Product Leadership Advice for First Time Founders

We asked 6 Product Leaders across the US and Canada: What do you want first time Founder or CEO to understand about experienced product leaders to ensure they make the right CPO or VP Product hire?

Here is what they said:

If you've managed to get to the point where you need a CPO you've likely done a whole lot right! However, if things have not been going right, the hire of a CPO is not intended to be a saviour. If that's the perception, then there is likely a root cause problem.

 A CPO is about elevation and as noted, freeing time from every decision to have someone else at the tillar for customers, the team and carrying forward your vision of the company, not dreaming up a new one.

- Brian MacDonald, VP Product at Craftt


I would want the CEO/Founder to reflect on and discuss openly what decisions they think they have already made versus what decisions they are hiring the VP/ CPO to own going forward.

Too many times, CEO/Founders have a vision so broad that it’s not actionable at all. Others have painted the picture for 5 years down the line very clearly, but they feel like the team is struggling to deliver it. Either way, they hire a new product leader to ‘make things happen.’ 

Building a common understanding of where the product is truly at helps establish the best course of action, and avoids disappointment when the newly hired leader wants to take a step back to clarify the vision, or when they develop a plan with the team which involves tradeoffs. 

The best CEO/Founders I’ve worked with understand that a strategy means making choices. They hire a product leader to help make these choices. The power of the experienced product leader is to know where to focus and when. 

- Christine Dupuis, Director at APM Canada (Former VP Product at


There are many things, but I'll mention one that is probably less obvious. Hire someone who has not been successful - let me explain. We collectively put a lot of value on creativity and big ideas, but as a Founder you already have great ideas. What you need is someone who can help you avoid the bad ones.

With limited time/money/runway as a startup, your success is a function of time spent building good ideas. Because there are always more bad ideas than good ones, there's real value in someone who can filter out the bad.

People who have failed, done the necessary post-mortems, and updated their models of the world have the ability to see around corners, and the intuition to do it fast.

If all someone knows is success, they don’t really understand the world. Complex systems can only be understood through trial and error. Interview for success, but also for failure, and what’s been learned through it.

- Mark Rabo, Founder at Revere App (Former Head of Product at Responsible)


If you wait too long to hire a Head of Product, you'll end up with a very disjointed user experience which will be tough to dig out of.

A great Head of Product will lean into the collective customer needs and create workflows to solve problems. The right hire is more interested in the pulse of the customer vs. how to create a product process in the early days. You'll need a process expert at a later stage. Don't get bogged down in the "art of product management" with the first hire. 

- Erica Jenkins, Former CPO at Crayon


One common reason a Founder might be thinking of hiring an executive-level product person is that they got the product launched and it’s time to prioritize selling or fundraising again.

Product strategy gets harder once you launch because ideas come from all over the place, and some come with sales pressure. Experienced product leaders know how to build a strategy that takes both the Founders’ vision and the market into account. They also know how to prioritize the right problems to solve to get you closer to product-market fit. It’s often hard for CEOs to really let go of driving this prioritization based on instinct— it can be pretty emotional for them.

If you’re a CEO, VPs or CPOs need your trust in their ability to make the hard decisions, and you need to let them do it. Sometimes they are going to be wrong, and you still need to not only let them do it but reinforce that you trust them.

Good product leaders are right a lot, but if they’re never wrong, they’re probably not taking enough risks for you to be perceived as unique in the market. Make sure you hire someone you can trust to make good data-and strategy-driven decisions, and who’s not afraid to make mistakes they can learn from.

- Mike Mitchell, CPO at Trigr Innovation (Former CPO at PetScreening)


First time Founders and CEOs should understand that experienced product leaders, especially when selecting their inaugural VP Product or CPO, bring more to the table than just analytical and strategic capabilities. 

Equally vital is their ability to cultivate connections, ignite inspiration, motivate teams and execute strategies effectively across cross-functional groups, aligning the entire organization toward a common and understood objective.

- Jennifer Buchanan, Former VP Product at Axonify

Thinking of making that key strategic product leadership hire? Here are the top 5 signs that signify your startup is in need of dedicated product management expertise.