Cailey Heffley

Trip Prep Specialist


Caily Heffley

Where do you call home and what were you doing before Backroads?

I am from Albany, NY. Before Backroads I lived in Ireland and went to school for my Masters in International Tourism. Previous to that I worked as a steward on a small cruise ship.

What about the TPS position interested you?

What initially caught my eye about the TPS position was that it was a non-guest facing behind the scenes role. It is rare to find a position in a travel company that allows you to remain behind the scenes while still traveling. I am more interested in the operations and logistics of tourism and saw the TPS role as a great learning opportunity with potential to grow in the company.

Where did you work as a TPS this season?

This past summer I worked in Jackson Hole, WY – the biggest region in North America and in the fall I worked in Charleston, SC.

What were the overall highlights of the job/lifestyle?

The biggest highlight of the lifestyle is getting to live in an amazing place for months at a time with equally amazing coworkers. The TPS position allows you to really get involved with the community you are living in if you so choose. The job itself includes a lot of independence and responsibility. With that comes the flexibility to structure your own workweek, meaning there are endless opportunities for adventure if you can manage your time well. Overall the TPS role offers more stability and routine than other field positions and the opportunity to really settle down and explore a new place.

What was your best memory from your summer working for a travel company?

The best part of my summer is where I had the opportunity to live. Living in Jackson Hole, WY is something some only dream of – which can be said of all Backroads regions! For me Jackson was an unexpected surprise and I loved the access to the outdoors with hiking, biking, and rafting opportunities just minutes from the Field Staff house. It is also one of the busiest regions in the company and there were always people around to go on adventures with from floating down the creek in town to camping in Yellowstone!

What were some of the challenges of the job/lifestyle?

Working in a busy region has a lot of benefits, but also comes with some challenges. One of my biggest challenges of the summer was keeping track of everything. With a lot of people in and out of the warehouse and vans/trailers equipment often disappeared. It was helpful to be present when Trip Leaders returned from trips to ensure everything made it back in the correct place. I also learned to begin each prep day expecting the unexpected! Issues and challenges often popped up out of nowhere and it was important to be flexible and patient with equipment and coworkers. Another key challenge stems from the fact that the TPS role is still relatively new within the company. I had to explain to some Trip Leaders exactly what the position entailed. It was important to set expectations early on and not over commit myself to duties outside of the role. TPSs are often the only constant in a region and the expectations we set play a role for how the season will progress.


Tell us about TPS training and the skills you learned as a TPS in the field!

Coming in with limited bike skills I knew I had a lot to learn in training. Luckily the head bike mechanics are not only some of the most knowledgeable and patient individuals at Backroads but also the kindest. I felt supported throughout the training process and encouraged that I would develop the hard skills necessary for the job. In the field, I was fortunate to work with a team of TPSs and continued to learn from them. Apart from the bike skills I also learned a lot about communication in the field. It is not rare to work with different leaders each week and with that comes a variety of work and communication styles. As a TPS it is easy to get into a work routine, but it is also important to remain flexible to changes. Overall training is a great opportunity to learn about the company, what to expect in the field, and the hard skills necessary to be successful in the role. It’s a busy ten days but I left training feeling as though I would be successful in the field. The most important quality someone can have coming into training is with a positive and open mind.


What do you plan on doing next season?

I plan to remain part of the operations side of things and either return as a second year TPS or move into an Operations Expert role.


Do you have any insight or advice for anyone interested in applying for this position?

Do it! The TPS role is a great way to learn about what goes on behind the scenes at Backroads and you’ll gain a lot of experience that will serve you well if you chose to move up within the company. My biggest piece of advice would be not to let limited bike experience hold you back from applying. If you are mechanically inclined (and patient) the bike skills can be learned. If you are an independent, responsible, and resourceful individual you will do well in this position.


TPSs are greatly appreciated by others in the field and while we don’t specifically go on trips the work we do helps to make them run smoothly. TPSs often know the region the best and are a key point person for those with questions. During a typical season, Trip Leaders move throughout regions – which are all unique and have their own ways of operating. As a TPS you know your region the best and can help set other Field Staff up for success not only on prep days but also in the field. It’s very satisfying knowing the job has a real impact on the guest experience even if we are not present on trips!


Overall experience working for a company like Backroads? What’s it like?

Backroads really encourages open and honest feedback with the intent to help each employee grow both in their position and personally. Being surrounded on a daily basis by people who are striving to be their best is infectious. I have yet to meet a Backroads employee who is not excited about their job or life in general! It is a great community to be a part of and the saying “work hard, play hard” has never been more accurate than in Backroads!