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

Role overview A Staff Software Engineer role on the Go-to-Market Engineering team, which builds the systems, automations, and AI-powered experiences that help sales teams cut manual work and focus on customers. The position owns the technical strategy and architecture of the GTM technology stack while leading engineers through complex, high-impact sales problems alongside Sales, Sales Strategy and Operations, Product, Data, and Engineering leadership.

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, breaking down complex problems, reviewing designs, and helping engineers deliver high-quality solutions. - Stay hands-on across the full software lifecycle, from prototyping and architecture through implementation, testing, deployment, and production operations. - Establish the patterns, evaluation methods, and guardrails needed to build AI systems that are reliable, observable, secure, and safe with sensitive business data. - Make thoughtful build-versus-buy decisions and guide integrations across internal platforms, CRM systems, data services, and third-party tools.

Requirements - 12+ years of related experience with a Bachelor's degree, or 8 years with a Master's, or 5 years with a PhD, 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, or workflow orchestration. - Track record moving AI capabilities from prototype to production, including evaluation, observability, security, reliability, and human oversight. - Strong software engineering and system-design skills, with an AI-native approach to development.

Benefits and work setup - Remote role based in Canada; published range of $222,900 to $334,300 CAD depending on zone, skills, experience, and location. - Benefits include remote work, medical insurance, flexible time off, retirement savings plans, and modern family planning programs. - Equal opportunity employer with reasonable accommodations available during the recruitment process.