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 150,000 people create wills and powers of attorney, establishing us as a trustworthy and innovative leader in the legal tech space. Featured in The Globe and Mail, Global News, and Dragons’ Den, we’re transforming how Canadians prepare for the future.

We’re looking for a customer experience director who shares our vision and can deliver exceptional service and support to our customers. As part of our team you will develop and implement a strategic, AI-first strategy for customer experience that delights customers and accelerates Willful's growth.

Your Role at Willful

As Director of Customer Experience, you’ll be accountable for proactively implementing new processes, innovations, tools, and automations that educate customers and empower them to create their end-of-life plans. You’ll also build, lead and scale a human-powered services offering to complement our self-serve online process. You’ll report to Willful’s Chief Operating Officer and work closely with the operations, product, and marketing teams to ensure a cohesive customer experience that empowers customers to check “get a will” off their list.

Key Responsibilities:

Implement a proactive, AI-driven strategy across the customer journey that directly impacts key metrics like sign up, conversion rate, revenue, and referral
Lead the Customer Experience team to deliver best-in-class customer support, as measured by CSAT and NPS
Set departmental rocks and KPIs, ensuring they are consistently met and aligned with the company’s quarterly goals
Automate the customer service experience using AI and other technologies
Manage a departmental operating budget to effectively allocate resources
Champion the voice of the customer by continuously gathering and integrating customer feedback into product development and service improvement process
Analyze and interpret data to identify opportunities and inform the CX strategy

Who You Are:

Experience leading and coaching CS teams, preferably in B2C organizations
Expertise in designing, implementing, and managing multi-channel inbound and outbound customer support programs
Experience implementing automations through phone, chat/SMS, email, and web channels using AI or other emerging technologies
Experience implementing or leading a referral program to amplify customers’ experiences via word of mouth
Proficiency with CX systems and/or automation tools such as Zendesk and Ada
Strong data analysis and visualization skills
Ability to think and operate at a strategic level but drive execution on a tactical level with the desire to be hands-on
Empathy is one of your top traits: You navigate sensitive customer interactions with compassion, and you value collaboration and diversity of thought
Articulate, persuasive verbal and written communication skills with the ability to engage and influence others at all levels of the company
Ability to manage multiple projects in a fast-paced environment
Extra credit if you have experience working with the principles of rapid experimentation, conversion rate optimization and/or product-led growth

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 leading and scaling customer support teams.

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 include 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 pilot 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 (this 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, 2SLGBTQIA+ 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 will be required to attend in-person company retreats and meetings.

Start date: Nov 1

Interviewing at Willful

Here’s what you can expect.

Phone screen (10-20 min)
Interview with Chief Operating Officer (1 hour)
Interview with interim Customer Support Manager (30 min)
Short at-home assignment (1-hour max)
Assignment review and final interview with Chief Operating Officer and Customer Support Manager (45-60 min)
References
Meet the CX team
Offer