Product strategy & customer discovery for funded B2B startups
Building products people actually want and will pay for — with evidence
I've spent nearly 15 years helping funded B2B teams — from early-stage startups to enterprise — figure out who their customers actually are. Most teams skip straight to solutions before understanding the problem — building features based on internal debates instead of customer evidence.
My approach starts with listening — you, your team, and customers. We test assumptions quickly and connect product decisions directly to what moves your business forward. Whether that's through workshop facilitation, product strategy, or team coaching, the work is collaborative and focused on outcomes you can measure.
I'm Skipper
Who you'll actually work with
I operate on a single belief: only humans buy anything. Not markets, not personas, not your bias.
And so I help teams replace internal debate with actual customer evidence. Not surveys. Not assumptions hard baked into a roadmap. Real conversations with real people — no pitching — while your whole team watches.
As a product strategist, designer, and workshop facilitator, my approach draws on Rob Fitzpatrick's The Mom Test, Teresa Torres' continuous discovery work, and a few others worth mentioning — but the difference is your whole team is in the room, not waiting on a research summary.
Engagements are led by me. And depending on what the work needs, other trusted specialists may come in — researchers, designers, strategists. But you'll always know who's involved before anything starts.
I didn't come up through design school or an MBA program. I studied playwriting and English Lit, which taught me that the most compelling story is told with clarity and heart — whether that's words, visuals, or both. I also ran a door-to-door car wash business in middle school and spent three semesters as a reporter for a Gannett newspaper. Nothing teaches deadline discipline like an editor waiting on your copy.
And yes, Skipper is my actual name. I don't go by Skip, Skippy, or chief. It's a longer story — ask me about it. Unless you're an identity thief, in which case: never mind.
Ready to turn assumptions into evidence? Book a 25-min chat.

Perspective from other humans I've worked with

Rates & engagement models
No hourly rates, generally
Transparency matters. While each engagement is customized, here are a few typical investment types and ranges:
- Bullseye Customer Sprint
$20K all in; two mos, including recruitment costs - Listening Cycle
$7.9K/mo, up to 2 interviews per week, 2-3+ mos
- Team development and coaching
$1.5K/mo for structured individual coaching programs — team packages available - Workshops, strategy, fractional & retainers
Scoped to the work — hours, involvement, and duration all factor in. A year-long engagement is priced differently than three mos of intensive work. We'll figure it out together before anything starts.
Incomplete work and shelfware never make an impact. All engagements include documentation and follow-up — and are structured as fixed-scope packages, ongoing retainers, or fractional arrangements.
How we work together
No productivity theater
Every engagement starts with a quick conversation — after that first call — to get up to speed on your situation and get clear on what success looks like. From there, we'll follow up with a short note on what was heard and what makes sense next — via email, no 10-page SOW required.
Sometimes we need another call. Sometimes we go straight into a SOW to keep things clear — but you'll never feel like you're signing something that appeared out of nowhere. No surprises about who's doing the work or what it costs.
Once we're in motion, expect regular check-ins. But no meetings for the sake of filling up the calendar. No productivity theater, we have a bias for action.
And when the engagement wraps, there's always next steps — using the what/who/when framing.
The whole point is work that actually serves your team — not our process, not our preferences.

This is a no pitch zone
Tell us where you're at
We'll talk through your situation and be straight about whether our approach makes sense for you and your team
Phone: +1 917-720-6388
Email: heythere@howthisworks.co
Book a call: howthisworks.co/start
Based in San Francisco, CA, working globally
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