About Willful

At Willful, we’re on a mission to make estate planning simple, affordable, and accessible for Canadians. Since 2017, we’ve helped hundreds of thousands of Canadians create wills and powers of attorney documents.

We’re transforming the way Canadians protect what matters most through an accessible 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.

About This Role

Here's what we've learned: thousands of Canadians start creating their will every month but get stuck somewhere along the way. Maybe they need to have a tough conversation with their partner about guardianship. Maybe they're overwhelmed by the beneficiary decisions. Maybe they just need someone to tell them it's okay to start simple and update later.

That's where you come in.

We're hiring someone to be the human voice that helps these families get unstuck. You'll reach out to people who started but didn't finish, have real conversations about what's holding them back, and guide them to complete one of life's most important (and avoided) tasks.

This isn't your typical support role. You're not waiting for problems to come to you, you're proactively calling and helping people before they even ask. And yes, you'll also jump in to help the team with regular support when things get busy, but your main job is calling our customers and turning "I'll do it later" into "Done, and it feels great".

Key Responsibilities:

• You'll call people who started but gave up. Not to sell them anything new, they already want this. You're calling to find out what made them stop. Maybe they disagree with their spouse on guardians for their children. Maybe they got overwhelmed by the beneficiary page. Maybe they just forgot. Your job is to help them get unstuck.
• You'll jump in when things get busy. When people are out sick and the queue is exploding, you're the cavalry. Phone, email, chat, whatever the team needs for reactive support. Think of it as being the reliable teammate everyone's grateful for.
• You'll become our resident detective. Why do people with kids under 5 convert differently than empty nesters? What voicemail actually gets callbacks? You'll test everything and track what works.
• You'll translate customer pain into company action. When you notice the fifth person this week is confused about executors, you don't just note it, you grab the team and say "we need to fix this". Your insights will literally change the product.
• You'll become great at estate planning knowledge. Within a few months, you'll know why wills are about so much more than just who gets your stuff, what happens when someone dies without a will in each province, and all the tricky questions about guardians versus executors. And more importantly, you'll know how to explain it without putting people to sleep.

Who You Are:

• You have zero fear of picking up the phone. Calling strangers doesn't make you sweat. You actually find it energizing. While others stare at their call list procrastinating, you're already dialing. You know the first three seconds set the tone, and you nail them every time.
• You genuinely care about people. Not in a "corporate values" way, but actually. You can talk to someone about their kids' future guardians without making it weird or pushy.
• You're curious about why things happen. When someone says "I'm not ready", you want to understand what's really behind that. Is it the price? The complexity? An uncomfortable family dynamic?
• You can explain complicated things simply. Estate planning has lots of jargon. You can translate "testamentary trusts" into "a way to control when your kids get their inheritance" or explain that an executor is basically "the person who handles all the paperwork after you're gone".
• You see patterns others miss. After a week of calls, you'll notice that everyone with teenage kids asks the same question, and you'll have ideas about how to address it.
• You're comfortable with uncertainty. This is a new role. We have some ideas about what works, but you'll be figuring out a lot as you go. That excites you rather than stresses you out.
• Rejection doesn't crush you. Some people won't be ready. Some will decide to see a lawyer instead. You understand that's valuable information, not personal failure.
• You think strategically. You understand this isn't just about individual calls, it's about building something that scales and transforms how we help customers.

Nice-to-Have:

• Past experience in a customer-facing role such as retail, hospitality, support, sales, or customer success

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 one in-person company retreat per year.

Start Date

ASAP

Interview Process

1. Phone Screen
2. Experience + Role Deep Dive
3. Customer Call Challenge
4. Meet the Team
5. References and Background Check
6. Offer