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. We’re transforming the way Canadians protect what matters most—through an intuitive online platform, support from human estate planning experts, and relentless innovation toward our vision of the future. Our partnerships with Canada’s most trusted brands, including Wealthsimple, Scotiabank, CIBC and Amazon help us bring estate planning within reach for every Canadian, making it easier than ever to get the protection and peace of mind of having an estate plan in place.

We believe that thoughtful, user-friendly content can empower people to take charge of end-of-life decisions. By combining intuitive technology with expert legal insights, we help individuals and families protect what matters most.

Your Role at Willful

We’re looking for a Content Writer to lead Willful’s content strategy across multiple channels, including email, direct response, long-form editorial, and in-app copy. You’ll be the voice of Willful, ensuring a consistent and engaging brand experience at every touchpoint. This is a fully remote role for a writer who thrives on both strategy and execution and is ready to impact how Canadians approach estate planning.

Key Responsibilities:

Own the brand voice: Refine and maintain Willful’s voice across all communications, from product tooltips and marketing assets to customer support resources. You’ll train and support cross-functional teams, ensuring every written asset aligns with our guidelines.
Email and direct response copy: Develop compelling email and direct response ad copy that reaches users at various touchpoints, driving engagement and conversion.
Long-form content: Research and write in-depth articles and guides that educate and empower readers to plan their futures while employing SEO best practices. Collaborate with our PR team to support thought leadership initiatives, industry reports, and earned media opportunities.
In-app copy: Partner with our Product team to craft user-centric messaging that resonates with users at various stages of their journey
Collaborate across teams: Work with content, product, customer success, PR and design stakeholders to align messaging and campaign goals

What Success Looks Like in the First 90 Days:

Audit all Willful communications; identify gaps, and deliver a refined style guide.
Launch at least two email campaigns aimed at driving conversions.
Partner with Product and CRM stakeholders to improve the early user onboarding journey
Develop copy for at least two paid social campaigns
Oversee the editorial planning and development for an edition of Willful’s monthly newsletter
Develop an editorial calendar that speaks to Willful’s audience across multiple channels

Who You Are:

Experience and expertise: You have 4–6 years of professional writing experience in B2C tech, SaaS, digital marketing, or editorial publishing. Your portfolio showcases compelling email, direct-response, editorial, and in-app copy, backed by strong storytelling, editing, and SEO skills.
Detail-oriented: You can produce error-free, fact-checked content that reflects a consistent brand voice in various formats with minimal editing.
Customer-centric mindset: You have a deep understanding of customer needs and aspirations, and excel at crafting content that educates, motivates, and drives meaningful action. You adapt tone and style to ensure each piece resonates with diverse audiences.
AI-native mindset: You see AI and emerging technology as a creative sidekick, not just a tool. You’re curious about how it can level up your process, from sparking ideas to speeding up research.
Collaborative spirit: You thrive in cross-functional environments—partnering with designers, product managers, and senior executives. You gather feedback efficiently, manage revisions with ease, and consistently deliver on time.
Analytical mindset: You’re eager to use data and experimentation to improve content performance.
Curious and empathetic: You question assumptions, explore new ideas, and remain true to Willful’s core brand values. You prioritize empathy and inclusivity, valuing diverse perspectives and collaboration.

We’re looking for the right person to join our team! We don’t care where you went to school—or if you went to school—as long as you have a proven track record of marketing success.

Even if you don’t check off all the boxes but you think you’d be a good fit for the team—we encourage you to apply.

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
Fun and inclusive virtual team events
In-person team and company-wide events

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

Ready to apply?

If you’re ready to help shape Willful’s voice and engage Canadians on a topic that truly matters, we’d love to hear from you. Please submit:

A couple of sentences explaining why you’re excited about Willful and how your experience aligns with our needs.
2–3 writing samples, including at least one email or direct-response piece. Feel free to share published or speculative content (and label accordingly).

Interviewing at Willful

Here’s what you can expect.

Interview with hiring manager
At-home assignment
Final interview
References
Meet the Marketing Team
Offer