Jon Skaggs

Critic
DISC Type : C

Director of Engineering at Jama Software

Greensburg, Pennsylvania, United States

Overview

Jon Skaggs is the Director of Engineering at Jama Software, bringing a unique background in biomedical and electro-mechanical engineering from his time at Philips. A Penn State University alumnus, he is a Certified SAFe® Advanced Scrum Master with expertise in test automation, strategic planning, and engineering leadership.

Demonstrating a strong growth mindset, Jon consistently pursues new knowledge through certifications in areas like generative AI, DevSecOps, and agentic AI. He also explores non-traditional asset development and passive income strategies through a senior partnership role outside of his primary career.

Jons career uniquely transitioned from developing life-support ventilators to leading software engineering teams that help innovators succeed.

Personality Overview

Precise

Negotiator

Critic

Unless the value is proven by data, they are unlikely to value fancy features.  It is very likely that they will negotiate pricing or other important terms. They enjoy working alone and do not rely on others very often.

Topics They Care About

Generative AI
Shows a strong, recent interest by completing courses on Agentic AI and Spec-Driven Development with GitHub Spec Kit in the last year.
Engineering Leadership
As a Director of Engineering, he focuses on strategic planning, cybersecurity, and fostering a quality-first mindset within his teams.
Medical Device Development
Previously worked as a lead engineer on the Trilogy Evo life-support ventilator at Philips, focusing on design, verification, and validation.

Media Appearances

Jon has no verified media appearances

Work History

12-2024
Director of Engineering at Jama Software
5-2022 - 12-2024
Software Engineering Manager at Jama Software
2-2021 - 5-2022
Sr. Embedded Software Engineer in Test at Philips
5-2014 - 2-2021
Sr. Design V&V Engineer at Philips
8-2011 - 5-2014
Automation Engineer at Philips

Education

2007 - 2011
Bachelor's Degree from Penn State University
General Studies from Penn Hills Senior High School

More Information

Social Presence :

Prographics :

Exp : 17 Location : Greensburg, Pennsylvania, United States Job Level : Mid-senior Designation : Director of Engineering at Jama Software
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Insights For Selling To Jon

During A Call Or A Meeting

DO's

  • Keep some extra margin while sharing pricing, they are likely to negotiate later
  • Don’t forget to mention how you compare to competition on both features and pricing
  • Be ready to answer many clarity-seeking questions and requests for information

DONT's

  • Don’t rush them till they have clearly gotten all the necessary information
  • Avoid phrases like ‘trust me’, ‘others just love’ etc.
  • Don’t try too hard to build a relationship with them

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Jon is

  • Strong evidence of ROI, effective pricing, and proven data points matter the most to them.
  • Will you ever get a clear answer from Jon

  • It is not very hard for them to say no if they are not convinced about the decision.

Insights For Deal Planning

    How fast (or slow) will Jon move?

  • Their decision-making is neither very fast nor very slow, they are somewhere in between.
  • Can Jon take some risk or not?

  • They can take risks if their analysis shows that it would be worth it.

You And Jon

Personality Compatibility


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