Darren Pettyjohn

About

As Chief Sales & Marketing Officer and Co-Founder of Wister Insurance®, Darren Pettyjohn brings over 15 years of experience in risk management and insurance innovation. He is also the Co-Founder of Proper Insurance® (est. 2014) and Waivo® (est. 2020), and is widely recognized as a leading expert in the short-term vacation rental industry.

Darren has played a pivotal role in shaping modern insurance solutions for vacation rental property managers and owners across the United States. Under his leadership, Proper Insurance quickly scaled to insure tens of thousands of properties nationwide, helping define a new standard for coverage in the rapidly evolving short-term rental market.

A proven organization and team builder, Darren has developed successful businesses across disability insurance, marine cargo insurance, and vacation rental insurance. His career includes leadership roles at companies such as CBIZ and Trade Risk Guaranty, where he built a strong foundation in complex risk solutions before launching his own ventures.

At Wister, Darren leads with a clear and disciplined philosophy: discover the problem first, find a better solution, and finish with exceptional service—an approach that continues to drive innovation and customer-focused outcomes.

Darren holds a Bachelor of Science in Marketing from Montana State University-Bozeman and began his career in the insurance space shortly after.

He lives in Bozeman, Montana with his wife and their two sons. Outside of work, Darren enjoys fly fishing, skiing, and spending time outdoors with his family.