Staff Software Engineer - AI Agents & Sales Tech

Square, a core brand of Block, Inc., empowers sellers of all sizes to run and grow their businesses through integrated, omnichannel commerce, software, and financial services.

As a Staff Software Engineer on the Go-to-Market Engineering team, you will serve as the overarching technical owner of Square's GTM technology stack. In this high-impact, hands-on role, you will architect, build, and operate production-grade AI agents, retrieval systems, tool-calling pipelines, and automated workflows. Partnering directly with Sales, Sales Strategy & Operations, Product, Data, and Engineering leaders, you will eliminate manual sales overhead, establish AI safety guardrails, and elevate engineering standards across application, integration, and data layers.

Key Responsibilities

• Technical Strategy & Architecture: Own the technical vision, system architecture, and long-term evolution of Square's go-to-market technology platform.
• Production AI Agents & Automation: Design, build, and maintain production LLM workflows, AI agents, tool-calling systems, and automated pipelines that optimize sales productivity and revenue execution.
• Hands-On Lifecycle Execution: Remain hands-on across the entire development lifecycle—from rapid prototyping and system architecture to coding, testing, evaluation, deployment, and live operations.
• AI Guardrails & Observability: Establish evaluation frameworks, observability, security models, human-in-the-loop oversight, and guardrails to safely deploy AI systems handling sensitive enterprise data.
• Cross-Functional Collaboration: Partner with Sales Strategy & Ops, Product, and Data leaders to translate sales workflows (e.g., lead scoring, opportunity management, forecasting, account planning) into scalable technical solutions.
• Build vs. Buy Decisions: Guide integration strategy between internal Block infrastructure, CRM platforms, customer data platforms, and third-party SaaS vendors.
• Technical Mentorship: Lead technical execution across engineering teams through design reviews, architecture alignment, and mentorship without needing formal reporting authority.

Requirements

Experience & Education

Must meet one of the following education/experience milestones:

• Bachelor’s degree with 12+ years of related software engineering experience; OR
• Master’s degree with 8+ years of related software engineering experience; OR
• PhD with 5+ years of related software engineering experience (or equivalent practical experience).

Production AI & Software Craft

• Demonstrated experience designing, building, and operating production software utilizing Large Language Models (LLMs), AI agents, tool calling, retrieval-augmented generation (RAG), and workflow orchestration.
• Proven track record of taking AI capabilities from initial prototype to production—including evaluation benchmarks, observability, security, and human oversight mechanisms.
• An AI-native engineering mindset, leveraging AI tools in daily development while exercising strong engineering judgment regarding when to use deterministic code versus probabilistic AI models.
• Deep hands-on experience across backend service design, integration layers, APIs, and data architecture.
• Track record of leading complex, multi-team technical projects through influence, mentorship, and architectural leadership.

Preferred Qualifications

• Direct domain familiarity with Go-to-Market platforms, sales technology, or Customer Relationship Management (CRM) systems (e.g., Salesforce, lead management, opportunity tracking, or revenue operations).
• Experience evaluating and integrating external SaaS APIs alongside proprietary internal data services.

Total Rewards & Benefits

• Compensation & Equity: Market-based base pay range of $263,600 – $395,400 USD + Block equity grants.
• Workplace & Flexibility: Fully remote work options paired with flexible paid time off (PTO) and paid holidays.
• Health & Family Care: Comprehensive medical, dental, and vision insurance; modern family planning and parental support programs.
• Financial & Retirement: 401(k) retirement savings plan with company match.