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

Ron Shepherd, Shepherd and Associates
Ron Shepherd
Founder and Treasurer

Ron has managed Shepherd & Associates since its founding in 1994 until 2018. His background includes founder and Chief Operating Officer of an insurance services company that was one of INC’s 500 fastest growing companies each year it was eligible; officer positions in organizations that specialized in insurance program development, implementation, and management; and 10 years in public accounting with a ‘Big 4’ accounting firm. Ron holds both a Fire & Casualty and Life license.

Christopher D. Shepherd


Anna M. Dobson
Executive Vice President

Anna is Executive Vice President of Shepherd & Associates and responsible for the day-to-day management of Shepherd & Associates. She joined the company in 2015 as the Manager of Employee Benefits from Epic Insurance Brokers. She has spent 12 years helping Bay Area organizations build strategic plans, manage risk, compliance, administration, and the rising cost of health benefits. Anna specializes in benefit plan design, human resources and compliance risk, including the Affordable Care Act. 

Anna holds an Associate Degree in English and a Certificate in Written Communications from Foothill College in Los Altos Hills, California. She has her Life and Health Agent license and acquired multiple designations including the Certified Corporate Wellness Specialist (CCWS), Certified Healthcare Reform Specialist (CHRS), and Certified Workers Compensation Specialist (CWCS). Anna is bilingual, fluent in English and Spanish.

Naomi Bliven
Account Manager

Naomi is an Account Manager with Shepherd & Associates. Prior to joining the firm in 2011, Naomi spent 15 years with State Farm as an agent for all lines of personal and commercial insurance. She is an expert in benefit technology and handles client proposals, account maintenance, new and renewal policies, and more. Naomi also manages personal line accounts, including auto, home, and umbrella policies. Naomi holds a Health, Life and Property Casualty license.

Chris Shepherd, Shepherd and Associates
Chris Shepherd

Chris is the President of Shepherd & Associates and responsible for day-to-day management of the firm. He joined Shepherd & Associates in November of 2004 after spending eight years as a Senior Client Manager, AVP with two large international insurance brokers. Chris has worked with clients ranging from small to large multi-state corporations. He provides a proactive and transparent approach when assisting his clients with their property/casualty insurance needs. Chris is an experienced consultant in a wide array of industries including technology, professional services, and non-profits. Chris enjoys learning about a company’s risks and prides himself in finding the most comprehensive and cost-effective insurance solutions.

Chris received his B.S. in Management with an emphasis in Finance from Santa Clara University. He holds a Fire & Casualty license.

Christopher D. Shepherd


Pam Wess
Account Executive

Pam is a Commercial Lines Account Executive. She joined Shepherd & Associates in February of 2013 after more than 20 years as a client manager for various regional brokerage firms and claims representative for personal and commercial lines for several insurance carriers. Pam holds a Property & Casualty and a Life & Health license. She has a strong focus on customer service and her continuing education.

Diana Medina
Account Coordinator

Diana is an Account Coordinator with Shepherd & Associates. She joined the firm in 2021 and specializes in benefits administration for medical, dental, vision, and life insurances among other employee benefit policies.  Diana holds a license in Life & Health. 

Shepherd & Associates believes in old-school customer service and the convenience of today’s technology. Our high-touch service model was founded on the values of integrity and honesty too often missing in the insurance industry. We make it our mission to ensure that every client and employee receives the same quality of service, regardless of company size.

We work tirelessly to ensure our clients are comfortable throughout the entire insurance placement process. With access to over 100 insurance companies, we have the relationships and experience to provide knowledgeable, ethical, and cost-effective insurance services.