Derek Gary

Commander
DISC Type : D

Director of Information Technology at Sherwood Companies

Owasso, Oklahoma, United States

Overview

Derek Gary serves as the Director of Information Technology at Sherwood Companies, where he drives a cloud-first strategy to modernize infrastructure and security. He previously led a complete AWS migration from four data centers at Vital Energy, significantly enhancing resilience and reducing costs. He holds an MBA and a CISM certification.

There is no publicly available information about his personal life.

He recently earned the Certified Information Security Manager (CISM) certification from ISACA.

Personality Overview

Decisive

Strong-Willed

Candid & Clear

They like to act fast and expect others to do the same.  They like to be in a position where they can control the conversation and terms. They respond better to strong and respectful interactions.

Topics They Care About

Cloud Transformation
He led a full cloud migration to AWS in a previous role and is now implementing a "cloud-first" strategy at his current company.
Cybersecurity Strategy
As Director of IT & Cybersecurity and a certified CISM, he focuses on identity management, governance, and strengthening digital resilience against threats.
IT Modernization
His work involves establishing clear roadmaps to reduce technical debt and replace legacy systems, enabling the business to operate more efficiently.

Media Appearances

Derek has no verified media appearances

Work History

1-2026
Director of Information Technology at Sherwood Companies
6-2025 - 1-2026
Director of IT & Cybersecurity at Vital Energy
2-2023 - 6-2025
Director of Information Technology at Vital Energy
3-2021 - 2-2023
Manager - IT Infrastructure at Vital Energy
9-2020 - 3-2021
Information Technology Solutions Architect at Vital Energy

Education

2010 - 2011
MBA from Hamline University
1995 - 2001
Bachelor of Science in Electrical and Computer Engineering from University of Minnesota Duluth

More Information

Social Presence :

Prographics :

Exp : 21 Location : Owasso, Oklahoma, United States Job Level : Mid-senior Designation : Director of Information Technology at Sherwood Companies
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Insights For Selling To Derek

During A Call Or A Meeting

DO's

  • Hold your ground without indulging in one-upmanship
  • Make sure that you circle back fast on any action items, it wins their trust
  • Objectively showcase the impact that your product creates

DONT's

  • Don't try too hard to forge relationships with them
  • Don’t be in a rush to invite them for a social meet and greet
  • Don’t focus on process and rules, give the impression of being a ‘gets it done’ person

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Derek is

  • Conviction around the impact matters the most to them, followed by a sense of achievement and ROI.
  • Will you ever get a clear answer from Derek

  • If they are not convinced, they will say no without any hesitation.

Insights For Deal Planning

    How fast (or slow) will Derek move?

  • They can take decisions very fast if you manage to convince them.
  • Can Derek take some risk or not?

  • The risks don’t matter much to them.

You And Derek

Personality Compatibility


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