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Jesse Whitcomb


I grew up skiing and recreating on the central East Coast, watching my father serve as Director of Risk Management for 3 local ski resorts and running an outdoor school with a focus on high adventure. I started working in the outdoor recreation industry before I could legally drive, primarily "pushing rubber" (rafting) down the Shenandoah and Youghiogheny rivers in the summer and working at the local ski resorts in the winter. 


After college and several positions within the outdoor recreational industry, I found one that I was truly passionate about - ski resort insurance.   I joined the Wells Fargo Special Risks team (now Safehold Special Risks) in 2012 and the Mountain Guard Insurance Program in 2018 handling claims, litigation management and loss control which provided a segue to launch this next chapter.

Skiing and high adventure sports are in my blood.  My passion and knowledge have played a pivotal role in my success handling insurance claims and building relationships across North America.​


Tiffany Whitcomb

The mountains are a big part of my life and Jesse's.  In fact, our first date and Jesse's proposal both took place on the top of a mountain. 

I grew up in Massachusetts in a town with a small ski area.  Although the ski area wasn't the biggest of mountains, it was my 2nd home growing up.  My dad taught me to ski when I was 3 years old and I simply fell in love with it.  My enjoyment of the sport continued throughout my childhood, as you would typically find me on the slopes on school nights and weekends.   
Once in college, I followed my dad’s passion of entrepreneurship as I earned a Bachelors degree in Business - Entrepreneurship from the University of New Hampshire.  But don’t let that fool you, I selected UNH to keep me close to the mountains. 
Post-college I navigated my passion for sports and business and became a Sports
 Director and then a Business-Entrepreneurship teacher for over 10 years.  Now, you will find me mentoring new teachers through my professional development company and working on the business operations for Whitcomb Resolution.  When we do have a free moment, you can find Jesse and myself hanging with our 3 young daughters and our vizsla dog named Brewski - yes, our pup's name speaks exactly to how much the two of us love this industry  (and another tasty industry)!

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