Running an Offsite, Carted-Style

Holly Cardew
9 min readFeb 7, 2022

When we decide to do something, we go all-in at Carted. Planning our first company offsite was no different. Not only did we face the challenge of organizing fifteen people scattered throughout the globe, but also we had to deal with the COVID-19 pandemic ever-present in the background. Call me crazy, but even with these challenges, it was the best thing we could have done to kick off 2022!

All together now

Our remote team makeup has many advantages. We’re not restricted by geography when looking for top talent in a specific business niche. There’s more flexibility for team members in balancing their work and personal life. Our favorite company perk is Carted’s ‘work from anywhere’ policy, where Carters can travel to, and work from, any location that other employees are based. Australia, United States, England, India, Germany, and on- the possibilities are endless as our team grows.

As much as we love the freedom and opportunities remote work provides, finding ways to connect outside of Zoom calls are essential to building a strong company culture and creating trust between team members. I particularly felt it was important to bring everyone together at this formative stage in our company’s history. The rest of the Carted team agreed, eager to do whatever it took to make this event happen.

Offsite Down Under

I had initially dreamed of getting the Carted team together for Christmas, (somewhat) joking that I wanted the offsite to take place in a European ski lodge, next to a fire, with us all wearing matching onesie pajamas.

The Omicron variant had other plans.

Suddenly, navigating the latest strain of COVID-19 in a foreign country felt like too much of a risk. Despite this setback, we remained optimistic that this could still happen. We quickly pivoted to our ‘Plan B,’ which involved hosting the offsite in our home city — Sydney! Not only could we host everyone safely, but the entire team could experience Carted House and everything there is to love about Australia.

For those wondering, this of course included Vegemite and Tim Tams.

Day 1: Welcome to Carted House

“This is the true story of seven strangers picked to live in a house, work together, and have their lives taped — to find out what happens when people stop being polite and start getting real.”

-MTV’s Real World

The above tagline from MTV’s Real World series is tongue-in-cheek but illustrates how we all felt descending upon Carted House for the first time. We certainly weren’t reality-tv contestants. However, we were a group of fifteen unique individuals, from all cultures and backgrounds, that had never before spent time together as one group.

We had our first moment of “realness” while showing the international team members Carted House for the first time. A huge Huntsman spider was nestled into one corner of the office. Thanks to the heroics of Kimia and Mykola, the spider was trapped in a bin and safely escorted outside. An unintentional way to break the ice, but effective nonetheless.

More importantly, we now knew who to call for future insect removal — a true necessity in Australia!

Welcome to Australia!

While the spider might not have been everyone’s idea of a warm welcome, custom goodie bags created by Gilbert certainly were. Full of Aussie treats, a QR code was included on the tag linking to the meaning behind each item.

He also personally designed some amazing Carted swag — a beach towel and a t-shirt — as a way to commemorate our first-ever offsite.

Tim Tams, Vegemite Shapes, ANZAC cookies - what more could you ask for?

After settling in, we kicked off the offsite with a Q&A with Robyn Denholm, Chair of Tesla and Operating Partner at Blackbird. Big thank you to Blackbird for arranging this session.

It was incredible for us to have access to Robyn, whose time is mainly spent with people such as Elon. Not only did she share insights into her childhood and career journey, but she also touched on how to build company values and culture in a fast-growing environment.

One piece of advice that really resonated was to not be afraid of pursuing a different path from others if we believed in what we were doing. This reaffirmed our vision for Carted, as we are building a completely new approach to commerce. We left feeling even more inspired and energized by the opportunity in front of us.

Day 2: Thinking outside the box

Want to really get to know your coworkers? Do a scavenger hunt together! Our ‘Welcome to Sydney’ scavenger hunt was planned by local Carter, Michael (with help from his partner, Roldan). Breaking into teams of three, we were tasked with completing a list of riddles and challenges that had us (literally) running all over the city.

Team activities as part of our scavenger hunt

We quickly learned that none of us like to lose, which made for some hilariously unsuccessful attempts at team sabotage.

We also learned to never challenge Mykola to a race, as he’ll win every time.

Post scavenger hunt excitement, we took a break to eat lunch and recharge before beginning our afternoon sessions.

We began with a core values brainstorm, arguably one of the most important discussions of the offsite. Values serve as the foundation upon which everything else in a company is built. Hiring, development, leadership, you name it — which is why creating and sticking to a strong set of values requires guts.

However, this doesn’t (and shouldn’t) have to be a daunting task taken on alone. When creating our values, we found it helpful to identify which beliefs and practices are not just meaningful to ourselves, but also shared across team members.

Key themes emerged, which led us to craft a set of core values that were authentically Carted.

Stay tuned for a future blog post sharing our updated Carted values!

Defining Carted’s core values

Next up was a design thinking workshop. By going through the process of designing a car for another team member, we learned how to ask the right questions in order to create the best solutions for our customers.

We closed the day with a team dinner and drinks in Surry Hills. This is where we learned about Calum’s strict “no sauce” rule.

Well, only unless the sauce is “absolutely integral” to the dish. Ask him to explain it!

Team dinner

Day 3: Planning and painting

Fully caffeinated from oat milk lattes (the unofficial drink of Carted), we were ready to dive into the third day of offsite.

We divided the morning into three presentations: a demo session where a rep from each function shared an update of what they were currently working on, takeaways from customer calls, and best practices for meetings.

Morning engineering demo session

This really helped the total team better understand each other’s initiatives and how to maximize time when collaborating together.

As a result, members of separate teams organically found ways to share ideas and offer support. Nil, Mykola, and Sayak found some potential ML automation opportunities for Kara’s categorization work. As leaders of engineering, Calum and Miroslav gained valuable insights from Kimia’s customer feedback session, which spurred additional team conversations.

This collaborative spirit carried into the afternoon’s session where we reviewed our topline company goals and 2022 roadmap. With the trust and space, we had created from three days together, we were able to improvise and riff off each other.

Post our working sessions, it was nice to relax with a little painting and pinot.

Interestingly enough, the Engineering team ended up being the best artists. We joked that it was due to their ability to break down a complex problem.

Our inner Picassos released during paint n’ sip night

Day 4: Communication is key

Day four of our offsite was a fun one.

First, Melia Rayner, Community and Communications Manager at Blackbird, put our inner PR managers to the test. Melia’s session focused on best practices in communications. We learned how to build credibility with our audience and to find our voice. We walked away feeling more confident in how to talk to friends, family, and others about all things Carted.

After sharpening our external comms skills, it was time to focus on how we would be speaking to those within Carted.

Vanessa, our Head of People, led a discussion on how to best give and receive feedback.

Feedback was something we wanted to build into our culture from the very beginning. Why leave it for an outdated review process that happens only once a year? Regular feedback is proven to improve engagement, performance, and relationships.

Learning how to effectively give and receive feedback

Last up was our team Strengths Profile session. After completing the online questionnaire, we were given both an individual and a total team profile of our realized and unrealized strengths.

We discovered our hidden potential as a comedy improv group due to so many team members showing “Humour” as a top strength. More importantly, we found where we could leverage our skills to drive maximum results.

As best illustrated by Vanessa’s Captain Planet cartoon clip, with our powers combined, we are unstoppable!

Day 5: Sharing perspective

We began the final day of our offsite with a call from another Aussie-based Entrepreneur, Sascha-Manuel Reuter. Sascha discussed his founder story and how he built and sold his company Doctape to Atlassian. He and the rest of his team actually relocated from Germany to Sydney. Sascha talked about how great of a move this was for him.

Funnily enough, a few international Carters were already discussing moving to Australia after spending some time here.

Thanks for helping to further sell the team, Sascha!

After our great chat with Sascha, we took a ferry from Circular Quay (pronounced “kee” for you non-Aussies) to the other side of Sydney — Manly.

Lunch at Manly

Over lunch, the team shared more about their respective cultures and home country.

From Sayak and Nil, we learned that Bengali is considered the sweetest language. Of course, we then had to try out some phrases.

From Vanessa and Kimia, we learned that “How you going?” and “hectic” are hallmarks of Australian slang. We also received some advice on the best place to find a kangaroo in the wild.

From Mykola, we learned how beautiful the city of Kyiv is (where he currently resides).

From Kara, we learned that San Diego has the best burritos in all of California.

From Michael, we learned that New Zealanders might just be the nicest people in the world (or at least the most polite).

From Miroslav and Calum, we learned the importance of a good pub, pint, and curry in Birmingham.

We closed out our offsite with a deeper appreciation for the passionate, intelligent, unique, and a little crazy, individuals that make up the Carted team.

Better together

We learned a lot about ourselves and each other during our offsite. The biggest realisation I had was that despite our obvious differences, we complemented each other extraordinarily well.

We got into a quick and easy rhythm of working together, planning for the future, sharing ideas and jokes, and overall enjoying each other’s company.

It wasn’t just at Carted House. The majority of us even chose to spend our free nights and weekends hanging together as well. We celebrated birthdays, went on outdoor adventures, and hosted team dinners.

This level of bonding and trust was made possible by bringing everyone together and planning creative ways for us to really get to know each other, and our work.

Weekend outings in the Blue Mountains and Bondi Beach

When you bring a group of different fifteen people together from around the world for the first time during a pandemic, you can’t ever be sure of the end result. If the outcomes from our first offsite are any indication, then Carted has an incredible 2022 in store!

The dream team of Carters (minus a couple)

A side note - A massive thank you to my team for pulling this together so quickly! I couldn’t have done it without you. 🙏

And we are always looking for more people to join our team! Read more about life at Carted and our opening roles.



Holly Cardew

Building solutions for the next generation of shopping