Top Tech Jobs & Startup Jobs in Chicago, IL

Own the full sales cycle for Stripe’s startup and SMB customers, from prospecting and lead generation through closing and product adoption. Identify high-potential prospects, understand customer pain points, propose solutions, manage complex sales cycles, and exceed sales targets. Collaborate with product, sales, risk, operations, and other internal teams to address client needs and ensure customer success.

Acquire new SMB customers through outbound prospecting, lead generation, solution selling, and full-cycle sales execution. The Account Executive will identify prospects, understand customer pain points, develop business cases, close new business, drive product adoption, and collaborate cross-functionally to improve customer solutions. The role requires success in high-velocity sales environments, comfort with ambiguity, strong communication, technical understanding, and a proven record of exceeding sales targets.

Own the full sales cycle for Stripe’s SMB customers, including prospecting, renewals, upsells, product adoption, negotiations, and retention. Build consultative relationships, understand technical customer needs, generate leads, close opportunities, and coordinate with cross-functional product, sales, risk, and operations teams to improve customer outcomes and revenue.

Own the full sales cycle for upper-middle-market and enterprise software platforms, from prospecting through close. Manage named accounts, build C-level relationships, lead complex consultative sales and negotiations, develop account plans, conduct product workshops and financial analyses, and collaborate with Product, Engineering, and Finance. Contribute to platform partnership strategy, sales processes, value propositions, and scalable engagement models while maintaining accurate CRM and forecasting practices.

Leads and develops a team of Account Executives focused on acquiring SMB customers. Owns revenue growth, sales performance, pipeline generation, forecasting, coaching, hiring, and customer relationships up to the C-level. Collaborates cross-functionally to improve products and solutions, while building scalable sales programs in a high-growth technology environment.

Build and maintain customer-facing Stripe demos by translating Product Marketing messaging into compelling narratives and multi-product experiences. Use AI-assisted tools to prototype and develop production-quality demos, track product launches, curate the demo library, and scope executive and strategic customer demonstrations with Solutions Architects and the Executive Briefing Center team.

Schedule high-volume interviews globally, coordinate with recruiters and interviewers, support hiring operations, protect sensitive information, adapt to changing priorities, and provide a welcoming onsite candidate experience. The role requires strong organization, communication, discretion, attention to detail, and the ability to manage multiple stakeholders and tasks in a fast-paced environment.

Owns global HR compliance operations, including audits, regulatory filings, HRIS data integrity, SOP documentation, vendor management, and process improvement. Partners with Legal, Employee Relations, Procurement, and other Centers of Excellence to meet compliance obligations and resolve complex operational issues. Maintains Workday records, coordinates audit evidence, monitors regulatory changes, and translates requirements into clear procedures and stakeholder communications.

Manage complex customer renewals in partnership with Account Executives and cross-functional teams. Analyze pricing, usage, performance, and contract data; build financial models and renewal scenarios; identify retention risks and expansion opportunities; support deal strategy, negotiations, quotes, and proposals. Track renewal milestones, report performance, and improve scalable workflows through tooling, automation, and responsible AI use.

Manage complex customer renewals by analyzing pricing, usage, performance, and contract data; build financial models and recommendations; support negotiation strategy; identify retention risks and expansion opportunities; coordinate with Sales, Customer Success, Deal Pricing, and other teams; report renewal performance; and improve scalable workflows through tooling, automation, and AI-assisted solutions.