Charles Oppermann

Commander
DISC Type : D

Senior Director of Windows Engineering, Consumer Group at Malwarebytes

Dunedin, Florida, United States

Overview

Charles Oppermann is a veteran software engineering leader at Malwarebytes, specializing in Windows security products. His extensive career includes pivotal roles at Microsoft, where he worked on Windows and Internet Explorer, and was an original author of the JAWS screen reader. He is a University of South Florida alumnus and a licensed Private Pilot. People describe him as passionate, customer-focused, and a leader with deep technical knowledge.

Outside of his technology career, Charles is a licensed pilot and a published author of two technical books on Microsoft Active Directory programming. He focuses on engineering to help others and is a proud father. His work history reflects a deep commitment to creating software that serves humanity, from accessibility tools to cybersecurity.

An interesting fact: Charles is a key inventor on multiple patents related to software accessibility, fundamentally improving how users with disabilities can interact with technology.

Personality Overview

Risk-Taker

Impact-Driven

Decisive

They take a lot of pride in personal achievements.  More than the product, they care about the impact of the product. They like to move fast and expect the same from others.

Topics They Care About

Software Accessibility
He was an original author of the JAWS screen reader, holds multiple accessibility patents, and worked on accessibility initiatives at Microsoft for nearly 15 years.
Product Quality
He is passionate about shipping high-quality software. His focus is on end-user experience, customer satisfaction, and resolving customer pain points quickly.
Engineering Leadership
Leads a large international engineering team at Malwarebytes and is praised in recommendations for mentoring and investing in the growth of his team members.

Media Appearances

Charles has no verified media appearances

Work History

5-2025
Senior Director of Windows Engineering, Consumer Group at Malwarebytes
11-2019 - 5-2025
Director of Windows Engineering at Malwarebytes
5-2015 - 11-2019
Senior Software Development Manager at Malwarebytes
2-2014 - 4-2015
Director Of Software Development at ThinkDirect Marketing Group
3-2013 - 12-2013
Program Manager at ThreatTrack Security Inc.

Education

1985 - 1986
Computer Engineering from University of South Florida
1984 - 1986
Mathmatics from Pasco-Hernando Community College

More Information

Social Presence :

Prographics :

Exp : 15 Location : Dunedin, Florida, United States Job Level : Senior Designation : Senior Director of Windows Engineering, Consumer Group at Malwarebytes
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Insights For Selling To Charles

During A Call Or A Meeting

DO's

  • Help them weigh the risks by sharing objective proof points without becoming too analytical
  • Get to the point quickly instead of spending time doing small talk
  • Hold your ground without indulging in one-upmanship

DONT's

  • Do not spend too much time focusing on product tech or features
  • Avoid being a storyteller and don’t try to oversell
  • Don't try too hard to forge relationships with them

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Charles 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 Charles

  • If they are not convinced, they will say no without any hesitation.

Insights For Deal Planning

    How fast (or slow) will Charles move?

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

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

You And Charles

Personality Compatibility


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