Looking Back: Our 2022 Leadership Off-Site

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The 2022 Order Desk Leadership Team

Working for a remote company has its perks, like being able to spend more time with your family (and your furry family!), but one aspect of remote work that many companies struggle with is the lack of in-person human connection. We’ve found ways of staying “close” and building community despite our truly global physical distance, but we’ve also found that getting together every now and then solidifies our already pretty close bonds.

Since the inception of Order Desk, there has been a single time where leadership has met for an extended period of time, and because it was at the height of the COVID-19 pandemic, we opted to remain in separate locations and call in for an intensive, weekend-long session. So this time, now that international travel restrictions have become more relaxed and vaccinations are more readily available, we opted to gather the five members of Order Desk leadership together for the first time, three of whom we’d never met in person before!

The Destination

Bloomingburg, New York isn’t a household name, but we were thrilled by the area’s sprawling farmland, memorably-delicious food, and hometown hospitality. Similar to our last company retreat, we opted to visit New York State because some serendipitous travel plans had one of us in the area at the time and two others lived close enough by that we jumped at the opportunity.

We had folks travel in from Jamaica, Idaho, Pennsylvania, and New Jersey to attend, and as one of us put it, “everything that could have gone wrong, did.” Skipping past the multiple delayed flights, the rental car agency being closed, laundry mishaps, missed turns, power outages, and even a brief run-in with the law, we were able to make it to our mountain haven house in Bloomingburg with only a few bumps and bruises.

Our awesome accommodations for the weekend!

The Work

Candidly, we had a lot of ground to cover. As the world heads into a possible “mild recession” in the coming months, we needed you, friend of Order Desk, to know that you’re in good hands. As a bootstrapped company, we have no outside investors, so every bit earned by Order Desk goes toward supporting the app in one form or another. Our team, our infrastructure, and our resources all come directly from you. Have we told you lately that we appreciate you?

We also needed to ensure that our team was healthy, happy, and thriving. We recently surveyed Order Desk employees to get a gauge for how we’re doing, and the team shared some invaluable, actionable feedback that we were able to pore over and analyze together.

We covered topics like the future of the Order Desk app and features we’d like to see, the future of the Order Desk team and what growth opportunities we could create for the folks who already add so much value to you and your business, ways we can better present ourselves to reach people who may not recognize that our app could help them work less and relax more, and even some super secret projects that we’re not quite ready to share publicly yet…

Was this dinner? Lunch? Both? We’ll never tell.

The Fun

It wouldn’t be an Order Desk gathering without some fun! Our team from outside the area got to enjoy local delicacies, like the best bagels in the world and Taylor Ham (sorry New Jerseyans, it’s not “pork roll”), a real 24-hour diner, homemade burgers with farm-fresh ingredients, the biggest crepes we’ve ever seen, and an incredible homemade ice cream spot where a “small” cone included three scoops.

We also got to spend a good amount of time with my wife and kids, which was a treat for everyone involved, and even my dog got to join in on the fun for a while.

The last time we did one of these blog posts, this section ended up being only about food, too… and we’re pretty okay with that, to be honest.

Jamilah with the Italian ice sampler
A banana split posing with Adam
Blog author and professional ice cream eater Dan in his natural habitat

The Future

Our last company retreat had all of Order Desk in attendance—all seven of us at the time. We’ve tripled the size of our company since early 2020, and we’re dying to meet the people who’ve become wonderful colleagues and friends over the course of those two years. Until we can get everyone together again, we have a lot of work to do.

Using the team’s feedback and our leadership team’s vision for the future of Order Desk, there are so many things we plan to implement to make the Order Desk app more powerful and useful to you, and some exciting improvements to our team structure to make us more scalable and motivated to grow with you and your business.

Despite all the improvements and changes we’d love to make, one thing remains the same: we exist to provide essential ecommerce tools because the world is a better place when everybody has an opportunity for success. That means you too!

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