Staff Software Engineer, Go-to-Market Systems & AI

Since we opened our doors in 2009 the world of commerce has evolved immensely and so has Square. After enabling anyone to take payments and never miss a sale we saw sellers stymied by disparate outmoded products and tools that wouldnt work together.

So we expanded into software and started building integrated omnichannel solutions to help sellers sell online manage inventory offer buy now pay later functionality book appointments engage loyal buyers and hire and pay staff. Across it all weve embedded financial services tools at the point of sale so merchants can access a business loan and manage their cash flow in one place. Afterpay furthers our goal to provide omnichannel tools that unlock meaningful value and growth enabling sellers to capture the next generation shopper increase order sizes and compete at a larger scale.

Today we are a partner to sellers of all sizes large enterprise-scale businesses with complex operations sellers just starting as well as merchants who began selling with Square and have grown larger over time. As our sellers grow so do our solutions. There is a massive opportunity in front of us. Were building a significant meaningful and lasting business and we are helping sellers worldwide do the same.

The Go-to-Market Engineering team builds the systems automations and AI-powered experiences that help our sales teams spend less time on manual work and more time serving customers. As a Staff Software Engineer you will be the technical owner of our go-to-market technology stack setting its architecture and long-term direction while leading engineers through complex high-impact sales problems. You will partner with Sales Sales Strategy & Operations Product Data and Engineering leaders to deliver reliable scalable solutions that improve sales productivity and business performance.

• 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.

• A minimum of 12 years of related experience with a Bachelors degree; or 8 years and a Masters 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.
• A track record of moving AI capabilities from prototype to production including evaluation observability security reliability and human oversight.
• An AI-native approach to engineering using AI tools throughout development while applying sound judgment about when to use models deterministic software or human review.
• Strong software engineering and system-design skills with the ability to work hands-on across application service integration and data layers.
• Experience leading technical execution through influence mentorship architecture and direct contribution without relying on formal reporting authority.
• The judgment to navigate ambiguous problems evaluate technical and business tradeoffs and influence senior engineering and business partners.
• Familiarity with sales processes or go-to-market systemssuch as lead management opportunity management forecasting account planning or customer relationship management platformsis helpful but not required.

Were working to build a more inclusive economy where our customers have equal access to opportunity and we strive to live by these same values in building our workplace. Block is an equal opportunity employer evaluating all employees and job applicants without regard to identity or any legally protected class. We also consider qualified applicants with criminal histories for employment on our team and always assess candidates on an individualized basis.

We believe in being fair and are committed to an inclusive interview experience including providing reasonable accommodations throughout the recruitment process. If you require an accommodation let your recruiter know. Want to learn more about what were doing to build an inclusive workplace Check out our Inclusion & Diversity page.