About Willful

At Willful, we're on a mission to make estate planning simple, affordable, and accessible for Canadians. Since 2017, we've helped over 400,000 people create their estate plans and plan their legacy. Through partnerships with Wealthsimple, Scotiabank, CIBC and Amazon, we're transforming how Canadians protect what matters most.

Your role at Willful

As a Product Manager at Willful, you'll play a key role in shaping how Canadians plan for their legacy. Reporting to our Director of Product, Sarah, you'll take ownership of core areas of the Willful experience. You'll tackle ambiguous problems and define solutions that help families across Canada. Partnering closely with Design, Engineering, and other teams, you'll prioritize opportunities, define customer-centred features, and deliver experiences that have an impact on people's lives.

What you'll do

Decision-making & problem-solving

• Leverage various inputs to identify opportunities within your areas of responsibility.
• Use frameworks, data, and other tools to prioritize your product backlog to maximize business and user impact.
• Test, refine, and validate solutions with our customers.

Execution

• Leverage experimentation and iterative product development to build a successful product.
• Drive product development from ideation through development to launch.

Communication & Collaboration

• Clearly communicate product plans and priorities to the broader organization.
• Help other teams understand product priorities and how they impact their work.

Product Team & Culture

• Create and optimize processes, frameworks, and tools that improve how we build products.
• Coach and guide others across the organization on how to make product-driven decisions.

What you'll bring

• Strategic problem framing. Ability to work on ambiguous problems, explore multiple solution paths, and choose the highest-leverage approach.
• Data depth. Hands-on with product analytics (e.g., Amplitude and Hotjar), experimentation, and instrumentation; comfortable building dashboards and making decisions with data.
• Customer empathy. Strong instincts for user research, interviews, and usability testing; you translate insights into clear requirements.
• Influence & collaboration. Excellent written and verbal communication; you bring stakeholders along and value diverse perspectives.
• Ownership mentality. Self-directed, resourceful, organized. You set clear priorities and follow through.

Nice-to-haves:

• Experience in fintech/insurtech or other regulated or trust-centric consumer domains
• Background in growth/conversion optimization.
• Comfort using Figma to review designs, give structured feedback, and collaborate effectively with design teams.

What success looks like in the first 90 days:

• Understand the context: You've built a deep grasp of our users, product, market, and metrics—reviewing past research, talking to customers, and digging into data to spot opportunities.
• Build strong partnerships: You're collaborating tightly with Design, Engineering, Marketing, CX, and stakeholders.
• Deliver early impact: You've led at least two product initiatives or experiments from discovery to launch, with clear hypotheses and success metrics.
• Improve how we work: You've introduced or refined PM processes (e.g., discovery cadence, experiment tracking, decision logs, KPI dashboards) that help the team move faster with fewer surprises.
• Raise the bar: You've brought in product best practices and fresh ideas—elevating our product thinking, customer empathy, and use of data across Willful.

Perks + What We Offer

• Competitive salary and participation in employee stock option plan (ESOP)
• Comprehensive benefits plan, including health, dental, and vision
• Flexible perks including the choice of a health spending account (HSA) or RRSP matching
• A $500 wellness budget to support your physical, mental and emotional health
• Monthly meal and entertainment budget
• 4.5 day work week and flexible work hours to accommodate both work and home life
• Company-wide “recharge” days off in December in addition to your vacation time
• Competitive parental leave policy
• Inclusive virtual team events
• In-person team and company-wide events (last year we went to PEI)

We're building a diverse team

Willful is committed to building a diverse team and encourages applications from individuals from underrepresented groups, including but not limited to women, racialized individuals, Indigenous people, LGBTQ+ individuals, and persons with disabilities. We are also committed to providing reasonable accommodations to applicants with disabilities during the recruitment process.

Work where you want to

We're looking for the right person to join our team so this role isn't limited by geography and will be 100% remote. The only requirement is that you must be legally able to work in Canada. You'll attend approximately two in-person company retreats per year.

Start date

ASAP - This role is to address an existing vacancy on the team.

Interview process

• Phone screen with a member of the team

• Experience Deep Dive with Sarah and another member of the team

• Product Challenge with Chris (Chief Product and Technology Officer) and Andres (Director of Engineering)

• References

• Offer

• Meet the Engineering, Product, and Design Team