Go-to-Market AI Systems Lead, Staff Engineer

Square; Oakland (CA); On-site; USD 264,000 - 395,000; Full time

Job summary

Square in Oakland, CA is seeking a Staff Software Engineer to own the go-to-market technology stack and define its long‑term direction. You will lead AI agents, automated workflows, and production systems that boost sales productivity and optimize decision‑making.

You will collaborate with Sales, Strategy & Operations, Product, Data, and Engineering to deliver scalable solutions, mentor engineers, and set high engineering standards while maintaining hands-on involvement across the full software

Qualifications

• 12+ years of related experience with a Bachelor’s degree.
• Experience setting technical direction across multiple teams.
• Experience designing and operating AI-based production software.
• Track record moving AI from prototype to production with observability & security.
• AI-native engineering approach using AI tools judiciously.
• Strong system-design skills across apps, services, data, and integrations.
• Leadership through influence and mentorship, not formal authority.
• Ability to navigate ambiguous problems and tradeoffs with leaders.
• Familiarity with sales processes or go-to-market systems is a plus.

Responsibilities

• Own the technical strategy, architecture, and long-term evolution of the GTM tech stack.
• Design, build, and operate AI agents and automated workflows to reduce manual work.
• Lead cross-team execution, reviewing designs and guiding engineers to high-quality solutions.
• Stay hands-on through prototyping, architecture, implementation, testing, and deployment.
• Collaborate with Sales, Strategy & Operations, Product, Data, and Engineering.
• Establish patterns and guardrails for reliable, observable AI systems handling sensitive data.
• Define success measures using data and user feedback to boost impact.
• Make build-vs-buy decisions and guide integrations across platforms and tools.

Skills

Technical direction

AI agents

Production software

System design

Mentorship

Hands-on coding

Cross-functional collaboration

Executive communication

Education

Bachelor’s degree

Job description

Square in Oakland, CA is seeking a Staff Software Engineer to own the go-to-market technology stack and define its long‑term direction. You will lead AI agents, automated workflows, and production systems that boost sales productivity and optimize decision‑making.

You will collaborate with Sales, Strategy & Operations, Product, Data, and Engineering to deliver scalable solutions, mentor engineers, and set high engineering standards while maintaining hands-on involvement across the full software