USAA’s Chief Claims Officer Joins Lemonade

Burgess joins Lemonade after more than 25 years at USAA, serving the military community and their families. In his new role at Lemonade, Burgess will oversee the company’s key claims functions across the US and EU, and report to Gavin Blair, SVP, Customer Operations.

‘We have a lot of respect for USAA, their values, trusted brand, and great customer satisfaction,’ said Shai Wininger, Lemonade CEO and cofounder. ‘Sean led one of the best claims teams in the world, and his joining not only marks an important milestone for Lemonade, but also sends a strong message to the industry. Sean’s knowledge, coupled with our technology, will allow Lemonade to continue redefining what a state-of-the-art 21st century claims organization looks like.’

Most recently, Burgess held the role of Chief Claims Officer at USAA, where he led a high-performing team that built and managed some of the company’s digital-first products, including touchless auto claims experiences. During Sean’s tenure, the company doubled in size, becoming the third-largest homeowners and fifth-largest auto insurer in the US, all while delivering world-class service and industry-leading loss adjustment expense (LAE).

‘I’ve followed Lemonade over the years since it launched, and have always admired all that Lemonade is known for - its customer-centric products, technology and AI, socially impactful business model, and so much more,’ said Burgess. ‘As a veteran of the insurance industry, it’s exciting to be leading the charge now with Lemonade. The technology and use of AI, alongside what the team has built in their claims functionality and experience, is best-in-class.’

As part of this move, Burgess will be filling the role of Jim Hageman, Lemonade’s first hire in this role when founded six years ago and famously known among customers as the face of ‘AI Jim.’

‘Saying hello to Lemonade was easy; saying goodbye was much more difficult,’ said Jim Hageman, outgoing Chief Claims Officer. ‘Lemonade has been like family to me for the last six years, so when I decided to move on, we had, well, a family talk, and found a really great fit for the future of Lemonade Claims. Sean brings the perfect blend of experience and humanity, and I am very confident he will continue to build on Lemonade’s success.’

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Lemonade offers renters, homeowners, pet, car, and life insurance. Powered by artificial intelligence and behavioral economics, Lemonade’s full stack insurance carriers in the US and the EU replace brokers and bureaucracy with bots and machine learning, aiming for zero paperwork and instant everything. A Certified B-Corp, Lemonade gives unused premiums to nonprofits selected by its community, during its annual Giveback. Lemonade is currently available in the United States, Germany, the Netherlands, and France, and continues to expand globally.

For more information about Lemonade, visit and follow @lemonade_inc on Twitter.

Natalie Gerke