Principal Software Development Engineer - Applied AI - Wagepoint

At Wagepoint, we're good people. It's easy to feel that way when you're surrounded by folks doing the best work of their careers, building great payroll software for small businesses across Canada.

Our team brings together diverse backgrounds, perspectives, experiences, and ideas to make payroll the easiest part of running a business.

We're remote-first, growing, and looking for passionate people who don't settle for the first solution or the way it's been done before. We care deeply about our customers and each other, and understand that when it comes to payroll, getting it right matters.

Our values guide how we work and what we expect from one another:

Cultivate Impact by focusing on what matters most and delivering meaningful outcomes for our customers.

Unify as One Team by collaborating openly, communicating clearly, and rallying around shared goals.

Stay Curious and Kind by challenging assumptions, learning quickly, and leading with empathy.

If you want to build the future of payroll in a place where your ideas are welcomed and your contributions matter, look no further!

The Role:

We’re looking for a talented Principal Software Development Engineer - Applied AI , who enjoys tackling hard problems and wants to create meaningful impact for small businesses across Canada. You’ll set the technical strategy for AI Products at Wagepoint, authoring the architecture decision records that define platform boundaries, persistence standards, and quality gates for every team building AI features, and setting the guardrails that let Engineering teams experiment with agentic AI. You will report directly to our VP, Engineering.

Your decisions are the ones other engineers’ proposals must cite and align to. Other teams’ roadmaps depend on getting your calls right. You’ll keep Wagepoint’s AI platform choices current against a fast-moving landscape, articulate tradeoffs in terms leadership can act on, and multiply the org through mentorship, pairing with and unblocking the engineers building on your standards.

Like every Principal Engineer at Wagepoint, you also carry broad architectural leadership beyond AI, including well-architected, highly performant distributed systems, and AI-augmented development practices across the SDLC.

Like every engineer at Wagepoint, you do not write software by hand. You’re a major contributor to the software factory, the agentic pipeline of specs, agent implementation, agent review, and human approval that produces our software. You’ll own specific agents within it and work with your teammates to constantly improve the factory itself.