B2B product strategy & customer discovery

What if every product decision your team made was grounded in what an actual customer told you?

Most teams build on gut feel and good intentions. And those instincts are usually close, but close doesn't close.

Even a small founding team debating who they're building for burns roughly $40K a month in misaligned work. That's not a people problem. That's a signal problem — and silence is expensive. Speed in the wrong direction is a mistake whose price keeps climbing.

Here's what fixing it looks like. The Bullseye Customer Sprint gets you to a staked customer hypothesis in about two (2) months — five (5) live interviews your whole team watches together, no more "I think," just "they said." A Listening Cycle keeps that clarity from expiring while you build — weekly interviews, immediate debriefs, no reports nobody reads.

Only humans buy anything. Stop building for the wrong one.

Book a 25-min intro call — no pitch, just a conversation about where you're at.

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Clients & collaborators

Built for teams at

Replay.io logo
Shep logo - horizontal
Sesame logo
Karmascore logo
Anova logo
Waterpik logo
Deloitte logo
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Bank of America logo
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Services

How we help B2B teams move from intuition to evidence

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Product strategy & design

Create products customers want using tested methods that turn insights into business results

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Workshop facilitation

Turn ideas into action through focused sessions — from our signature Bullseye Customer Sprint to a Listening Cycle to a Design Sprint

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Team development & coaching

Build stronger teams that solve problems together through structured coaching and proven frameworks

Here's what it sounds like when a team stops guessing

"Skipper excels as a workshop facilitator, guiding teams through structured and highly productive sessions. His ability to unite remote teams and foster collaboration makes him a remarkable leader."

Snizhana Bezhnar, design director

"His calm, collected demeanor and thoughtful approach have profoundly shaped my problem-solving and client interactions. Skipper's mentorship is transformative."

Brian Heltsmith, senior product designer

"Working with Skipper at Replay.io, I saw firsthand how he cuts through the noise when a team is stuck between a product they believe in and a customer they haven't quite found yet. He has a rare talent for helping teams identify their bullseye customer — and making that clarity stick across the whole team, not just leadership."

Filip Hric, developer relations manager

"Skipper brings a human-centric approach to transformational change for clients, with a rare ability to empathize with diverse perspectives, leading to solutions that genuinely work for all."

Gerard Welikala, vice president of digital transformation

"Skipper listens to his customers, leveraging their insights to initiate ideation and innovation. His ability to distill complexity into simple, elegant solutions is remarkable."

Marley Sirman, account executive

The How This Works co approach

Moving from founder intuition to evidence-based conviction

We help teams move from founder intuition to evidence-based conviction. The case studies below show what that actually looks like.

Pivoting to survive a market collapse

At Shep, we built a browser extension for business travel compliance. Our first hypothesis — small and medium businesses — failed after a year of iterations: fragmented budgets, impossible unit economics. We pivoted to enterprise. Then COVID killed 92% of business travel overnight. Instead of folding, we went back to listening. Enterprise still had duty of care problems. We retooled around safety and health notifications, piloted with Adidas and Discovery Channel, and Flight Centre acquired Shep in 2021.

Finding the customer with real stakes

Replay's initial hypothesis: ops managers need help building automation apps but a Bullseye Customer Sprint with five (5) discovery/user testing interviews told a different story. The customer who actually buys is an independent builder with a production app (not a test) and real money on the line — someone who needed to understand what broke and why, not just have it auto-fixed. So we shifted the Bullseye hypothesis, validated with a Listening Cycle, and they relaunched as Replay Builder. Specificity creates clarity. Clarity creates focus. Focus creates revenue.

Listening past the CFO

A tier 1 bank-integrated fintech's pipeline had stalled — sales down 23% over 18 months. We ran a Bullseye Customer Sprint targeting CFOs at $50M+ SaaS firms. By the third Listening Cycle interview, a CFO handed us the real answer: "That's an audit problem — I kick it to my controller." Right pain, wrong customer. We repositioned for controllers at $30–$100M firms and ran 13 more interviews to confirm. Higher retention, shorter sales cycles, wider swathe of accounts.

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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

Book a 25-min call

Insights & perspectives

Stories on customer discovery and product strategy

Stories and conversations on customer discovery, product strategy, facilitation, and the messy middle of building and making right now — including the How This Works show.

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Based in San Francisco, CA, working globally

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