Jesse Stafford

Judge
DISC Type : Dc

Vice President of Technology at Evergreen Financial Technology Group

Pittsburgh, Pennsylvania, United States

Overview

Jesse Stafford is the Vice President of Technology at Evergreen Financial Technology Group, where he leads high-level technology initiatives and roadmaps across the groups companies. His background includes infrastructure and platform engineering leadership roles. He holds a Master of Science from the Georgia Institute of Technology.

Jesse follows the regional economic impact of technology, such as the growth of AI and data centers in the Pittsburgh area. He is interested in major tech trends, including cloud platform choices like GCP and AWS, and the effects of technology on workplace culture and privacy.

In 2026, he moved from a subsidiary to the parent company to oversee the technology strategy for the entire group.

Personality Overview

Demanding

Objective Thinker

Fast But Wary

They respond better to strong and respectful interactions.  They are very proud of what they do. They are not focused on building rapport and relationships.

Topics They Care About

High-level Tech Roadmapping
His current role involves leading technology initiatives and focusing on the high-level roadmap for the entire Evergreen Financial Technology Group.
AI's Regional Impact
He has shown interest in the impact of AI on the Pittsburgh region, particularly the development of new data centers in Pennsylvania.
Cloud Platform Strategy
He follows the strategic decisions organizations make when choosing between major cloud providers like Google Cloud Platform (GCP) and Amazon Web Services (AWS).

Media Appearances

Jesse has no verified media appearances

Work History

1-2026
Vice President of Technology at Evergreen Financial Technology Group
6-2025
Vice President of Infrastructure at Sharetec Systems
8-2022
Innovation Advisory Council Member at Vation Ventures
7-2023 - 6-2025
Vice President of Technology at Clerri
1-2023 - 7-2023
Head of Platform and Reliability Engineering at CallRail

Education

2000 - 2004
Bachelor of Science from University of Pittsburgh
Master of Science - MS from Georgia Institute of Technology

More Information

Social Presence :

Prographics :

Exp : 3 Location : Pittsburgh, Pennsylvania, United States Job Level : Senior Designation : Vice President of Technology at Evergreen Financial Technology Group
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Insights For Selling To Jesse

During A Call Or A Meeting

DO's

  • Be respectful but crisp
  • Use phrases like ‘it’s your decision’, ‘strategic impact’ etc.
  • Get to the point quickly instead of spending time doing small talk

DONT's

  • Avoid being too verbose
  • Don’t be in a rush to invite them for a social meet and greet
  • Do not hesitate from asking counter questions, just avoid challenging their authority

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Jesse is

  • Conviction around the impact matters the most to them, followed by a sense of achievement and ROI.
  • Will you ever get a clear answer from Jesse

  • If they decide not to use your product, they will say no clearly.

Insights For Deal Planning

    How fast (or slow) will Jesse move?

  • They can take decisions very fast if you manage to convince them.
  • Can Jesse take some risk or not?

  • The risks don’t matter much to them.

You And Jesse

Personality Compatibility


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