In December I left my full-time role leading the Product Org at Included Health.
My first roles in what became “Product Management” started 25 years ago, so Charlene and I decided 2026 was the right time to take a longer than usual beat and think through what I (and we) wanted to do next.
The catalyst was personal in two ways:
First, our two sons are launching into adult life, so family time is especially precious since they are home less often. Tim Urban’s blog post “The Tail End” is a good read on this topic. When a kid graduates from high school, about 93% of in-person time with a parent is over. At this stage, you’ve got about 7% left.
Related, we wanted to experiment with inverting how our life was organized, focusing on the life part first and building work around that. For years I’d done the opposite. Let’s just say I was less successful fitting “everything else” in as well as I wanted.
We’ve taken the last few months to catch up on travel, spend more time outdoors, learn new skills, and see family and friends. (Still working on this last part, so let’s have coffee!)
Professionally, I’ve shifted into coaching and advisory work. Leaving a large leadership role to build something solo is equal parts exciting and humbling. Some days I’m energized. Some days I’m figuring it out as I go.
Why do it?
I’d worked with executive coaches throughout my career. I found it helpful and, at times, transformational to how I thought about work. At the time, I noted this and filed it away as something that would be interesting to do later.
As I’ve worked with increasingly larger teams, I found more of my time spent coaching leaders. Helping people improve and get where they wanted to go was often among the most fulfilling and alive parts of my job. Increasingly, I was also coaching people outside of my core work.
A natural thought over time became: What if I focused here?
It all comes together in the work I’m doing now: helping senior product and R&D leaders through moments where what got them here stops working. That’s often a larger job scope, working to communicate better at new levels, leading hard transformations, or just a decision about what’s next.
This started with 1:1 exec coaching, and has recently expanded into advisory work with small startups. For my clients, I’m in the role of a trusted, neutral thought partner. For me, it’s being of service. That’s the throughline.
I’m in flight on coach training towards credentialing as an ICF-Certified Coach. It lets me blend a coaching mindset and skills with 25 years operating in product environments. As good as coaches I’ve had were, I always wished I could find one who had operated in environments like mine.
You can follow the latest here, or reach out to me directly. I’d love to hear from you, whether I can help you, someone you know, or to just catch up. If you’re in the Bay Area, let’s connect over coffee.
🧭 Free 30-minute coaching sessions: I’m opening a small number of free 30-minute coaching sessions this summer — for folks who’d like to sample coaching, or for whom price may be a barrier. If you’re working through a hard stretch or transition — a bigger role, a complex situation, or you just want a thinking partner for half an hour — just reply or visit me here. If someone you know could use this, feel free to share with them. I’d love to help.\
I smiled reading this because I realized how many more people are about to benefit from something your teams have long known.
Great product leaders build products.
The best leaders build people.
You were always doing both.
Congratulations on this next chapter, Jeff.
I understand the impulse. Part of my struggle over the last three years is that my personal relationship with my work self has changed in the last 10 years. I worked harder on anything I have done since my Ph.D at a Series A startup. I was asked to be a founder in a next venture. I went on to work at one of the most technically capable companies I encountered in my career (which sadly did not work out.) After summits like that, the question comes: what is left to do? How does one balance work and life, and still be effective? Plus, my chosen field seems to have set itself on fire in the last four years in search of AI.