Image credit: DALL-E “Interviewing at a startup, man and woman sitting across from each other, one-line drawing”

Last week a reader asked about “Hiring Product Managers in Startups.”

What to look for in early hires? How to balance finding the right person with the reality of short timelines and limited budgets?

These are great questions, so over the next few weeks, we’ll discuss this topic in 4-parts.

  1. What to look for in early hires
  2. How to gain alignment on budget and role
  3. How to run a startup recruiting process
  4. How to increase your offer acceptance rate as a startup

What to look for in early hires

Over the years, I’ve made (and seen) many good and bad startup hires. I’ve seen remarkable individuals with deep expertise, that struggled in the Transition Stage (between $1-10M). I’ve also been fortunate enough to find remarkable people that, no exaggeration, altered the trajectory of the startup with their contributions. What I want to offer here are 5 attributes that I believe are make-or-break attributes for talent entering a Transition Stage startup that’s between $1M and $10M.

1. Pragmatic & Adaptable

Product Managers are coming into a “half-baked” product org at this stage. You’re in the middle of your startup’s awkward adolescent years. You’re big enough to be considered a real company, but not yet big enough to fully execute and operate at a level that most “Big Co” teams would expect you to.

People joining at this stage, need to see this “organizational immaturity” as a career opportunity – not a reason to complain. They should see this as an opportunity to help build out a mature product org. They need to embrace the fact that priorities are going to shift and that company strategy is still being refined and clarified quarter-by-quarter. They cannot bring a self-righteous or dogmatic air to the team – turning up their nose at the state of the org. They need to enthusiastically embrace the immature present state, and be excited to become a part of the organizational up-leveling process.

2. Bias for Action

At this stage, credibility is earned by action and impact. Therefore I look for people who want to come in and immediately dive in. Ideally, they have the maturity to know that strategy is important, but they don’t need to spend 3-months doing discovery and getting strategic alignment, before truly jumping into execution mode. They don’t need all the answers, they simply need permission to jump into the deep end with the team. They join, execute, and then adapt the product strategy and roadmap based on real-world learnings and feedback. These folks have a “learn-as-we-execute” vs “learn-then-we-execute” mindset. If Product Managers can’t adopt this bias for speed and action, they lose credibility and often don’t make it long in the role.

3. Independent & Self-Sufficient

Startups have limited resources and tight timeframes. Every month matters. So Transition Stage startups are generally the wrong place for first-time Product Managers. There just isn’t enough time and management structure for this dynamic to work well for the business and for the new hire.

Whoever joins needs to be able to carry their own weight, and operate reasonably independently. You can’t wait 12 months for someone to start producing business impact. You need impact now. That’s why I focus initial hires on strong, seasoned PMs as my first layer and then include earlier career PMs once the core foundation of talent, skill, and experience has been established.

One possible exception to this rule is that startups may have internal candidates that have operated in quasi-product roles without the formal title. If these individuals have the trust of the team and deep knowledge of the customer, it may work for these individuals to transition into a formal product role. It’s still a risk, but it could work.

4. Versatility & Mental Agility

Change is the only constant during the Transition stage. The company isn’t predictable enough to have well-established North Star Metrics and team charters. You should work towards those things, but the reality is it often takes the entire Transition stage, from $1M-10M for those metrics and charters to settle in.

This means you need product managers that can switch gears often. Your focus will change at least quarterly, often more. One quarter you’re focused on retention, while the next you’re focused on increasing sales conversion rates. Sometimes you’re doing both at the same time. If someone wants to settle in and stay focused on one part of the product and one set of metrics, then they’re going to struggle.

Individuals that have a background in startups or other “high change” environments like consulting, will likely do better than someone coming from a big company background with ownership of a deep, narrow slice of the product.

5. Problem Space Overlap

The last thing I look for is problem-space overlap. I don’t mandate that Product Managers have domain expertise, but I do look for Product Managers who’ve solved similar problems in the past. Because of this, I spend a lot of time asking candidates “What were the biggest challenges you had to overcome in your prior roles?” For PM candidates you’ll want to tune your ear to both “product challenges” and “organizational challenges” because PMs normally have to overcome both to drive results.

Be discerning here. Many times more polished candidates are skilled at navigating large, complex stakeholder environments to get results. They know how to sell a vision and work across teams to get things done. While valuable, this skillset is fundamentally about navigating the “organizational challenges” of a large company and translates less directly to a 40-person startup. It’s certainly a useful skill set but has less overlap than, for example, someone who was assigned a small team and asked to build out a brand new product line and bring it to Product Market Fit. Applying the lens of problem space overlap, also helps you recognize exceptional, non-traditional talent — individuals with fewer credentials or big tech logos on their resume — but who’ve spent several years solving very similar problems.

At the end of the day, we’re trying to increase the odds that someone will succeed in our environment.

These five attributes have helped me and I hope they help you too!

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