# Sean Taylor

> Sean Taylor is the CEO of Healthcare.com and the founder of Jaroop, a Connecticut software company that began with a whiteboard in his living room in 2010 and was acquired by Healthcare.com in 2022. His career connects management consulting, enterprise software, community theatre and health-insurance distribution; at Healthcare.com he has overseen the launch of Autopilot, an AI-driven platform designed to match insurance shoppers with distributors using more than 100 million data points.

- **Role:** Chief Executive Officer at Healthcare.com
- **Organizations:** Healthcare.com, Jaroop, Connecticut Theatre Company
- **Education:** BA in Economics, University of Connecticut, MBA in Strategy and Finance, University of North Carolina at Greensboro
- **Known for:** Founded Jaroop and grew it from one client and a living-room whiteboard into a software company serving clients nationwide., Led Jaroop through its 2022 acquisition by Healthcare.com., Became CEO of Healthcare.com in 2022.

## Career timeline

- **2004-2010** — Worked for six years as a management consultant, where he saw companies struggle to identify technology that fit their needs.
- **2010** — Co-founded Jaroop with college friend Chris Shields from Taylor's living room in Connecticut.
- **2011** — Moved Jaroop from the living room into a small one-room office in Middletown, Connecticut.
- **2013** — Expanded Jaroop into a larger Berlin, Connecticut office after growing from one client to clients nationwide.
- **2014** — Jaroop received Berlin's New Business of the Year Award; Taylor also led Connecticut Theatre Company as it acquired the New Britain Repertory Theatre.
- **2016** — Was listed as Jaroop's CEO at a U.S. government trans-agency technology workshop.
- **2022** — Healthcare.com acquired Jaroop on March 21; Taylor became Healthcare.com's CEO in June.
- **2025** — Healthcare.com launched Autopilot after two annual enrollment periods of pilot testing; Taylor also joined a Medicarians panel on AI in Medicare distribution.

## Achievements

- Founded Jaroop and grew it from one client and a living-room whiteboard into a software company serving clients nationwide.
- Led Jaroop through its 2022 acquisition by Healthcare.com.
- Became CEO of Healthcare.com in 2022.
- Oversaw the 2025 launch of Autopilot, an AI-driven insurance enrollment acquisition platform built on more than 100 million data points.
- Helped Jaroop earn Berlin, Connecticut's 2014 New Business of the Year Award.
- Served as president of Connecticut Theatre Company during its acquisition of the New Britain Repertory Theatre.

## Latest updates

- **2025-04** — Moderated and joined a Medicarians panel on how AI is changing Medicare distribution and operational efficiency.
- **2025-03** — Announced the full launch of Healthcare.com's Autopilot platform after two annual enrollment periods of pilot testing.

## Links

- Website: https://healthcare.com
- LinkedIn: https://www.linkedin.com/in/seanpatricktaylor

---

Profile page: https://yespress.io/sean-taylor
Published by YesPress — https://yespress.io
Last updated: 2026-09-28