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Block

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

Block

. Own the technical strategy, architecture, and long-term evolution of the go-to-market technology stack.

Posted 11/5/2026full-timeRemote • CanadaLead💰 CA$222,900 - CA$334,300 per yearWebsite

Core Competencies

Role fit
Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates expertise in designing and operating production-grade AI systems, with a strong focus on technical strategy, architecture, and the integration of AI capabilities into business-critical workflows. Proven ability to lead technical execution and mentor teams while navigating complex technical and business challenges.

Highest-signal resume keywords
AI System DesignTechnical Strategy DevelopmentProduction Software EngineeringMentorship and LeadershipSales Process Familiarity

ATS Keywords

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Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills
Large Language ModelsAI AgentsWorkflow OrchestrationSystem DesignSoftware DevelopmentData EvaluationObservabilitySecurity PracticesReliability EngineeringHuman Oversight
Soft Skills
InfluenceProblem-SolvingCommunicationMentorshipJudgment
Tools & Technologies
CRM SystemsData ServicesIntegration PlatformsPrototyping ToolsDeployment Tools
Industry Keywords
Go-To-Market StrategySales OperationsLead ManagementOpportunity ManagementAccount Planning

About the role

Key responsibilities & impact
  • 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, improve decision-making, and give time back to sales teams.
  • Lead technical execution across initiatives by setting direction, breaking down complex problems, reviewing designs, and helping engineers deliver high-quality solutions.
  • Remain hands-on throughout the software lifecycle, from prototyping and architecture through implementation, testing, deployment, and production operations.
  • Partner with Sales and Sales Strategy & Operations to understand workflows, identify high-value opportunities, and translate business problems into scalable technical solutions.
  • Establish patterns, evaluation methods, 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 complex tradeoffs, and raise engineering standards through mentorship and design reviews.

Requirements

What you’ll need
  • A minimum of 12 years of related experience with a Bachelor’s degree; or 8 years and a Master’s degree; or a PhD with 5 years 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 that uses large language models, AI agents, tool calling, retrieval, workflow orchestration, or related technologies.
  • A track record of moving AI capabilities from prototype to production, including evaluation, observability, security, reliability, and human oversight.
  • An AI-native approach to engineering, using AI tools throughout development while applying sound judgment about when to use models, deterministic software, or human review.
  • Strong software engineering and system-design skills, with the ability to work hands-on across application, service, integration, and data layers.
  • Experience leading technical execution through influence, mentorship, architecture, and direct contribution, without relying on formal reporting authority.
  • The judgment to navigate ambiguous problems, evaluate technical and business tradeoffs, and influence senior engineering and business partners.
  • Familiarity with sales processes or go-to-market systems—such as lead management, opportunity management, forecasting, account planning, or customer relationship management platforms—is helpful but not required.

Benefits

Comp & perks
  • Remote work
  • Medical insurance
  • Flexible time off
  • Retirement savings plans
  • Modern family planning