Your Head of Product and Your CEO

The relationship between the CEO and Head of Product is one of the most important pillars of a scaling startup. The CEO is most startups’ original Head of Product – setting the roadmap, hiring PMs, defining the features that you’ll build. But as a company grows it becomes too taxing to manage both the complexities of the Product organization and everything else on a CEO’s plate. The company needs to add a Head of Product in order to scale, and do so without screwing up their product quality or momentum.

Defining this relationship understandably leads to challenges. If the product is the CEO’s baby then hiring a Head of Product is the first day of daycare – how do you know you’re not placing your child into the hands of some clown who’s going to play Candy Crush all day? But at the same time it has to be done. You can’t keep your baby at home forever. Here are a few things I’ve learned about this critical element of a growing company.

There are Many Right Answers

There’s a wide spectrum for the product involvement that a CEO can take on, from being the sole decision-maker on all or most decisions to taking a backseat and letting the Head of Product largely run the show.

At one end of the spectrum you have CEOs who unilaterally set the product roadmap for their companies and are highly involved in a wide range of product decisions. This is more common in simpler consumer products – consumer companies often have much simpler workflows, and don’t require the same executive attention to sales and marketing that you’d find in an enterprise business. In this world, the Head of Product focuses on operationalizing and executing on the CEO’s vision.

At the other end of the spectrum there are companies where the CEO is effectively hands-off. This is more common in enterprise SaaS where products are more complex and CEOs are highly involved in go-to-market activities, and particularly with non-technical CEOs. Even at the most enterprise-first companies, most technical CEOs maintain a strong advisory relationship with the product and are an important source of input into the roadmap.

Some key questions to help sort out this balance:

  • Who will set the overall product vision?
  • Who will set the product roadmap?
  • How much oversight should the CEO have over the roadmap? (Can they unilaterally decide that something must be built or should not be built?)
  • How involved will the CEO and Head of Product be in specific product decisions?
  • Do all product decisions need to be run by the CEO, or will the CEO step in for exception handling?

Tasmanian devil going crazy There’s only one CEO, but there are a lot of ways to make the relationship work

Everyone has a Role to Play

While a wide spectrum of product ownership can work, there are a few areas that the CEO or Head of Product must handle in any arrangement.

The head of Product must:

  • Make sure that they are on the same page with the CEO about the product vision and strategy (regardless of who does what). Alignment is the head of Product’s job; the CEO has more important stuff going on.
  • Communicate upwards to the CEO, proactively, about major product decisions before they’re finalized.
  • Provide consistent paths for the CEO’s product feedback to be incorporated into product plans. These can range from formal product or roadmap reviews to a handshake Slack agreement that “we’ll talk about the roadmap at our 1:1s” or “I’ll Slack you if I see something f’ed up.”
  • Execute on hiring, operating, and building the culture of the product team. One of the Head of Product’s primary jobs is to take this off of their CEO’s plate, full stop.

The CEO must:

  • Set a consistent vision and strategy for the company to execute on. Product strategy is highly related to company strategy and takes a long time to reach fruition. For the Head of Product to be successful they need to be able to map to a company-wide plan that is consistent over time. The strategy can be very detailed or very high level, but it must be consistent.
  • Be consistent in the space that they give the Head of Product. While there’s a spectrum of arrangements that can make sense, expectations can’t flip flop erratically.

Present a Unified Front

The CEO and the Head of Product must close ranks for two important sets of decisions: the roadmap and how to handle one-off customer requests (for B2B companies).

The CEO and Head of Product must present an aligned front in the roadmap for morale reasons. If they have irreconcilable differences, people will either view the Head of Product as going rogue or will view the CEO as unable to let go. Both cause confusion and negatively impact morale. A red flag that you’re living in this world: the CEO has a “pet project” team that works on areas that they personally feel are important, but the rest of the product org doesn’t believe in.

The pull to bend the roadmap for critical strategic clients is a serious pressure in enterprise businesses. Regardless of how these decisions are made, the product leaders at a company must figure how to disagree and commit. Otherwise, you risk a tidal wave of salespeople petitioning the most pliant executive on behalf of their clients.

Evolve Over Time

As a company grows, the CEO/Product relationship needs to grow with it.

Both products and businesses grow more complicated as they scale. For the entire company to grow efficiently it’s critical that the CEO steps back from product and the Head of Product steps up. If trust isn’t increasing to make this possible, likely either the CEO or the Head of Product unfortunately needs to be replaced – either the Head of Product is not performing or the CEO is unable to let go. Neither will work at scale. This is a never-ending process, eg some Heads of Product who can effortlessly make it to $50M ARR can’t make it to $150M ARR, some of those can’t make it to $1B ARR, etc.

As this transition occurs, it’s also critical that the CEO and senior product leads who report into the Head of Product build rapport and a close working relationship. This allows the CEO’s strategic perspective to drive the product in a direct, unfiltered way.

Keep it Cool

Lastly, the relationship between a CEO and Head of Product can get tense. The product’s health is both important and subjective, and egos can easily get bruised. So the final advice is to keep a cool head so that you can continue to build a productive working relationship that gets stronger over time.