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

Block builds technology and integrated commerce and financial services solutions through brands including Square. The Staff Software Engineer will own the architecture and long-term strategy for go-to-market systems while designing and operating AI-powered agents and workflows that improve sales productivity. The role also leads technical execution, partners with sales and engineering stakeholders, and establishes reliable, secure, and observable AI engineering practices.

Responsibilities:

• Own the technical strategy, architecture, and long-term evolution of our 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 of varying sizes 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 the patterns, evaluation methods, and guardrails needed to build AI systems that are reliable, observable, secure, and safe to use with sensitive business data
• Define success measures and use data, evaluations, and user feedback to improve the accuracy, adoption, and business impact of new capabilities
• Make thoughtful build-versus-buy decisions and guide integrations across internal platforms, customer relationship management systems, data services, and third-party tools
• Build alignment with senior technical and business partners, communicate complex tradeoffs clearly, and raise engineering standards through mentorship and design reviews

Requirements:

• 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