howdy.
I help founders and executive teams turn messy growth into clear, aligned execution.
Not as a consultant with slides — but as someone who works inside the organization, alongside leaders and teams.
I’ve been through the same turning points you’re facing now: the moment when intuition stops being enough and systems start to matter.
How I Got Here
I’ve spent over 25 years as a product, design, and technology leader with experience as a CPO, CPTO, CEO, and executive operator at companies ranging from high-growth startups to global platforms.
I’ve shipped things, broken things, fixed things, and learned (often the hard way) what actually scales — and what doesn’t.
At heart I’m a builder and designer who cares deeply about how decisions get made, how teams work together, and whether we’re actually solving the right problems.
I started in computer science. Moved into design and UX. Studied sociology, psychology, & anthropology. Ran or helped run a bunch of businesses.
Different lenses — one question: How do people, technology, and organizations actually work together?
At IBM and Atlassian, I saw how orgs scale successfully and last — explicit and concrete culture. I also saw how they lose alignment and how they rebuild it.
At WooCommerce (Automattic), running P&L made it clear: clarity at the top shapes everything underneath. It is dysfunctional to separate “the business work” from “the product work.”
In growth-stage companies — ShipHawk, Qualio, Remote, Auctane — I saw talented people working harder than necessary without seeing the expected outcomes because the systems weren’t helping them.
I’ve seen the same challenges show up again and again across growth-stage companies — different industries, different personalities, different cultures, different funding profiles.
Inevitably, companies end up feeling like things almost work — but not quite.
How I Work
My core values are empathy and truth-seeking. I care deeply about the human systems (practices, incentives, relationships, etc.) and I will always drive the conversation toward ground truth rather than consensus or intuition.
What makes me different from your advisors, your board, a consultant, or a full-time hire:
I’ve explicitly chosen fractional partnership and coaching because it works best _for you_. Close enough to understand reality. Independent enough to challenge assumptions.
Unlike most founders, I have a large sample size. I’ve been _inside_ so many of these companies, I’ve learned the patterns that actually repeat and the solutions that work to address them.
Unlike most consultants, advisors, or, frankly, board members, I’m an operator. I’ve had real skin in the game. I’ve owned outcomes and the _how_ of getting to them.
I don’t just give advice or sell frameworks. I help build muscles.
If you’re navigating growth, transition, or strategic complexity — and want a partner who’s been there, will tell you the truth, and care for you and your team — let’s talk.
Outside Work
I love to camp, hike and run on trails but do all of that less than I’d like. There’s nothing like cresting the top of a rocky hill, covered in sweat, after dodging a couple of rattle snakes. (True story.)
I still build things, especially outside with my hands. I love software but building in the physical world is very grounding.
I live in an old stone farm house with my wife and 6 kids (10yo to 20yo). Our youngest has profound special needs. It has defined so much about our family in all the best ways — it is a blessing much more than a burden.
Our house is never quiet, never clean, but always filled with music and love.
Get in touch
Send me a message
You will get a reply. Promise.
schedule a call
Schedule a session to talk over your situation and challenges. I guarantee I can give you some help in this first hour. It’s the best way to find out if I can help you longer term as well.
I will review all your information before our session and come prepared to help.
Note: if you are not in a leadership position (exec, manager, or senior IC), then we are likely not a good match.
© 2026 Todd Wilkens. All rights reserved. · Photo by Ron Lach