Announces New CEO and CFO, Positions Itself for Continued High Growth in 2021

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Updated on March 1st, 2024

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Seasoned executives with experience helping lead two of the highest-growth stories in the history of consumer eCommerce will join’s leadership team

New York, N.Y., March 3, 2021 –, a leading insurtech company providing data-driven shopping solutions that help consumers enroll in individual health insurance and Medicare plans, today announced two critical additions to its growing leadership team. Don Loonam has assumed the role of Chief Executive Officer (CEO) and Bryan Lewis is the company’s Chief Financial Officer (CFO). Howard Yeh, co-founder and former CEO, will assume the position of Chief Operating Officer (COO) and will remain a member of the executive team. Jeff Smedsrud, co-founder, will continue in his role as President of Insurance Services.

Since 2014, has become one of America’s fastest-growing insurtech companies, revolutionizing how consumers shop for health insurance. Leveraging advanced technology and data science, the company has developed customized proprietary products to better fit consumer requirements, enhance customer satisfaction and take some of the guesswork and inefficiencies out of buying insurance. Building on this momentum, the full-stack, next-generation insurance company is extending its platform, augmented by various artificial intelligence and machine learning approaches, to provide more personalized user experiences for both consumers in its omnichannel direct enrollment path, and for sales agents of its more than 12,000 external distribution partners.

Prior to joining, Loonam was COO of Assurance IQ, one of the fastest-growing insurtech startups ever founded. He worked closely with Assurance’s founders to bootstrap the company without outside capital, playing an integral role in rapidly scaling the company. In September 2019, during Loonam’s tenure, Prudential Financial acquired Assurance for $3.5 billion, the largest strategic insurtech exit in history and one of the fastest multi-billion dollar technology exits for any technology startup.

Prior to Assurance, Loonam was CEO of AcademixDirect, a provider of marketing solutions for higher education. Earlier, he ran sales, marketing, and operations at AccuQuote, delivering 24 consecutive profitable quarters while dramatically increasing customer lifetime value (LTV). He joined AccuQuote from Washington Mutual, where he tripled regional sales volume from $600 million to $1.7 billion.

“My career has been about interacting with innovators in health insurance and financial wellness products who wanted to be creative about their growth model,” said Loonam. “I’ve been impressed by for a while, looking at how it has scaled in all the right ways. Its approach to technology and commitment to customer experience is what excited me the most about this opportunity. I look forward to leading the company to new heights in the insurtech space.”

Bryan Lewis joins from eNett International, a global travel payments solution provider. During his five years at eNett as COO and CFO, eNett tripled in size while profits grew 10x. The company was sold to Wright Express, Inc. in a transaction that settled in December 2020.

Previously Lewis served in several management roles at Booking Holdings after they acquired in 2007. He was the CFO of and, earlier, he held simultaneous roles as the CFO, Chief Marketing Officer (CMO) and co-founder of In his six years at Agoda, he helped scale the business from $70 million to more than $3 billion in sales, and the company expanded from a small base in Bangkok to employ more than 2,000 people in 25 countries around the world. Prior to Agoda, Lewis held several senior finance and marketing roles at Lexmark International in Paris, Hong Kong, Beijing and Singapore.

“I am incredibly excited to join a company with the broad ambitions of,” said Lewis. “The company’s commitment to data science meshes well with my passion for data-driven decision making, and I’m confident my experience in scaling global marketplaces will accelerate its already very impressive growth. Partnering with Don and the founders is an incredible opportunity and I can’t wait to get started.” board member Jim Sanger applauded the hires. “Don Loonam and Bryan Lewis have previously been senior contributors to two of the greatest growth stories in the history of online consumer business. I can’t wait see them come together to bring their considerable leadership skills, expertise and vision to helping guide’s already disruptive insurtech platform toward even more tremendous growth in the future.” co-founder Howard Yeh also welcomed the addition of Loonam and Lewis to the leadership team, sharing “I’m excited to be working alongside these leaders, and am excited as ever about the company and team as we reach the next stage of business growth. Our goal is to merge together software, data science, and tech-enabled sales and marketing with deep insurance expertise, and then wrap it in a simple consumer experience,” said Yeh. “We continue to see massive disruption offered by the digital distribution of insurance products to the consumer, and Don and Bryan’s collective experiences position to be at the forefront of new health insurance distribution models.”

About is an online health insurance company providing a data-driven shopping platform that helps American consumers enroll in individual health insurance and Medicare plans. also develops and markets a portfolio of proprietary, direct-to-consumer health insurance and supplemental insurance products under the name Pivot Health. Founded in 2014, the company is headquartered in New York City, and is backed by PeopleFund, Second Alpha Partners, Link Ventures, Axis Capital, and individual investors including current and former executives of and Priceline. is a 5-time honoree of the Inc. 5000 list of America’s fastest-growing companies. For more information, visit

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