Jessica Orkin

Chief Executive Officer

Clay

Jessica is CEO of SYPartners, where she leads business transformation grounded in humanity, creativity, and purpose—for both clients and the firm. Since joining SYPartners in 2013, she has partnered with and advised CEOs across organizations including AARP, Ageas, Airbnb, the Aspen Institute, Eileen Fisher, Hyatt, the Obama Foundation, Ralph Lauren, Starbucks, and UnitedHealthcare, bringing a background that began in public policy with the City of New York, the Ford Foundation, and leading think tanks.
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A frequent speaker on emergent leadership, creative audacity, and purpose-driven growth, Jessica brings a deeply personal perspective shaped by her upbringing in rural New Hampshire. She now divides her time between New York City, Sintra, and the many places where SYPartners’ teams and clients operate. She serves on the board of Gehl, is a senior advisor to Proto Collective and beta-i, and is an avid open-water swimmer—preferably in cold water.

What Name has been thinking

The power of a courageous question

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May 21, 2025

In an era where old playbooks no longer hold, leadership demands a different kind of courage. Speaking at the Fortune Most Powerful Women International Summit, SYPartners CEO Jessica Orkin explores how bold questions—rather than fast answers—help leaders navigate uncertainty, unlock innovation, and design organizations for both performance and humanity.

The pull back. The call forward

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November 7, 2022

As work and life resettle after the pandemic, many leaders feel a quiet tension between old habits and new possibilities. This essay explores the pull back to familiar ways of working—and the call forward to more human, sustainable leadership. It offers a reflective lens on the future of work, behavior change, and purposeful transformation.

Recent media

Airbnb’s Brian Chesky became a billionaire by knowing how to find the right question, says leadership advisor

May 30, 2025

Some of the most successful people got to where they are not by having all the answers, but by knowing how to find the right questions, according to SYPartners CEO Jessica Orkin. It’s an increasingly important business strategy—and survival skill—amid growing uncertainty about the future.

President of SYPartners explains how practicing design thinking transforms company culture

June 26, 2019

This profile spotlights Jessica Orkin, President of SYPartners, and her approach to transforming company culture through design thinking. Drawing from public policy and business experience, it explores how she balances empathy and aspiration to guide leaders, teams, and organizations through human-centered, purpose-driven change.

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