When and How to Make Your First Product Hire

I get one question from founders all the time: When is it time to make my first product hire?

Normally a startup founder is a visionary who is deeply involved in the product experience. She is the person closest to the problem the startup is trying to solve and intimately familiar with what needs to be built. But eventually, that’s too much for one person to manage alone.

I joined Airbnb as the first product manager (PM) when the company was 35 employees. The eighth engineer joined the same day I did. The business was woefully ahead of the team at the time, and as a result we were immediately underwater. Most startups are scaling like crazy at this stage, and early team leaders will feel woefully behind. It’s a feeling that may not go away for a while as you continue to build out the team.

My advice is that it’s time to hire your first product manager when all three of the following are met:

• You’ve achieved product/market fit and need to scale

• Your engineering team is greater than seven people

• You are mentally ready to let someone else control the roadmap at some level

This stage normally happens right after a Series A financing. The team sees the work ahead of them and the founder realizes that her number-one priority needs to be hiring for and building out other functions of the business. This doesn’t mean that the founder doesn’t still set the vision of the business or the product—she should. It means that she is finally ready to let go of the day-to-days of product management and the marshaling of the tech team toward goals. Letting go can be a challenge, but it’s critical to do so when the demands of the broader business are just too much to handle.

Once you know that you are ready to make your first product hire, you need to figure out the right profile for the team. I have seen founders orient too junior, where the first PM is out of their depth and doesn’t know how to wrangle the team. I have also seen founders orient too senior, where the first PM previously carried a big title at a large tech company but didn’t actually do any work.

My advice is to find a builder, not a maintainer. Look for a PM who has actually built a new product, not someone who was handed a well-established product to manage. The builder had to think about the problem they were solving and brainstorm to create a solution. This is far different than a manager of managers who simply watched dashboards to make sure that their product hummed.

The Criteria for Your First PM

Any PM hire—your first or your fiftieth—needs to bring certain critical skills to the table. The framework below hits on the essential criteria: product leaders need to be able to articulate a vision for how to solve a problem, develop a roadmap, get buy-in from the team, and then actually execute, hopefully surpassing the outcome they set out to achieve. This sounds basic, but many PMs don’t possess all of these skills.

These four key skills, though, are table stakes for a good product leader. Your initial PM hire will face the additional challenges of scaling, and needs an even more nuanced skill set to successfully launch a product organization.

For starters, an early PM should be particularly attuned to the balance between chasing growth and getting the overall product in a stable position. Making this tradeoff of resources is often contentious, but startups can ignore overall product health for only so long. A product leader needs to develop a framework to make these decisions.

When a company is getting started, most product efforts are binary builds (a.k.a. “We just gotta build this out”). It’s taking a product from 0 to 1, defining it from scratch. The first PM should think through building an A/B framework to test ideas and inform these foundational product decisions.

In addition to building a product, the first PM is building a team. She needs to think through the cadence of the team and understand how to evolve that cadence as the team expands. She also needs to know when and where to place milestone markers for the team to tie the work to actual, relevant results.

The early days of a startup are 90% execution. Your first PM has to want to get their hands dirty. They can’t rely on other functions being developed. Again, I’ve seen numerous PMs from established tech companies flounder because there isn’t a full data science or design team in place. It’s the PM’s job to fill in the gaps, even if the gaps are very large at the beginning. Ideally, your first PM will understand these gaps and look to actually build solutions and inspire the team to move faster.

Hiring Your First PM

Finding that nuanced skill set and can-do disposition is, of course, no small feat, and a rigorous interview process is essential. As you interview, though, my number-one piece of advice is to focus on how a candidate thinks about a problem and not what the right answer is. The first PM should be a master of the conceptual. There are so many “start from scratch” problems to deal with in the early days, with no existing products, policies, or frameworks to help tackle those challenges.

I prefer an in-person case interview, as I don’t want people getting help outside the office nor spending days solving a simple case study that can be completed in one hour. Base the case study on a current problem you’re facing or just solved. But watch out for the internal team dinging a candidate because they didn’t get to the exact right answer. They don’t have as much context as actual employees at the startup. It’s more important that they have—and articulate—a process for getting to the right answer.

Look for an orientation toward outcomes and not just implementation. For instance, a good indication you’ve found the right individual is when the candidate articulates what success might look like and defines what needs to be achieved with the product.

The hardest skill to teach is judgement—and a product manager’s job is all about judgement. To get at this, look for answers that demonstrate the candidate has tried to understand your questions at a higher level. For instance, they might respond by asking, “Is there a bigger problem that we are trying to address?” or “What’s the underlying cause of the issue?” They are constantly trying to up-level the scope to make sure they are focused on the highest-priority problem. A solid PM should always be stack ranking problems, solutions, and costs in their mind to get to the highest-leverage work.

In Summary

The first PM is a critical hire. A builder, though, can come from many different places, as long as they truly have a track record of building. This could be a super senior product leader who remembers building something long ago and wants to do that again. This could also be a junior PM who is just getting going but has amazing potential. More commonly it is a PM who has seen a startup get off the ground before and is ready to commit to it again. She has seen many fires before and isn’t fazed by putting them out. She provides the steady hand guiding the team forward in challenging moments.

As your startup grows, there will be constant organizational changes. Scaling demands that teams constantly up-level, and it takes a herculean effort for anyone to grow in their role at the same pace the company is growing. There will be a handful of team members who are able to grow with the organization, and they will become some of the most important contributors in the early years—as well as the later years—of a startup’s journey. If you take your time to hone in on a PM that is a builder, more likely than not they will be able to scale with you.

Follow me on Twitter @jpgg.

*Also published on Jonathan's Medium Page