Benjamin Woodruff

Collaborator
DISC Type : is

Board Member at OATH

Greater St. Louis, United States

Overview

Benjamin Woodruff is the Chief Revenue Officer at Flywheel Digital, leveraging an extensive background in senior sales leadership roles. A graduate of the United States Military Academy at West Point, he is recognized for his professional approach to sales and developing client relationships that drive exponential growth.

Outside of his executive role, Benjamin is a board member at OATH, an organization supporting military veterans. He maintains a strong connection to his alma mater, frequently expressing passionate support for Army athletics and the military community.

Unique fact: Benjamin is a West Point graduate, bringing military leadership principles to his corporate sales career.

Personality Overview

Fair-minded

Good Listener

Consensus Builder

Scenarios where both sides can come out as winners appeal to them greatly.  They are more likely to opt for solutions that are proven in the market. Unlike D or C types, they are calm as well as friendly and can give the impression of being more receptive than they actually are.

Topics They Care About

Sales Leadership
As Chief Revenue Officer, he focuses on team development, highlighted by his enthusiasm for the "Flywheel Academy" leadership graduates.
Veteran Support
Serves as a Board Member for OATH, a non-profit organization dedicated to assisting veterans, reflecting his personal commitment to the military community.
Army Athletics
An enthusiastic supporter of his alma mater's sports teams, as shown in his social media posts cheering for Army.

Media Appearances

Benjamin has no verified media appearances

Work History

2-2026
Board Member at OATH
10-2023
Chief Revenue Officer (CRO) at Flywheel
8-2021 - 10-2023
Executive Vice President of Sales at Flywheel
9-2019 - 8-2021
Chief Sales Officer (CSO) at MTM, Inc.
5-2019 - 9-2019
Senior Vice President of Sales at Pace Industries, LLC

Education

1998 - 2002
BA from United States Military Academy at West Point

More Information

Social Presence :

Prographics :

Exp : 10 Location : Greater St. Louis, United States Job Level : Leadership Designation : Board Member at OATH
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Insights For Selling To Benjamin

During A Call Or A Meeting

DO's

  • Be visibly appreciative of their actions during your interactions
  • Show genuine interest in solving their problems
  • Summarize the key points at the end of the conversation

DONT's

  • Don’t give the impression of being unproven or risky
  • Don’t sound very transactional
  • Don’t ask too many questions that sound too dry and objective

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Benjamin is

  • Relationships can sway their decisions, followed by the low risk and the presence of good evidence.
  • Will you ever get a clear answer from Benjamin

  • They are diplomatic when needed and rarely say no directly.

Insights For Deal Planning

    How fast (or slow) will Benjamin move?

  • Even if they are engaged and friendly, they can take their time to make decisions.
  • Can Benjamin take some risk or not?

  • They probably won’t put a lot at risk.

You And Benjamin

Personality Compatibility


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