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Conduct field-based, full-cycle sales across Brooklyn by prospecting local businesses, performing live demos, building partnerships, managing Salesforce pipeline, and closing Square software, hardware, and financial-services deals. The role requires extensive in-person outreach, consultative selling across restaurant, retail, and service verticals, accurate forecasting, onboarding collaboration, and consistent quota achievement.

Own a local sales territory for Square, spending approximately 80% of the week in the field. Generate pipeline through door-to-door outreach, networking, events, and partnerships; conduct product demonstrations; consult with businesses; close full-cycle deals; and exceed sales quotas. Build relationships with restaurants, retailers, and service businesses, maintain accurate Salesforce records and forecasts, and support successful customer onboarding.

Field-driven full-cycle sales role owning a geographic territory: prospecting door-to-door, running demos, closing deals across Square products, building local partnerships, and maintaining pipeline and Salesforce rigor to consistently exceed quota.

Own the architecture and technical direction of Square’s go-to-market technology stack. Design, build, and operate production AI agents and automated workflows that improve sales productivity. Lead complex initiatives through architecture, implementation, testing, deployment, and operations; establish AI evaluation, observability, security, reliability, and human-oversight practices. Partner with Sales, Product, Data, and Engineering teams to translate business needs into scalable solutions, guide integrations and build-versus-buy decisions, and mentor engineers through influence and technical leadership.

Own the full sales cycle for SMB merchants, converting inbound leads and generating outbound opportunities. Qualify prospects, conduct demos, close deals, provide consultative solutions, maintain accurate Salesforce forecasts, collaborate cross-functionally, and consistently achieve revenue targets.

As a Business Development Rep, you will engage with prospective sellers, managing outreach and promoting Square's services to enhance merchant growth. This role emphasizes evidence-based sales techniques and supports career development within the sales organization.

Lead and develop a remote team of Account Executives to drive predictable revenue through KPI-driven coaching, hiring, training, pipeline management, forecasting, and cross-functional GTM collaboration using data to improve performance.

Lead and develop a remote mid-market account executive team to drive revenue. Hire, train, coach, and manage KPIs, forecasting, and pipeline; participate in client meetings; refine sales strategy and processes; use customer feedback to improve products and scale repeatable sales practices.

Lead full outbound sales cycle for mid-market merchants: prospect, build pipeline, run discovery and demos, negotiate multi-product deals, and close revenue. Partner cross-functionally, manage forecasts in Salesforce, and consistently meet or exceed monthly and quarterly targets while acting as a trusted advisor.