Top Tech Jobs & Startup Jobs in Chicago, IL

Leads and scales Square’s Central Region Field Sales organization, managing Sales Managers and Territory Account Executives. Responsibilities include territory and go-to-market strategy, pipeline and KPI management, field coaching, consultative selling, product expertise, team development, cross-functional collaboration, and regional revenue growth. The role builds a competitive, accountable, high-performing sales culture while representing Square with local business leaders and partners.

Own the full outbound sales cycle for mid-market merchants, from prospecting and pipeline development through discovery, demonstrations, negotiation, and close. Build multi-product solutions, acquire new logos, manage complex multi-stakeholder deals, maintain Salesforce forecasting accuracy, collaborate cross-functionally, and consistently achieve revenue targets.

Owns mid-market merchant sales opportunities from prospecting through contracting, launch, and handoff for Cash App Pay and Afterpay. Responsibilities include account planning, outbound pipeline generation, discovery, business-case development, commercial negotiation, cross-functional deal coordination, Salesforce forecasting, and meeting revenue targets. The role requires consultative selling to senior commerce, marketing, finance, and technology stakeholders, plus market insight sharing and occasional travel.

Own the full enterprise sales cycle for Block’s commerce and payments portfolio, from prospecting and account strategy through negotiation, launch, and expansion. Build executive relationships, develop commercial strategies, negotiate complex agreements, coordinate cross-functional teams, and deliver revenue targets. The role requires strong enterprise selling, strategic thinking, financial analysis, deal management, and familiarity with payments, fintech, or digital commerce.