About Willful
At Willful, our mission is to ensure every Canadian has a comprehensive end-of-life plan in place in order to reduce burden on families. We make creating a will and other estate planning documents accessible, affordable, and easy, using technology and empathy to simplify the process. Since launching in 2017, we’ve helped more than 350,000 Canadian families get peace of mind through our digital estate planning products.
And we’ve built a respected, recognized brand - we’ve been featured in top-tier publications like The Globe and Mail and the Toronto Star, we’ve partnered with top-tier brands like Scotiabank and CIBC, and we even struck a deal on Dragons’ Den. Transforming estate planning into an accessible, convenient, and affordable option drives us daily. Now, we’re hiring an additional software developer to further our mission.
About the role:
We are looking for a senior technical expert with deep experience designing and maintaining complex, scalable web applications. In this role, your focus will be hands-on technical work, digging into codebases, solving high-level architectural challenges, and improving system performance, reliability, and scalability.
This role is ideal for someone who loves solving hard technical problems, enjoys working across multiple systems, and thrives in an environment where you can focus deeply on architecture and implementation.
What you l'll do:
- Design and refine architecture for our applications and systems to ensure scalability, maintainability, and security.
- Solve complex technical problems, including performance optimization, infrastructure reliability, and code scalability.
- Own key components of our codebase, contributing high-quality, well-tested code.
- Evaluate and introduce new technologies or frameworks as needed to improve efficiency and stability.
- Work closely with other senior engineers and the technical lead to plan and execute technical projects.
- Ensure best practices for testing, monitoring, code quality, and CI/CD pipelines.
- Provide technical direction within projects through code and design contributions, not through people management.
Required Skills and Experience:
- Experienced software engineer with extensive expertise in backend and full-stack development.
- Proven track record of designing scalable, maintainable architectures for web applications.
- Expertise with backend frameworks and languages (Ruby on Rails experience is a strong plus).
- Solid frontend understanding (React experience is a plus).
- Deep experience with RESTful API design and development.
- Strong database skills, including schema design, performance tuning, and optimization.
- Familiarity with cloud infrastructure and deployment practices (Heroku, AWS, or similar).
- Passion for solving complex technical challenges.
- Strong written and verbal communication skills.
Preferred Skills:
- PostgreSQL expertise and experience scaling relational databases.
- Experience working on multiple applications or services simultaneously.
- Familiarity with generative AI tools for development workflows.
- Knowledge of CI/CD tooling and DevOps best practices.
Who you are:
- Deep Technical Expert: You’re passionate about solving technical problems at a system level and thrive on digging into complex codebases.
- Architecture-Focused: You’re driven by technical correctness and long-term maintainability, and you’re comfortable making architecture trade-offs.
- Independent Contributor: You prefer deep technical work over people management or leadership roles.
- Pragmatic & Product-Aware: You balance technical excellence with practical product needs.
- Collaborative: You enjoy working with other technical experts and product-minded peers, and you communicate clearly and constructively.
- Detail-Oriented: You care about high-quality code, clean architecture, and robust systems.
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 success building software. If you don’t check every box, but you can show us a product you’ve successfully built in the past, apply.
We’re building a diverse team
Willful is dedicated to fostering a workplace that values and celebrates diversity in all its forms. We believe in the power of inclusion and are committed to creating a work environment that embraces individuals of diverse backgrounds, including but not limited to race, ethnicity, gender, sexual orientation, age, religion, and disability. We encourage all qualified candidates to apply, and we are committed to providing equal opportunities and a supportive, inclusive atmosphere for all employees. We are proud that over 50% of our team, and 50% of our Senior Leadership Team, are women; and over half of our team comes from diverse ethnic backgrounds.
Work where you want to
We’re looking for the right developer 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, and be able to align with our team’s core working hours. You will be required to attend one in-person company retreat per year.
When
September 2025 (flexible start date)
Why Willful?
- Competitive salary and participation in employee stock option plan;
- Sun Life benefits plan including health, dental, and vision;
- Annual $500 wellness budget;
- Monthly meal and entertainment budget;
- Choice of $500 perk: a health spending account (HSA) or $500 annual RRSP; contribution through Wealthsimple for Employees;
- 4.5-day work week (every Friday afternoon off), plus paid time off over December holidays and occasional extra-long weekends;
- Competitive policies, including parental leave and bereavement policy;
- Flexible work hours to accommodate both work and home life;
- Annual team-wide retreat
Interviewing at Willful:
- Phone Screen
- Experience Deep Dive (60 minutes)
- Skill Assessment (15 minutes for Q&A, followed by 30 minutes to present your solution)
- Culture Interview (30 minutes with members of our Engineering & Product team)
- Offer
All recruiting activities, including interviews and new hire onboarding, will be conducted virtually.
How to apply:
Breezy
