Who we are: 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 on a team of other Principal and Staff level engineers. 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 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. Your primary mandate is to build customer-facing AI products. About 85% of your time will go toward designing, coding, shipping, and supporting AI experiences used directly by Wagepoint customers, along with the platform capabilities needed to power them. The remainder will support Wagepoint’s internal use of AI and our software factory. This is a hands-on product engineering role with broad technical leadership scope. You will lead by building, stay close to customers and production, and make architecture decisions grounded in real product delivery. Your impact will be measured by the customer value you ship, the quality of the systems you build, and your ability to raise the capabilities of engineers across Wagepoint. What You'll Be Expected To Own: Build, ship, monitor, support, and continuously improve customer-facing AI products that solve meaningful payroll and workforce problems.



Turn ambiguous customer needs into intuitive AI experiences, combining strong product judgment with rapid prototyping, production code, and direct learning from usage. Lead the architecture of distributed, customer-facing systems where AI intersects with the product stack, using Clean Architecture to establish clear boundaries. Build the production services, shared libraries, critical integrations, and platform capabilities required to deliver reliable AI products at scale. Make consequential decisions across models, orchestration, evals, observability, persistence, and vendors using product requirements, prototypes, benchmarks, and cost models. Establish and implement quality gates for customer-facing AI, including evals in CI/CD, drift monitoring, release criteria, operational observability, and customer-impact measures. Stay close to production by reviewing critical code and designs, diagnosing incidents, improving performance, and supporting the AI products customers depend on every day. Build security, resource-isolation, and agentic-workflow guardrails appropriate for payroll, tax reporting, and other sensitive customer experiences. What You Bring To The Table: At least 18 months of recent, continuous experience personally building, shipping, and supporting active customer-facing AI products in production. Strong product taste, with a record of turning emerging AI capabilities into useful, trustworthy experiences that customers understand and choose to use. Significant software engineering experience with Staff-level scope or equivalent, plus a explicit desire to remain deeply involved in coding and delivery. Experience owning the full lifecycle of AI products, from customer problem and prototype through evaluation, launch, production op

📌 Principal Software Development Engineer (Winnipeg)
🏢 Wagepoint
📍 Winnipeg