Randy Pickering, President is both an alumnus of Black Hawk College, where he completed his AA degree and Western Illinois University, where he earned an ASE/BA degree in Business and Education. Randy is past President and current member of the San Diego Association of Health Underwriters (SDAHU), current member of the National Association of Health Underwriters (NAHU), Health Insurance Agents and the National Association of Life Underwriters. Also, he is a past member of the Tri City Hospital Corporate Council that works closely with North County businesses and their employees. Lastly, he is a Registered Representative (stockbroker) and Registered Investment Advisor (RIA) for Pro Equities Corporation. He directs investments of 401(k) and Pension and Profit Sharing monies. Employers and employees appreciate this value added service.

Randy started Pickering Insurance Services, Inc. 10-1-1980. For the last 38 years Randy has grown Pickering Insurance Services, Inc. into one of the largest privately held Benefit Firms in San Diego County. High Touch and personalized service has set his firm apart. Business owners enjoy the fact that they actually work with the President and owner of the firm.


Rooted in Southern California and extending a global reach, Pickering Insurance Services, Inc. works with partners ranging from individuals to mid-sized companies. Our Focus is on finding the perfect insurance solutions for our clients, with an optimal balance between coverage, benefit and savings. Our wealth of experience and widely varied services provide the knowledge, security and Foresight you need.


The consultants and support staff at Pickering Insurance Services are trained, licensed and experienced in all facets of employee benefit planning and service. Licensed in multiple states, Pickering Insurance Services, Inc. professionals design; implement and support integrated health and welfare benefit plans and qualified retirement programs. Specializing in health insurance cost management, Pickering Insurance Services has maintained over 100 large clients for 20 consecutive years or longer. Pickering Insurance Services, Inc. small business and administrative services division provides benefits services to hundreds of business and professional organizations.

Pickering Insurance Services, Inc. is an exclusive partner of ThinkHR an electronic Human Resource Assistant. Through its partnership with ThinkHR, Pickering Insurance Services can provide information on legislative changes as well as employee communications and consumer related healthcare information.

In 2000, Pickering Insurance Services launched a direct to employer, online group insurance product search engine and benefit enrollment and administrative service for employers with less than 100 employees through its website at

Whether contemplating a new benefit plan or seeking a more efficient alternative to an existing program, Pickering Insurance Services, Inc. provides decision makers with a finished product that reflects employer philosophy, conforms to budgetary requirements and preserves employee morale.