Reimagining healthcare for business
Careers at Clearwater
Help us make a splash in healthcare.
Join the team that's transforming healthcare by making it transparent, affordable, and empowering for individuals and small businesses to thrive.
Our mission is clear: be the nation’s #1 trusted one-stop-shop for quality, affordable, and transparent health plans. These plans are designed to keep both individuals and small businesses happy, healthy, and thriving.
We want to transform the perception of healthcare in America by trailblazing astonishingly affordable, high-quality health plans that people actually feel empowered to use.
Help us make a splash in healthcare.
Our mission is clear: be the nation’s #1 trusted one-stop-shop for quality, affordable, and transparent health plans. These plans are designed to keep both individuals and small businesses happy, healthy, and thriving.
Our Values
Transparency
We strive to demystify the complex healthcare industry by simplifying jargon, clarifying concepts, and consistently ensuring members feel supported and informed.
Compassion
We are absolutely obsessed with understanding the needs of our members, clients, and colleagues — and meeting them where they are to ensure they feel supported and empowered to succeed.
Excellence
From our products and services to our member support, we strive to provide the best experience possible to the clients and members who entrust us with their healthcare.
Innovation
Healthcare in America is broken, and fixing it is no small task. That’s why we hire the most innovative minds in the industry to continue to build plans, services, and experiences that break barriers and rise above the rest.
Wellness
We recognize that a healthy lifestyle improves quality of life, reduces healthcare needs, and fosters creativity. Therefore, we provide employees and members with the support and access to wellness services they need to help them stay well.
Our Values
Transparency
We strive to demystify the complex healthcare industry by simplifying jargon, clarifying concepts, and consistently ensuring members feel supported and informed.
Compassion
We are absolutely obsessed with understanding the needs of our members, clients, and colleagues — and meeting them where they are to ensure they feel supported and empowered to succeed.
Excellence
From our products and services to our member support, we strive to provide the best experience possible to the clients and members who entrust us with their healthcare.
Innovation
Healthcare in America is broken, and fixing it is no small task. That’s why we hire the most innovative minds in the industry to continue to build plans, services, and experiences that break barriers and rise above the rest.
Wellness
We recognize that a healthy lifestyle improves quality of life, reduces healthcare needs, and fosters creativity. Therefore, we provide employees and members with the support and access to wellness services they need to help them stay well.
Top 10 Reasons to Join Clearwater
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Why Join the Team
- Competitive pay
- Remote first workplace
- 401(k) plans with employer matching contributions
- 100% paid employee medical benefits and large employer contributions for families
- Free access to virtual care and mental health services
- 3 weeks of PTO; for select departments, unlimited PTO
- Paid parental leave
- Awards shoutouts, and recognition for achievements
- Annual performance reviews with bonus incentives
- Opportunities for advancement and internal mobility
What our employees are saying
I joined Clearwater in the summer of 2022 and it was the best decision I have ever made. When anyone asks me where I work now, I tell them about a wonderful healthcare company, Clearwater Benefits. A company that cares for their members and for their employees. I share how this company is always offering some ideas and opportunities for the employees. My goal is to continue to see the wonderful ideas and goals upper management offers to us here at Clearwater Benefits.
Cynthia Piasta
I joined Clearwater in November 2022, attracted by the visionary and revolutionary leaders, talented teammates, as well as the corporate mission of providing top-quality and affordable health care to the under-serviced population. Clearwater embodies a transparent corporate culture that promotes innovation, fulfillment, and professional growth for all employees. I appreciate the endless opportunities at Clearwater to continuously streamline and enhance our processes and truly enjoy growing with our most amazing teammates!
Yan Chen
I joined Clearwater in August 2021 because I was passionate about the company’s mission to help people and excited about the career opportunities associated with joining a fast-paced startup. In the years since, I have thoroughly enjoyed being a key part of the company’s incredible growth, seeing my colleagues excel in their careers, and watching my own career flourish. Professionally, it was the best decision I’ve ever made. I have been able to shape my own role and future, taking on new responsibilities and following my passions. I have been surrounded by smart, experienced mentors who are experts in their fields and also genuinely invested in my growth and success. The company culture at Clearwater is truly special, and Clearwater’s commitment to innovation, putting members first, and making a positive impact creates an environment where your contributions will truly matter.
Mandy Sohaney
At Clearwater, I wear many hats in underwriting, proposal generation, marketing, sales, and as a program manager. I joined in February 2024 because the product offering and culture are unmatched. Our collaborative and innovative environment encourages everyone to share ideas and make a real impact. I love providing better benefits at a better price and working with people who genuinely want to make a difference. Since joining, I’ve grown both personally and professionally, enhancing my teamwork, communication, and strategic problem-solving skills. I’m proud to be part of a team that makes a meaningful difference in our clients’ lives in a supportive environment. For those considering a role at Clearwater, come with a solution-oriented mindset, embrace challenges, and stay client-focused to thrive here.
Ryan Carter
Executive Leadership Team
Jason Sherman
Chief Executive Officer
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.
Madeline Smith
President
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Don Collis
Chief Financial Officer
Don Collis, 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.
Jessica Price
Strategic Advisor
Jessica Price is a dynamic strategic advisor and the operational right hand to the CEO at Clearwater, where she plays a pivotal role in ensuring seamless execution of initiatives and fostering effective communication across the organization. With a robust background in Fortune 100 consumer packaged goods, including 15+ years of experience at PepsiCo, Cadbury Schweppes, and Sara Lee, Jessica brings a unique blend of entrepreneurial spirit and corporate expertise. She is passionate about developing innovative marketing strategies, launching new products, and elevating brands. As the founder and CEO of an emerging nutrition food startup, Jessica is committed to making a meaningful difference in people's lives by revolutionizing the healthcare benefits market for contractors and small businesses. Outside of work, she enjoys skiing, Pilates, beach outings with her family, and supporting her children's sports activities.
Jack Hawthorne
Chief Revenue Officer
Jack Hawthorne, CRO 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.
Stacey Koehn
Chief People Officer
Stacey Koehn, CPO at Clearwater, leads the company’s human resources, talent acquisition, and culture strategy. She is passionate about Clearwater’s mission to transform healthcare through innovative solutions that provide high-quality, affordable care. Stacey drives recruitment, retention, and alignment with Clearwater’s core values. With over 20 years of experience, including roles at Accenture, Slalom, and as COO of 3Sage Consulting, Stacey brings a consultative approach to people strategies. Outside of work, she’s a mother of five, enjoys designing homes, and is currently working on her fourth project in the past decade.