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Roger Caballero, Jr

Roger Caballero, Jr

Director of Operations

Born in San Antonio, Texas to Roger and Nora Caballero, I am the oldest of 3 children with my younger Sister Becky and Brother Rudy.

I have been married for 22 wonderful years to my beautiful Wife Roxann Caballero and the Good Lord has blessed us with 3 Beautiful Children:

  • Alexandra Leilani Caballero
  • Roger Caballero III
  • Josefina Rosa Caballero


I joined the Secure Benefits Team in 2006 directly out of the United States Marine Corps after serving two tours. In addition to a hard-working, can-do attitude; after my tour with 2nd Battalion 6th Marines in Camp Lejeune North Carolina, I gained administrative and human resources experience at Quantico Virginia while serving as the Chief Admin Officer, responsible for over 250 officers (students O4-O5) and International Officers from over 24 different countries around the world each academic year. In addition to Chief Admin Officer, I also held the billets of Security Manager, Government Purchasing Agent and Supply Officer. I managed and oversaw the colleges’ security program, maintained inventory of classified material, processed clearance requests, ensured classified briefs were conducted within regulations, requested/tracked all purchases for the college’s student curriculum and was responsible for maintaining a budget for the colleges’ student program and day to day operations. Now a licensed insurance agent and the Director of Operations for Secure Benefits, my principal duties include overseeing a team of 7 team members, coordinating, administering, and selling group employee and individual benefits ranging from medical, dental, vision, life, disability insurance, retirement benefits, along with a wide range of work site products. (accident, cancer, etc.) I am also responsible for training, tasking and assisting our team with our clients on the day to day assistance with admin, payroll deductions, claims, billing issues, etc. I work with individual clients and families to include employer groups ranging from 2 employees to 5,000.


After leaving the United States Marine Corps…I can say with pride that I could not have joined a better team that gives me the same love and support that I received from my brothers and sisters in the Corps!  


Together, we are called to serve others, helping them focus on a more secure future!


“Once a Marine, Always a Marine”

                     Semper Fi