Jason Druding

Captain
DISC Type : DS

Career transition at Career Break

Greater Tampa Bay Area, United States

Overview

Jason is a dynamic executive leader and USMC Veteran with extensive experience in organizational and workforce development in the Tampa Bay region. Described by colleagues as a professional, caring, and dedicated leader, he has managed multi-million dollar budgets and is a Certified Workforce Development Professional (CWDP). He holds a Masters from Barry University.

Outside of his professional life, Jason is a passionate advocate for veterans and individuals with disabilities. He dedicates his time to volunteering with Largo Little League and provides pro-bono guidance to two veteran-focused nonprofits, demonstrating a deep commitment to community service and creating opportunities for others.

As a unique way to network, he has also worked as an Uber/Lyft driver.

Personality Overview

Decisive But Calm

Long-Term Thinker

Consummate Professional

They exhibit a rare combination of being result-oriented but patient at the same time.  Reading between the lines and seeing beyond your words comes naturally to them. They might take some time to make their mind up but once they do, they don't change it easily.

Topics They Care About

Workforce Development
His entire career, including director-level roles, has focused on managing and implementing federal and local workforce programs like WIOA and Wagner-Peyser.
Veteran Advocacy
As a USMC Veteran, he actively supports veteran-focused nonprofits and has designed and implemented veteran services programs in his professional roles.
Disability Inclusion
Previously served as a director at Lighthouse for the Blind & Low Vision, managing services and staff dedicated to supporting the visually impaired.

Media Appearances

CareerSource Hillsborough Pinellas Appoints Jason Druding. Featured in CareerSource Tampa Bay

See Now

Work History

2-2026
Career transition at Career Break
10-2022 - 2-2026
Director of Business Services at CareerSource Tampa Bay
4-2022 - 10-2022
Director of Program Services at Lighthouse for the Blind & Low Vision
1-2022 - 4-2022
Director-Seeking New Opportunities at Self-employed
1-2019 - 1-2022
Director of Operations at Lighthouse of Pinellas

Education

Master's of Arts from Barry University
Bachelors from University of South Florida

More Information

Social Presence :

Prographics :

Exp : 24 Location : Greater Tampa Bay Area, United States Job Level : N/A Designation : Career transition at Career Break
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Insights For Selling To Jason

During A Call Or A Meeting

DO's

  • Let them know of potential risks but suggest mitigation methods alongside
  • Focus on the results that your product produces, expect some strategic questions in return
  • You can spend time on BANT (or other qualification methodology) but keep it to the point

DONT's

  • Don't focus too much on mutual contacts or bother about other stakeholders, focus on them
  • Avoid putting conscious effort into relationship-building
  • Don't take their patience for granted, avoid long-winding sermons

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Jason is

  • Strong proof of impact and their conviction will matter the most, but they wouldn't want to act unilaterally either
  • Will you ever get a clear answer from Jason

  • They will say no if they are not convinced but you will have to prompt them.

Insights For Deal Planning

    How fast (or slow) will Jason move?

  • They will want to understand things well but can move fast once they have a clear picture.
  • Can Jason take some risk or not?

  • They have good risk tolerance but are likely to think it through once or twice.

You And Jason

Personality Compatibility


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