Remote work isn’t just a management fad that we’re trying out at Jilt; it’s been in our DNA since day one. Being a fully distributed company means we make sure our team members feel they can fit work into their lives, and not the other way around. It also means, however, that we can get a little lonely without some in-person bonding time.
So once each year, we bring our whole team together to explore, play games, eat delicious food, and simply enjoy one another’s company.
Our main goals for the retreat are to get to know each other, have fun, and relax, but this year we also put more emphasis on learning something new together. Past retreats have all been in the U.S., but as we continue to grow the team internationally, we expanded our location search outside America, as well.
This year, we decided on Scotland, a place most people on our team had never been! Getting to bring the team together to explore a new corner of the world together was a really beautiful thing.
At just around 20 people, we’re still at the point where it’s just barely feasible to get one big house for everyone. Similar to years past, we really don’t want to compromise on our policy of giving every team member their own bedroom and bathroom. As remote workers, we’re used to having a lot of alone time—and on top of that, it’s just plain professional and empathetic to give people their own space to unwind and recharge after a long day of team bonding!
We generally followed the same location and venue selection process as last year, so of course we assumed we’d have plenty of time. Spoiler alert: You rarely have as much time as you think. We quickly transitioned from, “We got this” to “Oh no, our retreat is really soon and we have no place to stay!” at the end of last year.
Through some frantic late night AirBnB scrolling, we were very lucky to come across Dunskey Estate in Portpatrick, Scotland. In the future, we plan to have several potential locations for our next retreat lined up nine or 10 months before the retreat. (Yes, that means we’re already scouting for our 2020 retreat!)
We weren’t necessarily planning on Europe while looking for a spot for the week—we focus first on the house itself being big and comfortable enough for everyone, and then factor in location after that. We actually ended up breaking a few of our ideal location guidelines for this year’s trip (more on that later), but after my scouting trip to Dunskey I knew those tradeoffs would be worth it. Additionally, we were planning to grow the team in between booking Dunskey and the actual retreat week. So, we wanted a place that could expand with us if needed. Startup hiring can be somewhat unpredictable, so I highly recommend building in that flexibility.
This year, that meant we were able to bring our newest team member, Artan, out to join us at the last minute for his very first week on the team. Quite the first week! 😂
As I mentioned above, we broke a few of our ideal location guidelines in order to make our magical Scottish week a reality for the team.
Longer than usual flight times for the majority of the team
We prefer to keep flight times within reason for the majority of the team. This year, with the bulk of us coming from North America, this meant most of the team was flying overnight, with at least one connection. To make all that extra travel worthwhile, we extended the length of the retreat. In years past we’ve had team members arrive on a Sunday and depart on Saturday—this year we had people fly out on Thursday evening, arriving Friday morning in Glasgow, and depart from Glasgow on the following Saturday morning. We booked a block of rooms at the Marriott in Glasgow for everyone to recover from jet lag that first night. While it made for a longer week, we felt strongly that having that first night in Glasgow to rest and recover individually before formally kicking things off on Saturday morning was essential to taking care of our team members both mentally and physically.
On the flip side, that extra length means being away from family for a longer time, and that can be really challenging/impossible for some team members. We made sure team members knew it was completely fine to shorten the trip if needed, especially for a couple people on the team who have very young (or even brand new!) children. We handled that on a case-by-case basis.
Longer than usual drive from major airport to Dunskey
Travel to get to retreats is already long for most team members, so we try to keep a driving distance of no more than one hour from the nearest major airport to wherever we’re spending the week. Dunskey ended up being about a three hour drive from Glasgow. But good news: The ride was absolutely stunning, so it certainly didn’t feel that long on the way out. We spent the entire time driving along the coast, passing by fields filled with frolicking sheep and lambs (omg, the lambs!), and listening to historical tidbits about the area from our driver. Anne from Dunskey had even sent along bags of homemade baked goods in case we got hungry along the way. The drive was actually a perfect way to settle into what was to be a week of stunning Scottish scenery.
More remote area vs. being near a city
For previous retreats, we’ve always found places that are located in or near at least a mid-sized city, which allows us to have easy access to grocery stores, activities, etc. Dunskey is far more secluded than we’ve done in the past, so we were a bit concerned about feeling cooped up. (Narrator: we did not!)
At Jilt, we like to “surprise and delight” our customers, which means going the extra mile to solve problems and bring a smile to our users’ faces. That philosophy is one we embrace internally, too. I really took this to heart for our 2019 retreat, and had several surprises (some big, some small) throughout the week for the team. My favorite part of the week was getting to see the team’s reactions!
These are a few of my favorite surprise and delight moments.
Swag bags waiting in Marriott rooms
Our designer, Kim, did some truly phenomenal work on our retreat swag this year, which resulted in us being decked out like this for a solid part of the week:
Improbable continuation of our Denny’s kickoff breakfast tradition
All of our retreats so far have started with a kickoff breakfast at cofounder Max’s favorite restaurant—Denny’s. Much to everyone’s shock, and Max’s outrageous delight, in December, Denny’s opened their first U.K. location a mere 15-minute drive from the Marriott. Clearly it was a sign. So on Friday morning, the whole lot of us rocked up to a suburban Scottish Denny’s, and only slightly overwhelmed the waitstaff. Every dish came with American flag toothpicks, and much hilarity ensued.
For the full Scottish experience, on our first night at Dunskey, we had a local bagpiper come out to the estate and surprise the team by playing for us as we came out onto the terrace for our welcome cocktail and appetizer hour. (Oh, we also had a welcome cocktail and appetizer hour.) The sun was just beginning to set, and Ali (whose family owns Dunskey and was our gracious host) had just finished leading us on a wonderful tour of the house. We were trying to keep the bagpiper a surprise, so we kept having to rush him around corners as the team was walking through the house. That’s definitely a favorite memory of mine.
We had two surprise picnics planned throughout the week. On Sunday, Ali took us on a guided walk of the grounds, and we ended in the walled garden. The team knew that part, but they did not know that two of Dunskey’s fabulous staff members, Aggie and Dave, were there waiting for us with hot dumpling soup, melted brie sandwiches, and heavenly brownies. Lady Beecher, the world’s best dog, graced us with her presence, and was kind enough to pose for some headshots while we ate.
Our second surprise picnic was after what we thought was another “walk” (in quotes because in reality it turned out to be a five mile hike). It all felt very Lord of the Rings, so of course our head of product, Beka, pulled up the soundtrack up on her phone, and we hiked along to that for a bit as one does:
In the middle of the hike, we rounded a corner to find a gorgeous coastline and Dunskey staff Aggie and Becky waiting with thermoses of coffee, roast beef sandwiches, and more of those heavenly brownies! Since this was our last day of the trip, we all sat quietly, gazing out over the ocean and contemplated how we could possibly reintegrate with normal society the next day. It was awesome.
Surprise turn down service
Who doesn’t want the greatest chocolate of all time, After Eights, on their pillow every night? (Actually it turns out Beka doesn’t, which is weird, but I wasn’t too mad because it meant I got a chocolate at night, plus her extra chocolate each morning. Good times.) This was a lovely little touch for the team to end each day on the right, sweet note!
Since we were a bit more secluded this year, we erred on the side of having more scheduled activities than on previous retreats. This kept everyone engaged and moving throughout the week. Our week included, but was not limited to:
Guided “walks” around the estate
The Dunskey Olympics
We usually try to do something new at each retreat. In 2016, we set the team loose at Disney World, two years ago we took over mission control at the Kennedy Space Center, and last year we dodged bears while zipping around a mountain on snowmobiles.
This year, we held the Dunksey Olympics, a four “sport” event that pitted us against each other in (mostly) good natured competition and was a ridiculous amount of fun. (And that’s coming from someone who is not the slightest bit athletic.)
Dunskey hooked us up with a great company who came out to the estate and ran an afternoon full of events. I split the team up into three smaller teams, making sure to put people who don’t typically work together on the same team, as well as making sure physical abilities were evenly distributed. (Though we learned we’ve got more than a few ex-athletes around—I am not one of them!)
We channeled our inner Katnisses for archery, conspired to bring Beka down in Zorb ball, hid behind giant inflatable shapes during laser tag, and learned that Justin and I make an unbeatable canoe racing duo. [Ed. note: 🙄]
My favorite way to live is with planned spontaneity. It took a little legwork beforehand, but we made sure to have a list of ad-hoc activities team members could easily set up depending on how they were feeling. This allowed the team to feel in control of their time, and use free time however they saw fit in the moment. For us, this list looked like this:
We made sure to leave plenty of blocks of free time in the schedule so the team could take advantage of these activities if they wanted to. That’s the beauty of planned spontaneity. If you wake up and feel like heading off-site to go horseback riding or clay pigeon shooting and trying your hand at trotting and getting a double cross back shot (not at the same time), you can. If you’d rather hang back by the fire and play a board game with coworkers, that’s fine, too.
Anne and Ali, the proprietors of Dunskey Estate, will tell you that one of the highlights of staying there is the food. They are absolutely, without question, correct on that count.
They have an in-house chef and source almost all of their ingredients direct from the property, which means we ate and drank like royalty all week.
Having all our meals catered was new for us this year. In previous years, we’ve usually mixed cooking for ourselves (we had a team potluck last year), takeout dinners, and team meals at restaurants. With the exception of the first night in Glasgow, where we all gathered at the hotel restaurant, and the kickoff breakfast at Denny’s, that wasn’t feasible this year.
The catering thing was, in a word, fantastic. Not only is the food at Dunskey as good as advertised, it took a lot of pressure off our team and allowed us to spend more time hanging out and bonding instead of cooking or driving to restaurants. (Plus, no question of whose responsibility it is to empty the dishwasher!)
Based on feedback from last year, we wanted to keep breakfast casual and self-serve. The idea was people would grab some food and head into the informal dining room (what are our lives, even?) to eat while working on customer support. Dunskey would also offer a hot breakfast option for those who wanted it.
In reality, more people than anticipated opted for the hot breakfast, which led to more people hanging out in the breakfast room while eating. That meant our planned support hour took a hit.
It wasn’t a disaster, by any means, but it’s something we’ll address in the future, if we do catered breakfasts again, by keeping the meal totally separate from work time.
Surprise. Picnics. For. Life. When not a surprise picnic, a gourmet buffet works too:
Cocktail and hors d’oeuvre hour
Yep, this was real life. For a week, at least. Almost every night we gathered out on the terrace to toast to another great day, and prepare ourselves for yet another memorable dinner. We made sure Dunskey included vegetarian appetizers and non-alcoholic cocktail options so everyone could partake. (We also discovered a Dunksey secret: You can access the drawing room directly from the terrace via a side window. Fun!)
Similar to last year, our nightly team dinners were some of the best times for bonding. As our team members work all across the world in our own spaces and places, it’s really such a special thing for us to be able to physically gather around a table and share a good meal with one another.
While last year we had several activities competing for the team’s attention post dinner (games room, movie theater, pool, etc.), there weren’t as many of those at Dunskey. Team members still brought their own board games and gathered to play most nights, but without a lot of the modern day bells and whistles, we were free to simply sit and talk with one another.
For a group that spends all day tethered to their electronics, the lack of screens (and often finicky wifi) was perfect for team bonding and relaxation. Dinners were, on average, three hours long, and people lingered far after that by the fire, or in the drawing room next door. It was magical!
While planning, I was a little concerned that having dinner in the same room every night would get to feel a bit monotonous. But Anne and the Dunskey staff transformed the room new themes each night, and we spent a few dinners in different spots around the estate, including:
After a brief hike through more magical fairytale land, we ended up on a beach, where Dave and Chef Oliver were waiting with a seaside BBQ! This was absolutely one of the highlights of the week:
Pub quiz in the library
Because the jocks shouldn’t get all the glory, we rounded out our Dunskey Olympics day with another friendly competition, one a bit more intellectual in nature. I divided the team up into smaller groups, and Ali drafted the trivia questions and played game show host for the night. Jury’s still out on whether ‘gridiron’ is an acceptable answer for “another name for American football….” [Ed. note: It’s not.]
Pizza and movie night in the theater room
Even in the best planned and executed retreats, energy naturally tends to take a dip mid-week. With that in mind, Anne and I decided one dinner would be a pizza and movie night.
Being in Scotland, obviously we only had one real movie choice: Monty Python and the Holy Grail. Coconuts were not provided, but we did have a feast of gourmet pizzas, a full bar set up, and the Dunksey staff even surprised us with fresh popcorn.
A “casual” farewell pasta feast
Last year, our final dinner was a bit more relaxed, and that worked well for the team, especially for those who had early departures the next day! We had a very early morning (6 AM wakeup call, woof) on Saturday in order to make it back to Glasgow in time for everyone’s flights, so we kept a similar plan for this year.
This is Dunskey, though, and as they’d showed us all week, they don’t take half measures! We shared a family style meal of several different types of pasta, played a hilarious dinner game that had us all acting extremely silly, had cocktails in the drawing room one last time, and headed to bed early.
The only miss in terms of food, based on our post-retreat team survey, were the snack options. After planning out the menu with Anne, I truly thought we’d be so stuffed from all our amazing meals that we wouldn’t even be looking for snacks at any point. False! Never skimp on the snacks. While there were snack options available, we could have done more here to make sure there was never a point in the day during which someone was left wanting for a snack. Lesson learned.
The main goal for retreats is bonding, but we’re still running a company and so we do manage to get some work done.
Despite what it may look like, it’s not all fun and games! Ok, it’s almost all fun and games, but it’s important to us not to leave our customers hanging. That’s why we scheduled an all-hands-on-deck, 90 minute support block every morning.
We had delays in getting started most days because of our team’s voracious appetite for cooked breakfast, as mentioned earlier. When those delays were paired with a significant increase in support volume due to the Mailchimp/Shopify breakup (what’s that? you haven’t heard? we can help! 😁), it made for a heavier workload than anticipated during the week. The team did some excellent work, though, and we also had a few team members who couldn’t come to Scotland due to family conflicts and pulled some serious weight from back home.
Based on feedback from last year, we switched things up a bit here. As the team grows, we’re constantly thinking about what scaling effectively and efficiently looks like. This year, instead of broad presentations about the company’s progress and goals, we had each head department share a brief retrospective of their Q1 goals, wins, and losses, as well as an upcoming overview of their goals for Q2, followed by a Q&A from the team.
We’re planning to keep iterating on this part of the retreat based on team feedback. Next year, for example, we’ll likely try to do a “year in review” session for each department, instead of focusing on a single quarter.
The hackathon has been a part of our team retreat from the very beginning, and this year we learned a few important things about scaling a hackathon for our changing team dynamics. Our post-retreat survey indicated that this was one of the least successful parts of the week.
In the past, we’ve simply split the team up into smaller groups, and assigned each group a specific project/area to work on. This year, however, we realized that as we continue to expand the team beyond just engineers, the groups can start to feel imbalanced. We’re planning to revisit how we run our hackathon and its purpose, and next year we’ll spend more time planning and making sure teams are balanced and projects are varied.
Another thing that made the hackathon a bit more challenging than usual this year was some of our “planned spontaneity” time conflicted with time we set aside for the hackathon. While our schedule was the same as prior years, the two offsite activities we had available (clay pigeon shooting and horseback riding) required a hard exit time. This made certain teams a bit more time-gated in their work, whereas others were not. This is something we’ll keep a closer eye on when crafting the itinerary for next year.
It’s funny to put our videographer in the “work” category, since having Sean around all week hardly felt like work for us! But shooting hours of video from our team retreat was specifically for the goal of showing the world what it’s like to work at Jilt.
Our team retreat is the perfect time to get that kind of video—otherwise it would just be a lot of footage of us sitting in our respective homes in our team onesies (yeah, we have those), typing away on our laptops. Sean made the official video for the Dunskey Estate, so he came highly recommended by our hosts—another spot on recommendation. Sean quickly felt like one of the team and was with us day in and day out, filming all week.
This year’s grand total was $90,838, so about $5,300 per person. That’s quite a jump from last year’s $3,300 per person, which is due to a few things:
- The majority of our team is based in North America, so we spent a lot more on flights than last year to get everyone to Europe.
- When we were making initial projections for the week, we thought we’d have 2-3 new team members onboard by the retreat, but recruiting timelines changed and this wasn’t the case. Additionally, we included the entire team in our planning headcount, but not everyone could make it! These things led to a lower headcount than we initially planned for.
- This grand total includes the cost of working with Sean for the week. While technically it was a retreat expense, we’re treating it more as a marketing/recruiting expense—our goal for all that footage is to show off our fabulous team!
The full breakdown:
- Flights: $16,846
- Lodging: $36,753
- Food/Drink: $17,462
- Activities: $3,462
- Transportation (Ubers, rental cars, gas, etc): $4,213
- Misc (plane wifi, baggage fees, SIM cards, etc): $2,011
- Swag: $1,451
- Photographer: $840
- Videographer: $7,800
We found it interesting that total cost for accommodation (which includes the additional night at the Marriott in Glasgow) was pretty close to what our Lake Tahoe house cost last year.
The one major increase from last year (outside of flights) was food and beverage. We spent more than double on that! However, considering last year we grocery shopped and ate out only a few times, whereas this year we had incredible catered meals 3x/day, plus drinks, it’s not surprising. We’re thrilled with how the week went, and the extra cost feels worth the amazing experience. That said, given the current size of our company and our business goals, this is about the upper tier of what we expect to spend on retreats in the next few years.
Fun fact: I actually left last year’s retreat with a fair amount of dread. I thought there was no possible way to top Tahoe, with its gorgeous mountain vistas and 70 bajillion room mansion.
Well, Dunskey sure proved me wrong!
We’re all still adjusting to life after Dunskey (most of our Slack chatter the following week was about how we had all apparently forgotten how to feed ourselves without a steady stream of surprise picnics), I’m already scouting spots for next year. I’ve got my eye on a few, but the majority of the team said they would be more than happy to return to Dunskey.
We’ve always taken more of a DIY approach in the past, so we came into this retreat not completely sure what a fully catered week would be like. In the end, we had nothing to worry about. The staff at Dunskey felt like part of our team, Anne and Ali are the world’s most gracious hosts, and though we did miss Tahoe’s Barb the Bear (and kids), we were more than thrilled to welcome a new furry friend, Lady Beecher, into our lives.
The reviews from the team in our post-trip survey were glowing. Turns out, we love coming together and we’ve already gotten several ideas from the team on how to preserve the magic of our team retreat throughout the year. Though it may be a happy hour held over Zoom instead of on a Scottish terrace, we’re excited to keep the warm fuzzy feelings of spending time with a group of hardworking, passionate, genuine folks alive and well! 😁
A huge thank you to our wonderful photographer, Mark Pacura, for capturing so many of these moments. We certainly kept him laughing, as our group was not his typical wedding party clientele. Also, huge thanks to everyone Dunskey Estate for making this our best team retreat yet!