Matthew Stewart, CPCU

Questioner
DISC Type : c

VP, Insurance Strategy Enablement at CCC Intelligent Solutions

San Antonio, Texas, United States

Overview

Matthew Stewart is the Vice President of Insurance Strategy Enablement at CCC Intelligent Solutions, leveraging over 26 years of experience from USAA. His expertise lies in claims operations, digital transformation, and leveraging technology to enhance customer satisfaction. He completed a General Management Program at Harvard Business School Executive Education.

Outside of work, Matthew has a deep-seated commitment to the military community, stemming from his long career serving military families. He frequently expresses pride in veterans, including his own family members serving in the U. S. Army, and has participated in community events providing support to veterans.

He joined CCC Intelligent Solutions after being their client, having led the implementation of their technology while he was a VP at USAA.

Personality Overview

Systematic

Not Easily Convinced

Value Seeker

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 prefer to fully evaluate every situation.

Topics They Care About

Claims Digitization
He is passionate about simplifying the claims experience by leveraging technology for intelligent digitization, automation, and creating greater transparency for customers.
Supporting Veterans
He actively promotes initiatives supporting the veteran community and has represented his company in events that provide tangible assistance, like reliable transportation, to military families.
Insurance Innovation
His career focuses on the intersection of innovation, data, and digital transformation to build next-generation insurance operating models and improve operational efficiency.

Media Appearances

Matthew has no verified media appearances

Work History

11-2025
VP, Insurance Strategy Enablement at CCC Intelligent Solutions
1-2021
Head of Casualty Claims, Vice President of Injury & Claims Litigation at USAA
9-2018 - 1-2021
AVP, Senior Experience Owner at USAA
3-2017 - 9-2018
AVP, P&C Chief of Staff at USAA
8-1996 - 6-1999
Casualty Claims Adjuster at MetLife

Education

General Management Program from Harvard Business School Executive Education
Bachelor of Business Administration - BBA from University of the Incarnate Word

More Information

Social Presence :

Prographics :

Exp : 11 Location : San Antonio, Texas, United States Job Level : Senior Designation : VP, Insurance Strategy Enablement at CCC Intelligent Solutions
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Insights For Selling To Matthew

During A Call Or A Meeting

DO's

  • Emphasise more on facts and measurable benefits
  • Emphasize on objective proof of ROI, help them do a thorough evaluation
  • Tell them that you will come back if you don’t have a good answer for a question

DONT's

  • Avoid rushing them, be polite and patient
  • Avoid phrases like ‘do not worry about’, ‘no one compares to’ etc.
  • Don’t depend too much on anecdotal evidence, it reduces their confidence

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Matthew 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 Matthew

  • 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 Matthew move?

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

  • If they believe that they have analyzed the situation well, they can take a little risk.

You And Matthew

Personality Compatibility


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