Principal Software Engineer
Wagepoint
Software Engineering
Canada · Remote
USD 150k-190k / year
Posted on May 10, 2025
Who We are:
At Wagepoint, we’re good people. Sure, maybe we’re biased. But that’s only because Wagepointers bring the best versions of ourselves to do some of the best work in our careers.
We’re an authentic team who bring our diverse backgrounds, ideas, experiences and cultures together to make payroll magic. Speaking of, we “pull rabbits out of hats” for thousands of small business owners across Canada who rely on our payroll software to pay their employees and process their payroll taxes. And we’re just getting started.
We’re growing and looking for more awesome people to join our merry band of misfits. We are looking for people who share our understanding that when it comes to our commitment to our customers: we mean business. Especially given that the consequences of getting payroll wrong can sometimes be dire.
If you are the kind of person who has always wanted to make a difference and be heard at work, Wagepoint will give you plenty of opportunity to do just that.
The Role at High Level:
We’re looking for a talented Principal Software Engineer who doesn’t shy away from tackling hard problems and interesting (well, most times) subjects like payroll and HR technology. You’ll play a pivotal role in evolving how we build software at Wagepoint by leading technical innovation, embedding AI into development workflows, and mentoring teams across the org.
This role is highly dynamic—you’ll rotate into product teams as needed, support critical initiatives, mentor peers, and align execution with strategic goals. You will report directly to our Engineering Leadership Team.
- Department
- Engineering
- Employment Type
- Full Time
- Location
- Canada - Remote
- Workplace type
- Fully remote
- Compensation
- $150,000 - $190,000 / year
- Reporting To
What You'll Be Expected To Own:
- Lead end-to-end full-stack development for key product features from design through deployment.
- Architect scalable, distributed systems using microservices and domain-driven design (DDD) principles.
- Design and deliver AI-powered features and embed automation across the software development lifecycle.
- Refine DevOps and CI/CD practices to improve deployment confidence and system observability.
- Provide senior technical leadership, participate in architectural reviews, and mentor engineers.
- Drive engineering architecture strategy and contribute to long-term technical planning.
- Promote AI literacy and champion AI tooling adoption across R&D.
- Guide and coach technical leads and senior engineers, raising engineering maturity across the board.
- Lead cross-functional initiatives that improve platform scalability and developer velocity.
What You Bring To The Table:
- 10+ years of full-stack software development experience with increasing technical leadership.
- Deep expertise in distributed systems, DDD, and microservices architecture.
- Proven ability to design and deliver customer-facing AI-powered features.
- Skilled in frameworks such as React or Angular and back-end technologies like C# and .NET Core.
- Proficient in relational and NoSQL databases, with strengths in schema design and data integrity.
- Experience with cloud platforms (AWS, Azure, GCP), IaC tools (Terraform, CloudFormation), and Kubernetes.
- Committed to clean code, automated testing, design patterns, and high code quality standards.
- Exceptional communication skills and ability to translate complex concepts to varied audiences.
- Passionate about continuous learning, innovation, and mentoring others.
Bonus points if:
- You’ve implemented advanced AI techniques such as RAG, vector search, and prompt engineering.
- You’ve contributed to the adoption of AI tools in software delivery (e.g., Cursor, Copilot).
- You have led initiatives around service decoupling, platform modernization, or cross-team architectural refactors.
- You’ve facilitated domain modeling workshops or event storming sessions.
- You’ve built enablement playbooks, shared technical talks, or driven engineering cultural improvements.
What We Bring To The Table:
- Impact: Roll up your sleeves and directly contribute to the growth and success of Wagepoint by shaping our workforce.
- Culture: The opportunity to work with the world’s friendliest team, solving interesting problems together with an endless amount of laughter (We work hard, but we always have time for a bad joke or two).
- Growth: Opportunities for professional development and career advancement - we are always, always learning with a growth oriented mindset.
- Innovation: Work in an environment that encourages creativity and new ideas.
- Remote: The ability to work from home, forever! Wagepoint is a remote company, so you don’t have to worry about commuting to an office. Plus, more time with your pets is always a bonus!
Ready to embark on an exciting journey with us? Apply now and help us build the future of Wagepoint!
About Wagepoint
Wagepoint is a simple and fast online payroll app, backed by the world's friendliest team.
The app is ideal for small businesses across North America (US & Canada) who are looking to pay their employees easily and quickly.
The app is ideal for small businesses across North America (US & Canada) who are looking to pay their employees easily and quickly.
Next Steps:
If all the above feels right and proper, please don’t feel like you need to send us an uninspired cover letter. Just send us your updated resume and perhaps a few lines on what excites you about the job - we really want to get to know who you are, not just about how we can work together. If we believe you’re a good match, someone from our team will reach out to schedule a call.
Psssst!
Wagepoint is an equal opportunity employer. We welcome and appreciate all applicants with diverse backgrounds, races, religions, genders, identities, ages, experiences (the list goes on!). We are committed to making not only our workplace safe and inclusive for everyone, but also ensuring our recruitment process reflects that. We are a remote company, so there's no need to travel to an office for an interview, but if you require any special accommodation during our recruitment process, please let us know. We are more than happy to assist!
Not quite right? Register your interest to be notified of any roles that come along that meet your criteria.