Own the full outbound sales cycle for mid-market merchants, from prospecting and pipeline development through discovery, negotiation, and close. Sell tailored, multi-product Square solutions in complex, multi-stakeholder deals, maintain accurate Salesforce forecasts, collaborate cross-functionally, and consistently exceed 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 scalable integrations that improve sales productivity. Lead complex technical initiatives across teams, establish AI reliability and security guardrails, define evaluations and success metrics, and guide build-versus-buy decisions. Remain hands-on across prototyping, implementation, testing, deployment, and operations while mentoring engineers and influencing senior business and technical stakeholders.

Own end-to-end reconciliation and reporting for card networks, banks, processors, and internal ledger data. Build SQL-based reporting, dashboards, exception queues, metrics, controls, and automated solutions; investigate discrepancies, improve data quality, support month-end close and audits, and partner with Engineering, Product, Accounting, Treasury, Tax, and Compliance. The role also defines requirements and test plans, maintains data pipelines, mentors analysts, and drives automation across payment settlement and money-movement processes.