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Episode 1: Matt Winter – The Uncharted Course to Career Management


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Matt Winter is the retired president of The Allstate Corporation and retired chief executive officer of Allstate Life Insurance Company.

During our link-up, Matt shares valuable lessons from his journey during his time in the Military, AIG during some of America’s most difficult financial times, as well as how he drove change at the Allstate Insurance company.

Most significant is Matt’s approach to career management, The Unchartered Course, or what his Army superior instructed him to do, “saw the wood in front of you.”  Matt’s principles and stories help bring this to life in terms of practical application.

Detailed Show Notes

Early Life Overview [2:00]

  • Early education – Wildlife Management and Forestry (who knew?)
  • Military Life
  • Law School program within the Army and Ft. Dix as a prosecutor
  • Moves into becoming a criminal defense attorney
  • Shifts into a career in insurance by starting as an attorney within an insurance company

Matt’s Keys to Career Management [16:00]

  • The idea of meritocracy: Matt received counsel from his General to “saw the wood in front of you, you are given a task, pay attention to that task and do it flawlessly.” Matt elaborates on this in terms of how he became an opportunist in managing his career with a focus on three things:
    • Could he learn from the role?
    • Did he like, respect and trust the people he worked with.
    • Something he could do and make a positive impact.
  • Don’t change what you do, change where you are. Matt discusses that if you are not in an environment where the practice of meritocracy and doing the right things has its own rewards, then you should change environments versus changing yourself.

Assuming the responsibility of the Allstate Agency distribution system.  [24:00]

  • Matt spends time talking through his initial assessment of the changes required, the most significant of which was demonstrating more respect of the agents to the agents. Further, Matt discusses his personal respect for entrepreneurs more broadly.

The introduction of diversity into the Allstate Agency distribution system.  [34:00]

  • Matt changed the model, introducing a system where agents were asked “what size do you want to be,” a counter-cultural shift from the traditional “one-size-fits-all” model.

Matt discusses two myths about entrepreneurship [38:00]

  • All entrepreneurs are motivated by money. Matt counters with several points such as the importance of money, cash flow, etc. and that the motivators vary.
  • Entrepreneurs don’t need a feeling of affiliation or support. Matt counters that this is not true.  Further, he mentioned a phrase started in a prior role that people need to feel “in business for themselves, but not by themselves.”

Matt discusses his role at AIG during the financial crises in 2007-2008.  [42:45]

  • As he describes it, he ran most of the “toxic” assets at the time. Running operations in 162 countries (his first international job by the way), he mentions that he learned to:
    • “Let go,” as the reality is that you cannot control everything – counter to your original thinking growing up into the CEO role, which is that you must dive deep into everything.
    • Taught him a different style of leadership – get great people in place, give them guidance, tools, and resources and let them go.
    • “Treat people as if they were what they ought to be and you will help them become what they are capable of becoming”- Goethe
    • Framing the work as a noble purpose and weathering through a tough time.

Retirement [52:30]

  • Matt speaks to what he has retired to and reflects on the reality that balance had gotten out of whack during his career and some of the things he has done since.
    • Giving more time to community and family.
    • He and his family have started a foundation together, directing funds together, allowing his children to learn philanthropy.
    • He and his wife are active trainers in a non-violence curriculum that follows the principles of Dr. Martin Luther King, working with Bernard Lafayette.
    • Took a seven-day silent meditation retreat.

Stress and self-care [64:00]

  • Matt expresses that it is a fallacy that you can just deal with this. People need active stress management, it needs to be managed consciously.

Matt Winter’s Bio

As of February 2018, Matthew Winter is the retired president of The Allstate Corporation and retired chief executive officer of Allstate Life Insurance Company. During his tenure, Matt led all business operations and distribution for the Allstate Personal Lines (APL) business, which includes 15 field offices located across the United States and in Canada.

Matt joined Allstate in 2009 as president and CEO of Allstate Financial. In 2012, he was named president of Allstate Auto, Home and Agencies and was promoted in 2014 to the president of The Allstate Corporation and CEO of Allstate Life Insurance Company.

Before joining Allstate, Matt served as vice chairman of American International Group. He also served as president and CEO for AIG’s American General domestic life companies; as executive vice president at Massachusetts Mutual Life Insurance Company; and as vice president and chief ethics and corporate compliance officer for Connecticut Mutual Life Insurance Company.

Previously, Matt spent more than 12 years on active duty with the United States Army. He earned a Bachelor of Science from the University of Michigan, his JD from the Albany Law School of Union University, and a Master of Laws from the University of Virginia School of Law. He is also a graduate of the Harvard Business School Advanced Management Program.

In addition to Feeding America’s national board, Matt currently serves on the boards of directors of H&R Block and the ADT Corporation.

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