[Hiring] Principal Software Development Engineer - Applied AI @Wagepoint

Role Description

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.
• Report directly to our VP, Engineering .
• Your decisions are the ones other engineers’ proposals must cite and align to.
• Keep Wagepoint’s AI platform choices current against a fast-moving landscape.
• Articulate tradeoffs in terms leadership can act on.
• Multiply the organization through mentorship, pairing with and unblocking the engineers building on your standards.
• Carry broad architectural leadership beyond AI, including well-architected, highly performant distributed systems.
• Contribute to the software factory, the agentic pipeline of specs, agent implementation, agent review, and human approval that produces our software.
• Own specific agents within the software factory and work with teammates to constantly improve it.
• Focus 85% on customer-facing AI products and the platform beneath them, with the rest on building Wagepoint’s internal use of AI and our software factory.
• This role is measured by scope of influence, not just personal output.

Qualifications

• 10+ years of professional software engineering experience with progressively increasing impact.
• Multiple years designing and operating production LLM/agentic systems at Staff-level scope or above.
• Proven technical leadership designing distributed systems and microservices for complex domains.
• Full-stack breadth, spanning modern front-end frameworks and a Python back-end.
• Track record of authoring architecture standards adopted beyond your own team.
• Demonstrated quantified build-vs-buy decisions against named vendors.
• Deep fluency in the current AI platform landscape.
• Experience defining platform boundaries between AI stacks and an existing product stack.
• Security and governance leadership in a regulated, money-movement domain.
• Executive communication skills.
• A high degree of agency in building net-new systems and optimizing API performance.
• Demonstrated multiplier effect through mentorship.
• A passionate and key contributor to Wagepoint’s software factory.

Requirements

• Author the decision records that define how AI gets built org-wide.
• Define and maintain the boundary between AI services and the product stack.
• Make quantified platform calls against named vendors with cost models.
• Define how every AI team gates quality.
• Set resource-isolation and agentic-workflow guardrails.
• Keep platform choices current against the landscape.
• Lead design of large-scale, distributed, customer-facing systems.
• Be a go-to technical resource across teams.
• Set the org-wide path from today’s baseline to Level 4 of the agentic development ladder and beyond.

Benefits

• Impact: Dig in and directly contribute to Wagepoint’s growth and success.
• Culture: Work alongside a team that genuinely enjoys solving problems together.
• Growth: Commitment to helping you Get Better Every Day through professional development.
• Innovation: Curiosity and experimentation encouraged.
• Remote: Work from wherever you do your best work.