Jason Waldrop in

Jason Waldrop

President of Managed Services at Red River
📍 Chantilly, Virginia, United States

Jason Waldrop is the President of Managed Services at Red River, leveraging his expertise in scaling mid-market managed services. He was previously the CEO of CWPS, a company he grew into a regional powerhouse before its acquisition by Red River in 2019. He holds a Bachelor of Science from Virginia Tech.

Outside of his executive role, Jason is active in his community, supporting local youth sports and the Prader-Willi Foundation. He is recognized as a leader within the top 1% of the Managed Service Provider industry.

His career is highlighted by the successful sale of his company and his subsequent transition into a key leadership role within the acquiring firm, Red River.

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Experience
29 Years
Current Role
President of Managed Services
Location
Chantilly, Virginia, United States
Personality Overview
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Priorities

Topics Jason cares about

MSP Growth Strategy
As a former MSP owner, he frequently discusses scaling managed services, M&A strategy, and the transition from owner-led sales to dedicated sales teams.
Business Integration
Successfully merged his former company, CWPS, into Red River and speaks on the importance of cultural and business alignment post-acquisition.
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Career

Work history

10-2019 - 6-2025
President of Managed Services
Red River
5-1996 - 10-2019
Chief Executive Officer
CWPS
In the press

Media appearances

Jason Waldrop | Red River | Technology Decisions Aren’t Black and White. Think Red.. Featured in Red River
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Education
1992 - 1996
Bachelor's degree
Virginia Tech
Social presence
in

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