Building products people actually want — with evidence, not assumptions
I've spent nearly 15 years helping early-stage startups (along with enterprise companies and SMBs) figure out who their customers actually are and what to build for them. 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. We talk to actual customers, 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.
Who you'll work with: Sometimes it's just me. Sometimes I bring in trusted partners depending on what the work needs. Either way, you'll know exactly who's involved before anything starts.
WHO'S BEHIND THIS?
I'm Skipper
I operate on a single belief: only humans buy anything. Not markets, not personas, not your bias.
I'm a product strategist, designer, and workshop facilitator who's spent nearly 15 years helping teams replace internal debate with actual customer evidence. Not surveys. Not assumptions baked into a roadmap. Real conversations with real people — while your whole team watches.
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 (3) 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.


Rates and engagement models
Transparency matters. While each engagement is customized, here are a few typical investment types and ranges:
- Workshop facilitation
$5K to $19K based on scope and duration - Product strategy engagements
$10K to $39K based on scope and deliverables - Team development and coaching
$2K per month for structured individual coaching programs, typically done in three-month increments, three weeks on, one week off — team packages also available - Weekly/monthly retainers
$5K/$19K
All engagements include documentation and follow-up support. After all, incomplete work and shelfware never make an impact.
How we work together
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. Probably via email, don't need a 10-page statement of work out of the gate.
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.

READY TO WORK TOGETHER?
See if our approach fits your needs
Book a 25-min call to talk through your situation. We'll be straight about whether our approach makes sense — and what working together might look like (if we work in tandem).
Phone: +1 917-720-6388
Email: heythere@howthisworks.co
How This Works show, our podcast
Subscribe to our newsletter, How Might We...
Not spammy or salesy, just ideas worth your time — written and assembled weekly-ish
© 2017-2026 How This Works, Inc. All rights reserved.

