Inside Drift: Why We Have Sabbaticals (and Where Our Team Has Gone)

Many of Drift’s Leadership Principles focus on seizing opportunities to grow and staying curious. Our Drift team also works REALLY hard. That’s why in 2017, we announced a very unique Drift perk for those who have been at the company for at least three years: sabbaticals.

Our sabbatical program provides employees with up to four weeks of paid time off to rest, rejuvenate, and try new experiences. Not to mention, it gives them the chance to exercise our Leadership Principles in their own way outside of work, too.

Over the past few years, Drifters have embarked on some very exciting adventures. I recently chatted with a few members of our team who used their time off in some pretty special ways. Here are some of their trip highlights and lessons learned along the way.

Matt Bilotti

Role at Drift

I’ve worked at Drift for six years and currently work on the product team.

Where He Went on Sabbatical

I booked a one-way trip into Bangkok where I spent three days, and then another one-way trip into Ho Chi Minh city, in South Vietnam. I drove on a motorbike, solo, through the entire country.

Trip Highlights

My favorite part of my trip was being in a new place and meeting different people. I would sometimes just take a random turn here and there to explore, without the weight of any major responsibilities.

Lessons Learned

My whole mode of operation has always been excessive planning. I would over-plan stuff in the product team, and we would wind up not getting to it, which would frustrate me.

But on my trip, I didn’t know any of the places I was going to stay at beforehand. I didn’t know how I was going to get from point A to point B. I was able to just go with the flow and realize I could figure it out along the way. Now in my role, I still do need to plan ahead, but I think the realization that it’s okay not to have everything planned out perfectly was a good lesson for me.

One more thing I’d like to add: Having that month off gave me the chance to do something I’ve always wanted to do, even back when I was in college. If you find yourself in a similar situation, I recommend documenting your time in some way, whether that’s a blog post like I did or journaling because it will be meaningful to look back on one day.

Frank Schepps

Role at Drift

I’ve worked at Drift for almost four years and am on the operations team.

Where He Went on Sabbatical

I went to Hawaii. I stayed with my sister and brother-in-law in Oahu, and then I traveled to the Big Island of Hawaii and Maui. Half of my time there was my sabbatical and for the other half, I utilized Drift’s digital-first policy and worked from a new location.

Trip Highlights

I loved going on the Haleakalā volcano on Maui. But, in general, I just really enjoyed the freedom of doing exactly what I wanted to do each day. You get used to a continual schedule of waking up Monday through Friday and logging into work, doing your work, and then having two days off on the weekend.

It was refreshing to wake up and read, or watch five episodes of Below Deck, or go sit on the beach. This was something I hadn’t been able to do in a long time – and something I truly appreciated. Plus, it was nice knowing that it wasn’t just a week-long break. I had a whole month.

Lessons Learned

In my role, there’s a lot that happens and changes over the years. Taking a step away forced me to rely on my teammates and realize that some of what I was doing could be done even better, or that I didn’t even need to be doing those things at all.

When I first started at Drift, I heard about the sabbatical perk and I thought three years is so far away. But, every day I was so caught up in the minutiae of everything that when I got to three years, a sabbatical was a really nice reset. And when I returned to work, it was like a new beginning. I was mentally much more relaxed and had a completely different perspective.

Amanda Walters

Role at Drift

I’ve worked at Drift for four years and am a solutions consultant.

Where She Went on Sabbatical

I went to Charleston, South Carolina and stayed in an Airbnb.

Trip Highlights

My sabbatical was a great opportunity to experience life in a different part of the country. I grew up in New England and have lived in Boston since graduating college. So I haven’t spent a ton of time down south. There’s a lot of history there, and Charleston is such a cool city.

After college graduation, I started my first job right out of the gate and have been working ever since. On sabbatical, it was great to wake up and feel like I could do anything I wanted. I worked out a ton, read a bunch of books, and spent time at the beach with my dog.

Lessons Learned

I’ve never been good at planning long vacations. In a sales role, you have to be very responsive. I started to struggle with cutting things off at the end of the day. Taking a sabbatical was a nice forcing function to reset and come back to work with a better work-life balance – and really focus on turning off at the end of the day. Although work at Drift is fast-paced, I realized I can’t be my best self if I’m not taking time for myself.

Final Thoughts

A sabbatical is an incredible opportunity for our team to take a well-deserved break, partake in new experiences, learn something new, be creative, and explore the world (or your backyard). This time off is an incredible benefit of working at Drift and one that we hope everyone takes advantage of when the time comes.

We love celebrating our Drifters and their hard work, and it’s amazing to see what the team does with this special perk. Plus, it gives us inspiration for our own sabbaticals someday 🌴

What would you do with a month off?!

Want to join the team? We’re hiring. Check out all our open positions here.