Top Tech Jobs & Startup Jobs in Chicago, IL

Designs and scales global manager enablement, onboarding, leadership development, coaching, and performance programs across Customer Care and Customer Success. The role establishes coaching standards, partners with senior stakeholders, develops AI-powered training and simulation tools, supports organizational and process change adoption, and measures learning impact against operational and commercial KPIs using analytics and AI. It serves as a global center of excellence for manager effectiveness and scalable talent development.

As a Senior Principal Engineer, you'll define and drive the technical strategy for customer experience platforms, lead architectural decisions, and mentor engineering teams to enhance customer and agent experiences.

Build and ship production software for Toast’s retail platform, partnering with engineering, product, and customers. Responsibilities include identifying opportunities, designing and prototyping end-to-end solutions, making foundational technical decisions, incorporating customer feedback, tracking industry trends, and deploying AI-powered experiences. The role supports large grocery and convenience-store customers and may involve visiting stores to understand operator workflows.

Build and productionize agentic workflows, RAG pipelines, AI services, backend systems, and ML pipelines for sales automation. Integrate Salesforce, quoting engines, data lakes, and internal platforms using scalable, event-driven architectures. Lead 0-to-1 development of tools for account research, lead prioritization, and quoting while ensuring reliability, observability, performance, and resilience across the GTM technology stack.

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.

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.

Leads Toast’s AI and analytics strategy for Enterprise Care. Owns the roadmap, evaluates and deploys AI-assisted support tools, develops operational intelligence products, and partners with Product, Engineering, and Data teams to move pilots into production. Establishes complexity and workload intelligence, assesses AI readiness, translates AI performance into measurable operational outcomes, and builds organizational AI literacy. The role requires extensive enterprise support or service-delivery leadership, hands-on production AI experience, operational data fluency, and the ability to drive trusted adoption among agents and executives.

Design, scope, and implement scalable backend and platform solutions for a reservations and waitlist product. Improve performance and usability, collaborate with Product and Design, identify high-impact opportunities, and contribute across the stack including APIs and front-end integration.

Own end-to-end bookkeeping for pilot restaurant customers, including account setup, monthly close, reconciliations, accruals, consolidation, tax support, and financial statements. Serve as the restaurant-accounting expert while partnering with product and engineering to define workflows and requirements. Build bookkeeping SOPs, controls, and QA processes from scratch, support restaurant operators, and help establish scalable tooling, automation, and hiring practices.

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.