Top Sales Jobs in Chicago, IL

The role involves leading and scaling the Central Field Sales organization, driving performance and operational rigor, and collaborating with teams to achieve regional growth.

Manage a portfolio of ~175 mid-market retail sellers to drive retention, expansion, and satisfaction. Consult with owners to uncover cross-sell and technical solution opportunities across payments, POS, business management, and banking tools. Negotiate contracts, project-manage implementations with cross-functional teams, deliver white-glove service, and advocate seller needs to Product, Engineering, and Operations.

The Strategic Account Manager will manage relationships with Square's largest Food and Beverage sellers, drive revenue growth, and collaborate with product teams on solutions for complex business needs.

Manage a mid-market book to retain and grow revenue for Cash App and Afterpay. Build data-driven account strategies, negotiate expansions and renewals, deepen executive relationships, coordinate cross-functional teams, and represent merchant feedback internally to drive product and commercial outcomes.

Manage and grow an SMB Food & Beverage customer portfolio by understanding client needs, cross-selling Square products, retaining revenue, resolving issues, and collaborating with Sales, Support, and Product to improve merchant outcomes.