Cliff Sentell brings more than 25 years of entrepreneurial and operating experience in the software and services sectors, including launching, growing, and exiting a successful healthcare technology company. He participates in all facets of Cypress’ investment process and actively supports portfolio companies.

Before joining Cypress, Cliff co-founded Compass Professional Health Services, a software-enabled healthcare engagement company. From its early start-up phase, Compass grew to 350 employees, supporting 2,000+ companies, when it was acquired by Alight Solutions in 2018. Cliff led the integration of Compass products into the Alight platform, resulting in 300% revenue growth post-acquisition. In 2020, he was recognized as one of the top 20 digital innovators in the United States by Employee Benefits News. Cliff holds a patent for AI that selects and recommends physicians for patients.

Cliff’s leadership in technology, product, and strategy, combined with his boot-strapped startup experience, provides him with a broad and deep lens for investing in and advising Cypress’s portfolio companies. Cliff is a graduate of Duke University, where he received a B.S. in mechanical engineering.