Staff Go-to-Market AI Systems Engineer

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

Benefits offered by this job

Remote work

Medical insurance

Flexible time off

Job summary

Square seeks a Staff Software Engineer to own the go-to-market technology stack, shaping its architecture and direction. You will lead engineers, partner with Sales, Product, Data, and Engineering to deliver reliable AI-driven solutions that boost sales productivity and business performance.

You will design and operate AI agents, guide complex initiatives, and stay hands-on across the lifecycle from prototyping to production, ensuring security and scalability for sensitive data.

Qualifications

• Experience setting technical direction for complex, business-critical systems.
• Proven ability to move AI capabilities from prototype to production with reliability and security.
• Strong hands-on software engineering and system-design skills.
• AI-native approach to engineering with judicious use of AI tools.

Responsibilities

• Own the technical strategy, architecture, and long-term evolution of the go-to-market tech stack.
• Design, build, and operate production-grade AI agents and automated workflows.
• Lead cross-functional execution and review designs for high-impact sales initiatives.
• Remain hands-on through prototyping, implementation, testing, and production ops.
• Translate business problems into scalable technical solutions with Sales and Ops.
• Establish guardrails for reliable, observable, secure AI systems handling sensitive data.
• Define success metrics and use data to improve capability adoption and impact.
• Make build-vs-buy decisions and guide integrations across platforms and CRM systems.
• Mentor and raise engineering standards through reviews and collaboration.

Skills

Technical leadership

AI/ML systems

System design

Hands-on software

Cross-functional collaboration

Mentorship

Decision making

Architectural vision

Education

Bachelor’s degree (or higher)

Job description

Square seeks a Staff Software Engineer to own the go-to-market technology stack, shaping its architecture and direction. You will lead engineers, partner with Sales, Product, Data, and Engineering to deliver reliable AI-driven solutions that boost sales productivity and business performance.

You will design and operate AI agents, guide complex initiatives, and stay hands-on across the lifecycle from prototyping to production, ensuring security and scalability for sensitive data.