Cliff Webster


Clifford Webster is a successful IT entrepreneur, executive, and advisor to business owners in matters of value planning, growth planning, and exit planning.

After holding key engineering positions with leading IT companies, Cliff founded Webster Data Communication in 1998 as a one-man shop. Over the next 12 years, he grew that business into an award-winning, 100-person company with double-digit annualized growth. He successfully sold Webster Data Communication to STG, Inc. in 2010.

Now a Certified Merger & Acquisition Advisor, Cliff has turned his attention to helping fellow business owners understand and benefit from the full and complex range of exit planning options and activities. Cliff’s personal mission as an advisor is to protect the seller’s interests and increase the transaction value of the seller’s business. Having seen firsthand many of the pitfalls and hazards associated with the sell-side, he has dedicated his practice to changing the paradigm for the middle-market mergers and acquisitions by bringing structure, transparency and integrity to the process.


Webster Data Communication’s notable awards include:

  • Entrepreneur Magazine’s Hot 500
  • Washington Technology Magazine’s Fast 50
  • Virginia Chamber of Commerce Fantastic 50
  • Fairfax County Economic Development Authority’s Celebration of Northern Virginia Business Success

Certifications and Registrations

  • Cliff Webster holds his FINRA Series 82 Registration with Stillpoint Capital LLC.
  • Certified Merger & Acquisition Advisor, Pepperdine University, AM&AA