Executive Team

Smarter coverage, backed by people who know your business.

Scott Wolf

Chief Executive Officer

    • Graduate: Harvard University, Bachelor of Science in Economics

    • Co-Founder: Proper Insurance®

    • Co-Founder: Waivo®

    • Executive Vice President: CBIZ

    • President: Wolf Innkeeper’s Insurance Program

    • Basketball: Harvard University

    • Chairman: Legion Baseball

    • Eagle Scout

  • 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 home and abroad as possible.

Mike Zimmerman

Chief Financial Officer

    • Graduate: Virginia Tech, Bachelor of Science in Accounting

    • Certified Public Accountant

    • Surplus Lines Insurance Producer

    • Co-Founder:Proper Insurance®

    • Co-Founder:Waivo®

    • Past President and Board of Entrepreneur Council: Frederick County for 18 years

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

Darren Pettyjohn

Chief Sales & Marketing Officer

    • Graduate: Montana State University, Bachelor of Science in Marketing

    • President: Habitat for Humanity Campus Chapter

    • Co-Founder: Proper Insurance®

    • Co-Founder: Waivo®

    • Board Member: Rent Responsibly

    • Author: VRM Intel

    • Volunteer: Salvation Army

  • As the Chief Sales & Marketing Officer, Darren brings 15 years of risk management experience to the Wister 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, Wister 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. When Darren’s not working on insurance or spending time with his family, he is passionate about fly fishing, skiing, and all things outdoors.

Christy Wolf

Chief Product Officer

    • Graduate: University of Maryland, Bachelor of Science in Business

    • Graduate: PIA Insurance Program at Drake University

    • Founder: Innkeeper’s Insurance Review

    • Co-Founder: Wolf Innkeeper’s Insurance Program

    • Program Manager: CBIZ

    • Certified Insurance Counselor, CIC

    • Head Coach: Boys Basketball

    • Volunteer: All Things Equine

  • 1984, after graduating from the University of Maryland with dual degrees, Christy Wolf began her career with the Fidelity & Deposit Company as a surety, fidelity and judicial bond underwriter; she was the first female hired in this capacity by the Baltimore office.

    Christy co-founded the Wolf Innkeepers Insurance Program in 1989, a national program for the Hospitality industry insuring B&B’s, Inns, Boutique Hotels, Resorts, and Event Centers. Prior to the program’s acquisition by CBIZ in 2008, the Wolf Insurance For Innkeepers program was endorsed by local, state, regional, and national associations and became the largest insurer of bed & breakfasts in the US.

    After the acquisition, Christy was retained to run the program. In 2018, Christy opened Innkeepers Insurance Review, an insurance consulting firm for the Hospitality Industry. For decades, Christy has been a thought leader in the Hospitality industry, having her expertise and advice featured in countless publications.

    Christy is now proud to be the CSO of Wister Insurance.

    Together with her husband and 2 children, Christy operates a small farm in the foothills of Western Maryland. She is very active in 4-H and is the leader of the Frederick County 4-H Goat and Equine Clubs.

    Christy is active at church and leads the Youth Group, Youth Choir, and Mission trips. She coaches youth basketball and enjoys boating, the outdoors, sports, and being on the farm.

Jackie Bachman

Chief Operations Officer

    • Graduate: Belmont University, Bachelor of Business Administration

    • Surplus Lines Insurance Producer

    • International Director of Sales: Waivo Damage Protection

    • Account Executive: Waivo Damage Protection, Wister Insurance

    • Co-Owner: Tru North Cafe (Montana)

    • Worship Leader: Journey Church (Montana)

    • Internships: The Grammy Awards, The Country Music Hall of Fame, Sony Music Entertainment, Capitol Christian Music Group

    • Coach: Intramural Girls Lacrosse

  • As the Chief Operations Officer at Wister Insurance, Jackie helps vacation rental managers across the country navigate insurance and risk in a way that actually makes sense. She spends her days improving processes, supporting the team, and making sure clients have a smooth experience from their first quote through renewal and beyond.

     

    Before moving into operations, she worked directly with vacation rental managers as an Account Executive at Wister and previously led the sales team at Waivo Damage Protection. This hands-on experience over the past 5 years has helped her understand what Wister’s clients are dealing with day to day.

     

    Jackie is based in Bozeman, Montana, where she enjoys spending time outdoors with her husband and two stepdaughters. She loves songwriting and playing music, traveling, skiing, hiking, and getting out on the water - whether on mountain lakes or Montana’s blue-ribbon trout streams. 

Alyssa Piliero

Chief Compliance Officer

    • Graduate: Virginia Tech, Bachelor of Science in Meteorology

    • Graduate: North Carolina State University, Master of Atmospheric Science 

    • Data analyst in R, Fortran and Matlab

  • As the Chief Compliance Officer, Alyssa brings a data-driven approach to regulatory oversight and risk management. With five years of experience in federal air quality compliance, she has worked closely with state and federal agencies to interpret complex regulatory frameworks and ensure national adherence to evolving standards. Alyssa is a skilled analyst with experience using R and modern AI tools to interpret large datasets, streamline compliance, and support executive decision-making. 

    Outside of work, Alyssa is married and the mother of one boy. She enjoys yoga, spending time outdoors biking and hiking, and spending time with friends and family. 

The Wister Difference

We view insurance as a strategic risk mitigation plan. Our three-pillar approach ensures that we meet the unique needs of our vacation rental managers and co-hosts with precision and reliability. We are dedicated policymakers.

Identify

Every vacation rental manager or co-host has unique insurance needs. Our job is to understand your business operations and identify your specific risks.

Customize

Insurance is a transfer of risk, and every business has a different risk tolerance level. A customized coverage plan is essential for the right protection.

Deliver

When you purchase insurance, you are purchasing a future claims experience. We customize your insurance and deliver it with world-class service.

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