Top Sales Jobs in Chicago, IL

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.

Field-driven Territory Account Executive responsible for full-cycle, self-sourced sales across Square's product suite. Spend ~80% of time in-market conducting 50–60 targeted visits weekly, running demos, closing deals, building pipeline via door-to-door outreach, events, and partnerships, and using Salesforce to manage pipeline and forecasts.