Top Tech Jobs & Startup Jobs in Chicago, IL

Manage enterprise customer accounts, deliver insights and support post-sale engagements to drive account health, retention, and growth.

Lead technical presales engagements with enterprise customers: design platform payment architectures, demonstrate Stripe solutions (Connect, Payments, Billing), perform discovery, run proofs of concept, influence executives, expand account footprint, and coordinate cross-functional teams to secure technical wins and accelerate adoption.

Own post-sale lifecycle for Revenue & Finance Automation customers: drive retention, expansion, adoption, and account health. Act as trusted advisor on payments, billing, tax, and invoicing; partner with account teams and internal stakeholders to optimize value, surface feedback, and identify growth opportunities.

The Account Executive will identify potential customers, develop sales strategies, manage the sales cycle, and collaborate cross-functionally to address user needs.

The Hardware Solution Specialist will support complex Stripe Terminal users, troubleshoot hardware issues, collaborate with teams, and optimize documentation.

Provide high-level administrative support to two People leaders: manage complex calendars, travel and expenses, organize meetings and offsites, track project milestones and action items, improve administrative systems, and handle sensitive information with discretion while acting as a trusted strategic partner.

The Payments Performance Strategist will lead discussions on payment optimization with merchants, create analysis tools, and collaborate with various teams to enhance Stripe's payment strategies.

The Billing Account Executive will drive revenue, lead sales conversations, and collaborate with teams to enhance Stripe's product offerings and customer success.

Own full sales cycle for enterprise and upper-middle-market B2B software platforms. Manage named accounts, build C-level relationships, develop outbound strategies, lead complex multi-party negotiations and product workshops, collaborate with Product and Engineering, and drive repeatable platform partnership processes and sales forecasting.

Lead, recruit, coach, and scale an enterprise sales team across AMER. Set strategy and day-to-day operations, drive net revenue and activation targets, work cross-functionally to shape solutions, and mentor direct reports while engaging directly with prospective customers.