"I'm More Open To A Fully Remote Company": How COVID-19 Changed This Entrepreneur's Perspective



Welcome to Remotely Inclined, a newsletter about remote work and remote entrepreneurship. If you’d like to sign up, you can do so here. Or just read on…

In the first edition of Remotely Inclined Chats, Erin Bury, CEO of legal startup Willful explained how she keeps creative energy flowing in her company remotely, maintains company culture, and how she gives back in a time of crisis.

I captured the highlights here, but listen in or read the edited transcript below for the full story:

Creative juices

Erin keeps creativity flowing by digitally mimicking behavior she would do in the office.

  • Instead of walking over to a desk, she’ll send a quick Slack message.

  • Instead of in-person meetings, she’ll use Zoom.

  • When it’s time to whiteboard, she’ll encourage everyone on the team to take part just as they would in the office.

Company culture

For Erin, a key part of company culture is the conversations and time spent not on work things. It’s the happy hours (both alcoholic and non-alcoholic options available), the team lunches, and the fun anecdotes from everyone’s lives. She’s keeping that alive with:

  • Virtual team lunches.

  • Encouraging personal chats on Slack.

  • Always being there to have a life chat with her team.

Giving back

Willful is in a unique position - it’s actually growing due to the COVID-19 pandemic, which is pushing people to think about end of life planning. With that privilege, Erin gives back by:

  • Promoting local businesses on her social media.

  • Giving away free wills and other legal documents to healthcare workers.

  • Supporting local businesses by giving her team gift cards to buy local.

And in the end?

“I’ll have a lot more of an open perspective to fully remote people and - potentially even a fully remote company - based on this experience.”


Remotely Inclined Chats with Erin Bury

Transcript edited for brevity and clarity.

Stefan: Can you share a bit about who you are and what you’re up to at Willful?

Erin: For sure! I have a decade of experience in marketing, communications, and business operations. I ran a marketing and branding agency in the past and I was on the founding team of startup publication BetaKit

I’m now the co-founder and CEO - alongside my husband - of legal startup Willful, where we help people get estate plans in place. 

Since you’re building a tech company and sell a digital product, were you a fan of remote work before the COVID-19 pandemic?

I’ve always been a fan of flexibility. When you’re building a digital product, there’s no reason that anyone should be forced to be in an office. We’ve always had a really flexible policy around things like working remotely or working from home. 

That said, we’ve never had a fully remote company. I’m an extrovert, so I love the energy of an office. Things like the impromptu happy hours or white boarding sessions -- all of the things that come with being in an office. But I’ve never been the type of person to say you have to be in an office to be productive. 

If you hire smart people and give them quantitative metrics, let them do their thing and trust that you hired them for a reason. 

A lot of people talk about the “energy” in an office - have you found that’s been lost now that you’re working remotely? 

I think there are definitely energy shifts. You can’t necessarily have those impromptu conversations or just chat about personal things. You’re also not interacting as much with people on a daily basis. 

But I haven’t found that it’s affected our ability to be creative other than maybe not having a physical white board. 

Tools like Zoom make it so easy to feel like you’re in the room with someone. We do a lot of impromptu Slack calls and touch bases so you can still have those conversations with people. So instead of walking over to someone’s desk, I ping them on Slack. 

As a leader, are there things you find you can’t do remotely that you could do in an office?

Well, I can’t distract people! As an extrovert who’s constantly sharing memes and talking about things in the office, I know that I’m a source of distraction for our team members who really like uninterrupted periods of deep work. So I think it’s a good thing in some ways. 

But the things I can’t do mostly revolve around culture. We always had a Friday happy hour, for example, where you could get an alcoholic or non-alcoholic beverage and we’d have demo days for people to showcase their projects. That’s a bit more difficult now. 

Instead of the in-office culture stuff like Friday happy hour, we’ve switched gears to Friday Games where we’ll play Jackbox games or trivia virtually. We also still do those demos, now just using video instead of in-person. 

To counteract the lack of impromptu chats, we have virtual lunches for people to pop in - even just for 10 minutes - to get face time with other human beings. 

A ton of headlines talk about businesses going through hard times, but Willful is growing - how do you balance that excitement while also realizing why the growth is happening? 

It’s interesting. We didn’t know if COVID would send our sales plummeting as people stopped spending money or if it would grow. It turned out to be the latter. We’ve seen an incredible increase in traffic and demand, especially from older folks who can’t go into a lawyer’s office right now because they’re in an older segment of the population.

I’m very fortunate and grateful that we are in a position where we have this increase, but I’ve struggled with it because I have friends and peers who are shutting down their businesses or losing their jobs. So success is not something I celebrate publicly because people are buying our products out of fear and anxiety, not a desire to have peace of mind. 

It’s been weird to juxtapose those emotions. I don’t know that I’ve solved for them yet. 

But what I am trying to do is support local businesses where I can. We give gift cards to our team to buy from local restaurants and I give some attention to the small business community with shoutouts on my Instagram. Willful is also giving away 1,000 plans to healthcare workers - we can’t make masks, but a lot of doctors and nurses are being urged to create these legal documents.  

How did you get these different ideas? What resources did you turn to?

A lot of the ideas were from the Upside Foundation, which put out a resource guide for remote workers and entrepreneurs

I just felt like I had to do something, even if that’s just using my platform. I’m not Oprah - I wish I was - but every little bit counts. 

On the business side, it was a direct response to the feedback we had from doctors and nurses, who told us their hospital administrators were asking them to get the documents done. It felt like it was only appropriate to help these people out who are risking their lives to help us. 

And on a more personal side - you were forced to move in the middle of everything. How did that go?

Erin: Yeah. These are all first-world problems, but: we had purchased a pre-construction condo in 2014. It was delayed by three years and is now delayed again by COVID. But we had to move out of our rental. Luckily, we could stay at our family home in Prince Edward County. 

But it was weird because we had to that dance with movers. We all had masks on and were moving things around but trying to not get too close to one another. It made me think about all the people who are still working, bagging our groceries and things. They are not paid six figures to do that. I think it’ll be on us as a society to reflect on the value we place on some of these essential jobs. Hopefully, there’s some positive change that can come from that. 

Alright - three rapid fire questions. Number one: favorite book, or a book that changed the way you think about the world? 

Number two: favorite podcast? 

A tech podcast called Reply All.

Number three: favorite movie? 

The fifth instalment of the Fast and Furious franchise - Fast 5.

In closing, what’s something you’ve learned about remote work that you didn’t know before?

I’ve learned you can easily do it - and do it effectively. 

I always had a lot of trepidation about remote work - would the team stay connected? Would we get as much work done? Now, I’ve seen the huge benefits of it. 

I think I’ll have a lot more of an open perspective to fully remote people and potentially even a fully remote company based on this experience. 

Amazing, thank you! 

You can connected with Erin on: 

Photo of Erin courtesy Be The Next Her.