Episode 25: CEO, Woody Bradford

E25: Woody Bradford is Chief Executive Officer and Chair of the Board at Conning, a global investment firm founded in 1912 with a long history of serving the insurance industry.

Prior to joining Conning, Woody was an Operating Partner with Advent International, a global private equity firm.

Previously, he spent 12 years at Putnam Investments where he held multiple roles, including Head of Corporate Development and Chief Operating Officer of Global Distribution.

He is a graduate of Worcester Polytechnic Institute and of the Harvard Business School, where he graduated as a Baker Scholar.

He is a member of the Worcester Polytechnic Institute (“WPI”) Board of Trustees and participates on The Greater Boston Food Bank Emeriti Board, where he has served as Chair of the Board.

Woody Bradford’s LinkedIn Profile



  • Woody’s personal story of helping establish the first food bank in Maine when he was a teenager.
  • The bet he took that ended up with him getting into Harvard Business School.
  • The unique distinction of graduating as a Harvard Baker Scholar (top 5%) and the study skills he used to achieve it.
  • The skill Woody developed to create his own luck.
  • The surprising career strategy that helped him find his way to the Financial Services industry.
  • Why humility is the one trait he’d like to instill in every employee.
  • What important things Conning is doing to prepare for the workforce of the future.
  • How individuals from under-represented groups have distinguished themselves as potential future leaders, including C-suite positions, and the encouragement they offer to others with similar aspirations.
  • A helpful resource for having uncomfortable conversations.
  • The one word you should keep in mind when presenting your idea to the C-Suite.
  • A positive strategy to use with an employee who is feeling burned out.
  • Books for inspiration.
  • How to improve your mental and physical health.
  • Woody’s favorite Metallica album.


What characteristics should you look for in a mentor:

  • Someone who can give you honest feedback.
  • Someone who can point you in a direction that helps you think through your strengths and weaknesses and find opportunities in an organization.

Advice for people in under-represented groups in the C-Suite:

  • Do your job well.
  • Try to be in an organization that understands and practices diversity and inclusion.
  • Find a manager or a mentor who values you and who will give you opportunities.


"Allow people to bring their whole selves to work."

"I learned to be ruthless about time management. There's no way you can do everything. You must be able to decide what's important and what's not.


Uncomfortable Conversations with a Black Man, Emmanuel Acho,


Why We Sleep, Matthew Walker

How Not to Die, Michael Greger

Indianapolis, Lynn Vincent and Sara Vladic

Jaws: The U.S.S. Indianapolis Speech

Robert Ludlum books

Endurance: Shackleton’s Incredible Voyage, Alfred Lansing

Metallica Black Album

Pyramid Principle (the book he’s gifted most), Barbara Minto


Apply to be on the show


Connect with Ben: