A Tampa native Sierra graduated from Berkeley Prep. After attending Florida State University, he entered the insurance industry as an account executive. Sierra went to work for the Jack Nicklaus Development Corporation in 1985, as a construction manager, and has been in land development since that time. Sierra has worked on numerous developments in the last 30 years including: Avila, Tampa Palms, Lakeview Village, and Cypress Creek Town Center in the Tampa Bay area. Some of the developments Sierra was involved with outside of the Tampa Bay area include: The County Club of the South in Alpharetta, Georgia, Wynstone Golf Club in North Barrington Illinois, and Rotunda in Charlotte County Florida. Sierra has also served on numerous property owner boards through the years, generally as a developer liason.

Charitable Works:
As a director for the Sierra Family Foundation Sierra been involved with dozens of local and national non-profits. Including being a board Member of First Tee of Tampa Bay and Academy Prep Tampa.

Sierra enjoys Golf and his dogs, Lolly and Chica, in his spare time.