top of page
  • Writer's pictureDrew

What do you do when you have a gap in Product leadership?

Every company, at some point, experiences a gap in Product leadership. Attrition is an obvious empty seat, but there are a lot of other times and reasons for this gap:

  • Too Early — a reasonable ratio of PM to Engineer at a web/mobile company is 1:10. At four engineers, you definitely don’t need to hire a full-time Product leader, but the team still needs focus and leadership.

  • Initial Product/Market fit — where Product may be led by an individual contributor who hasn’t run the function before or co-founder who doesn’t have a background specifically in Product.

  • Recruiting — it’s hard enough for a non-PM to hire a good PM, but what does a good VP of Product look like?

  • New initiatives — where the head of product wants to bolster expertise in a specific area or just lacks the time and resources to address it properly.

  • Planning and alignment — facilitation of the critical and potentially contentious work aligning on company vision, product vision, mission, and values.

In most businesses, but especially in startups, things that are ignored deteriorate exponentially (see: diversity). An inexperienced leader may be able to maintain a steady state if you don’t expect the company to grow or change.

Companies don’t grow or change, right?

No, the truth is you don’t just need to manage gaps in leadership, you must accelerate during the gaps. I could get alarmist about the potential consequences, but suffice to say that failure to do so leads to stagnation and stagnation is bad.

Okay, so now I’ve freaked you out. I’m sorry. I know leaders don’t need more existential anxiety. Thankfully, I’m writing above about things I can, have, and want to help with.

How I can help

I’ve spent the past eight years working and leading B2B2C products, advising companies and mentoring PMs working on hundreds of products. I’ve developed a skill set that ranges from enterprise to consumer, from two to 1,000 engineers, pre-revenue to over $100M run rate.

I’m currently freelancing and hopefully help a lot of companies. I’d like to help teams anywhere from series A to public with:

  • Interim/fractional head of product — the most obvious situation. Maybe you don’t have enough engineers to justify a full time leader and just need someone to check in a 1–2 days a week. Maybe your leader just departed and you’re staring at one ore more quarters without one. This is work I’m quite comfortable with and happy take on. I can also help hire the full-timer when you’re ready.

  • Product co-founder support — Product Management is deep philosophically and can only truly be learned through apprenticeship. I wouldn’t be half the Product person I am without the crucible that was Product Review with David Sacks and Jim Patterson. I can provide that guidance and help build systems and processes to help the product co-founder through the next stage of growth.

  • Discovery/development of new initiatives—I can help validate/invalidate new feature ideas before the company spends significant resources on them (including product co-founder time), provide research-driven feature prioritization, deliver a roadmap, even assemble the team to execute the project.

  • Organizational design—building a great product is as much about the communication structures and org chart (another communication structure) of the team building it as the idea itself. Here I’ve been fortunate to learn from Adam Pisoni and Kris Gale and apply those lessons to transform how we conceived of, built, delivered, and communicated product at Fond and Skedulo.

  • Process improvement — process is often a dirty word at startups and often what makes or breaks them. Because of this, companies tend to lurch right from “ship or die” to “this is how we did SCRUM at Google” and wonder why everything grinds to a halt. A couple observations from dev teams from two to two thousand: 1. There’re core elements that don’t change at any scale. These things aren’t rocket surgery, but they do require experience, effort, and careful implementation. 2. Everything. else. changes. every. time. Just “doing SCRUM” usually means people put their brains on autopilot and don’t consider whether what they’re doing works for their people or their company.

  • Facilitation — the most important thing for a Product team to do is say “no.” Therefore, the most important thing a head of product can do is align the leadership team around a common set of goals and priorities. This starts with mission and vision, then company and product vision, and tactically at the roadmap. These conversations are critical. They provide air cover for PMs and inspire all of Product Development by aligning their work the goals of the organization.

There’s a lot more I could do that would be more situational to the business, but these are the biggest needs I’ve seen from mentees and companies I’ve advised.

I’d love to talk to you about your needs in Product leadership and how I can help. My goal is to line up contract gigs, but I’m also open to a limited number of mentee and advisory relationships.

162 views0 comments

Recent Posts

See All


bottom of page