As CEO of CareerSource Tampa Bay, Flanagan works closely with business, government and educational entities to find workforce solutions for the more than 1.5 million Hillsborough County residents and businesses.

In the first year as CEO, he launched a youth summer jobs program, dubbed Summer Job Connection, which placed 560 youth into paid work experience positions with 90 Hillsborough County employers.

Flanagan is a member of Tampa Mayor Jane Castor’s workforce advisory committee, the U.S. Conference of Mayors, later being elected among his peers to serve on the board of trustees.

He serves on the community impact committee with the United Way of Tampa. He also sits on the Junior Achievement board of directors, the Early Learning Coalition of Hillsborough County and One Tampa.

1. College alma mater? Gannon University in Erie, Pa. 

2. Last book you read? There’s No Such Thing as a Bad Kid, by Thaddeus Bullard.

3. Last place you vacationed? Couer D’Alane, Idaho.

4. PC or Mac? Both.

5. Guilty-pleasure food? Strawberry ice cream.

6. We’ll find you on the weekend doing?. Golfing, riding my bike with Jack, watching Jack’s baseball games, walking the dogs.

7. Biggest fear? My son not having a full and amazing life.

8. Proudest moment? The birth of my son, Jack.

9. Dream dinner companion? My dad.

10. Any pets? Stella—a boxer, and Gretta—a Boston terrier/pug mix.

11. Who did you last text? My wife, Emily.

12. What is your cellphone wallpaper image? My son listening to his Beats.

13. What do you listen to in the car? Anything and everything. I love music.

14. What is your go-to drink order? Diet Coke most of the time. Adult time? Guinness.

15. Favorite candy? Romolo’s Sponge Candy. (It’s an Erie thing.)

16. Do you suffer from Primenesia (the act of ordering from Amazon and forgetting about it)? No. Buy local!

17. Pool or beach? Pool, but I love the beach.

18. Charity you support? St. Jude’s Children’s Hospital, United Way, Junior Achievement of Tampa Bay.

19. Favorite childhood memory? The precious few moments I shared with my dad.

20. Words of advice? “The pessimist sees difficulty in every opportunity. The optimist sees opportunity in every difficulty.” — Winston Churchill