Join Us in Revolutionizing Health Benefits

We are on a mission to change the health benefits industry and we need your help.

Jason Sherman

CEO

As the CEO of Clearwater, Jason is dedicated to ensuring the company remains true to its mission: helping members save money on their health insurance while securing better coverage. With a deep passion for Clearwater, Jason has spent years observing small businesses and independent contractors struggle with inadequate health insurance, and now leads a company that successfully addresses these challenges, impacting thousands of lives.

Jason values Clearwater’s strong sense of purpose, which resonates deeply with the team, fostering a high-engagement environment where empathy and customer experience are prioritized. For those looking to make a meaningful impact and join a mission-driven company, Clearwater offers an incredible opportunity.

With over 20 years of experience in starting and running high-growth companies, Jason has consistently focused on compassionate, people-centered solutions across various industries, including insurance. Outside of work, Jason enjoys attending his kids’ sports events and traveling.

Doug Sherman

Cofounder

Doug Sherman, Co-Founder of Clearwater, is dedicated to providing innovative solutions that reduce health insurance costs for individuals and employers while expanding coverage. Doug’s extensive background includes consulting for Fortune 500 companies and leading two high-growth firms. His consulting firm, DSG Consulting, served clients like Boeing, Caterpillar, Siemens, and Citrix across over 30 countries, gathering a wealth of best practices and proven results. After leading three high-growth companies, Doug entered the health insurance sector as a C-level officer at The Boon Group, gaining firsthand insight into major medical insurance challenges. Observing rising premiums and out-of-pocket costs, he pursued innovative solutions for affordability.

Don Collis

Chief Financial Officer

Don Collis, the CFO at Clearwater, oversees critical financial operations like fundraising, cash management, budgeting, forecasting, and investor relations. His role ensures Clearwater's sustainable growth and operational excellence. Don is dedicated to the company's mission of providing affordable, effective health plans to alleviate financial stress for millions. With 35 years in financial management, including roles at Standard Oil and Dell Technologies, Don's expertise shapes Clearwater's financial strategies. Outside work, he enjoys hunting, boating, diverse music genres, and mentoring young people in their spiritual growth.

Steve Howe

Chief Technology Officer

Steve Howe, CTO at Clearwater, leads technology innovation and AI development. He drives insights through advanced data analytics and enhances Clearwater's data lakehouse capabilities, scaling IT operations and improving efficiencies. Steve ensures a secure, compliant technology ecosystem while guiding Clearwater's tech roadmap. Focused on innovative AI solutions, he enhances customer experiences and optimizes processes. With a background in cutting-edge technology and software solutions, Steve scales Clearwater's business to deliver exceptional benefits. Passionate about AI's real-world impact, he also enjoys time with his two children, woodworking, and sand volleyball.

Jack Hawthorne

Chief Revenue Officer

Jack Hawthorne, Chief Revenue Officer at Clearwater, aims to expand awareness and adoption of the company's innovative health benefits solutions. By leading outreach and engagement strategies, he helps boost revenue without increasing consumer costs. A seasoned sales professional, Jack understands the challenges of confusing and expensive health benefits and is dedicated to Clearwater's mission of providing accessible, cost-effective solutions to independent and small business owners. Before joining Clearwater, Jack grew his own law firm and spent eight years in real estate as a sales executive and consultant. He enjoys spending time with his wife and two young sons, often filled with the joyful chaos of their adventures.