Trail to onX: Kaitlyn Jeszenka

Everyone’s trail to onX is a little different, but whether a senior executive, a fixed-term customer experience agent, or somewhere in between, we’re a company of passionate professionals with a deep love for the outdoors. We’re also proud to have a range of voices across our leadership corps, including a strong commitment to women in leadership from the CEO on down. This series highlights some of the female leaders at onX in a range of departments and roles. Read more and find out how to join the team at

Kaitlyn Jeszenka, Manager II, Software Development

Basecamp Missoula

Tell us a little bit about your professional “trail” to onX.

I joined onX shortly after college. At the time, I was running a mobile app business and met Eric Siegfried, the founder of onX, at a networking event where he showed us his prototype of the Hunt App he had built himself. The prototype was rough, but I was blown away at the concept. I later learned my father had already been using the chip in his GPS for years. I started at onX as one of our first QA engineers and quickly transitioned to a web developer working on our Webmap product for several years before moving up to manage our Backcountry engineering team. 

What’s the most exciting part of your job?

As a developer, I love the endorphin rush you get after solving a really difficult bug. But I also love hearing friends and family talk about using something you’ve built. After moving into leadership and management, I’ve found it pretty amazing to watch those you’ve mentored and coached grow and develop into successful and confident developers.

onX software development manager Kaitlyn Jeszenka

When you began your career, did you ever imagine that you would have a leadership role in this profession/organization?

It was always a hope of mine to eventually move into a leadership role, either as a senior engineer or management. I certainly wasn’t imagining it would happen quite so quickly when I decided to transition into management, but then the Backcountry App was born and we needed help managing it.

How do you adventure using the onX App (and which one do you primarily use)?

I’ve always enjoyed hiking and skiing, so I was excited to learn we were making the Backcountry App. While not a hunter myself, I’ve grown up around hunting and also have done my fair share of off-roading, but the Backcountry App is more up my alley. 

Are you a morning person or a night owl?

Night owl, definitely!

What was your first job?

I started as a banquet server during school at our local Hilton conference center.

What’s something you find challenging about your work?

I think the nature of tech always changing and rapidly improving can be challenging. It can be overwhelming at times, hard to keep up with or stay ahead of competitors, and is impossible to keep tabs on every new innovation. However, I think that’s also what makes working in tech so interesting—it’s never dull if you’re innovating, and I love working in a field that constantly challenges and pushes me. Plus it’s good for job security!

onX software development manager Kaitlyn Jeszenka.

What are you most excited about professionally for the upcoming year? 

We just released a big feature with our Beacon Guidebooks for backcountry skiers. I think we’re set up to do well this winter with this addition and the other snow features we’ve added, so I’m very excited to see how this carries us into next year. It will also be exciting to see how we apply this work and continue this momentum forward into our summer activities for Backcountry.

What’s the top destination on your must-visit list?

I would love to visit Australia and New Zealand.

What advice would you give young women in the workplace?

Mentorship. That has been one of the biggest impacts in helping me grow as a leader and engineer throughout my career. Early in your career, finding a good mentor can have an immense impact in helping you build up your technical and soft skills, as well as connecting you with others that can also help on your journey. Once you’re further into your career, I’ve found being a mentor has also helped me grow in ways I wasn’t anticipating. In the day-to-day, we often forget how far we’ve come since our early days and mentoring someone is a huge reminder of just how much you’ve learned and grown yourself. This was immensely helpful in improving my Imposter Syndrome. What also helped me with Imposter Syndrome was learning more about it and learning that nearly everyone around you has experienced it in some fashion, regardless of gender.

What is your favorite thing about working for onX?

I love how we’ve made getting outdoors a primary part of our culture. Not only does that encourage a healthy work life balance, but it’s so cool to use what we’ve built to get out and have fun.