Square Offices

Own the full outbound sales cycle for mid-market merchants, including prospecting, pipeline development, discovery, product demonstrations, negotiation, and closing. Build tailored multi-product solutions across Square’s ecosystem, acquire net-new customers, manage complex multi-stakeholder deals, forecast accurately in Salesforce, collaborate cross-functionally, and consistently achieve revenue targets.

Supports global sales and account management enablement through ongoing learning programs, centralized knowledge resources, training content, stakeholder coordination, internal communications, and feedback tracking. The role operationalizes everboarding, maintains learning assets, localizes content for Canada, and measures adoption, knowledge retention, and performance impact while collaborating with Product, Marketing, Sales, and subject matter experts.

Lead approximately 10 senior Account Executives on an outbound mid-market sales team. Responsibilities include hiring and developing talent, coaching through pipeline and performance data, forecasting, improving sales processes, establishing operating rhythms, and partnering with Sales Leadership, Marketing, Enablement, Operations, and Product. The role focuses on building a high-performance organization, strengthening pipeline quality, improving execution, and developing future sales leaders.