Senior Content Marketing Manager

About Willful

Willful makes estate planning simple, affordable, and accessible for Canadians. Since 2017, more than 400,000 people have trusted us with their estate planning journey.

Estate planning is a high-trust, high-empathy space. Accuracy, clarity, and tone matter. We believe that good content can make complex decisions feel more manageable and help people take action without pressure, fear, or unnecessary complexity.

The role

We’re looking for a Senior Content Marketing Manager who cares deeply about words, judgement, and outcomes.

This role is for someone who can balance strategy and execution, and who wants clear ownership over their work. You’ll be responsible for shaping how Willful communicates, writing and editing key pieces yourself, and ensuring our content is accurate, consistent, and effective.

This is a senior individual contributor role, reporting to the Head of Marketing. You’ll be trusted to make decisions about what to prioritize, how work gets done, and how success is measured, and you’ll be accountable for the outcomes.

You’ll work across long-form editorial, SEO-driven content, email, and marketing copy, partnering closely with other teams to make sure content supports real user needs.

This is a newly created role, and starts as a 6-month contract, with a clear opportunity to transition to a permanent position based on performance and mutual fit.

How you’ll make an impact

• Content strategy and ownership: Set direction, make decisions, and be accountable for outcomes.
• Editorial planning and execution: Own the learn centre and blog, from prioritization through publication.
• High-impact copywriting and editing: Write and refine marketing copy across emails, paid ads, and landing pages.
• Content performance optimization: Use data and experimentation to improve what’s working and fix what isn’t.
• Brand voice and standards: Own Willful’s tone and quality bar across all customer-facing content.
• Content accuracy and subject-matter expertise: Build and maintain strong working knowledge of estate planning topics, stay current on relevant legal changes, and ensure content is accurate and trustworthy.
• Freelance resourcing and scale: Bring in external support when it makes sense and manage quality end‑to‑end.
• Cross-functional partnership: Work closely with Product, CRM, CX, and Design to ensure content supports real user needs.

What success looks like

• Content decisions are focused, intentional, and tied to measurable outcomes.
• Writing quality and accuracy are consistently high with minimal rework.
• Content contributes to measurable improvements in conversion rates across priority funnels.
• The Learn Centre is clearer, more effective, and easier to improve over time.
• Stakeholders trust content to be well‑reasoned, on‑brand, and correct.

Who you are

• You bring 5–7 years of experience writing and leading content in consumer tech or direct-to-consumer (DTC) environments.
• You’re an excellent writer and editor with strong taste and a bias toward clarity.
• You have hands‑on experience with SEO‑driven content, including search intent, on‑page optimization, and iterating content over time.
• You operate with ownership and agency, not just execution.
• You’re comfortable with metrics and care about whether your work actually works.
• You’re detail‑oriented and take accuracy seriously, especially in high‑trust subject areas.
• You communicate clearly, manage stakeholders well, and push back thoughtfully.
• You use AI as a tool to improve your work, not replace judgement.

Perks + What we offer

• Anticipated salary range of $85,000 to $115,000. The exact salary will be dependent on the successful candidate’s relevant skills, experience, and qualifications.
• 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 year‑round, and flexible work hours to accommodate both work and home life
• Company‑wide paid “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. If you require an accommodation at any stage of the application or interview process, please let us know and we’ll work with you to ensure a fair and accessible experience.

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:

1. A few sentences explaining why you’re excited about Willful and how your experience aligns with our needs.
2. 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.

1. Interview with Head of Marketing (45 min)
2. At‑home assignment (compensated)
3. Final interview with CRO (45 min)
4. References
5. Offer

AI Disclosure Statement

Willful uses artificial intelligence tools for internal note‑taking purposes only. These tools do not influence candidate screening or hiring decisions and are used solely to support accurate documentation and efficient communication.