Jobs at Square

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 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.

Develop and manage Square’s always-on B2B content engine across social, thought leadership, customer stories, partner content, and industry narratives. Build content calendars, formats, briefs, campaigns, and AI-assisted workflows; coordinate cross-functional teams and external partners; oversee production through launch; and analyze performance to optimize messaging, formats, and distribution.

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.

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.

Lead data science initiatives for Risk and Support Operations by analyzing customer and product data, defining metrics, forecasting demand, evaluating experiments and risk policies, and building decision frameworks. Use AI tools and agent workflows to improve analytical efficiency. Partner with product, engineering, and risk teams, communicate insights to senior stakeholders, establish technical standards, mentor data scientists, and support hiring.

Own the architecture and technical strategy for Square’s go-to-market systems. Build and operate production AI agents, automated workflows, and integrations that improve sales productivity. Lead complex initiatives through architecture, implementation, testing, deployment, and operations while establishing AI evaluation, observability, security, reliability, and human-oversight practices. Partner with Sales, Product, Data, and Engineering leaders to translate business needs into scalable solutions, make build-versus-buy decisions, mentor engineers, and improve business impact through data and user feedback.

Own a Santa Clara territory through primarily in-person field sales. Generate pipeline via business visits, networking, events, partnerships, and cold outreach; run full-cycle sales from prospecting through demos and closing; build seller relationships; support onboarding; maintain Salesforce activity and forecasts; master restaurant, retail, and service verticals; and consistently exceed quota.

Own and grow an Oakland territory through primarily in-person field sales. Generate pipeline via business visits, cold outreach, events, networking, and partnerships; conduct demos; sell Square’s software, hardware, and financial solutions; and close full-cycle deals. Build relationships with local businesses, support onboarding, develop referrals, manage pipeline and forecasting in Salesforce, and consistently exceed quota across restaurant, retail, and services verticals.

Build and operate ingestion and reconciliation pipelines that match card-network and partner reports against internal transactions. Develop reporting products, produce standardized journals for accounting, support tax and regulatory filing systems, handle sensitive PII for compliance, debug production issues, and collaborate with finance, product, and data teams to automate and scale reconciliation and reporting.

Lead pricing modeling and experimentation to optimize margin, conversion, and retention. Build elasticity and willingness-to-pay models, design A/B and bandit experiments, develop pricing automation (DealBot) and monitoring for AI-driven rate recommendations, own ETL/analysis/visualization, and partner with Finance, Risk, Product, and GTM teams to operationalize pricing intelligence.

Convert inbound leads and prospect outbound opportunities to close SMB merchants. Own full sales cycle, qualify, demo, and forecast in Salesforce, collaborate cross-functionally, and consistently exceed monthly and quarterly revenue targets.

The Strategic Account Manager will manage a portfolio of mid-market sellers, negotiating contracts, identifying growth opportunities, and ensuring seamless client service alongside cross-functional teams.

Lead and build Square's global commercial operating system, owning Deal Desk, pricing operations, strategic deal support, and commercial governance. Drive pricing execution, approval workflows, AI-enabled automation, reporting, and cross-functional alignment to increase deal velocity, consistency, and profitability while managing a global team.

The Business Development Rep Associate will drive sales efforts by reaching out to prospective sellers, promoting Square's value, and managing a diverse business pipeline. Success will lead to growth opportunities within the sales organization. Candidates need to possess excellent sales instincts and a desire to grow in a sales career.