Jonathon M.

Questioner
DISC Type : c

AI Capability Leader - Claims IT at Progressive Insurance

United States

Overview

Jonathon is a versatile AI/ML leader, applying his expertise across both the insurance and neuro-oncology sectors. As an AI Capability Leader at Progressive Insurance and a published scientific author, the Harvard University graduate specializes in algorithms and statistical modeling to drive technological advancements in complex domains.

He is a firm advocate for positive psychology, believing in the power of consistent daily effort to create meaningful change. A family man, he enjoys hands-on projects like building and programming robots with his child. Jonathon is also an avid and self-proclaimed "above-average" softball player.

Unique fact: He includes "Above-Average Softball Player" directly in his professional headline.

Personality Overview

Cautious & Analytical

Value Seeker

Not Easily Convinced

It is quite likely of them to ask for pricing or other concessions.  While they don't hesitate to ask questions, they are generally risk-averse and tend to be late adopters. They generally do not appreciate an overfriendly approach and prefer to stay to-the-point.

Topics They Care About

AI in Insurance
As the AI Capability Leader for Claims IT at Progressive Insurance, he is directly involved in applying AI and machine learning to the insurance industry.
AI in Healthcare
Identifies as an AI/ML Leader in the neuro-oncology technology sphere and previously served as Chief Technology Officer for GrAI Med.
Data Science Education
He actively promotes demo days and open houses for data science bootcamps, indicating a passion for developing emerging talent in the field.

Media Appearances

AI‑Proof Your Future | Jonathan Mast (AI Capability Leader – Claims IT, Progressive Insurance). Featured in Apple Podcasts

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Artificial Intelligence at Progressive Insurance – Two Use Cases. Featured in Emerj

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Work History

1-2025
AI Capability Leader - Claims IT at Progressive Insurance
6-2020 - 12-2024
Lead Machine Learning Engineer at Progressive Insurance
1-2019
Chief Technology Officer at GrAI Med
8-2017 - 7-2020
Senior Engineer - Enterprise Data & AI at University Hospitals
5-2012 - 8-2017
Software Engineer Mid at Medical Mutual

Education

2019 - 12-2023
Master's degree from Harvard University
2012 - 2015
Bachelors of Business Administration from Cleveland State University

More Information

Social Presence :

Prographics :

Exp : 13 Location : United States Job Level : Mid-senior Designation : AI Capability Leader - Claims IT at Progressive Insurance
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Insights For Selling To Jonathon

During A Call Or A Meeting

DO's

  • Keep some extra margin in hand as they will likely negotiate the pricing
  • Back up any claims with data and numbers
  • If you have a lower priced product compared to the competition, call out the same

DONT's

  • Don’t overhype the product/pitch, keep it measured
  • Don’t depend too much on anecdotal evidence, it reduces their confidence
  • Avoid phrases like ‘do not worry about’, ‘no one compares to’ etc.

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Jonathon is

  • Ensuring that the product delivers ROI, cost-effective pricing and process compliance are very important for them.
  • Will you ever get a clear answer from Jonathon

  • It doesn’t come naturally to them but they can say no if they are not convinced.

Insights For Deal Planning

    How fast (or slow) will Jonathon move?

  • If they have the information that they need, they can move fast at making their decisions.
  • Can Jonathon take some risk or not?

  • They can take risk if they are convinced that they have analyzed the circumstances well.


You And Jonathon

Personality Compatibility


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