HealthSherpa Announces New Hires Jeff Pollock and Rob Fitzgerald, Formerly of GuideWell Connect

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Fitzgerald and Pollock join HealthSherpa’s efforts to help carrier partners leverage new technology and grow their business

HealthSherpa, the largest private channel for Marketplace enrollment, today announced the appointment of Jeff Pollock as Director of Sales and Rob Fitzgerald as Senior Director of Solutions Engineering. Rob Fitzgerald and Jeff Pollock both spent several years at GuideWell Connect. At GuideWell Connect, Rob directed the execution, delivery and support of white-labeled web sales solutions to issuer clients for their Individual U65 and Medicare market segments. He played a strategic role in successful approval as the 3rd Enhanced Direct Enrollment (EDE) primary entity as well as the original development of the Direct Enrollment program. Jeff Pollock was responsible for developing new carrier sales partnerships through sales of Marketing Services, Telesales and an Enrollment & Application SaaS platform.

“We’re very excited to welcome these two highly qualified members to our sales organization.” said George Kalogeropoulos, CEO of HealthSherpa. “Both bring a wealth of experience, comprehensive market knowledge and a deep understanding of carriers’ pain points and needs. They have the skills needed to help our carrier partners make the most of our technology to grow their business.”

HealthSherpa is one of few companies approved to use the Department of Health and Human Services’ innovative Enhanced Direct Enrollment (EDE) technology at the highest level, and was the first company granted approval on November 28th, 2018. EDE permits private companies to carry out all quoting, shopping, enrollment and related activities for on-exchange health coverage. HealthSherpa can process all Marketplace health insurance applications end-to-end on HealthSherpa hosts an EDE platform for more than 45,000 insurance agents and more than 40 insurance carriers.

Pollock said, “I am thrilled to be a member of the HealthSherpa family. George is a pioneer in our industry and has created the most innovative, nimble and well respected organization in healthcare, whose mission is to ensure that affordable healthcare can be enjoyed by all. It is an honor to be part of that mission and work alongside George, Ning, Cat and everyone at HealthSherpa.”

Fitzgerald, who is set to start in January, said, “Over the past 8 years, I have seen HealthSherpa grow into a dynamic and thoughtful market leader in the On-Exchange market. I am very excited to join a technically savvy and mission-driven organization and look forward to a journey that will bring expanding value to all consumers seeking coverage, issuer clients, and the tremendous agent/broker community.”

About HealthSherpa

HealthSherpa is a health insurance enrollment platform that serves consumers, 30+ insurance carriers, and more than 45,000 agents. HealthSherpa only sells ACA marketplace plans, which have built-in consumer protections. Since its founding in 2014, HealthSherpa has enrolled over 6 million Americans in Affordable Care Act coverage. HealthSherpa processes more than ⅓ of total Marketplace enrollments. For more information, visit

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Divya Raghavan
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