top of page

Shepherd & Associates Names New Leadership Team

Founder Ron Shepherd Will Step Aside After Launching Insurance Consultancy 23 Years Ago

San Jose, CA – April 24, 2018 – Shepherd & Associates Insurance Services, Inc., the Bay Area’s premiere small business insurance consultancy, announced today that founder Ron Shepherd is stepping aside from day-to-day operations and has named a new leadership team. The fast-growing consultancy firm will now be managed by Christopher Shepherd and Anna Dobson.

Christopher Shepherd who joined Shepherd & Associates in 2004 has been promoted to President after 14 years as Vice President and Manager of the Property/Casualty. Prior to joining Shepherd & Associates, he was an Account Manager with two global benefits firms – Willis Group and Marsh - in their property/casualty departments. Chris is an expert in risk assessment and identifying comprehensive and cost-effective business insurance solutions.

Anna Dobson (nee Uscanga) has been named Executive Vice President, responsible for employee benefits. She joined Shepherd & Associates two years ago as Manager of Employee Benefits after two years with EPIC Insurance Brokers & Consultants. Anna has been improving the cultures of Bay Area businesses for over thirteen years with innovative and cost-effective executive and employee benefits.

“Chris and Anna are both creative and innovative professionals in small business insurance with more than 30 years of combined experience in the industry,” said Ron Shepherd, Founder & former President of Shepherd & Associates. “I have tapped them because I am confident that they will maintain the high standard of client service that I have established and because of their insights into the technology solutions and insurance products for Bay Area small businesses now and in the future.”

In addition to managing operations, Chris and Anna will lead the expansion of technology applications to grow the business and better service Bay Area small businesses. “Chris and I are committed to providing our clients with the technology solutions that make sense for our customers,” said Anna Dobson, Executive Vice President of Shepherd & Associates. “Technology cannot and should not ever replace personal client service, but we believe that intuitive online solutions can ease the burden on HR professionals and fulfill the demands of the younger, web-native workforce.”

“Job number one has always been and will always be client service,” said Chris Shepherd, President of Shepherd & Associates. “That means finding ways to simplify and improve the lives of our clients and their employees. It is not enough to us that we meet their needs and expectations today, we will help them identify the right mix of insurance and technology solutions that do nothing short of helping them meet their business goals.”

Ron Shepherd has managed Shepherd & Associates since launching the business in 1994. After 30 years in the industry, including ten in public accounting, he is stepping aside and shifting his focus to supporting the leadership team as the Treasurer and advisor to the company.

About Shepherd & Associates

Shepherd & Associates offers comprehensive employee and insurance solutions to Bay Area businesses, non-profits, and public-sector organizations, including employee benefits, business insurance, personal policies, and individual coverage. Our high-touch service model was founded on the integrity and honesty too often missing in the insurance industry. This model was designed to ensure that every client and employee receives the same quality of service.

If you are ready for a strategic partner that can deliver excellent service and solutions for your organization, contact us now at 1 (408) 526-1112 or visit

Press inquiries, please contact:

Dayna Verstegen

Profit in Clarity

Cell: (415) 215-2871


bottom of page