Top Tech Jobs & Startup Jobs in Chicago, IL

Own new-business sales for Stripe Connect with upper middle market and enterprise software platforms. Manage named accounts, prospect outbound opportunities, build C-level relationships, lead complex consultative sales cycles, conduct product workshops and financial analyses, negotiate commercial agreements, and close deals. Partner with Product, Engineering, Finance, and company leaders to refine sales processes, shape platform strategy, and develop scalable engagement models.

Drive new customer acquisition for Stripe's Startup and SMB segment by owning full sales cycles from lead to close, prospecting inbound and outbound, solving client needs cross-functionally, and driving product adoption while meeting sales targets.

Manage enterprise customer relationships after sale, focusing on retention, account health, product adoption, payment optimization, renewals, growth, and satisfaction. Conduct business reviews, advise customers on payments and product value, identify expansion opportunities, advocate internally, and share customer insights with product, engineering, support, marketing, and sales teams.

Lead Stripe’s enterprise Platform Sales team, driving revenue growth and global expansion across SaaS platforms. Responsibilities include managing and developing account executives, shaping deal strategy, building executive relationships, improving pipeline and forecasting, supporting product roadmap decisions, creating sales processes, and delivering revenue attainment. The role also involves hiring, coaching, organizational planning, and developing scalable sales playbooks for payments monetization.

Lead and scale Stripe’s commercial sales team focused on growing existing mid-market accounts. Responsibilities include hiring, coaching, and managing Account Executives; driving product adoption, revenue growth, and share of wallet; developing go-to-market strategy; forecasting performance; building executive customer relationships; and collaborating cross-functionally to improve sales efficiency.

Lead and grow a high-performing team of Customer Success Managers supporting Stripe’s strategic enterprise customers. Responsibilities include recruiting, coaching, developing customer engagement strategies, driving adoption, renewals and growth, managing account risks, advising on account strategy, serving as an executive sponsor, and establishing operating rhythms such as account planning and health reviews. The role also requires cross-functional collaboration, executive relationship management, and solving complex customer and business problems in a high-growth environment.

Lead and grow a team of Account Executives focused on acquiring venture-funded technology startups. Responsibilities include recruiting, coaching, sales strategy, revenue and acquisition growth, pipeline improvement, customer relationship management through executive levels, forecasting, and cross-functional collaboration to shape Stripe products and solutions. The role combines people leadership with direct involvement in complex sales cycles and requires experience scaling technology sales teams in high-growth environments.

Lead and scale a commercial sales team focused on acquiring and expanding mid-market accounts. Responsibilities include hiring, coaching, forecasting, managing sales performance, developing go-to-market strategy, driving revenue growth, building customer relationships, and collaborating cross-functionally to improve team efficiency and product alignment.

Drive new business growth for Stripe Terminal by prospecting, managing the full sales cycle, closing strategic deals, and expanding existing customer relationships. Lead complex product and technical sales conversations involving hardware, software, and payments. Develop go-to-market strategies, negotiate bespoke agreements, advise customers and internal teams, and collaborate with Product, Engineering, Marketing, and User Operations to accelerate adoption.

Lead and coach an enterprise sales team focused on acquiring new customers across AMER. Develop sales strategy, train representatives in consultative and solution-based selling, manage revenue and activation targets, build strategic client relationships, collaborate cross-functionally, and support direct reports’ career development. The role requires extensive technology, SaaS, banking, or payments sales experience and a proven record of scaling high-performing teams.