Christopher Lee

As a startup founder you’re always the first product manager, but just because you start as the de facto PM doesn't mean it will stay that way forever. At some point, you need to hand that title off to someone you trust to continue scaling effectively. One of the most common questions I get asked by founders is when?

Unfortunately, there is no one size fits all answer, and in my experience many don’t ask themselves this question until it’s too late - after growth has already started to stall.

Every startup is different and product management is different in every startup so there’s no simple heuristic. Take a look at these wildly different examples:

Ramp’s first product hire was employee #16 in year 1

Coda’s first product hire was employee #4 in year 1

Stripe’s first product hire was employee #220 in year 5

That’s a huge spread, right?

Three Signs To Watch Out For Instead of playing the numbers game, here is my framework for how I guide the startups in timing their first Product Leader hire. We look for three key signs based on your unique circumstances:

1. The product team needs to scale

As your company grows, the product management workload expands exponentially. What started as quick decisions between co-founders evolves into coordinating multiple teams, managing competing priorities, and maintaining development velocity at scale. If you're seeing signs that your informal processes are starting to crack – like scattered product decisions, misalignment across teams or building the wrong thing– you're already feeling the pain. The key is to spot these signs early and bring in someone who can build the foundation for scale before these issues compound.

This is what I see most frequently with the founders I work with. These founders have successfully gotten their product from 0-1, but now need someone who lives and breathes product management to take it to the next level and unlock the next stage of growth.

2. The rest of the company needs to scale

As a founder, you're not just the first product manager – you're also the first salesperson, marketer, and everything in between. When you start seeing real traction, other parts of the business may need more of your attention. Maybe you need to focus on building out the sales organization, or perhaps the engineering team needs stronger technical leadership. Product is crucial, but it's also something that can be delegated to give you leverage elsewhere. The trick is making this move before other parts of the business start to suffer.

This is particularly common among founders who don't have a product background. If product isn't your superpower, bringing in someone who lives and breathes product frees you up to focus on areas where you naturally excel.

3. You're Not Great at It (And Don't Have Time to Get Better)

Product Management, like all other functions, is a skill. If you don't have a product background, you're learning on the job. And while that's admirable, your startup might be growing faster than your PM skills. If you find yourself constantly playing catch-up or making costly product mistakes, it might be time to bring in someone who eats, sleeps, and breathes product management.

This often comes down to self-awareness – recognizing that things just aren't working as well as they could. Sometimes founders need a gentle nudge from their team to see how everything could run more smoothly with a dedicated product manager at the helm.

The Three Questions Every Founder Should Ask So, founder, it's time for some self-reflection. Ask yourself these three questions:

Are your product processes breaking under scale?

Is your attention needed more urgently elsewhere in the business?

Are you good at product management?

If any of these questions surface some uncomfortable truths, it might be time to find your first PM.

Wrapping Up Hiring your first PM isn't about hitting a certain company size or stage – as we saw with Ramp, Coda, and Stripe, that timing varies dramatically. It's about recognizing when you need to evolve your role as a founder. Remember, your job is to build a company, not just a product. Sometimes that means letting go of the day-to-day product work to focus on bigger challenges.

So, are you starting to see the cracks in your product processes? Are other parts of the business crying out for your attention? Make sure you spot these signs early – your startup's future might just depend on it.

If you need a thought partner, someone to help you think through these three steps, you can schedule a free 30 minute consultation with me.

Christopher Lee

San Francisco Bay Area 3K followers 500+ connections

Experience

Product Scout

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Education

The Wharton School

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San Francisco Bay Area
3K followers 500+ connections