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 involves important, often emotional decisions, which means how and when we communicate with customers really matters. Lifecycle marketing at Willful supports customers through complex moments with clear, relevant, and thoughtful communication.

The role

We’re looking for a Senior CRM & Lifecycle Marketing Manager who cares deeply about judgment, ownership, and outcomes.

You’ll set the strategic direction for CRM and lifecycle marketing, own lifecycle performance across email and SMS, and manage one CRM Specialist, while working cross-functionally to improve the end-to-end customer experience.

This is a newly created role designed to blend responsibilities that are often split across CRM, lifecycle, growth, CX, and product marketing. You’ll be expected to recognize opportunities across the full customer lifecycle and work cross-functionally to turn them into results, even when you don’t own every lever directly.

This is a senior, hands-on role with clear ownership. You’ll set direction, make trade-offs, and remain close to execution. You’ll be accountable for lifecycle outcomes, not just activity or output.

This role reports to the Head of Marketing and is best suited to someone who has operated in an agency, startup or high-growth environment, is comfortable with ambiguity, and prefers building and fixing over managing at a distance.

How you’ll make an impact

• CRM strategy and leadership: Define the lifecycle vision, priorities, and roadmap across email and SMS, aligned to business goals and customer needs.
• Lifecycle ownership and accountability: Own lifecycle performance across onboarding, conversion, and referral, with accountability for efficiency, effectiveness, and ROI.
• Coaching with accountability: Manage and mentor a CRM Specialist with clear expectations, direct feedback, and follow-through.
• Execution oversight: Oversee production of email and SMS programs using strong judgment around segmentation, triggers, experimentation, and messaging.
• Lifecycle opportunity recognition: Identify when lifecycle challenges are rooted in product experience, CX workflows, or operational friction. Partner with Product, CX, Ops, and Marketing to unlock improvements.
• Resourceful execution: Make progress with imperfect data, limited time, or constrained resources. Make clear decisions without waiting for perfect conditions or alignment.
• CRM tooling ownership: Own the CRM tech stack and roadmap. Manage vendors and ensure tools support execution.

What success looks like

• Lifecycle priorities are focused and tied to outcomes.
• High-impact improvements are shipped quickly.
• Lifecycle performance is clearly owned, measured, and improving.
• Cross-functional partners trust your judgment and follow-through.
• CRM execution quality is high, with minimal gaps between strategy and reality.

Who you are

• You bring 6–8 years of experience in CRM or lifecycle marketing, ideally in consumer tech or direct-to-consumer (DTC) brands.
• You’re comfortable with data and analytics, with hands-on experience pulling reports, interpreting performance data, and using insights to drive strategy.
• You have experience operating in an agency environment, startup or high-growth companies and are comfortable with ambiguity, shifting priorities, and limited resources.
• You act like an owner and take accountability for results.
• You diagnose problems before jumping to solutions and make trade-offs confidently.
• You’re comfortable working cross-functionally and influencing outcomes without formal authority.
• You communicate clearly, give direct feedback, and push back thoughtfully when needed.
• You use AI as a tool to support judgment and efficiency, not replace it.

Bonus experience

• Experience in regulated or trust-based consumer industries (financial, legal, health).
• SQL or advanced data access skills.

Perks + What we offer

• Anticipated salary range of $110,000 to $140,000. 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
• 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 excited to own lifecycle outcomes and help Canadians navigate important decisions with clarity and trust, we’d love to hear from you. Please submit:

1. A few sentences on why you’re interested in Willful and how your experience aligns with this role.
2. A brief description of a lifecycle initiative you personally owned, including what worked and what didn’t.

Interviewing at Willful

1. Interview with Head of Marketing (45 min)
2. At-home assignment (compensated)
3. Final interview with Head of Marketing and CRO (60 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, evaluation or hiring decisions and are used solely to support accurate documentation and efficient internal communication.