Michael Lehman

Trailblazer
DISC Type : DI

Advisory Board Member at BOLDIFI® Accredited Executive Microschool for Women Entrepreneurs

Greater Milwaukee, United States

Overview

Michael is a C-Level technology leader with over 30 years of experience, specializing in the retail and franchise industries. As the founder of Parachute CIO, he focuses on enterprise cybersecurity, strategic roadmapping, and process automation. Colleagues describe him as a thoughtful, insightful, and humble leader with an MBA from Marquette University.

Outside of his consulting work, Michael is actively engaged in the Wisconsin technology community, participating in groups like the Wisconsin Technology Association and IT Leaders Milwaukee. He is passionate about networking with local professionals and supporting the next generation of entrepreneurs, particularly women in business.

He was a featured keynote speaker on retail technology and cybersecurity at national conferences for TRG Solutions and Fortinet.

Personality Overview

Charismatic

Informal

Achievement-Oriented

If they come to believe in your value proposition, they will be your champion.  They are not against taking risks and can make tough decisions when required.
 They are charming and can persuade others to support their decisions.

Topics They Care About

Retail & Franchise Tech
Has over 20 years of experience leading technology for 730+ retail stores and has delivered keynotes on retail insights from the customer perspective.
Enterprise Cybersecurity
A Certified PCI Professional who has led cybersecurity practices, advised AI-powered security startups, and spoken at conferences on securing the future of retail.
Fractional CIO Services
His current venture, Parachute CIO, is built around providing fractional and interim CIO leadership, M&A due diligence, and strategic technology consulting to businesses.

Media Appearances

Michael has no verified media appearances

Work History

2-2026
Advisory Board Member at BOLDIFI® Accredited Executive Microschool for Women Entrepreneurs
1-2024 - 12-2025
COO & vCIO Practice Lead at TSR Solutions
11-2021 - 4-2026
Advisory Board Member at Lumeus.ai
8-2021 - 9-2023
Retail Customer Advisory Board Member at Fortinet
1-2021 - 1-2022
Retail Corporate Customer Council Member at Microsoft

Education

1988 - 1992
Master of Business Administration (M.B.A.) from Marquette University
1983 - 1987
Bachelor’s Degree from Carroll University

More Information

Social Presence :

Prographics :

Exp : 40 Location : Greater Milwaukee, United States Job Level : Leadership Designation : Advisory Board Member at BOLDIFI® Accredited Executive Microschool for Women Entrepreneurs
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Insights For Selling To Michael

During A Call Or A Meeting

DO's

  • Showcase existing customers and use case-studies to grab their attention
  • Display high self-confidence and expect them to have a strong personality.
  • Ask them for a lunch or coffee once some rapport has been established

DONT's

  • Don’t force involvement of other stakeholders unless it is critical
  • Don’t hesitate from asking them how they truly feel about your product
  • Avoid unnecessary negativity or slowness

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Michael is

  • Relationship and product conviction matter equally, followed by a sense of achievement.
  • Will you ever get a clear answer from Michael

  • If they are not convinced, they will say no though in a friendly way.

Insights For Deal Planning

    How fast (or slow) will Michael move?

  • If you earn their trust and they develop faith in the product, they can make decisions quickly.
  • Can Michael take some risk or not?

  • If necessary, they will be ready to take risks.

You And Michael

Personality Compatibility


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