Staff Go-to-Market AI 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

Retirement savings plans

Family planning

Job summary

Square is seeking a Staff Software Engineer for the Go-to-Market Engineering team in San Francisco. You will own the architecture and long-term direction of our go-to-market technology stack, leading engineers through complex, high-impact sales problems while partnering with Sales, Product, Data, and Engineering leaders.

You will stay hands-on across the lifecycle, design AI-powered agents, and build scalable, reliable solutions that reduce manual work and boost sales performance.

Qualifications

• 12+ years of related experience with a relevant degree or equivalent.
• Experience setting technical direction across multiple teams or areas.
• Experience designing and operating production software using AI/ML tech.
• Track record moving AI capabilities from prototype to production with observability and security.
• AI-native engineering approach with sound judgment on model use and deterministic software.

Responsibilities

• Own the technical strategy, architecture, and evolution of the go-to-market stack.
• Design, build, and operate production-grade AI agents and automated workflows.
• Lead technical execution across initiatives, reviewing designs and mentoring engineers.
• Remain hands-on from prototyping to deployment and production operations.
• Partner with Sales and GTM ops to translate business problems into scalable tech solutions.
• Define success measures and use data to improve accuracy and impact.
• Make build-vs-buy decisions and guide integrations across platforms and tools.
• Communicate tradeoffs clearly and raise engineering standards through reviews.

Skills

Technical leadership

Architecture

Hands-on software engineering

Mentorship

Cross-functional collaboration

Go-to-market systems

AI/ML systems

System design

Leadership without authority

Education

Bachelor's degree in related field

Master's degree

PhD

Tools

Large language models

AI agents

Tool calling

Retrieval systems

Workflow orchestration

Job description

Square is seeking a Staff Software Engineer for the Go-to-Market Engineering team in San Francisco. You will own the architecture and long-term direction of our go-to-market technology stack, leading engineers through complex, high-impact sales problems while partnering with Sales, Product, Data, and Engineering leaders.

You will stay hands-on across the lifecycle, design AI-powered agents, and build scalable, reliable solutions that reduce manual work and boost sales performance.