Staff AI-Driven Go-To-Market Systems Engineer

Square; New York (NY); Remote; USD 264,000 - 395,000; Full time

Benefits offered by this job

Remote work

Medical insurance

Flexible time off

Retirement savings plans

Job summary

Square is seeking a Staff Software Engineer for the Go-to-Market Engineering team. You’ll own the architectural direction of our GTM tech stack, build AI agents and automated workflows, and lead multi‑team technical delivery to improve sales productivity.

You’ll stay hands‑on through lifecycle phases, collaborate with Sales, Product, Data, and Engineering, and set guardrails for reliable, secure AI systems handling sensitive business data.

Qualifications

• 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.

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.

Skills

AI systems

System design

Technical leadership

Go-to-market

Hands-on coding

Education

Bachelor’s degree in Computer Science or related field

Tools

CRM systems

Workflow orchestration

LLM tooling

Job description

Square is seeking a Staff Software Engineer for the Go-to-Market Engineering team. You’ll own the architectural direction of our GTM tech stack, build AI agents and automated workflows, and lead multi‑team technical delivery to improve sales productivity.

You’ll stay hands‑on through lifecycle phases, collaborate with Sales, Product, Data, and Engineering, and set guardrails for reliable, secure AI systems handling sensitive business data.