About Willful

At Willful we’re known for bringing the mundane task of estate planning out of the shadows and into the same conversation as insurance, financial planning and filing your taxes. While end-of-life planning is a very sensitive subject, our mission at Willful is to use technology and empathy to make the process as simple and painless as possible. It’s a great day at Willful when a customer finishes their will and writes to tell us “Hey, that was kind of fun!”

Giving people an accessible, dependable and affordable option is the fuel that drives us every day. We’ve helped tens of thousands of customers create their wills and power of attorney documents since launching in 2017, and now we’re looking to hire our first head of legal to lead and grow our in-house legal team.

What your role will encompass

As Willful’s first Head of Legal, you will be responsible for the following:

  • Maintaining the quality of our legal documents: Conducting regular audits of our legal documents, and working in tandem with our provincial legal partners to review content in other provinces to identify ways we can improve and maintain the accuracy of our legal content. This also includes staying updated on relevant case law, and making ongoing recommendations for improvements.
  • Monitoring for and responding to legislative updates: You will monitor for legislative changes in all provinces, and be ready to work with our provincial partners to implement changes to our documents when necessary. You will also be on top of any digital will legislation that could impact our customers and inform future product updates.
  • Implementing document updates: You’ll work closely with our product team to implement any updates and improvements to our documents. This will include reviewing proposed changes with provincial partners, and working with legal translators to implement changes in Quebec.
  • Law Society program management: You will manage Willful’s participation in the Law Society of BC’s Innovation Sandbox, and in the Law Society of Ontario’s Access to Innovation program. You will also spearhead applications for similar programs in other provinces as they become available.
  • Product expansions and additions: You will work alongside the product team to develop new legal services offerings at Willful. You will provide input on priorities, pricing, process, and go-to-market strategies.
  • Resourcing: You will manage the relationships with Willful’s local legal partners in each province. This will include ongoing relationship management, ongoing audits and document improvements, and sourcing, augmenting, or replacing partners when necessary. This includes managing the relationship with our notary partner in Quebec. You will also be responsible for growing our in-house legal team as needed.
  • Legal content: You will work with our marketing and customer success teams to audit, improve, and add to our library of user-friendly, jargon-free educational content. This may include drafting written content, filming videos, or editing content. You will also review marketing and product copy for legal compliance.
  • Thought leadership: You will become Willful’s external estate planning expert, handling educational presentations, lunch and learns, media interviews, and other opportunities to build our brand and promote our expertise to Canadians.

This role will report to our Chief Operating Officer Julia Wilkie, and there will be a considerable amount of collaboration with our CEO, and with the product and marketing teams.

Who you are:

  • Proven expertise in estate law: You have at least 5-8 years of experience as a practicing LSO-licensed wills and estates lawyer in Ontario. You are very comfortable with drafting wills and power of attorney documents, regardless of the level of complexity. You are in good standing with the Law Society of Ontario.
  • Innovative mindset: You believe that technology is the future of estate planning, and that platforms like Willful improve access to justice for all Canadians. You believe digital wills should be adopted across Canada, and you believe that tools like ChatGPT has the opportunity to change the way we practice law (for the better).
  • Attention to detail: You care about the small details and are a stickler for grammar, wording choices, and accuracy in your legal content. You are practical, business minded and open to working in a fast-paced environment.
  • Strong communications skills: You’re an excellent written and verbal communicator, and you are excited by the prospect of honing your public speaking skills.
  • Entrepreneurial approach: You are excited to work in a small company with limited resources, and you recognize that you will not have the resources of a large law firm - but in exchange, you’ll have the opportunity to build out a team and to work on exciting innovative products that will change the estate planning landscape in Canada.


  • Bilingual
  • Experience in/knowledge of the Quebec legal system

Perks + What we offer

  • The opportunity to work in the nascent space of estate planning that is ripe for disruption
  • Competitive salary and participation in employee stock option plan (ESOP)
  • Comprehensive Sun Life benefits plan, including health, dental, and vision
  • Choice of $500 perk: a health spending account (HSA) OR as RRSP matching through Wealthsimple for Employees
  • An annual education budget to sharpen your existing skills or learn a new skill set
  • Shortened summer hours, and company-wide “recharge” days off in December in addition to your vacation time
  • Competitive parental leave policy
  • Flexible work hours to accommodate both work and home life
  • Fun and inclusive remote team events and in-person retreats twice a year.

We’re building a diverse team

Willful is an equal-opportunity employer. We celebrate our inclusive work environment and welcome members of all backgrounds and perspectives to apply. We are committed to providing reasonable accommodations and will work with you to meet your needs. We have a commitment to diverse hiring and are proud to say that 50% of our team, and 50% of our C-level executives, are female-identifying.

Work where you want to

We’re looking for the right person to join our team and this role will be 100% remote. The only requirement is that you must be legally able to work in Canada, and you must live in Canada full-time and be committed to working in the EST time zone. You must be licensed by the Law Society of Ontario, and you may be required to attend events and meetings in Toronto. You will also be required to attend in-person company retreats twice a year.

Interviewing at Willful
Here’s what you can expect.

  1. Phone screen (10-20 min)
  2. Interview with CEO Erin Bury (45 min)
  3. Interview with COO Julia Staffen (1 hour)
  4. Short at-home assignment (2 hours max)
  5. Assignment review and final interview with Willful co-founders Erin & Kevin, and COO Julia Staffen (45-60 min)
  6. References
  7. Offer

Note that Willful’s legal partners may be part of your assignment review. All recruiting activities including interviews and new hire onboarding will be conducted virtually.


July 4 2023 (or sooner)

How to apply:

Via Breezy HR