Top Sales Jobs in Chicago, IL

Designs and presents scalable technical solutions for enterprise merchants using Affirm’s payment platform. Leads technical discovery, solution architecture, custom integrations, demos, and pre-sales support while partnering with Sales, Engineering, Product, and partner teams. Builds customer trust, identifies technical risks, influences product development, creates enablement materials, and supports successful implementations. The role requires payments or fintech experience, strong API and enterprise architecture expertise, technical communication skills, and travel up to 30%.

Leads and develops a team of Sales Engineers while participating in enterprise technical sales, API integration discussions, solution presentations, and merchant onboarding. Builds, tests, and troubleshoots integrations; coaches teams on AI development tools; collaborates with Engineering, Product, and Revenue; translates merchant challenges into product improvements; and maintains relationships with technical and business stakeholders.

Leads and develops a team of senior enterprise Account Executives selling complex solutions to major retail merchants. Owns pipeline, forecasting, deal progression, merchant acquisition, expansion, and revenue outcomes. Coaches strategic deal execution, builds executive merchant relationships, shapes enterprise retail go-to-market strategy, and partners cross-functionally across Product, Client Success, Marketing, Finance, Legal, and RevOps. Uses data, AI, automation, and modern sales tools to improve effectiveness. Travel supports merchant meetings, events, and team gatherings.

Own the full sales cycle for complex upper-SMB and mid-market merchants, from territory planning and outbound pipeline generation through executive discovery, solution design, negotiation, contract, and launch. Build quantified business cases, coordinate cross-functional teams, manage forecasts in Salesforce, navigate legal, risk, technical, and implementation requirements, and acquire new merchant partnerships. The role requires consultative selling, commercial judgment, executive communication, and experience closing complex technology, fintech, payments, or SaaS deals.

Lead four Account Executives selling platform partnerships to ISVs and SaaS providers. Define the ISV go-to-market strategy, manage complex negotiations, oversee opportunities from creation through launch and activation, improve prospecting and forecasting, and represent partner insights in commercial and product decisions. Responsibilities include coaching, hiring, talent planning, performance management, executive relationship building, and driving revenue growth across the platform ecosystem.

Manage a portfolio of strategic merchant accounts, driving revenue, GMV, product adoption, expansion, and customer satisfaction. Lead complex contract negotiations, pricing initiatives, account plans, financing optimization, and executive relationships. Analyze partner performance, recommend growth programs, and coordinate Product, Technical, Credit, Analytics, Marketing, Risk, and Support teams. Serve as a strategic account-management leader and customer advocate across omni-retail.