Job Description

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 300,000 people create wills and powers of attorney documents. Through partnerships with Wealthsimple, Scotiabank, CIBC and Amazon, we’re transforming how Canadians protect what matters most.

Your role at Willful

As a Senior Product Designer at Willful, you’ll own the end-to-end user experience—turning complex problems into intuitive, accessible, and visually polished solutions. You’ll lead design from research through high-fidelity execution, working closely with Product, Engineering, and other stakeholders to shape our roadmap and deliver real impact. You’ll be a key voice in product strategy and a driving force behind our design culture. This role is ideal for a self-starter with strong visual design skills, someone who has a user-first mindset, and experience designing in fast-paced, collaborative environments.

The impact you'll have:

As Senior Product Designer at Willful, you will have a significant impact on the success of our product and the opportunity to help shape the team, design culture and processes. The role will encompass:

• Lead design from start to finish: Drive projects from discovery to final delivery, including prototyping and high-fidelity visuals. Build and maintain scalable design systems.
• Put users first: Conduct interviews, surveys, and usability tests to uncover insights. Use research and analytics to guide smart, strategic design choices.
• Collaborate cross-functionally: Partner with Product, Engineering, and other teams to align on goals and bring ideas to life. Champion user-first thinking across the org.
• Iterate and innovate: Solve complex problems through rapid testing and continuous iteration. Stay adaptable in a fast-paced startup environment.

What you'll bring:

• You are an experienced designer with the ability to execute on all phases of the design process.
• Passionate about accessible, user-centred design. You turn research into meaningful experiences.
• Comfortable working with and presenting to cross-functional teams.
• Entrepreneurial mindset with a drive to push boundaries, improve processes, and grow alongside the product.
• You think in terms of outcomes, validation, constant iteration and are great at simplifying complexity.
• You examine all processes critically and are always finding opportunities to streamline and improve
• You have a fine-tuned balance of accountability for results and customer empathy.

What success looks like in the first 90 days:

• Understand the context: You’ve built a strong understanding of our users, product, and space—reviewing past research and conducting your own discovery.
• Build strong partnerships: You’re collaborating closely with Product, Engineering, and stakeholders, and contributing meaningfully to team discussions and rituals.
• Deliver early impact: You’ve led design on at least two product initiatives, from discovery to delivery, with clear, user-centred design decisions.
• Improve how we work: You’ve introduced or refined design systems, processes, or tools that help us work faster with more consistent results.
• Raise the bar: You’ve brought in new ideas, best practices, or inspiration that’s elevated how we think about product and design.

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 the Dominican Republic)

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 in-person company retreats and strategic planning sessions a few times a year.

Start date

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

Interviewing at Willful

Here’s what you can expect.

1. Phone screen with Sarah Cook (Product Lead / Hiring Manager)
2. Portfolio Review with Sarah and Chris (CPTO)
   
3. Final Interview
4. References
5. Offer