Ryan Cleaver

Captain
DISC Type : DS

Senior Manager, AIA Program Management at Five9

Lake Forest, Illinois, United States

Overview

Ryan has no verified overview

Personality Overview

Consummate Professional

Output-Driven

Decisive But Calm

They exhibit a rare combination of being result-oriented but patient at the same time.  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.

Topics They Care About

Ryan has no verified topics they care about

Media Appearances

Ryan has no verified media appearances

Work History

12-2025
Senior Manager, AIA Program Management at Five9
2-2025 - 11-2025
Principal Program Manager at Five9
2-2022 - 1-2025
Senior Program Manager at Five9
2-2019 - 1-2022
Program Manager at Five9
1-2017 - 2-2019
Global Lead Program Manager at Mitel

Education

1999 - 2003
Bachelor of Business Administration (B.B.A.) from Michigan State University

More Information

Social Presence :

Prographics :

Exp : 22 Location : Lake Forest, Illinois, United States Job Level : Middle Designation : Senior Manager, AIA Program Management at Five9
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Insights For Selling To Ryan

During A Call Or A Meeting

DO's

  • Ask them at the end if they see a strong value prop in your product; expect an honest answer
  • Come across as a trustworthy professional and be respectful, they usually know their game
  • Let them know of potential risks but suggest mitigation methods alongside

DONT's

  • Don't take their patience for granted, avoid long-winding sermons
  • Don't shy away from asking hard questions, but be extra polite
  • Don't focus too much on mutual contacts or bother about other stakeholders, focus on them

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Ryan 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 Ryan

  • 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 Ryan move?

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

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

You And Ryan

Personality Compatibility


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