Our Team

Part 2B of Form ADV

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 to have eyes on accounts as the portfolio manager. He executes trades, leads our investment strategy, and collaborates on developing firm strategy. He uses skills learned at Linfield as a double major in Economics and Finance and a student of Scott.

He is our most ‘lettered’ employee earning his Certified Financial Planner™ (CFP®) designation, an MBA from University of Oregon Executive program, a Chartered Retirement Planning Counselor℠ (CRPC®), and a Chartered Retirement Planning Specialist℠ (CRPS®) designation from the College of Financial Planning. He uses all of this knowledge to help our clients navigate the tricky decisions surrounding retirement and estate planning.

Outside of the office, Tommy serves the community in a variety of ways. He is on the Board of Directors of Delta Psi Delta at Linfield College, one of the oldest local fraternities in the United States and is the Treasurer of the McMinnville Noon Rotary Club. He has completed Leadership Programs for both the Newberg and McMinnville Area Chambers of Commerce. Tommy has previously served as Treasurer for the Yamhill County Cultural Coalition. He also enjoys working with small businesses and start-ups as an advisor and mentor.

Tommy is a new father! Charlie James joined the Sherwood family in December 2017, and he keeps Tommy and his wife Rose plenty busy. They enjoy taking family walks, biking together, and trying out new recipes in the kitchen. When not with his family or at his trading station, you can probably find Tommy on the back nine of Michelbook Country Club.

Certified Financial Planner Board of Standards Inc. owns the certification marks CFP®, CERTIFIED FINANCIAL PLANNER™ and federally registered CFP (with flame design) in the U.S., which it awards to individuals who successfully complete CFP Board’s initial and ongoing certification requirements.

Member of the Headwater Investment Team since September 2006.

CB’s role at Headwater Investments allows her to meld her passions to create and organize. She manages the web-based and traditional marketing efforts, responds to client requests and inquiries, supervises and coordinates the firm’s information technology systems, and handles office administration.

After CB earned her BS in International Business from Linfield College, she held various roles at adidas in Portland, Oregon, in the Global Footwear Logistic and Apparel Marketing groups, including Product Line Manager, Merchandise Manager, and Operations Manager. These organizational and marketing skills have proven useful at Headwater Investments.

She stays active in the community as a group fitness instructor, a volunteer in the schools, and a mentor to Linfield students. CB has previously served as an advisor on the McMinnville Area Chamber of Commerce Leadership Committee and as President of the Board of Directors for Trinity Learning Center and the PTA of her sons’ elementary school. She currently serves on the board for the McMinnville Education Foundation and is co-chair of the 2019 Grad Night Committee for McMinnville High School.

Many evenings and weekends you can find CB and her husband, Jeff, at sporting events for their two boys. Although their oldest son is about to fly the coop for college, they hope their chickens all stay put – the family enjoys the farm-fresh eggs the chickens provide. In exchange, CB gladly accepts help from “the ladies” in her garden.