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Meet the leaders who help us stay true to our course.

Bruce Smith

CEO + Founder

Bruce is a lifelong entrepreneur and an accomplished rower and coach. A former Head of the Charles winner, Bruce coached the US Lightweight Eight to a Bronze medal at the 2015 World Rowing Championships. He is the former Executive Director of Community Rowing – Boston. He holds a BA in English Literature and Theory from McGill University.

Gretchen Saegh-Fleming

Chief Commercial Officer

Gretchen’s expertise lies in driving brand growth through digital innovation, strategic partnerships and new marketing models. Previously the CMO of L’Oréal USA, Gretchen also led DTC e-Commerce for the Luxe division, featuring brands like Yves Saint Laurent Beauté. She holds a BA in English Literature & Art History from Dartmouth College, and an MBA from Boston College.

Chris Paul

CHIEF TECHNOLOGY OFFICER

Chris’s expertise spans SaaS, healthcare, database platforms, and business intelligence. Throughout his career, Chris has led engineering efforts at startups including Brainshark, Blueleaf.com, InsightsSquared and OM1 (formerly Better Outcomes). He holds a BS in Mathematics and Computer Science from Carnegie Mellon University.

Amory Wakefield

CHIEF PRODUCT OFFICER

Amory is a strategic leader, who has built high-performing product teams and successfully launched key products at technology companies of all sizes, including True Fit, E Ink, MathWorks, and Texas Instruments. She holds a BS and an MS in Electrical Engineering from MIT.

Dan Dunn

CHIEF OPERATING OFFICER

An early-stage veteran of eight startups including HubSpot and Quantopian, Dan brings leadership experience in product management, customer experience, and member support. Dan holds a BS in Mechanical Engineering from MIT.

Matt Lehrer

CHIEF EXPERIENCE OFFICER

As the former Director of Coaching Education and Head Coach at Community Rowing – Boston, Matt has deep experience coaching athletes of all levels. He holds a self-design major from Denison University, and an MA in Sports Management from the University of San Francisco.

Ian Drummond

CHIEF FINANCIAL OFFICER

Ian’s experience lies in supporting fast-growing DTC tech subscription businesses. Most recently, Ian was the CFO of SimpliSafe, and facilitated its acquisition to Hellman & Friedman LLC in 2018. A former vice president at Barclays Capital and Lehman Brothers, Ian holds a BS in Economics from the Wharton School at the University of Pennsylvania and an MBA from Dartmouth College.

Ben Berman

CHIEF LEGAL OFFICER

Ben’s expertise lies in helping direct hyper-growth startups navigate significant corporate maturation, including public readiness, mergers and acquisitions, major financial events and global expansion. Ben has been in house for almost two decades, including many years as the GC at Kayak and, most recently, Jobcase. Ben also spent many years on the legal team at Orbitz. He holds a BS in Communications from the University of Illinois, and a JD in Law from DePaul University.

Adam Craft

CHIEF PRODUCTION OFFICER

With a background in mechanical engineering, Adam has made a career of leading product development and production for brands including WaterPik, Hasbro, and iRobot. He holds a BS and MS in Mechanical Engineering from Cornell University and the University of Michigan, respectively.

John Lees

CHIEF STRATEGY OFFICER

John’s experience as a strategic problem solver includes seven years at Boston Consulting Group, building a global marketing research and analytics function at Kimberly Clark, and building a pricing capability for Cengage Learning. John earned his BComm and LLB at the University of Melbourne, and his MBA from the Wharton School at the University of Pennsylvania.