Top Tech Jobs & Startup Jobs in Chicago, IL

Set technical direction for Toast’s Developer Experience platform, including local development, build tooling, shared libraries, testing frameworks, and developer portals. The role combines hands-on software engineering with architecture, cross-team technical leadership, AI-assisted development, developer productivity measurement, mentorship, and roadmap prioritization.

Leads Toast’s merchant liens, levies, garnishments, UCC, tax lien, and bankruptcy compliance function. Builds policies, governance, workflows, systems, KPIs, and a specialized oversight team while insourcing operations from a third-party partner. Manages complex escalations involving customers, creditors, attorneys, Legal, Risk, Finance, Product, and Engineering, ensuring compliant withholding, remittance, releases, and handling of high-risk cases.

Own the Talent Acquisition technology stack, including Greenhouse, GoodTime, and BrightHire. Configure systems, manage integrations, permissions, workflows, compliance, releases, reporting, automation, vendors, renewals, and roadmaps. Partner with recruiting, People Systems, Analytics, IT, Security, Legal, Procurement, and Finance to improve processes, data quality, system adoption, and monitoring. Evaluate recruiting technology, document architecture and runbooks, and resolve system issues. The role may eventually build and lead a small team.

Lead the design, development, and delivery of scalable payroll onboarding software. Drive technically complex initiatives, influence architecture and roadmaps, collaborate across product, design, and engineering, improve reliability, promote coding best practices, mentor engineers, and use AI tools to enhance development productivity.

Leads technical initiatives for Toast’s restaurant scheduling product, designing and delivering scalable full-stack software. Responsibilities include architecture, API and system design, roadmap influence, cross-functional collaboration, engineering quality, performance, and technical leadership. The role also promotes AI-assisted development and improved employee and customer experiences.

Associate Counsel supporting product, engineering, marketing, compliance, and sales teams on legal risks. Responsibilities include reviewing advertising and marketing materials, product development, labeling and certifications, trademark matters, privacy and regulatory issues, and legal processes. The role requires researching applicable laws, communicating legal guidance to non-legal stakeholders, managing deliverables, and collaborating cross-functionally in a technology company.

Manage full-cycle, high-volume recruiting for R&D and/or G&A roles, including sourcing, application review, candidate engagement, hiring-manager partnership, pipeline development, inclusive hiring, and recruitment metrics. The role requires adapting strategies to changing business needs, navigating ambiguous hiring situations, and delivering a strong candidate and stakeholder experience.

Lead the technical vision, architecture, and delivery of Toast’s pricing engine across multiple teams. Design and operate highly available distributed systems, APIs, databases, and event-driven services at scale. Serve as the pricing domain expert, improve correctness and performance, lead incident response and reliability initiatives, mentor engineers, establish operational excellence, and align technical priorities with Product and engineering leadership.

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.

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.