The Sidewalk Story

We started Sidewalk partly out of frustration for how quickly tour books grew stale, partly out of the joy of discovering a new place alongside to a local insider.

We built a platform that allows real people to share their favorite places and stories through authentic walking guides that can be updated in real time. And because Sidewalks are digital, anyone can access the chronicles, food, history and culture of a city whenever they want.

Sidewalk is a personal guide to the best a city has to offer - simple as that.


Leadership Team

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Jason Donahue

Co-Founder & CEO

Passions: local history, quirky architecture, dim sum eats, art heist true crime, cooperative board games.

Past: product @ Jawbone, Apple, Zeo

School: Harvard Business School; Brown University

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Dave Hotchkiss

Co-Founder & CTO

Passions: tasting menus, Oktoberfest festivities, backcountry skiing, speed reading non-fiction, tiny Tuscan wineries.

Past: engineering @ Twitter, Google

School: Boston University

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Corey Wood

Product Lead - Growth & Lifecycle

Passions: getting lost in new places, donuts, the pursuit of the perfect picture, street food on a stick.

Past: product @ Jawbone; finance @ E&Y

School: University of Texas - McCombs School of Business; University of California, Santa Barbara


Join Us

We’re looking for engineers, designers, builders and storytellers with a love of learning and a curiosity about what is just around the corner.

If that sounds like you, tell us why at careers@sidewalk.guide