Top Tech Jobs & Startup Jobs in Chicago, IL

Advise AI companies on payments, billing, metering, and monetization strategies. Architect custom Stripe solutions, support implementations, influence product roadmaps, engage technical founders and executives, and partner with sales, engineering, product, marketing, and professional services. Provide thought leadership through demonstrations and events, monitor competitors, and help position Stripe as a strategic AI monetization partner. Travel may reach 50% of the time.

Generate qualified sales pipeline through cold calls, email, social outreach, and marketing-generated inquiries. Research prospects, pitch Stripe products, book meetings, qualify business needs, maintain warm opportunities, update Salesforce records, meet outreach SLAs, and collaborate with Marketing and Account Executives. The role includes structured training through Stripe’s Sales Development Associate program and requires fluent English and Spanish communication in a primarily in-office Chicago environment.

Lead end-to-end integration engineering for strategic Stripe customers, from architecture through implementation and debugging. Collaborate with sales, solution architecture, and implementation teams; serve as the primary technical contact for enterprise users and partners; explain Stripe products and APIs; educate developers; provide technical thought leadership; and recommend improvements to product and engineering teams.

Designs and presents Stripe payment, billing, banking, and SaaS solutions for SMB customers. Builds trusted relationships with executives and technical decision-makers, identifies business and monetization opportunities, delivers demos and RFP responses, expands accounts into new markets, and collaborates with sales, product, marketing, partners, and professional services. Creates scalable customer-engagement assets and advises on technology strategy, architecture, and execution.

Manage enterprise customer relationships across the post-sales lifecycle, driving adoption, retention, renewals, expansion, and satisfaction. Deliver workshops, business reviews, payment performance insights, product guidance, and thought leadership. Partner with sales, technical account management, operations, product, engineering, support, and marketing teams to resolve issues, advocate for customers, and identify growth opportunities.

Leads Stripe’s Sales Development organization supporting Startup, SMB, and Commercial segments. Manages five managers and more than 50 SDRs, owns qualified pipeline and business outcomes, and drives forecasting, operational rigor, Salesforce data integrity, AI-enabled workflows, cross-functional strategy, hiring, coaching, and succession planning. Partners with Sales, Marketing, Enablement, Product Marketing, and Operations to scale high-performing teams and improve sales development processes, tools, and playbooks.

Lead end-to-end integrations for strategic Stripe customers, from high-level architecture through implementation and code-level debugging. Partner with Sales, Solution Architecture, and Implementation teams to drive customer outcomes. Serve as the primary technical contact for enterprise users and partners, explain Stripe products and APIs, educate developers, provide technical thought leadership, and share integration feedback with product and engineering teams.

Manage and grow named enterprise and upper-middle-market accounts for Stripe Connect. Own the full sales cycle, develop account and outbound strategies, build C-level relationships, close complex platform partnerships, and support implementation. Collaborate with Engineering, Product, and Finance on product workshops, financial analyses, sales processes, and product strategy.

Leads end-to-end RFP and RFI processes for large strategic pursuits, including bid evaluation, response strategy, proposal writing, contributor coordination, review management, and deadline delivery. Translates technical and business requirements into persuasive proposals, develops value propositions and commercial recommendations, and improves proposal processes, tools, templates, and performance reporting using win-loss data.

Leads Customer Success strategy and operations by designing operating models, planning processes, reporting infrastructure, OKRs, dashboards, AI-enabled workflows, and scalable technical solutions. Partners with senior leadership, analyzes performance, manages territories, improves systems and workflows, and drives cross-functional initiatives from requirements through implementation to increase efficiency and customer impact.