Top Tech Jobs & Startup Jobs in Chicago, IL

Lead product strategy and roadmap for a new venture from MVP through product-market fit and scale. Own outcome briefs, weekly planning, customer research, prioritization, success metrics, and launches. Partner closely with engineering, design, sales, marketing, support, and operations to simplify workflows, validate customer value, and build scalable onboarding, reliability, self-service, and integrations. Use data and AI tools to guide decisions, prototype, research, and improve product outcomes.

Lead a four-person engineering team building a new product from concept through MVP and beyond. Act as a player/coach by writing code, fixing bugs, triaging customer issues, shaping architecture, and driving rapid weekly sprints with Product. Establish lightweight engineering practices, coordinate cross-team dependencies, incorporate modern tools, and maintain close customer feedback loops while balancing speed, quality, and long-term viability.

Build and deploy statistical and machine learning models for the Toast platform. Collaborate with product, engineering, and business teams to identify opportunities, develop data-driven solutions, evaluate models, and communicate insights to stakeholders. Work in a fast-paced environment and contribute to production ML systems and experimentation.

Develop and scale full-stack web applications for Toast’s digital storefront, including online ordering and website products. Design solutions, improve performance and usability, collaborate with Product and Design, run experiments, resolve critical issues, and contribute to API design, testing, and cross-team product integration.

Staff Software Engineer responsible for leading design and delivery of large-scale order platform capabilities spanning cloud and point-of-sale systems. The role drives architecture, performance, reliability, API design, code quality, incident response, and technical roadmap alignment. It also requires cross-team collaboration, domain expertise in order processing and synchronization, mentoring engineers, and using AI-assisted development tools to improve productivity.

Support Toast’s enterprise data governance program by managing governance dashboards, business glossaries, metadata standards, compliance monitoring, documentation, stewardship training, and data quality tracking. Collaborate with Engineering, Analytics, Legal, and data catalog teams to translate business definitions into technical specifications, automate data discovery, facilitate governance workshops, and improve data management and AI governance practices.

Lead development of Toast’s consumer-facing web experiences, building scalable guest and restaurant features across the stack. Collaborate with frontend, backend, iOS, and Android engineers using React, TypeScript, Next.js, APIs, and backend services. Own projects from development through launch, monitoring, and analysis while experimenting with users and influencing consumer product strategy.

Own the technical infrastructure supporting paid media, including tracking pixels, conversion signals, CRM audience syncs, marketing automation, data pipelines, platform integrations, UTM governance, launch QA, monitoring, and reporting infrastructure. Partner closely with paid media teams to troubleshoot data discrepancies, improve campaign launch speed, maintain data quality, and support audience operations across multiple advertising platforms.

Lead end-to-end delivery of critical IT systems initiatives and integrations across identity, service management, infrastructure, collaboration, and compliance domains. Manage a project manager, coordinate cross-functional technical teams, unblock dependencies, define program metrics, build executive dashboards, drive user adoption, and communicate technical outcomes to business stakeholders. The role also oversees tooling consolidation, documentation, training, release communications, post-mortems, and enterprise IT roadmap execution.

Design, build, and operate production AI automations and agentic workflows for Toast’s customer care systems. Integrate LLMs with Salesforce Service Cloud, Amazon Connect, and workflow platforms; develop autonomous actions with human oversight; test, monitor, and improve system reliability, accuracy, latency, and cost. Collaborate with software engineers, Salesforce developers, and care operations stakeholders to translate workflows into scalable intelligent solutions.