At an early-stage startup the CEO and CTO do the bulk of the “product work”: positioning, planning, developing, iterating, and so on.

The team grows and eventually they hire their first PM. The product manager works with the engineers (and sometimes with sales) to help flesh out requirements and acceptance criteria for individual features and sprints.

This works for a while, but as the CEO and CTO face an ever-expanding scope of responsibilities they find themselves slipping on certain things. The product development process as it stands is prone to errors, the positioning hasn’t been updated in a few years, and deadlines have been slipping.

So the founders start the search for a product executive. They post a job listing along the lines of “product executive for high-growth startup”, and title it “VP Product” or “Product Director”.

One of two things tends to happen at this point:

They go through dozens of interviews without extending an offer, or
Or they hire someone that only lasts a few months

Mistakes were made. Let’s discuss the common ones:

What’s the Scorecard?

That’s the first question I ask CTOs looking to hire a product executive. What does the scorecard look like? (If you don’t understand this reference, go read Who: The A Method For Hiring by Geoff Smart and Randy Street.)

It’s surprising just how many CEO/CTO pairs neglect this step. They’re hiring emotionally, looking for a personal connection with the candidate. That’s fine, but not at the cost of ignoring the objective facts.

Before you write the job listing, you need to ask yourself:

What does success look like in this role?
What does the average day look like in this role?

In fact, I advise figuring out what the average day looks like and including that in the job listing itself. I give this advice for all job listings, but product executives are such troublesome hires that I think it’s doubly important to lay it all out on the table up-front.

Strategic vs Tactical

I find that product executives fall into two categories, and that in general, an individual strongly prefers one or the other.

Therefore, straight off the bat, CEO/CTOs tend to make an early mistake in expecting that one person can fulfill both the strategic role and the tactical role. This is a unicorn that you should not expect to find.

Things a tactical product executive does:

Takes measurements, designs A/B tests, looks at data;
Pays attention to the product development process and tweaks it to improve efficiency or correctness;
Gets on the phone with actual customers;
Develops KPIs to track productivity, judge what to build next, and keep the trains running on time.

Things a strategic product executive does:

Does constant market research to figure out the best positioning of your product;
Works closely with sales and marketing to execute on positioning;
Maintains the product and strategic roadmap over a period of years;
Figures out how to make the product a Purple Cow (see Seth Godin’s Purple Cow)

Again, don’t fall into the trap of thinking you can find someone who excels at both. Even if you find an executive who has proven themselves in both tactics and strategy, you’ll likely soon find that they have a preference for one or the other.

Before you start on this hire it’s important to understand whether you’re looking for a tactical or a strategic product executive. Don’t expect a unicorn.

Not Knowing How To Interview

Sometimes a founding team will get the above points right but still fail at hiring the correct person. This is usually a case of not knowing how to interview an executive when you don’t have the requisite experience in that field. A CTO who has never been a product professional simply might not know the right questions to ask. (Though, again, Who: The A Method For Hiring is a great read.)

The solution to this one is quick and easy. If you don’t know how to interview for a VP Product role, bring on someone who does.

Most likely you have an investor, advisor, or friend who understands both your company’s needs and this VP Product role very well. Ask them for advice, and then bring them in to an interview.

You’re hiring an executive. If there ever was a time to call in favors, this is it. Make sure you hire the right person, and if you need to go so far as to retain a consultant for the interview, then do so.

Clash With The Founders

Sometimes all of the above goes well but the relationship still sours. In many situations, this is related to the inability of the founders to let go of their ownership over product.

Imagine you’re a VP Product just hired by a CEO/CTO cofounder team. They promise you strategic ownership over the product. You, tapping on your decades of expertise, start making changes that you believe will position the product into a growing market. The founders, however, push back and ultimately veto you.

This doesn’t happen just the once, but nearly every time you try and make a strategic change to the product. “But this is what you hired me to do,” you nearly shout. After 6 months of rolling that boulder up the hill, you get frustrated and quit.

This happens a lot. If you’re a founder and you want to hire a strategic product executive, you will have to give up a good deal of your product ownership. If you have faith in the person you hired, you must allow them to run things their own way — at least until they show that your faith is undeserved.

It is very hard for an outsider to step into a startup and take product ownership away from the founding team. The outsider will either have to be bold, or the founders will have to be flexible.

If you think you want to hire a strategic product executive, but know you won’t be able to let go of your ownership, then you can either not hire a strategic product exec, or you can design guardrails for everyone. This really just comes down to the first point of having a good scorecard and clear expectations for what the role should entail.

In this case, the CEO/CTO must decide what parts of product and vision are still owned by them. They must learn how to identify when they’re pushing back because “it’s my baby”. They must learn how to have healthy, honest communication with the new executive they’ve brought into the inner circle. And finally, they must admit and accept that they can no longer run the entire company by themselves.

In Summary

The biggest pitfalls regarding hiring product executives center around a lack of clarity and communication. CTOs and CEOs, because they rarely have professional product management experience, think they can hire someone to “take care of product” at an executive level. It’s surprising how many intelligent people think that a role like this can be simplified that much.

Instead, recognize that this is a significant hire and you should do a lot of work before even writing your job listing. You should go into the process with a full understanding of exactly what this person’s daily responsibilities should look like, what’s in-bounds and what’s out-of-bounds for them, and what success looks like for you. You should have a scorecard and the first couple of major projects lined up. Discuss these with your candidates to make sure that they lie both within your candidate’s skill set and their proclivities.

Founders must also be careful of the emotional attachment they develop towards their product. If you need a strategic product executive, then you also need to let go of some things to make it work.

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