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100% office-based to remote-first: SquaredUp’s journey

Back when everyone was talking about the ‘new normal’ and what the future of work would look like post-pandemic, SquaredUp was having a rethink too.

SquaredUp has always been a 100%, office-based company with a heart for bringing people together. Richard Benwell, CEO, and the executive team had created a company that is truly fun, collaborative, and integrated, largely based on their drive to keep people connected and build an incredible community – in the office.

Whether it was sharing in the spoils of the weekly charity bun run, competitive poker nights after work, or a quick game of table tennis, there were always reasons to be gathering together at the office and nearby.

And it was brilliant…

…until the world was turned upside down.

In 2021, SquaredUp did a full U-turn. We decided to go remote-first.

But that’s no small decision when the whole of the C-suite have been championing in-person, office-working as the optimal way to work and build community and collaboration.

SquaredUp’s CEO, Richard Benwell, said, “Two years ago, it would have been impossible to believe that we’d become a remote-first business. The pandemic forced us to think differently and I’m glad it did – remote-first has been such a success there is no turning back.”

So how did SquaredUp achieve building a fully remote work force without losing its values?

Here’s how we made the shift to remote-first.

Recognizing the changes

The first step in the shift was recognizing the changes that were already in full swing.

The whole company had been forced, through lockdowns across the globe, to work remotely from home. Immediately, there were temporary changes put in place to help people adjust to a remote-first way of working.

But it soon became clear that the temporary measures weren’t going to be so short-lived.

Was the way we work going to change forever? Or would we eventually slowly go back to how things were?

SquaredUp decided not to passively wait and see, but chose to be active in designing the way the company worked to fit employees needs best.

SquaredUp has been on the front foot, recognizing that the way we work has changed forever. It's admirable that SquaredUp has been actively designing what we want the new way of working to look like. The desire for flexibility is wonderful and I genuinely feel that I would be as successful in my role regardless of whether I go to the office or stay at home.

Simon P

In addition, the pandemic came at a time when SquaredUp was expanding in the US. Richard Benwell, our CEO, was relocating to Boston, MA, with his family and we were scaling up the team simultaneously.

To our surprise, the pandemic and our switch to remote-first made all of that expansion and moving much easier. We’re now a larger group of people and geographically dispersed but still one cohesive team. It’s hard to imagine that being so successful if we were still office-based.

Consulting the entire company

Given SquaredUp cares so much about their people, they knew they couldn’t design a new way of working without in-depth consultations with every person in the business to find out what they wanted, what their struggles were, and what new joys had been discovered in the lockdowns.

“The decision to become a remote-first company wasn't made in a vacuum, but with feedback of the entire company. A lot of thought and intention went (and goes) into making this fun, productive, and sustainable. And we still make getting together a priority!”

Jason Baudreau

Surveys and in-person consultations gathered all the data that pointed to the wider company wanting flexibility in where they worked. Though some wanted the option to work from the offices, the office wasn’t wanted as a permanent place of work for most.

This reveal started the shift in SquaredUp to a remote-first focus while currently keeping offices open for those wanting to use them as their working location. The offices also provide a location for those that want to meet in person.

There were going to be plenty of challenges along the way. But SquaredUp is committed to listening to their own people first and delivering on what’s best to help people thrive.

Here are just some of the results from our 2021 Employee Engagement Survey.

Clear communication throughout the transition

Once the preferences for remote working became clear, SquaredUp needed to communicate clearly what the changes could and would look like, when the transition would happen, what support would be in place for the shift to remote-first, how to prepare for the change, and how we would change how we operated to champion remote-first working.

Such a huge transition can’t be done overnight without causing huge instability. So, through the already established, weekly all-company Wrap Up meetings, and through managers talking to their teams collectively and 1-to-1 with a feedback loop to HR, the company was able to clearly communicate each decision and next step. (Note that these regular meetings and opportunities weren’t new. They’d been established for years.)

The company has been transparent throughout the transition and kept everyone consistently up to date with what is happening and how we should prepare for it. The result of this is that, from my perspective as an engineer, there has been minimal disruption to our workflow or efficiency, and we have been able to continue to perform our roles unhindered.

Aaron Argent

SquaredUp also gave plenty of opportunity for employees to talk to HR and others so they could address all the concerns and consider the ideas of everyone in the company. This meant listening carefully to make sure nobody would be disadvantaged or left behind in the transition.

SquaredUp had a very smooth transition into a remote-first company and made sure everyone is informed and on board with every aspect of this process. We truly practise the "remote-first” concept and make sure there are equal opportunities regardless of the place of work. It is definitely superior way of working for me.

Tanja Matoska

Hiring the right people

This transition to working remote-first opens up a whole new recruitment market to SquaredUp, being able to employ anyone from anywhere.

But the ease of the transition to remote-first working and minimal disruption to day-to-day activities was, we believe, largely down to having hired the right people in the first place.

I would describe my experience of SquaredUp's transition to becoming a remote-first company as 'seamless'. This was, in my opinion, the combination of the excellent culture the company has developed with the excellent people the company has attracted and hired.

Steve Rowland

SquaredUp has been deliberate about who they hire. The company consistently hires talented people with humility, a pursuit of excellence, openness to change, and most importantly, those who care for others.

Because there was already a great culture of transparent communication, making sure everyone was included and provided for, and individuals were talented and adaptable, the transition to remote working – first due to lockdowns, then due to the remote-first change – was incredibly smooth.

Keeping everyone connected

Now we are all working remotely, it would be all too easy to separate into silos of teams and departments that we talk to regularly and not communicate with others across the company unless completely necessary.

However, by continuing the weekly Friday Wrap Up for all the company, which will have a spotlight on a different team and their work each week, everyone gets together regularly to share what they are doing and how others can be involved. We also all keep aligned on our company and team goals this way, keeping us all aligned on the bigger picture.

The official meeting is preceded by a time when everyone can just hang out for a while in Gather so you can chat with others you don’t regularly connect with.

Plus, there has been the occasional addition of 5 Minutes of Fun where teams competed in fun challenges.

I've been so impressed with SquaredUp's move to a remote-first culture. We've adapted so well and kept this great connection between teams. I love seeing everyone at the Friday Wrap Up.

Rachel Kelly

Weekly team and cross-team meetings, as well as 1-to-1s with line managers, are also the heartbeat of connecting people. Making time to catch up on life news as well as work means we keep the communications human.

I think SquaredUp has handled the transition into becoming a 'remote-first' company really well. It is easy to lose sight of the bigger picture especially when working from home but weekly, company-wide meetings keep us connected and give us a clearer picture of what we are working towards. My team's regular check-in calls have also helped ensure that I never feel isolated.

Lydia Shu

Fully committed to the cause

Finally, we’re fully committed to being remote-first. This isn’t an optional extra or a nice ‘flexible working’ perk. Too many companies use remote working as a perk but don’t truly support those who are remote – people are always left out.

We, in contrast, are going all-in and dedicated to providing equal opportunities for everyone, wherever they work.

That SquaredUp was willing to commit to being a remote-first company and then follow through on that despite having been 100% office-centric pre-pandemic speaks volumes about how the leadership listens to its employees and is able to adapt to changing circumstances.


From providing the right systems and equipment to great gatherings online and in person, we want to provide everything that’s necessary for each person to feel completely part of the SquaredUp team.

We know we’re only a few months into this decisive transition to working remote-first so there will be plenty we will be learning along the way. But we have made an incredible start and we only want to do better as the years roll on.