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Ryan Singer

Author of Shape Up; Fractional CPO and founder of Felt Presence (early 37signals/Basecamp)

SeniorLeads from the frontOld schoolProductSystemsAI
He is now translating his judgment-first methodology into open-source Claude Code shaping skills that keep humans in the decision loop — a model case of AI adoption that elevates the practice rather than hollowing it out.

Signature win. Wrote Shape Up, the product-development operating system (appetite, shaping, breadboarding, six-week cycles) that thousands of teams adopted worldwide.

The case

editorial · CCBEI · with sources
CraftAuthored Shape Up after 17 years at 37signals; invented breadboarding and 'fat-marker sketches' as judgment-first tools that hold the bar on what to build, not just pixels.9
CommunicationShape Up is one of the most-read, most-legible product methodologies of the decade — gave a generation of teams shared language (appetite, shaping, cool-down); a pure clarity-thesis win.10
BusinessMethodology directly ties design/build to shipping work that matters with bounded appetite; now Fractional CPO and coach helping real orgs adopt durable product operating systems.8
Education[Education recalibrated toward editorial baseline] Teaches 'Shaping in Real Life' course and hands-on shaping sessions so teams see what 'good' looks like; reskills product people, and open-sourced his AI skills for others to learn from.8
InnovationBuilding open-source Claude Code shaping/breadboarding skills that mirror the human flow and explicitly keep humans in the judgment loop — AI adoption that lifts the practitioner, not replaces craft. Passes the elevate test.9

Endorsed by peers

illustrative · opens with verified accounts
OverallI'd work for them116
CraftRaised my craft bar122
CommunicationMade the case for design135
BusinessMade design matter to the business108
EducationTaught me something I still use108
InnovationShowed me a new way to work122

Verified peers only — one tap with LinkedIn. Names stay private; we show role and industry. Bars are illustrative until the participation backend is live.

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