3 months ago
Remote, CanadaStaff+
Responsibilities
- Define and maintain organization-wide architecture decisions, AI platform boundaries, persistence standards, shared service kits, and quality gates.
- Lead architecture for large-scale, distributed, customer-facing systems where AI intersects with the product stack, applying domain-driven design to define boundaries.
- Make quantified build-versus-buy decisions involving evaluation, observability, persistence, vector stores, vendors, cost models, and rejected alternatives.
- Establish evaluation standards, drift monitoring, release criteria, resource-isolation controls, agentic workflow guardrails, responsible-AI practices, and auditability.
- Maintain current AI platform choices through dated verification notes, tradeoff analysis, and revisit triggers.
- Set the organization-wide path toward Level 4 and Level 5 agentic development while maintaining payroll and tax-reporting quality and compliance.
- Serve as a technical resource across teams, author RFCs and reviews, unblock high-impact initiatives, and mentor, pair with, and develop senior engineers.
- Contribute to Wagepoint’s software factory by directing and reviewing agentic development, owning specific agents, and improving the factory itself.
- Spend approximately 85% of focus on customer-facing AI products and their platform, with the remainder on internal AI use and the software factory.
Requirements
- 10+ years of professional software engineering experience with progressively increasing impact.
- Multiple years designing and operating production LLM or agentic systems at Staff-level scope or above.
- Proven technical leadership designing distributed systems and microservices for complex domains, with practical knowledge of DDD and Clean Architecture principles.
- Full-stack breadth across modern front-end frameworks and a Python back end; .NET or C# experience is a plus but not required.
- Experience authoring architecture standards and decision records adopted beyond the candidate’s own team.
- Demonstrated quantified build-versus-buy decisions involving named vendors, cost models, and explicitly rejected alternatives.
- Deep knowledge of stateful agent orchestration, MCP, A2A interoperability, evaluation-gated delivery, and vector-enabled persistence including PostgreSQL/pgvector and DiskANN-class indexing.
- A considered model-strategy perspective covering fine-tuned small language models versus frontier APIs and tradeoffs among cost, latency, and control.
- Experience defining boundaries between AI stacks and existing product stacks, including shared service-kit libraries consumed by other teams.
- Security and governance leadership involving resource isolation, agentic workflow guardrails, and responsible AI in a regulated money-movement domain.
- Executive-level communication of platform tradeoffs involving cost, risk, and optionality.
- Strong agency in creating net-new systems and optimizing API performance where established patterns do not exist.
- Demonstrated multiplier effect through mentorship, pairing, unblocking, and growing senior engineers.
- Commitment to directing and reviewing agentic development while maintaining high quality and compliance standards.
Benefits
- Remote-first work with flexibility to work from wherever the employee does their best work.
- Professional development, new experiences, and career-growth opportunities.
- A collaborative, inclusive culture that supports experimentation, learning, and responsible use of AI.
- Virtual interviews and accommodation support throughout the hiring process.
- AI-based tools support initial application review, with final progression decisions made by the People Ops team.
Tech Stack
Categories
About Wagepoint
Wagepoint builds cloud software that automates payroll, time tracking, and basic employee management for small businesses, primarily in Canada. It sells its tools on a subscription basis and integrates them into customers’ day-to-day operations to handle recurring runs and compliance. Founded in 2012 and headquartered in Calgary, it is privately held and part of the Providence Equity Partners portfolio.