Staff Software Engineer, Go-to-Market Systems & AI

Responsibilities

• Own the technical strategy, architecture, and long-term evolution of the go-to-market technology stack.
• Design, build, and operate production-grade AI agents and automated workflows that reduce manual sales work and improve decision-making.
• Lead technical execution across initiatives by setting direction, decomposing complex problems, reviewing designs, and supporting high-quality delivery.
• Remain hands-on across prototyping, architecture, implementation, testing, deployment, and production operations.
• Partner with Sales, Sales Strategy & Operations, Product, Data, and Engineering leaders to translate business problems into scalable solutions.
• Establish evaluation methods, patterns, and guardrails for reliable, observable, secure, and safe AI systems handling sensitive business data.
• Define success measures and use data, evaluations, and user feedback to improve accuracy, adoption, and business impact.
• Make build-versus-buy decisions and guide integrations across internal platforms, CRM systems, data services, and third-party tools.
• Build alignment with senior technical and business partners, communicate tradeoffs, mentor engineers, and raise engineering standards through design reviews.

Requirements

• 12+ years of related experience with a bachelor's degree; or 8+ years with a master's degree; or a PhD with 5+ years of experience; or equivalent experience.
• Experience setting technical direction and delivering complex, business-critical systems across multiple teams or functional areas.
• Experience designing, building, and operating production software using large language models, AI agents, tool calling, retrieval, workflow orchestration, or related technologies.
• Track record of moving AI capabilities from prototype to production, including evaluation, observability, security, reliability, and human oversight.
• AI-native engineering approach, with sound judgment about when to use models, deterministic software, or human review.
• Strong software engineering and system-design skills across application, service, integration, and data layers.
• Experience leading technical execution through influence, mentorship, architecture, and direct contribution without formal reporting authority.
• Ability to navigate ambiguity, evaluate technical and business tradeoffs, and influence senior engineering and business partners.

Nice to Have

• Familiarity with sales processes or go-to-market systems, including lead management, opportunity management, forecasting, account planning, or customer relationship management platforms.

Compensation and Benefits

• Annual salary range of $222,900–$334,300 CAD.
• Benefits include remote work, medical insurance, flexible time off, retirement savings plans, and modern family planning support.