About Old Glory

Old Glory Insurance Services, a comprehensive benefits brokerage, opened in 2010 to provide small businesses, human resource professionals, and individuals and families with personalized benefits planning and consultation services. Product offerings include:

  • – Health
  • – Dental
  • – Disability
  • – 401Ks
  • – Life Insurance
  • – C-Suite Benefits
  • – Financial Services
  • – HR Compliance
  • – Employee Advocacy
  • – Health Management
  • – Paperless Enrollment
  • – Community Support
  • – Industry Leadership

Lifelong friends Jason Cushing and Shawn Haney founded Old Glory based on the values they were raised with: honesty, integrity and service. They chose their company name and logo to reflect those values as well.

The concept of Old Glory started with their mutual interest in American history and a story they heard twenty years before from a friend who owned an antique American flag. Tattered and worn, the flag had originally flown proudly over the prow of one of the first U.S. Naval ships, circa 1775. This was prior to the forming of the 13 colonies, and the image of its bold anchor emblem representing honor, freedom, and time-tested initiative remained with them.

A proud member of the Silicon Valley Health Underwriters Association since 2010, Old Glory is committed to helping you navigate the comprehensive benefits planning process beginning right now- and for years to come. Let’s get started!

Meet The Team

Jason Cushing, CLCS


Jason is an employee benefits and executive benefits specialist, licensed with the State of California as a healthcare, property and casualty insurance broker. His practice focuses on small businesses in established and emerging fields, human resource professionals, and individuals and families.

The son of a retired police officer, Jason was born and raised in San Jose. He graduated from San Jose State University with a BS in Aeronautical Engineering and worked in technology sales for several years before co-founding Old Glory with lifelong friend, Shawn Haney. In Jason’s own words:

“Watching my father navigate his pension decisions, as well as my corporate experience, inspired me to enter the insurance benefits field. I have lived through what the average employee goes through: I was given a monthly budget annually at open enrollment, but no direction on how to spend it, or guidance on the levels of insurance that were appropriate based on my age and circumstances.”

Shawn Haney


Shawn is a licensed health and life insurance broker, specializing in individual health, life insurance and employee benefits planning. He launched Old Glory with lifelong friend Jason Cushing in 2010 after spending a decade in restaurant management, where he in part assisted employees navigating their benefits choices. Shawn is married with three children. He is active in his community, volunteering as a high school flag football and t-ball coach. Shawn says:

“Choosing benefits is one of the most critical decisions a person or business can make - as well as one of the most confusing decision pathways to navigate. That makes it a challenge - and one that inspires me every day. Helping clients arrive at the best decision for them and seeing them happy is the best part of my job.”