening the gap between them.

Experience tells you someone solved yesterday's version. Agility and range tell you they can solve tomorrow's, and cover for each other while they do.

Before you screen your next exec hire for experience, pull your criteria and check what they actually reward. If it's a matching CV, you're hiring for the last problem instead of the next one.

If you enjoyed this post or know someone who may find it useful, please share it with them and encourage them to subscribe.

This piece is based on one of the 40+ sessions that took place at Startup People Summit 2025.

SPS returns on 3 September 2026, with people leaders from the fastest-scaling companies showing exactly how they're building talent systems and going AI-native.

If this article was useful, 30 sessions just like it are happening for you. And the peers you’ll add to your network are worth as much as the content.

Tickets are live and selling fast. Grab yours while they last at this price.

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A roundup of the most interesting stuff from the week:

When you’re ready, here’s three ways I can help you:

1. Tools & resources
Resources and tools that give you what you need to build your own startup compensation practices.

2. Comp consulting
Building startup compensation practices that are clear, fair and competitive.

3. Startup People Summit
A 1-day annual event for People professionals in scaling companies. Creating the playbook for startup people practices. Grab recordings from past events, or subscribe to join the next summit.