Chicago, United States, September 2025 – Bryan Preston has joined Firefly Health as the new Chief Commercial Officer (CCO). In this leadership role, Preston will drive Firefly’s commercial growth strategy, strengthen partnerships, and expand market presence as the company continues to disrupt healthcare with its integrated, virtual-first model.
Before joining Firefly Health, Preston spent nearly 12 years at Castlight Health, where he played a pivotal role in advancing health plan sales and customer engagement. Most recently serving as Vice President of Health Plan Sales, he led strategic partnerships with employers and payers, enabling employees to make informed healthcare decisions that improved health outcomes while delivering cost savings. Earlier at Castlight, he served as Vice President of Customer Success, Senior Director of Key Accounts, and Regional Sales Director, driving growth across multiple business functions.
In addition to his time at Castlight, Preston founded Preston Strategic Advisors, LLC, providing business planning, due diligence, and strategic advisory services to early-stage companies, funders, and large nonprofits focused on social enterprise. He also held a senior fellowship at the Civic Consulting Alliance, where he collaborated on initiatives to improve city governance, livability, and competitiveness.
Previously, Preston served as President and CEO of Back Office Cooperative, a consortium of social service and community health providers. His leadership focused on leveraging scale and best practices to enhance operational efficiency and impact. He also held executive positions at Healthways as Vice President of Internet and Mobile Strategy and at CarePages, Inc. as Vice President of Business Development.
Earlier in his career, Preston’s professional journey spanned roles at the MIT AgeLab, where he conducted research on innovation in long-term care, as well as positions with The Lewin Group, HCR ManorCare, ThirdAge Media, and as Press Secretary for the 1995 White House Conference on Aging.
Preston is also a long-standing Board Member at Public Good Software, Inc., a role he has held for more than 11 years. He holds an MBA from Cornell Johnson Graduate School of Management and an MPA from Harvard Kennedy School, underscoring his blend of business strategy and public policy expertise.
About Firefly Health
Firefly Health is transforming healthcare delivery by removing barriers between primary care, specialty care, and plan coverage. Its integrated care model provides members with personalized clinical support whenever needed, ensuring a seamless and patient-first experience. With expert guidance and a strong focus on lowering costs while improving care quality, Firefly Health offers a virtual-first approach designed to deliver both better outcomes and better value. By making healthcare simple, accessible, and affordable, Firefly Health is setting a new standard in the industry.
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