When to Hire Your First VP of Product

I’ve been the first VP of Product hired by a founder, and I’ve been the founder who hired a VP of Product. Each was hard, for different reasons.

Short answer: hire when you’ve become the bottleneck and you can name what the person will own. The rest of this post is how I got there, and what I’d do differently.

It’s hard to join a company where the founder has been the head of product. Are they ready to hand over product responsibilities? How will they still be involved? What will you actually own? Who decides what gets built?

Some of those questions can be answered before you say yes. It’s worth understanding what the company needs and what the founder wants. In my case, it became clear that the company didn’t need a VP of Product. They needed a senior individual contributor who could execute and drive a product strategy forward. They didn’t need someone to define the strategy.

When it was my turn to hire, the reason was plain: I had become the bottleneck. I couldn’t keep up with the team. I was active in sales and fundraising, so I had less time for customer conversations. I wasn’t up to speed on the roadmap or releases. I needed someone who could lead and operate.

The person I hired ended up being a great fit, but I wish I had been more intentional about their onboarding and about crafting a transition plan for delegating things to them. Instead, we fumbled our way through, and it took more time than it should have. We got there in the end, but I could have saved us a bunch of time had I been smart about the handoffs.

In my case it showed up as a handful of small things before it showed up as a big one. Ask yourself:

• When did you last talk to a customer about the product, rather than a deal?
• Could you walk someone through the current roadmap and the last two releases today?
• Does the team wait on you to decide what to build, or to unblock a decision?
• Is sales and fundraising taking more of your week than product?

If most of those land, the question is no longer whether to hand something off. It’s what, and to whom.

The usual rules of thumb are stage-based. One common rule of thumb is to hire a product leader at around $3M to $5M in ARR, and to wait for repeatable product-market fit first. They’re good guardrails. But they tell you when the problem tends to show up, not whether you have it.

Part of what makes this question hard is that the answer keeps moving. Every few years the product role gets rethought, and the title shifts with it. I’ve lived through this myself. My title went from Sr. Producer to Product Manager, and my role was defined and then redefined as the company and the broader ecosystem shifted how to build products and teams. The takeaway is that first the roles are bundled together because you’re a small team and everyone is doing everything, then you grow and the roles get unbundled, and then it’s rinse and repeat through the decades. Right now, with AI, we’re back to bundling the product role into a builder role. I wrote more about this shift in From Producer to Builder.

The most visible recent example is Airbnb. In 2023, Brian Chesky said Airbnb was folding product management and product marketing into one function. The headlines said Airbnb had gotten rid of product managers. In practice, it looked to me like the PM function mostly went away, but only in name. In 2024, Paul Graham’s essay Founder Mode built on Chesky’s story. His argument, in short: the usual advice to hire great people and let them run is manager mode, and it can fail founders who need to stay close to the work.

I don’t think either camp is wrong. I do think “Founder Mode” is a silly phrase that, once again, glorifies the hustle-bro culture of Silicon Valley, but that’s typical of YC, so take it with a grain of salt.

It’s a pendulum. A founder-led product works until the founder becomes the bottleneck. Delegated product works until the vision gets watered down. Founder mode is right that you can’t hand product off and walk away. It’s easy to miss that you also can’t be everywhere. I learned that second part the hard way.

So the title matters less than the question under it: who holds the product vision, and do they have the time and context to do it? Ask that, whatever you decide to call the job.

There’s a practical consequence for your hire. Before you search for a VP, ask whether you need one at all, or whether you need a product-minded builder who can ship.

The first question isn’t the title. It’s the mandate. From the other side of the table, this is the one I wish had been answered earlier: does this person define the strategy, or drive one that already exists?

A strategy owner and an executor are different hires, with different profiles and different expectations of the founder, and a mismatch is hard on both people.

I explore the responsibilities and different hats a product leader wears in What Is the Role of a CPO?. Whether you call the role CPO or VP of Product, the useful question is which of those responsibilities your company needs this person to take on.

Before the search, write down:

• Which decisions does this person own outright?
• Which ones do I keep?
• When we disagree, who decides?
• Who does product report to?
• How involved will I be, and for how long?

For most founders, product is the baby. Hiring a VP of Product is handing your baby to someone else to hold. If you’re not ready, say so and wait.

Letting go is hard, and it should be. The key is that you aren’t fully letting go, so define what it looks like. I knew I was ready to hand over the reins, but I still had to let go emotionally. I’m a control freak. I care about every pixel and every detail and every interaction. I had to loosen my need for control and perfection, and I also had to teach and mentor my team that those things still mattered.

Be honest with yourself about control. If you plan to overrule most of their calls, you don’t need a VP of Product. You need a PM, or you need to keep the role.

This is the part I’d do differently. I wouldn’t wait until after I’d hired someone. I’d write the transition plan before the interviews even start: what I intend to hand off, what I intend to keep, and clear dates and milestones for each. I’d review it with a coach or trusted advisor for accountability, and keep reviewing it every 30 days for at least the first six months.

A few things I’d build into that plan:

• Hand off first the work you’re falling behind on, usually customer conversations, the roadmap and releases.
• Tell the team who owns what, so decisions stop routing back to you.
• Teach the standard, not just the task. If you care about the details, show them what good looks like.

The right time isn’t a number. It’s the moment the product needs more than you can give it, and you know what you want that person to own. In practice, all four of these are true:

1. You’re the bottleneck. Decisions wait on you, and you can’t keep pace with the team.
2. You can name the job: who owns strategy, who executes, and what you keep.
3. You have enough repeatable fit that product decisions no longer feel existential.
4. You’re ready to let someone else decide, and to live with their calls.

If you are a founder wondering if it’s time to bring on someone to help you lead the product, I’ve been there. It’s an exciting and terrifying moment. It’s hard to let go. I remember feeling sad that I wasn’t as close to the product as I once was. I love designing and building product. I was spending more and more of my time on fundraising and sales, and I was wishing I was still in the pixels. Ultimately, I found a balance that worked. I’m sure you will, too. If you want to talk, please get in touch.