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

Block
Toronto
Workplace: RemoteFull timeCAD 222,900 - 334,300 annuallyFunction: Software EngineeringExperience: 8+ yearsEducation: bachelorsSkills: ["Mentorship","Influence","Judgment","Problem-solving"]

Own the architecture and long-term direction of go-to-market technology while leading engineers to solve complex, business-critical sales problems. Build and operate production-grade AI agents and automated workflows that reduce manual sales work and improve decision-making. Partner across Sales, Sales Strategy & Operations, Product, Data, and Engineering to translate business needs into scalable systems, including reliable evaluation, observability, security, and production operations.

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FursaFursa
Block
Block
5 days ago

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

✓ Verified Job

Canonical indexed version, validated from employer's careers page.

Source: Company careers pageValidated by: Fursa AI
Last checked: 11 hours agoStatus: Live

Job Summary

Own the architecture and long-term direction of go-to-market technology while leading engineers to solve complex, business-critical sales problems. Build and operate production-grade AI agents and automated workflows that reduce manual sales work and improve decision-making. Partner across Sales, Sales Strategy & Operations, Product, Data, and Engineering to translate business needs into scalable systems, including reliable evaluation, observability, security, and production operations.
Location: Toronto
Workplace: Remote
Employment Type: Full time
Job Function: Software Engineering
Seniority: Mid level

Key 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 by setting direction, breaking down complex problems, reviewing designs, and helping engineers deliver high-quality solutions.
  • •Remain hands-on across the software lifecycle from prototyping and architecture through implementation, testing, deployment, and production operations.
  • •Partner with Sales and Sales Strategy & Operations to translate sales workflows and business problems into scalable technical solutions.

Pay and Benefits

Salary: CAD 222,900 - 334,300 annually
Perks:Remote WorkHealth InsuranceFlexible TimeRetirement SavingsFamily Planning

Key Requirements

  • •Minimum 12 years of related experience with a Bachelor’s degree; or 8 years with a Master’s degree; or PhD with 5 years experience (or equivalent).
  • •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 moving AI capabilities from prototype to production, including evaluation, observability, security, reliability, and human oversight.
  • •Strong software engineering and system-design skills across application, service, integration, and data layers.
Experience:8+ yearsAI
Education:Bachelor's
Skills:MentorshipInfluenceJudgmentProblem-solving
Languages:English
Tech Stack:Large language modelsAI agentsTool callingRetrievalWorkflow orchestrationCRMCustomer relationship managementObservabilitySecurityReliability

Company Brief

Block
Builds financial services and commerce tools to empower businesses and individuals, operating products such as Square, Cash App, Spiral (Bitcoin initiatives), TIDAL, and developer-focused payment and banking solutions.
Industry: Fintech Infrastructure
Company Size: Enterprise (1,001+ employees)
Revenue: USD 1B+
Growth: Public Company
Valuation: Public Company (Market Cap in USD)
Funding: IPO / Publicly Listed
Headquarters: San Francisco, United States
Founded: 2009
WebsiteLinkedIn