Top Tech Jobs & Startup Jobs in Chicago, IL

Source and close complex, multi-location retail technology deals across grocery, liquor, and convenience operators. Build pipeline, conduct executive discovery, deliver value-based demonstrations, structure and negotiate deals, manage multi-stakeholder sales cycles, and own contracts through close. Partner cross-functionally on implementations, product feedback, and repeatable sales processes while maintaining Salesforce discipline, forecasting accuracy, and long-term revenue quality. This remote role requires 30% or more travel.

Source and close complex, multi-location grocery, liquor, and convenience retail deals. Build pipeline, conduct executive discovery, deliver value-based demonstrations and business cases, negotiate contracts, and manage full-cycle sales. Navigate buying committees, RFPs, compliance, and lengthy sales cycles while partnering with internal teams on implementation, product feedback, and deal structure. Establish repeatable upmarket sales processes, maintain Salesforce discipline, and optimize long-term revenue.

Design, build, deploy, and maintain resilient, scalable software for Toast Delivery Services. Develop real-time delivery tracking, driver matching, pricing, refunds, and payment-related systems. Solve distributed-systems and scaling challenges, integrate with partner APIs, uphold production reliability, promote strong engineering practices, and mentor teammates.

Lead enterprise product marketing strategy for Toast’s hospitality platform, including positioning, messaging, launches, pricing and packaging, demand campaigns, customer proof points, sales enablement, and performance measurement. Build and manage the Enterprise Product Marketing team, collaborate with Product, Sales, Finance, Engineering, and Customer Success, represent the product externally, and use customer insights and data to drive pipeline, win rates, and revenue.

Lead the ToastNow engineering team in delivering high-quality native mobile experiences for restaurant operators. Drive planning, execution, cross-functional collaboration, backlog development, production quality, monitoring, and issue resolution. Hire, mentor, and develop engineers while fostering diverse, high-performing teams. Champion AI tools and practices to improve development speed, quality, and team velocity.

Lead architecture and technical execution for Toast’s Payroll and Team Management products. Own authentication, authorization, and organizational hierarchy across a multi-tenant SaaS platform. Drive high-scale, full-stack initiatives, modern agentic development practices, integrations, technical strategy, quality standards, deployment practices, and cross-functional collaboration. Mentor engineers across teams and leverage AI tools and LLM integration to improve software development velocity and quality.

Lead and build Toast Retail’s Mid-Market sales function from the ground up. Manage and coach Account Executives while personally closing complex grocery, liquor, and convenience retail deals. Develop repeatable sales processes, qualification frameworks, business cases, proposals, forecasting practices, and competitive positioning. Partner cross-functionally with Product, Marketing, Enablement, Finance, Deal Desk, and Onboarding to support enterprise implementations and product improvements. Hire and develop a high-performing team, establish benchmarks, and transition from a player-coach role to full team leadership.

Design, build, deploy, and maintain resilient, scalable backend services and platform components for Toast's Voice AI platform. Lead cross-cutting architecture and projects, integrate AI platforms (LLMs), implement observability and evaluation for AI systems, set engineering standards, and mentor engineers.

Manage post-sale onboarding for restaurant customers through remote site assessment, Toast POS implementation, staff training, go-live support, troubleshooting, and follow-up guidance. Build onboarding plans, document installations and deviations, improve restaurant operational efficiency, and manage multiple engagements simultaneously. The role requires Vietnamese and English fluency, restaurant or hospitality experience, strong customer satisfaction and business operations experience, autonomy, organization, communication, and goal achievement.

Onboards restaurant customers onto Toast POS from purchase through go-live and early post-launch support. Builds implementation plans, conducts remote site assessments, documents installations, trains restaurant staff, troubleshoots issues, and provides follow-up guidance. Manages multiple onboarding engagements and large customer portfolios while meeting activation goals, maintaining timelines and budgets, and improving restaurant operational efficiency. Requires fluent Thai and English, restaurant or hospitality experience, and at least three years in customer satisfaction or business operations.