Our Team
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Founder, CEO

Josh Levine

Josh is the founder and CEO of Cake & Arrow, an experience design firm he established in 2002.

With a career spanning over 25 years, Josh is an expert practitioner of human-centered design methodology, digital product strategy, and Design Thinking. He has led innovation initiatives for prominent insurance and financial companies, including MetLife, Citi, Travelers, Aflac, and Chubb, as well as notable retailers like Bose, Lowe’s, KIND snacks, and Saks Fifth Avenue.

A designer by trade, Josh is deeply passionate about helping insurance and financial services companies leverage design-driven mindsets to cultivate authentic and meaningful relationships with the customers and employees they serve. He is drawn to the challenge of helping traditional organizations unleash the humanity in their business and explore new ways of solving old problems.

Josh has won numerous awards, including being recognized in AdWeek’s Young Influencers edition, and as a three-time recipient of IMA’s Agency of the Year.  A frequent speaker, he has shared his expertise on customer experience, human-centered design, insurtech, and digital transformation at various industry events including ITC Vegas, Insurtech NY, Fintech Generations, Retail Innovation Conference, and ReSource Pro Annual Summit. His insights have been featured in AdWeek, Inc. Magazine, and CIAB’s Leader’s Edge.

Under Josh’s leadership, Cake & Arrow has earned a reputation for its people-first and design-driven culture, being recognized as a Best Place to Work by Ad Age, Crain’s, and Inc. Magazine.

Outside of work, Josh enjoys playing pranks, drawing with his daughter Olivia, attending Islander games with his son Julian, rubbing the belly of his French bulldog Big Joey Carmichael, raising money for the March of Dimes, and traveling the world with his wife, Paulina.