Jobs at Square

Own the full outbound B2B sales cycle for mid-market merchants, including prospecting, pipeline development, discovery, product demonstrations, negotiations, and closing complex multi-product deals. Build net-new business, tailor Square ecosystem solutions, forecast accurately in Salesforce, collaborate cross-functionally, and consistently achieve revenue targets.

Own the architecture and technical strategy for Square’s go-to-market technology stack. Build and operate production AI agents, automated workflows, and integrations that improve sales productivity. Lead complex technical initiatives across teams, establish reliable and secure AI evaluation practices, make build-versus-buy decisions, and partner with Sales, Product, Data, and Engineering leaders. Mentor engineers, guide design and implementation, and use data and feedback to improve system adoption and business impact.

Own full B2B sales cycle for mid-market merchants: prospect, build and manage pipeline, demo multiproduct Square solutions, negotiate complex contracts, collaborate cross-functionally, maintain Salesforce forecasts, and consistently exceed revenue targets.

Manage the full sales cycle for SMB merchants: convert inbound leads, proactively prospect to build pipeline, close high-volume short-cycle deals, deliver consultative solutions, collaborate cross-functionally, and consistently hit monthly and quarterly revenue targets using Salesforce.

Own the full sales cycle for SMB merchants in Canada: convert inbound leads, prospect outbound, manage pipeline in Salesforce, collaborate with cross-functional teams, and consistently hit monthly and quarterly revenue targets while improving conversion and deal size.

Own the full outbound mid-market sales cycle: prospect, build pipeline, run discovery and demos, negotiate multi-product deals, and close new logo business while collaborating cross-functionally and maintaining accurate Salesforce forecasts to exceed monthly and quarterly revenue targets.

Own the post-checkout customer experience for Square’s food ordering and retail ecommerce products. Set product strategy, prioritize investments, align cross-functional teams, define customer journeys, and ship improvements across tracking, delivery, refunds, and support. Use customer research, behavioral data, AI tools, prototyping, GitHub, and automation to improve product quality and outcomes. Lead decisions across engineering, design, sellers, customers, and external partners while measuring resolution time, satisfaction, inquiries, and repeat purchases.

Leads Square’s global external workforce and partner strategy for seller onboarding. Owns vendor, BPO, and third-party operating models; develops build-versus-buy recommendations, partner standards, SLAs, scorecards, governance, and performance mechanisms. Partners with Procurement, Legal, Finance, and regional operations on commercial terms, capacity, quality, cost, and scalability. Manages evolving partner operations teams and drives improved seller outcomes through operational discipline, workflow optimization, and AI-enabled improvements.

Leads the global operating system for seller onboarding by establishing KPI frameworks, reporting cadences, planning processes, capacity models, financial support, and continuous improvement programs. Partners with regional operations, Finance, Product, Analytics, and Enablement teams to standardize workflows, improve efficiency, and scale AI-enabled onboarding processes. Owns performance management routines, workforce modeling, vendor analysis, operational planning, and impact measurement across global delivery models.

Leads US seller onboarding operations across first-party and vendor-supported teams. Owns execution from post-sale handoff through go-live, including staffing, scheduling, routing, quality, service levels, and cost management. Drives operational excellence through KPI analysis, process redesign, tooling improvements, automation, and AI adoption. Partners with Sales, Product, Finance, and regional teams while managing multiple teams and developing operational leaders.

Leads international seller onboarding operations across Europe, the UK, Australia, and APAC. Owns regional execution, staffing, vendor performance, service levels, market readiness, operational scaling, and seller activation outcomes. Develops localized operating models and launch playbooks while maintaining global standards. Uses metrics, dashboards, financial analysis, and AI to improve workflows, cost-to-serve, speed, and quality. Partners with Sales, Product, Finance, Legal, Compliance, and GTM leaders while managing distributed teams and developing regional leadership.

Leads ambiguous, high-impact revenue strategy initiatives, including sales forecasting, pipeline health, capacity planning, organizational sizing, partnership modeling, and commercial deal economics. Builds repeatable operating processes, analyzes complex data, and delivers executive-ready recommendations. Partners across Sales, Finance, Partnerships, Services, Data, and Systems, influencing outcomes without direct authority.

Leads a team of Product Sales Specialists responsible for product adoption, cross-sell, expansion, pipeline, and revenue outcomes. The role coaches sellers, manages forecasting and performance, partners on complex opportunities, develops scalable sales motions, and enables broader sales teams. It also collaborates with Sales, Product, Marketing, Operations, Data Science, and Enablement to improve targeting, commercialization, product expertise, and seller outcomes.

Own the full outbound sales cycle for mid-market merchants, from prospecting and pipeline development through discovery, product demonstrations, negotiation, and close. Build net-new business through strategic outreach, sell multi-product solutions, manage complex multi-stakeholder deals, forecast accurately in Salesforce, and consistently exceed revenue targets. Collaborate with business development, product, marketing, implementation, and operations teams while serving as a consultative advisor to merchants.

Develop data science solutions for payments across Square and Cash App. Build AI-powered tools, ETL pipelines, dashboards, machine learning models, experiments, and cloud data systems. Partner with Product, Engineering, Finance, and Operations to improve payment success, cost efficiency, risk mitigation, and decision-making. Translate business needs into practical solutions, research questions independently, and operationalize data processes and infrastructure.

Design, build, scale, and operate high-volume payment APIs and distributed systems serving global traffic. Lead complex engineering projects from requirements through production, improve reliability, performance, observability, fault tolerance, and security, and participate in on-call and incident response. Collaborate across product and engineering teams, use AI-assisted development tools responsibly, and mentor engineers through technical reviews and documentation.

Leads Square’s US Business Development Representative organization through managers and frontline teams. Owns pipeline generation strategy, operating cadence, performance management, forecasting, capacity planning, outbound execution, and sales technology improvements. Coaches managers, develops BDR talent, hires and retains staff, and partners with Sales, Marketing, Revenue Operations, Enablement, Analytics, and Strategy to improve funnel conversion and revenue contribution. Uses data, automation, AI, and prospecting tools to improve productivity and scale successful programs.

Own Square Hardware sales and revenue across major U.S. retail partners. Build and scale retail partnership strategies, manage existing retailer and distributor relationships, source and negotiate new partnerships, lead cross-functional launches and forecasting, and manage retail marketing budgets through test-and-learn investments.

Coordinate cross-functional product go-to-market programs from planning through launch, adoption, and optimization. Build project plans, operating mechanisms, launch documentation, feedback loops, status updates, and decision logs. Partner with Product, Sales, Marketing, Enablement, Analytics, Finance, and leadership to align stakeholders, manage dependencies, identify blockers, and improve execution. Translate operational data and customer or field feedback into clear priorities and recommendations.

Lead global ecosystem partnerships for Block’s Afterpay, Cash App, and Square products. Develop partner strategies, build executive relationships, design scalable partnership programs, commercialize B2B and B2B2C payment products, negotiate agreements, and expand distribution through third-party platforms. Collaborate with Product, Engineering, Sales, Marketing, Finance, Compliance, and Legal teams to maximize partner performance and commercial growth.