Block
Staff Software Engineer, Go-to-Market Systems & AI
Toronto, Ontario, Canada +1 · Remote · Staff · Full-time · Posted Aug 31, 2026
- Location
- Toronto, Ontario, Canada
US - NY - NYC - Remote - Experience
- 12 years with a Bachelor’s degree; or 8 years with a Master’s degree; or a PhD with 5 years of experience; or equivalent experience.
- Education
- Bachelor’s degree, Master’s degree, or PhD as described; or equivalent experience.
About the job
Owns the architecture and technical direction of Block’s go-to-market systems, building AI-powered tools and workflows to improve sales productivity and business performance.
What you'll do
- Set the technical strategy and architecture for the go-to-market technology stack; lead complex initiatives and mentor engineers.
- Build and operate production AI agents and automated workflows, including evaluation, observability, security, and safety guardrails.
- Partner with Sales and cross-functional teams to identify opportunities, deliver scalable solutions, and measure their impact.
What they ask for
- Experience delivering complex, business-critical systems across teams or functional areas.
- Experience building and operating production software using LLMs, AI agents, tool calling, retrieval, workflow orchestration, or related technologies.
- Track record of taking AI capabilities from prototype to production, including evaluation, observability, security, reliability, and human oversight.
- Strong software engineering and system-design skills, hands-on across application, service, integration, and data layers.
Nice to have
- Familiarity with sales processes or go-to-market systems, such as lead or opportunity management, forecasting, account planning, or CRM platforms.
Pay
$222,900 — $334,300 CAD (base salary); $222,900 — $334,300 CAD (base salary)
Tools
large language models, AI agents, tool calling, retrieval, workflow orchestration, customer relationship management systems
AI focus
Build and operate production AI agents and workflows for sales; establish evaluation methods and safeguards, and improve accuracy, adoption, and business impact using data and feedback.
Model-written summary · the original posting is authoritative