Strong, clear teams build stellar products

At How This Works co, we partner with growing companies ($5-$95M) to take early product success — whether bootstrapped or through rapid investment — and parlay it into operational excellence. Through focused workshops, strategic guidance, and hands-on work, we turn bottlenecks and team silos into sustainable growth, without burning out.

Our sweet spot is where organizations: 

  • Grow from 3-30 product team members
  • Establish product operations and design systems
  • Build their first product leadership layer
  • Creating scalable team structures


Our mission is to unlock the power of working together. Because it's not what you build — it's how you build it.

Ready to achieve lasting outcomes? Schedule a 25-min call.

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Core services

An icon showing iteration and cycles on a black background - product strategy and design

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 a 1-Hour Power Hour to a Design Sprint 2.0

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Team development & coaching

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

"Skipper's exceptional leadership and innovative approach consistently elevate team performance. He expertly bridges design, engineering, and business to deliver outstanding results."
Rustam Magomedov, director of portfolio delivery

Why work with us?

  • Get answers that matter
    Understand what stakeholders need, customers will buy, and users will love
  • Focus on outcomes
    Deliver results that matter, not jargon or features
  • Adapt to your context
    Every team is unique; our approach adapts with you
  • Test and improve
    Start with proven methods, refine through feedback
  • Build lasting success
    Your team(s) will succeed long after we're not around
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How we work

When we meet, we'll ask, How does this work for you?

We start with curiosity. We ask questions to understand your challenges and goals. Then we work together to find and test solutions that fit your needs. 

Our iterative approach builds solutions that work by talking to the right people at the right time.

(And yes, we love that this question is also our name.)

Recent posts, media

We write about product, strategy, design, workshop facilitation, team dynamics, technology, and other hot topics (like AI), plus episodes of the "How This Works show."

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How might we begin?

Ready to see how this works for you? Schedule an initial consultation. And let’s map it out together (if we work in tandem).

How This Works show, our podcast

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Fresh ideas — written, curated, and assembled monthly-ish. Not spammy or salesy, it's about adding value while we grow and learn.

© 2025 How This Works, Inc. All rights reserved.

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