Rachel Whitcomb

Chief Of Staff at HealthSherpa

Rachel Whitcomb currently serves as Chief of Staff at HealthSherpa, a role assumed in January 2025. Prior to this, Rachel held the position of Director of Strategic Operations at Syllable, where leadership focused on product performance and account growth strategy from June 2022 to December 2024. Rachel's tenure at Boston Consulting Group spanned from September 2018 to June 2022 as a Project Leader, driving strategies and organizational efficiency in the healthcare sector. Earlier experience includes consulting at the University of Minnesota on residency and fellowship program management, and serving as a Registered Sales Assistant at Raymond James Financial Inc. Rachel holds an M.B.A. from the University of Minnesota - Carlson School of Management and a Bachelor's degree in English Language and Literature from Truman State University.

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St. Paul, United States

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HealthSherpa

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HealthSherpa's mission is to help every American feel the comfort and security of having health coverage. They use innovation, technology, and customer service by real people to make your healthcare options easier to understand, faster to sign up, and simpler to use. HealthSherpa is a Healthcare.gov certified web broker, giving consumers, employers, and nonprofits a simpler platform for enrolling individuals and families in subsidy-eligible health plans. They provide consumers access to tools to aid their plan selection and to make the best use of their insurance after they’ve enrolled. With support via phone, email, and chat throughout the enrollment process, consumers don't need to feel confused by the Affordable Care Act (ACA) anymore.


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11-50

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