Top Tech Jobs & Startup Jobs in Chicago, IL

Develop fullstack web applications, enhance platform performance, collaborate on high-impact opportunities, and ensure stable, scalable solutions. Engage in rapid iterations and be a committed team player.

Own and run the monthly release program for Toast IQ: set platform-readiness standards, manage technical dependencies and risk, coordinate cross-functional go-to-market and naming, instrument launch health and reporting, and establish governance and rhythms that scale multi-team agent launches.

The GTM Engineer will automate sales workflows using tools, build integrations, design a win/loss analysis program, and collaborate with sales teams to leverage AI insights.

Lead and coach a team of 6–8 Strategic Cuisines Account Executives across the West Coast. Drive sales productivity, pipeline performance, discovery, demos, and customized restaurant technology solutions in Thai. Partner with leadership to assess market opportunities, improve sales funnels, and coordinate delivery expectations across teams. This field-based role requires travel and local West Coast residence or relocation.

Lead Toast’s global privacy program across multiple jurisdictions, operationalize privacy requirements, assess vendor DPAs, mature privacy rights processes, oversee privacy reviews and DPIAs, manage risk registers, develop training and data governance initiatives, and report program KPIs. The role also drives automation using LLMs and collaborates with legal, technical, product, procurement, and business teams to implement privacy controls and mitigations.

Product Counsel will advise product, engineering, data science, marketing, compliance, and sales teams throughout the product lifecycle. Responsibilities include counseling on regulatory compliance, privacy, intellectual property, consumer protection, AI and machine learning, data rights, platform architecture, APIs, identity and account security, and marketing. The role translates legal requirements into technical guidance, supports AI governance, monitors evolving laws, and develops scalable legal processes for a fast-paced technology company.

Design, build, deploy, and maintain resilient, scalable production systems for Toast’s retail customers. The role sets long-term technical architecture and strategy, communicates technical direction, mentors senior engineers, improves engineering productivity, diagnoses performance issues, and drives initiatives amid ambiguity. Engineers collaborate directly with retail customers, visit stores, understand operational workflows, and use AI tools to improve development velocity and quality.

Source and close complex, multi-location retail technology deals across grocery, liquor, and convenience operators. Build pipeline, conduct executive discovery, demonstrate platform value, structure and negotiate deals, manage lengthy buying cycles, and ensure implementation handoffs. The role also develops repeatable sales processes, partners cross-functionally on product and commercial gaps, maintains Salesforce pipeline discipline, and represents retailer needs in product decisions.

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.