Todd Oakes

Commander
DISC Type : D

Chief Operating Officer (COO)-Fractional at Diogenes

Ashburn, Virginia, United States

Overview

As a fractional COO at Diogenes, Todd Oakes is a systems-thinking executive with over 30 years of experience in business strategy and strategic operations. He is currently focused on scaling the company by developing its operational systems for the launch of CyberGov™, an Agentic AI governance tool. He holds a BA from the Virginia Military Institute and an MS from George Mason University.

His social media activity suggests an interest in leadership dynamics and workforce trends, particularly concerning ageism and the role of introverted leaders. He also contemplates the future of corporate governance, pondering how data-driven boardrooms can bridge the gap between fiduciary decisions and operational reality.

People who have worked with him describe him as experienced in sales strategy, a good listener, and someone who possesses a strong communications style.

Personality Overview

Risk-Taker

Candid & Clear

Impact-Driven

They put a lot of effort into ensuring personal success.  They respond well to strong and respectful communication. They are less concerned about the product and more about its potential impact.

Topics They Care About

AI in Governance
He is the fractional COO for Diogenes, which is developing CyberGov™, an Agentic AI resource for governance, risk, and compliance.
Startup Scalability
His current role involves preparing his organization for accelerated growth and his headline identifies him as a "Startup & Early Stage Operator. "
Operational Systems
His primary responsibility is developing and implementing systems encompassing people, processes, and technologies to enable company growth.

Media Appearances

Todd has no verified media appearances

Work History

12-2025
Chief Operating Officer (COO)-Fractional at Diogenes
7-2022 - 12-2025
Strategic Planning Senior Leader at Verizon Business
11-2019 - 7-2022
Principal Consultant, Smart Venues & Public Safety at Verizon Business
11-2017 - 11-2019
Advisory Board Member at One Human Service Network (OneHSN)
10-2016 - 11-2019
Defense and National Security at Verizon Business

Education

BA from Virginia Military Institute
Master of Science - MS from George Mason University

More Information

Social Presence :

Prographics :

Exp : 36 Location : Ashburn, Virginia, United States Job Level : Leadership Designation : Chief Operating Officer (COO)-Fractional at Diogenes
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Insights For Selling To Todd

During A Call Or A Meeting

DO's

  • Use phrases like ‘it’s your decision’, ‘strategic impact’ etc.
  • Help them weigh the risks by sharing objective proof points without becoming too analytical
  • Get to the point quickly instead of spending time doing small talk

DONT's

  • Do not back off when challenged, respond with a confident, objective answer instead
  • Avoid being a storyteller and don’t try to oversell
  • Do not spend too much time focusing on product tech or features

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Todd is

  • Confidence in impact is paramount to them, followed by a sense of achievement and ROI.
  • Will you ever get a clear answer from Todd

  • If they are not convinced, they will have no hesitation in telling you the same.

Insights For Deal Planning

    How fast (or slow) will Todd move?

  • If convinced, they can reach decisions quite fast.
  • Can Todd take some risk or not?

  • They do not shy away from taking risks, but can be quite binary about them.

You And Todd

Personality Compatibility


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