About Us
Wayfinder Core Team

Shelly Jackson

Executive Assistant
Shelly Jackson

Shelly's professional journey has been anything but conventional—blending education, entrepreneurship, adventure, and global exploration. She began her career as an elementary educator, spending seven years teaching second grade at a Title I International Baccalaureate school in Colorado Springs, CO. When the opportunity arose to own a local coffee shop, Shelly embraced her entrepreneurial spirit and became a small business owner, fostering connections within her community.

But when the pandemic changed her course in 2020, Shelly embarked on an adventurous chapter of self-discovery. One of her most remarkable experiences took her to Antarctica, where she worked at McMurdo Station, training grantees and staff to operate PistenBully tracked snow machines. This wild and transformative journey fueled her passion for exploration. After leaving Antarctica, she traveled extensively across the southern hemisphere, soaking in diverse cultures and landscapes across New Zealand and Indonesia.

Returning to the US, Shelly utilized her organizational expertise and people-first mindset as an Executive Assistant, first for a private equity firm in Dallas, TX, and later for Wayfinder in her dream location of Bend, OR. Her role reflects her knack for cultivating meaningful relationships and managing complex operations with precision.

Shelly holds a Bachelor of Science in Elementary Education from the University of Wisconsin-Oshkosh and a Master’s in Curriculum and Instruction from the University of Colorado Springs. An avid outdoor enthusiast and trail runner, she has traveled to six of the seven continents, with Africa next on her list. She is now looking forward to her most exciting journey yet—motherhood. 

"My purpose is to cultivate relationships, embrace new challenges, and create impactful experiences."

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