Future of Work 
Part 2 of our interview series with Canadian Unicorns about the future of work: Matt Carlson catches up with Ada’s Chelsea MacDonald to see how the busy tech enterprise is charting its course for a post-pandemic workplace.
Canadian chat bot company Ada is no stranger to innovation. Pioneers in the AI space, Ada helps companies around the world elevate their customer service through personalized digital experiences. So when the pandemic hit, Ada did what it does best — it innovated. Once an in-person first company, Ada has now transformed into a permanent digital-first workplace for its 350 employees, which they hope to grow to 500 in the near future.
Matt Carlson: What was your pre-Covid policy for working away from the office?
Chelsea MacDonald: We were in-person first, and remote friendly. Most people worked an average of 2 days a month from home, often when they had appointments or personal reasons to be at home for a day. Less than 5% of our teams were remote-first prior to Covid.
MC: Tell us about your post-Covid return to work strategy (timing to return, whether you’re hybrid, remote, digital-first, etc.).
CM: We are now a digital-first company. What this means is that wherever you’re working, from your home office or a co-working space, you’ll work the same way as everyone else with the same tools as your peers. If it’s important, it should be happening digitally, not in-person.
MC: Did this strategy change from what you originally envisioned in the early days of Covid? If so, how/why?
CM: No. We were lucky in that we’d considered moving to digital-first before Covid and had been waiting for a push that would make the change more palatable. We were extremely early adopters of digital-first, within a week of Rudy Gobert’s Covid diagnosis.
MC: What was your process for developing this strategy, and how did you understand what’s important to your team?
CM: Pre-Covid, we had been reaching out to people who had experienced digital-first cultures and asked them what worked and what didn’t. We also relied on some of the larger data studies that have been done to supplement those anecdotal conversations.
Our team is growing really quickly, so it was important for us to understand what our teams said they wanted, but also, what the broader market was asking for, since most of the people who will work for Ada in the next 2 years don’t work for Ada yet.
Socializing and building intimacy remains one of the more difficult things to do digitally, especially if you have not met people in-person at all.
Chelsea MacDonald, SVP Operations at Ada
MC: When your employees provided information about their post-Covid work preferences, what trends did you notice? What surprised you?
CM: I don’t know if surprise is the right word. We saw confirmation of some of the data we’d seen in other places — the people who were most worried about working digitally were senior leaders, which is a small but important group; new grads were also relying on work for social expansion. These groups are still worried. Leaders have to add a new skill of leading digitally, which is a big ask from an already difficult job. Socializing and building intimacy remains one of the more difficult things to do digitally, especially if you have not met people in-person at all.
MC: How do you plan to build culture in this new digital-first environment?
CM: I think remote culture is not that different from in-person culture. It’s just way more deliberate. There’s serendipity in person that’s hard to re-create digitally, but over time, I’ve realized that serendipity isn’t all good. People have a tendency to talk to the same people, all of the time, and assume that they’re talking to ‘everyone.’ Digital tools make it easier to understand who ‘everyone is’ and create moments for interactions that are truly random in a way that’s very difficult to do in-person.
So we’ll over-communicate, we’ll repeat ourselves a LOT, and we’ll assume that we need to be constantly focused on creating intimacy across our teams.
MC: What is your company’s position on in-person work/collaboration, and how are you planning to connect employees in-person going forward?
CM: We will do almost all of our work digitally. In-person will be focused on building intimacy and social connections. We’ll also have in-person socializing for new hires, and all-employee meetings once a year, and we’ll have team meetings infrequently.
We’ll talk about work things in these spaces, but we’ll be primarily focused on developing intimacy and social connections to build trust. The focus will not be on making important business decisions. Covid taught us we could make those decisions digitally with no negative impact to our business.
An unexpected upside is that the diversity of voices in collaboration has changed, as we are more likely to have equal representation in collaboration because it’s asynchronous more often. We’re more likely to collect ideas and review than to do a physical brainstorm.
Quieter and more diverse folks, who might be drowned out in person, have the opportunity to contribute asynchronously and have their ideas heard.
Chelsea MacDonald, SVP Operations at Ada
MC: What tools will you employ to support a virtual workplace that you didn’t before?
CM: Our tools are not very different, but the importance of them has changed. Zoom and Slack are where we work now. We had these tools before, but they weren’t as important. We didn’t even give everyone a Zoom license until 2019. It’s unfathomable to think that was a thing now!
MC: Have you, or will you, change your physical workplace to address your new work strategy?
CM: Yes. Pre-pandemic we had planned to lease enough space to last us through 5 years of aggressive growth. Flash-forward to now, and we don’t currently intend to have any work space dedicated to Ada — employees can now work from home or from co-work spaces we plan to secure for our team.
MC: When you implement your strategy, do you have any contingencies if things don’t go as planned? What are they?
CM: We will be looking at our results as a company, our ability to attract talent and employee surveys to ensure we’re making the right choice for our people and our business. It is unlikely that we’d change our digital-first approach, but it’s highly likely that we’ll adjust our strategies to achieve those outcomes as we go.
MC: Do you think employee preferences will change from what is requested today?
CM: Yes and no. Do I think many people will want to work for all in-person companies? No. If I did, I would be choosing a return to work model. What I do think will change will be the importance that employees place on their organizations’ ability to handle digital and hybrid well. It’s such a fundamental part of how you work, and if it’s frustrating or unfulfilling, employees will exercise their agency with their feet. They’ll leave companies that don’t get it right, and they’ll flock to companies that do.
MC: If you look forward to fall 2023, how will things change with respect to in-office and at-home work?
CM: This next year is going to be a messy middle. Covid isn’t over, despite vaccines. Also, in my opinion, going hybrid is much harder to get right than going all in-person or all-digital. The data out there is pretty clear that most tech employees are looking for the flexibility and lifestyle advantages of working remotely, and I think a company’s ability to adapt to those changes will be a big part of their success.
About Ada
Ada is the new front line of your customer experience, empowering businesses to provide personalized experiences at scale – in a snap! Ada’s no-code, AI chatbot improves CX, reduces costs, and drives revenue – while freeing live agents to have greater impact. Learn more about open roles at Ada by visiting the career page -> https://www.ada.cx/careers
About Chelsea MacDonald, Senior Vice President Operations at Ada
Chelsea MacDonald is the SVP, Operations at Ada. In her role, Chelsea is responsible for ensuring that as Ada more than doubles in size every year, the company scales effectively and efficiently. She is an avid sprinter, back country hiker, traveler, advocate for mental health and diversity, and she makes a mean chicken nugget.
