Erin Bury named CEO of Willful

Erin Bury

Erin Bury, advisor and investor in Toronto-based Willful, is jumping with both feet into entrepreneurship, replacing her husband and founder Kevin Oulds as CEO of the company. Focused on end-of-life planning, Willful aims to simplify the process of estate preparation by getting more Canadians to create a will.

“Kev has done a really great job of building a brand around Willful. But we have big plans beyond that.”

Bury told BetaKit that she has operated as an “unofficial behind the scenes cheerleader [and] mentor” at Willful since day one, encouraging Oulds to take the initial leap in founding the company in 2017. Since then, Oulds has built a team that has raised less than six figures of friends and family capital, and has expanded into Ontario, BC, and Alberta.

During this time, Bury served as managing director of creative communications agency, Eighty-Eight, an advisor and investor to Pressed, and as a board member of Save the Children Canada and Tech4SickKids. Bury was also previously the founding managing editor of BetaKit.

“It seems scary to move into a CEO role for the first time,” Bury said. “But Kev always says to me, ‘you really were the CEO of Eighty-Eight for six years.’ To date, Kev has done a really great job of building the product and building a brand around Willful. But we have big plans beyond that.”

Bury said the decision to join was a combination of her looking for the next challenge and Oulds recognizing that the time would eventually come to bring in someone with more experience to scale the business.

“I was at the stage in my career where I was looking for a change from my agency,” Bury said. “I wanted to get back in-house, and I wanted to be part of a small early-stage team again. And [Kevin] was at a point where he had gotten to where he could with his own skillset and background.”


Bury said that what attracted her to Willful was a market guaranteed to always exist, but also one that had never truly been tapped into from a tech perspective. Oulds got the original idea for the company after the unexpected death of a family member. His family had never made a will, making an already difficult time more challenging for his family. Some near-death experiences for Oulds made him realize that he needed to found a company to encourage people to have a conversation about death, and beginning planning sooner than later.

“Death, which is the only inevitability in life, has been largely untouched by technology,” Bury said. “As we started diving into this problem, I realized that there was actually a huge business opportunity here. Both because the business is recession-proof, and secondarily, if you tried to name one player who has really owned or changed the experience of planning for and dealing with death, I think you’d be hard-pressed to name one.”

RELATED: One year later, Willful wants to make wills less scary

Bury and Oulds had spoken over the last few years about what would happen if she ever wanted to join the company. She said she always joked that she would have to come in as CEO, not only because her strengths lie in business operations and public relations, but also because there was a gap for her sort of skillset at Willful.

“[Kevin is] such an expert in estate planning, whereas my strength is more so on the business operations side,” she said. “So I think we have a good complement of skills.”

In his new role as head of business development, Oulds will be focusing on building out Willful’s partnerships with financial institutions, benefits companies, and life insurance companies. He has launched partnerships with the Ontario Teachers Insurance Plan and Honeybee Benefits, with additional partnerships expected to be announced later this year.

“The biggest challenge when you’re working with a husband and wife team is making sure that there’s a clear divide between work and personal, and making sure that you’re treating each other like colleagues when you’re in the office,” Bury said. “That will be the big challenge for us.”

Oulds told BetaKit that Bury’s business operations experience, combined with her storytelling expertise, will add a great deal of value to the organization, and will allow him to focus on growing the business with partners across Canada.

“Willful has grown from an idea I had based on a personal experience into a thriving estate planning platform that has helped thousands of Canadians,” Oulds said. “I’m excited to welcome Erin to the team as CEO. She knows the business inside out since she’s been advising us since day one, and I know she’s the right person to help us achieve our mission of ensuring every Canadian adult has an estate plan in place.”

So far, Willful’s strategy has involved partnering with local lawyers in each of their operational provinces to help create the legal content, and answer questions. Bury said she’s hoping to launch Willful across Canada by the end of this year.

“The expansion has gone slowly because Kev is reaching out to a lot of these lawyers, and they see us as competition,” Bury said. “Ultimately, we see it as a partnership, and the lawyers that we’ve partnered with today believe that. They understand that technology is the way that their industry is moving.”


The company also recently made its first full-time hire to its engineering team, Matt McFadyen, who was previously at Since launch, Willful has added additional features to its core product, like the ability to designate what happens to pets, and a charitable giving feature, which allows customers to designate a percentage of their estate to a charity of their choosing.

Willful is looking to build out a suite of products that not only help consumers prepare for death through a will, but also through other arrangements that are often overlooked, like wrapping up debt and online and social media accounts.

Bury said the company is also developing a hiring roadmap for people in product design and sales, and is expected to announce a series of strategic and affiliate partnerships. Bury added that Willful is in the process of closing its first round of angel financing. The investors are undisclosed for now, but Bury said the company is expecting to raise approximately $500,000 CAD.

“My goal is really to come in and help guide the next phase of the business,” Bury said. “There’s no time in history where death is going to slow down, so unless we achieve immortality, we have a business case that really will last forever.”

Image courtesy Kayla Rocca.

Isabelle Kirkwood

Isabelle Kirkwood

Isabelle is a Vancouver-based writer with 5+ years of experience in communications and journalism and a lifelong passion for telling stories. For over two years, she has reported on all sides of the Canadian startup ecosystem, from landmark venture deals to public policy, telling the stories of the founders putting Canadian tech on the map.

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