Garry Anzaroot in

Garry Anzaroot

Captain · DISC type DS
Director, Advisory Services at UPSTACK
📍 Washington DC-Baltimore Area, United States

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.

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Experience
7 Years
Current Role
Director, Advisory Services
Job Level
Mid-senior
Location
Washington DC-Baltimore Area, United States
Personality Overview

How Garry shows up

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.

Priorities

Topics Garry cares 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.
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Career

Work history

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

Media appearances

No media yetWe could not find public media appearances for this person.
Education
1980 - 1982
Business
University of Tennessee, Knoxville
1983 - 1984
Education details unavailable
Shelby State College Memphis TN 1983-84
Social presence
in
Behavioral profile

DISC profile (public)

D

Dominance (D)

Dominance (D) reflects how goal and task oriented a person is, and their ability to accomplish results irrespective of how demanding the circumstances might be. Those scoring high tend to be motivated by winning, competition, and success.

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