Derek Gillespie

Captain
DISC Type : DS

Chief Executive Officer at 365 Data Centers

United States

Overview

Derek is the CEO and CRO at 365 Data Centers, bringing over 25 years of executive experience in the Infrastructure as a Service (IaaS) industry. A graduate of the United States Naval Academy, he has a proven track record of transforming sales organizations at Zayo, Cosentry, and Savvis. Colleagues describe him as driven, strategic, and well-rounded.

Outside of his executive roles, Derek is committed to community involvement. He serves as a member of the Board of Trustees for the Henry Viscardi School, an institution dedicated to educating children with severe physical disabilities.

He has been globally recognized as a top sales leader, including being named one of the Top 20 CSOs by Clari in 2023.

Personality Overview

Long-Term Thinker

Dynamic But Sincere

Consummate Professional

They might take some time to make their mind up but once they do, they don't change it easily.  They are very professional in their approach and can weigh multiple perspectives together. Reading between the lines and seeing beyond your words comes naturally to them.

Topics They Care About

Edge Computing
He publicly predicted that edge data centers, SD-WAN, and SASE would dominate enterprise technology discussions and strategy in 2024.
IT Infrastructure
His career specialty is leading sales for IaaS, colocation, managed hosting, and cloud computing solutions for major industry providers.
Sales Transformation
He is known as a strategic change agent, consistently tasked with leading high-priority rebuilding efforts and revenue-generating initiatives for global sales teams.

Media Appearances

Legacy Investing Expands Data Center Connectivity With Zayo Group At T5@Minneapolis. Featured in PR Newswire

See Now

Work History

10-2025
Chief Executive Officer at 365 Data Centers
3-2024
Chief Revenue Officer (CRO) at 365 Data Centers
1-2021 - 3-2024
Chief Sales Officer - Enterprise Sales at Zayo Group
1-2020 - 1-2021
Chief Revenue Officer at Zayo Group
1-2019 - 1-2020
President, Global Head of Enterprise Sales at Zayo Group

Education

1992 - 1996
History-Political Science from United States Naval Academy

More Information

Social Presence :

Prographics :

Exp : N/A Location : United States Job Level : N/A Designation : Chief Executive Officer at 365 Data Centers
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Insights For Selling To Derek

During A Call Or A Meeting

DO's

  • Use phrases like 'your team deserves', 'best in class' etc.
  • Stick to your standard pitch and qualifying script, don't try to wing it
  • You can spend time on BANT (or other qualification methodology) but keep it to the point

DONT's

  • Avoid putting conscious effort into relationship-building
  • Don't get into pricing discussions early on, steer conversation towards proven results
  • 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 Derek 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 Derek

  • 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 Derek move?

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

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

You And Derek

Personality Compatibility


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