Top Tech Jobs & Startup Jobs in Chicago, IL

Lead Toast's consumer payments strategy, managing product vision and execution for payment experiences. Collaborate across teams to optimize guest and restaurant experiences with innovative payment methods.

The position involves providing legal support for FinTech products, negotiating partnerships, drafting agreements, and ensuring compliance with financial regulations. The role requires expertise in embedded finance and advising on financial products.

The Principal Technical Writer will design and deliver enterprise documentation, work on AI-driven content generation, and mentor other writers while collaborating with product teams.

Lead the end-to-end POS Ordering product strategy, maintain reliability and performance at scale, drive ordering workflow innovation (including AI opportunities), partner with restaurant operators and cross-functional teams, and steward a high-traffic domain to ensure coherent, reliable, and differentiated ordering experiences.

The Principal Product Manager, Voice AI will define the strategy for voice technology in restaurants, leading evaluations, vendor negotiations, product pilots, and creating a reusable voice platform. Responsibilities include driving commercialization, managing cross-functional teams, ensuring operational readiness, and mentoring other product managers.

Lead the technical direction of Care & Onboarding platforms by driving architectural decisions, overseeing large initiatives, and enhancing engineering quality.

Lead AI adoption and workflow redesign in Toast's marketing team, focusing on change management, governance, and measurable transformation programs.

The Director of Retail Engineering will lead architecture and development of Toast's Retail Platform, ensuring resilience and data integrity, managing teams, and driving technical strategy to support Grocery and Convenience Store demands.

Serve as strategic HR partner to a 2,000+ R&D organization, leading org design, performance calibration, people programs, engagement analysis, and coaching senior leaders to scale the org and improve talent outcomes.

The Senior Product Manager will own the strategy and execution of Toast's configuration platform, collaborating with engineering, design, and customer teams to enhance the user experience and support diverse business needs.