Waivo’s Executive Team

Waivo’s Success Starts with Leadership.

Scott Wolf

Chief Executive Officer

Scott began his insurance career in 1988, after graduating from Harvard University cum laude in Economics.

As the President of NAIS, Inc., Scott guided the Wolf Innkeepers Insurance Program, through organic growth and acquisitions, into the largest insurer of B&B and Country Inns in the US.

In 2008, Scott facilitated the acquisition of the Innkeepers Program by CBIZ, a publicly traded national insurance broker, and subsequently became the President of Program Insurance for CBIZ.

From 2008 to 2016, Scott managed CBIZ’s insurance programs for wineries, paddle sports, and the former Wolf’s Insurance For Innkeepers Program. In 2012, Scott created, developed, and managed the hugely successful Vacation Rental Insurance Program.

Throughout his career, Scott has been an expert source on insurance for publications such as the New York Times and numerous insurance journals.

Scott is highly respected in the international insurance industry, having worked extensively with Lloyd’s of London, Swiss Re, and Munich Re in London, the Caymans, and the US.

Scott and his wife Mary are the parents of three and reside in Southwest Montana where they enjoy the Big Sky country when not traveling the globe to visit their children. Scott is an avid outdoorsman and spends as much time in the field both at home and abroad as possible.

Resume Highlights:

  • Graduate: Harvard University, Bachelor of Science in Economics
  • CEO: Proper Insurance & Wister Insurance
  • Executive Vice President: CBIZ
  • President: Wolf Innkeeper’s Insurance Program
  • Basketball: Harvard University
  • Chairman: Legion Baseball
  • Eagle Scout

Darren Pettyjohn

Chief Operating Officer

As the senior operations officer, Darren brings 20 years of risk management experience to the Waivo executive team. Darren is an organization and team builder, having helped build successful businesses in the field of disability insurance, marine cargo insurance, and vacation rental insurance.

With Darren’s leadership and oversight, Waivo follows a simple three-point operational plan: Discover the problem first, find a better solution, and finish with service.

Darren is married and the father of two boys and a baby girl. When Darren’s not working on insurance or spending time with his family, he is passionate about fly fishing, skiing, and all things outdoors.

Resume Highlights:

  • Graduate: Montana State University, Bachelor of Science in Marketing
  • President: Habitat for Humanity Campus Chapter
  • Co-Founder: Proper Insurance & Wister Insurance
  • Co-Founder: Nonprofit, Found Guilty
  • Board Member: Rent Responsibly
  • Author: VRM Intel
  • Volunteer: Salvation Army

Michael Zimmerman

Chief Financial Officer

As the senior financial officer, Mike brings over 30 years of financial and risk management experience to the Waivo executive team. Mike is an entrepreneur and operational guru, having built successful businesses in hospitality insurance, vacation rental insurance, tax and consulting for businesses and individuals, and investment rental properties.

Mike is married and the father of two daughters. His hobbies include competitive and tournament pickleball, and anything outdoors including hunting, fishing, kayaking, shooting, hiking, and skiing.

Resume Highlights:

  • Graduate: Virginia Tech, Bachelor of Science in Accounting
  • Certified Public Accountant
  • Surplus Lines Insurance Producer
  • Co-Founder: Proper Insurance & Wister Insurance
  • Past President and Board of Entrepreneur Council of Frederick County for 18 years
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