Two of the people Caroline Dell used to report to are now investors in Goodword.

When our co-founder and CEO left Chief to start this company, both founders wrote angel cheques. They opened their networks to her as well, and she still calls them. We're opening there because it's the least discussed part of this decision and we think it's the most important. Most advice on when to hire a chief of staff treats the question as a workload problem. You're drowning, so you hire someone to help you swim. True enough, and it misses what the job actually is, which is the closest working relationship a founder builds, and one that keeps paying out long after the person moves on.

Caroline set out her thinking on A Chief of Staff, David Nebinski's podcast, alongside Lara Kuhn, who joined Goodword in April as our Head of Strategy and Operations. What follows is where she has landed after being a generalist, being a chief of staff, and then hiring one.

The timing answer is earlier than most founders want to hear

Caroline's position isn't subtle:

"For a startup, a venture-backed startup, a company should hire a generalist as early as possible. Definitely first five."

The one real exception she would make is a company building something deeply technical with no commercial motion yet. No paying customers, no go to market. Then you can probably wait until your first ten hires. Otherwise, get a jack of all trades in early.

The reasoning is simple and a little uncomfortable. In a startup you don't know what you don't know, so you can't write a job description for problems you haven't hit yet. What you can do is hire someone you can hand a problem to and trust to figure it out. That's a different hire from a functional specialist, and at the earliest stage it's usually the more valuable one.

There's a blunter diagnostic in the episode too. Are you underwater all the time? Are you not sleeping eight hours? Is your spouse annoyed you're never around anymore? There's your answer.

The question that tells you it's time

For us the moment came about six months after we launched our commercial beta. We had paying customers and a team that was almost entirely product and engineering, plus our CPTO and Caroline.

Everything external falls to a CEO. Podcasts, investors, events, the partnerships that only happen because someone showed up. Meanwhile there is finance, HR, customer insights, one-off projects, and whatever broke this week. The useful question isn't "what can I offload". It's this:

"What are my superpowers and what are the things that a CEO uniquely has to do? And then what are the things that I am holding onto just because maybe I have done it before, or because it is comfortable, or just because there is literally no one else at the business who I am going to tap to do it?"

That last category is the tell. When the list of things only you can do is mostly things you're keeping out of habit, you need a right hand.

There's a line Caroline uses as the real test of the hire. Great employees are the ones you can hand something to and then delete it from your brain. Not park it. Delete it. If you're still carrying it after you delegated it, either the hire was wrong or the handover was.

Why we didn't use the chief of staff title

Lara joined as Head of Strategy and Operations, which was Caroline's own title when she was the third employee at LOLA. We borrowed it on purpose.

The chief of staff title carries implications a startup should think through first. If there are two co-founders, whose chief of staff is it? Do you want someone who speaks for the CEO when the CEO isn't in the room, the way it works in government? Those are relational questions, and we wanted to build the relationship before answering them. Caroline and Lara had never worked together.

Lara is more relaxed about this than Caroline is. She's been a chief of staff twice and an early stage generalist three times, and her view is that titles matter less than what you actually own. None of those roles looked the same. At Goodword she's doing growth work she'd never done before.

One distinction is worth defending firmly. A chief of staff is not an executive assistant and shouldn't be treated like one. If you're hiring a chief of staff and you don't have an EA, know that going in. The confusion starts there, because the same three words can describe someone two years out of school or someone senior enough to be a C-level executive elsewhere. Those aren't the same job and shouldn't be scoped or paid as if they were.

Treat the chief of staff role as a tour of duty

Here's where Caroline differs from a lot of founders. Most roles are meant to be held. You hire a CRO and, absent a problem, that person stays the CRO. She doesn't think this one works that way:

"I actually prefer the idea that it is a tour of duty. That it is not necessarily a three to five year home for someone, but is an excellent one to two year home."

One to two years is long enough to see a whole business from the inside, which is a rare vantage point. After that, people usually know which function they want to run, or that they want to build something themselves. Both are good outcomes. Neither is a retention failure.

You're asking someone to be deliberately unspecialised for a couple of years, at a career stage when most of their peers are building a narrower and more legible track record. You owe them a plan for what that buys them.

What a founder owes the person who takes the job

About a year into Caroline's time at Chief, one of the founders took her for drinks and asked whether she wanted to be a CEO or a COO. The point was that they're different jobs, and the answer should change how they scoped her role.

She said CEO. The answer was taken seriously, and it shaped four years of decisions. Every time she was doing three jobs, the pieces handed off were the operational ones, so she kept the ground that pointed where she'd said she wanted to go.

Later, when a role she was running went away, the conversation was direct rather than managed. That honesty is what eventually led to her being told to go and build something of her own. Then both founders invested in it.

We don't think that's luck. It's what happens when someone runs a relationship properly over years, has the awkward conversations early, and treats an employee leaving as a next chapter, not a betrayal. The return shows up after the person walks out of the door, which is why so few people optimise for it.

It's also a large part of why we built this company. The outcomes that change careers come from relationships, not strategy or execution, and usually from people who are adjacent rather than close, a pattern we've written about in why weak ties are your biggest career advantage.

AI makes the generalist more valuable, not less

David asked how AI has changed Caroline's thinking on early hires. Her answer was that it has made generalists more valuable rather than less:

"A generalist who is AI curious is a secret weapon."

Note that's curious, not top ten percent of AI users. Curious is enough, because the tooling moves faster than anyone's expertise in it can settle. What matters is that they keep poking and bring back what they find.

There's a structural reason this lands hardest in this role. The job has almost never come with a team. Maybe they manage the EA, maybe one or two people. So a chief of staff has always had to be high agency and self-sufficient. Give them a set of agents to direct and you've changed what one capable generalist can hold. Lara went from not touching our codebase to opening pull requests against it within months. The teaching part matters as much as the doing, which is roughly what a super connector does with relationships.

If you're the one taking the job

Interview the founder. Ask whether they understand this is a tour of duty. Ask what happened to the last generalist they hired. Ask, directly, whether they'll spend their network and credibility on your next step when the time comes. The good ones say yes without hesitating, and mean it.

If you're the founder, the equivalent question is whether you're willing to have that conversation every year instead of at the exit interview. Deciding when to hire a chief of staff isn't really about getting an hour back in the calendar. It's about choosing to build one relationship with unusual care, then finding out over the following decade what that was worth.

The full conversation, including Lara on how she and Caroline split what they own, is on A Chief of Staff here.

And if the wider idea lands, that the people around you are the asset almost nobody has a system for, that's the problem we built Goodword to solve.