Erin Bury: Willful CEO


My Native Admission Statement: I describe myself as an entrepreneur, speaker, startup advisor, and former technology journalist. I’m the co-founder and CEO at Willful, an online estate planning platform that makes it easy for Canadians to create a legal will online in less than 20 minutes. At Willful I’m responsible for driving the company’s mission to make it easier for Canadians to prepare for and deal with death in a digital age. I’m also a professional speaker with Speakers’ Spotlight, a board member at Save the Children Canada, and I was named one of Marketing Magazine’s top 30 Under 30 marketers. I’m passionate about travel, and in 2019 I’m traveling to Australia, New Zealand, Singapore, and Scotland. My claim to fame is being retweeted by Oprah – twice.

How did you get into the industry?:

Willful was inspired by my co-founder (and husband’s) Kevin Oulds’s experience after a family member passed away. He realized so few people – about 56% of Canadian adults – don’t have a will, and even if you do, chances are it’s out of date due to a life event like the birth of a child or a divorce. Not only that, but we just don’t talk about end-of-life planning with our family, because of course it’s uncomfortable to think about death. Originally I was an investor in the company and a marketing advisor, and I ran a marketing agency that helped Willful with its naming, branding, and launch communications. When I was looking for a career change in early 2019, I decided to join the company as CEO.

Emerging industry trends?:

Estate planning is an industry that’s ripe for innovation. We plan for death the same way now that we did 50 years ago – by going to a lawyer during work hours and paying a lot of money for what is often a simple document. Just like Wealthsimple has changed the way we invest our money through a beautiful, user-friendly online platform, other financial processes like purchasing life insurance or getting will are also moving online. In the future, I imagine that not only will we prepare for our own passing using online tools, our executors will also be able to wrap up our life using online tools.

Industry opportunities and challenges?:

One big trend that is driving the industry is digital legacy – we leave a massive footprint when we pass away, from our emails to our social media accounts to our online subscriptions. I think a huge trend in the industry will be giving people an easy way to assign contacts to deal with our digital footprint.

Inspiration for the business idea, and your vision for the Business?:

My husband Kevin, who is also my co-founder, had a family member pass away unexpectedly, and while he did have a will, he had never discussed other end-of-life plans with his wife of almost 40 years. Kevin and his family were left scrambling, asking each other questions about his burial plans and funeral wishes, and guessing at what he would have wanted. It made Kevin realize that it’s a broken process to wrap up someone’s life, and it’s even harder if you don’t have a will in place. That can lead to long, drawn-out court battles, and the government deciding on how your assets should be distributed. He decided to launch Willful to make it easy for people to create a will – which we see as the “Painkiller” in estate planning, the thing that every adult with assets or children needs – while also allowing people to include other estate planning information like their burial preferences and preferred funeral wishes. Our vision at Willful is to help every Canadian create a legal will online easily and affordably, so no family is left scrambling when someone passes away.

What's next for the Business in the near future?:

We’re currently participating in the FounderFuel startup accelerator program in Montreal, and we pitch on stage at demo day on July 9th. We’re also expanding across Canada, and launching partnerships with financial institutions and life insurance companies to get our platform in front of millions of people.

How do you motivate others?:

I prefer to motivate with empathy and positivity. I believe that the best leaders are empathetic, and motivate with kindness, constructive feedback, and mentorship. The best leaders have a mix of warmth and competence – you can’t have one without the other, so I strive to have a balance of both.

Career advice to those in your industry?:

My biggest tip is to pay attention to your personal brand, and put time into growing it. A strong personal brand can help with everything from networking to new business, and it’s something that most people ignore until it’s too late.

What do you do best?

I’m a great storyteller. I’ve spent a decade as a journalist telling startup stories and interviewing amazing entrepreneurs like Mark Cuban, and as a marketer who has helped startups shape their stories.

What makes you the best version of yourself?:

The thing that makes me the best version of myself is getting enough sleep and getting enough exercise. Those two things don’t happen all the time – or happen consistently – but when they do, I always feel better.


Positivity is a choice! I’m an extremely optimistic person, and I truly believe that you can decide to look at the world as a half-full glass.

Favorite People/Role Models?:

My role model is my mom. She was a marketing executive at Nortel in its heydey, and she now owns her own communications consulting business. She taught me the value of hard work, and showed me what happens when you build an incredible career. She also imbued with a love for travel, and I’m very grateful for that.

Favorite Places/Destinations?:

It’s so hard to choose my favourite place! We just went on our honeymoon to Fiji, New Zealand, and Australia, so I would say right now New Zealand is at the top of the list. It’s incredibly beautiful, and everywhere you go is a wine region (bonus). But I would say South Africa and India are two of my other favorite places. Going on safari is one of the most special things you can experience, and my favorite travel day ever was going on a tour of the Chandni Chowk market in New Delhi, which is an incredible place.

Favorite Products/Objects?:

My favorite product is my AirPods. They truly changed my life! They’ve changed the way I listen to podcasts, work out, and conduct business meeting.

Current Passions?:

My passion has always been travel. I’ve been lucky to travel to incredible countries like Brazil, South Africa, and India, and while I don’t care about fancy cars or expensive possessions, I am obsessed with spending my disposable income on travel.

A Day in My Life:

What do you love most about Your City?

I’m from Toronto, but right now I’m living in Montreal for the FounderFuel startup accelerator, and I absolutely love this city. It feels very European, and it’s absolutely beautiful – every side street has colorful walk-up apartments, trees, flowers, and historical buildings. It also has an incredible restaurant scene, which I’ve been working on exploring!

Favorite breakfast meal & restaurant?

If I have a breakfast meeting, my favorite breakfast meal is avocado toast from Soho House in Toronto. If not, I eat the same thing every date for breakfast: whole wheat toast with peanut butter.

What are you doing at:

6:00 AM – Sleeping! I usually wake up at 7am to go for a run or hit a workout class, and I’m at my desk by 8:30am.

10:00 AM – Working.

12:00 PM – Favorite Lunch spot/meal? My favorite lunch spot in Toronto (where Willful is usually based) is Le Gourmand, a cafe at Spadina and Queen – they have the best grab-and-go sandwiches and salads.

7:00 PM – Either at a workout class, at an event, or watching Netflix.

11:00 PM – I would like to say sleeping, but more likely, scrolling through Instagram.

What drink do you need to get through the day and at the end (and how many)?

At least two coffees in the morning, and lemon-flavored Perrier at night (I can’t have caffeine after lunch or I bounce off the walls).

Most used App/Favorite Instagram Account?

I use Todoist, a to-do list app that helps keep me organized.

Where do you enjoy getting lost?

In any new city when I’m traveling. My favourite thing to do is explore a new neighborhood with my husband when we travel – walk around, grab a cocktail, and get lost.