Guided by Experience. Grounded in Trust.
The headwaters of a river shape everything that follows. We believe financial guidance should provide that same clarity and direction. Since 2004, we have served families and nonprofit organizations with unbiased investment management rooted in integrity and long-term thinking.
We are lifelong learners who stay engaged in our profession and active in our local community. Our clients trust us with their goals, their businesses, and their legacies, and we approach that responsibility with care every day.
Thomas J. Sherwood MBA, CFP®
Managing Partner & CCO
Member of the Headwater Investment Team since November 2011. Tommy is always looking for ways to help our clients and better our business. His primary responsibilities are as managing partner and chief compliance officer. He oversees...
Kevin W. Chambers MBA
Managing Partner & President
Member of the Headwater Investment Team since November 2013. Kevin proudly serves as President and Managing Partner at Headwater Investments. His primary role is to shape firm strategy and empower our advisors and clients to make...
Janet Sasaki CRPC®
Advisor & Operations Manager
Matt Dressel CRPC®
Advisor & Portfolio Manager
Member of the Headwater Investment Team since July 2021. Matt graduated with a Bachelor of Arts in History from Oregon State University. After 13 years of progressively advancing through management roles at Starbucks, he transitioned...
Jess Couser CRPC®
Advisor & Marketing Manager
Jess brings a diverse background in finance, client service, and marketing to her role as Advisor and Marketing Manager at Headwater. Her experience spans the wholesale mortgage industry, financial aid counseling, and business...
Rachelle Silis
Portfolio Trading Analyst
Scott W. Chambers Ph.D.
Founding Partner
Founding Partner of the Headwater Investments team. Scott initially pursued an academic career, achieving a Ph.D. from UC Davis. He later relocated to McMinnville, where he assumed the role of a Professor of Finance at Linfield...