Garry Anzaroot

Captain
DISC Type : DS

Director, Advisory Services at UPSTACK

Washington DC-Baltimore Area, United States

Overview

Garry is an Enterprise Technology Advisor at UPSTACK with over 25 years of experience leading high-performing sales organizations in the IT and telecom sectors. He focuses on a consultative, vendor-agnostic approach to help clients reduce costs and mitigate risk. Described by colleagues as an energetic, organized, and passionate leader, he holds a CCSE certification.

Originally from the Maryland area, Garry founded the Maryland Technology Group with a focus on exceptional IT services. He studied Business at the University of Tennessee, Knoxville and likely maintains an interest in the local professional sports scene given his long career in the Mid-Atlantic region.

He once led his sales team to increase production by 200% for three consecutive years.

Personality Overview

Output-Driven

Long-Term Thinker

Decisive But Calm

They are very professional in their approach and can weigh multiple perspectives together.  They exhibit a rare combination of being result-oriented but patient at the same time. Reading between the lines and seeing beyond your words comes naturally to them.

Topics They Care About

IT Fragmentation
He recently highlighted that the primary challenge for CIOs isn't the technology itself, but the fragmentation of contracts, spend data, and SLAs across multiple systems.
Effective AI Strategy
He is focused on helping organizations develop a clear AI strategy to avoid wasted investment and ensure they are choosing the right technology for their specific needs.
Maximizing Tech ROI
His professional headline emphasizes driving clarity, confidence, and ROI for technology leaders, aiming to help companies save 30% or more on their IT spend.

Media Appearances

Garry has no verified media appearances

Work History

10-2025
Director, Advisory Services at UPSTACK
2-2024 - 10-2025
President and Founder at Maryland Technology Group
4-2024 - 9-2025
Sr. Director, Strategic Accounts at Five9
11-2019 - 12-2023
Chief Operating Officer at Technology Trading Partners, LLC
4-2018 - 11-2019
Director of Enterprise Sales at CenturyLink

Education

1980 - 1982
Business from University of Tennessee, Knoxville
1983 - 1984
Education details unavailable from Shelby State College Memphis TN 1983-84

More Information

Social Presence :

Prographics :

Exp : 7 Location : Washington DC-Baltimore Area, United States Job Level : Mid-senior Designation : Director, Advisory Services at UPSTACK
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Insights For Selling To Garry

During A Call Or A Meeting

DO's

  • Suggest clear next steps with confidence, don't be vague or hesitant
  • During followups, use phone or text if needed, they should be fine
  • Let them know of potential risks but suggest mitigation methods alongside

DONT's

  • Don't shy away from asking hard questions, but be extra polite
  • Avoid putting conscious effort into relationship-building
  • 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 Garry 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 Garry

  • 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 Garry move?

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

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

You And Garry

Personality Compatibility


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