Jobs at Square

Lead and develop a remote team of Account Executives to drive revenue growth. Hire, train, coach, and manage KPIs, forecasting, and pipeline. Build repeatable sales processes, run pipeline and forecast reviews, collaborate cross-functionally, use customer feedback to improve products, and evolve sales strategy to increase revenue and customer success.

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.

Field-driven territory sales role responsible for full-cycle, self-sourced selling across Square's products. Spend ~80% of time visiting 50-60 targeted businesses weekly, run demos, build pipeline via door-to-door outreach and partnerships, manage Salesforce pipeline, and consistently exceed quota while supporting fast onboarding and cross-functional collaboration.

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 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.

Lead and develop a remote team of 8-10 SMB Account Managers to drive upsell, retention, software adoption, and churn reduction. Establish performance expectations, coach managers, run cadences and escalations, partner cross-functionally to improve customer experience, and support OKRs. Travel quarterly for team events or customer meetings.

Manage and grow a book of SMB merchants in Eastern Canada through relationship building, product education, cross-selling, upselling, pipeline management, and collaboration with Sales, Support, and Product teams to improve merchant outcomes and retention.

Field-driven Territory Account Executive responsible for full-cycle sales: 80% in-market activity with 50-60 weekly visits, self-sourced pipeline, demos, closing deals across Square products, building partnerships and vertical expertise, tracking activity in Salesforce, and consistently exceeding quota.

Lead end-to-end strategy and execution for Tier 1 trade shows and industry events in retail and food & beverage. Own event selection, budget management, ROI tracking, booth design/production, vendor relationships, lead capture processes, cross-functional alignment, and inventory/shipping logistics. Travel to key events (up to 25%) and collaborate with sales, creative, product, and partners to drive qualified leads and showcase Square solutions.

Lead and scale a Product Sales overlay team to drive adoption, expansion, and revenue for strategic products. Own commercial strategy, operating model, go-to-market plays, and cross-functional launch and enablement. Partner with AEs, AMs, Product, RevOps, and Marketing to prioritize opportunities, shape deal strategy, and deliver customer-facing executive engagement to maximize product penetration and outcomes.

Lead global referral and growth partnerships to drive seller acquisition. Define partnership strategy, source and negotiate complex commercial agreements, launch and scale integrations, manage C-level relationships, measure KPIs, and build a high-performing partnerships team across markets.

Lead growth through reseller channel partnerships: recruit, sign, launch, and scale reseller relationships; own deal execution and negotiations; build business cases; collaborate cross-functionally; and be accountable for partner-driven customer acquisition and revenue.

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 cross-team iOS engineering for Neighborhoods across Cash App and Square: define architecture, stay hands-on with SwiftUI/Workflow codebases, deliver integrated loyalty/ordering features, mentor engineers, and adopt AI-native workflows to accelerate development and quality.

Lead technical direction and architecture for Neighborhoods mobile experiences across Cash App and Square. Drive cross-organizational mobile initiatives, stay hands-on in iOS development, partner with backend/web/Android teams, mentor engineers, and apply AI-assisted workflows to accelerate feature development and quality.

The Senior Manager will define and drive the Services vertical strategy, enhance revenue performance, and ensure product alignment with sales efforts. They'll collaborate across teams, translate insights into actionable guidance, and shape product roadmap decisions, advocating for innovation and measurable impact on revenue.

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.

Drive growth and retention for Square's Retail Strategic Account Management program by advising retail executives, designing solutions, and managing key accounts.