Erin O'Leary

Commander
DISC Type : D

Director of Information Technology at Shapiro

Chicago, Illinois, United States

Overview

Erin OLeary is the Director of Information Technology at Shapiro, leveraging significant experience in logistics technology and IT strategy. A CargoWise Certified Professional and former CIO, she holds a Masters degree in Nonprofit Administration from North Park University. Colleagues describe her as a dedicated, creative, and compassionate leader with a strong work ethic.

Personality Overview

Candid & Clear

Decisive

Strong-Willed

They respond better to strong and respectful interactions.  They like to move fast and expect the same from others. They prefer to be the ones controlling the conversation or defining the terms.

Topics They Care About

Logistics Technology
A CargoWise Certified Professional, she specializes in technology evaluations, implementations, and integrations within the supply chain and logistics industry.
IT Strategy
As a former CIO and current IT Director, she is responsible for formulating and executing technology vision and strategy that aligns with business objectives.
Community Governance
She is a multi-term Elected Commissioner and current Vice President for the Dundee Township Park District, a volunteer role involving financial and fiscal oversight.

Media Appearances

Erin has no verified media appearances

Work History

1-2026
Director of Information Technology at Shapiro
8-2025 - 2-2026
Director, Information Technology at Scarbrough Global
11-2023 - 8-2025
Director, Enterprise Services at Scarbrough Global
9-2022 - 10-2023
Chief Information Officer (CIO) & Cargowise Certified Professional at Janel Group, Inc.
8-2020 - 9-2022
Vice President of Technology & Innovation, Cargowise Certified Professional at Janel Group, Inc.

Education

2006 - 2008
Master of Nonprofit Administration from North Park University
2006 - 2006
Nonprofit Management Certificate from Harper College

More Information

Social Presence :

Prographics :

Exp : 19 Location : Chicago, Illinois, United States Job Level : Mid-senior Designation : Director of Information Technology at Shapiro
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Insights For Selling To Erin

During A Call Or A Meeting

DO's

  • Use phrases like ‘it’s your decision’, ‘strategic impact’ etc.
  • Speak about competitive differentiation that your product offers
  • Hold your ground without indulging in one-upmanship

DONT's

  • Don't try too hard to forge relationships with them
  • Do not back off when challenged, respond with a confident, objective answer instead
  • 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 Erin 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 Erin

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

Insights For Deal Planning

    How fast (or slow) will Erin move?

  • They can reach decisions fairly quickly if they are convinced.
  • Can Erin take some risk or not?

  • They don’t mind risks but can be quite binary about them.

You And Erin

Personality Compatibility


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