Top Tech Jobs & Startup Jobs in Chicago, IL

Design and own end-to-end technical solutions and integration architecture for enterprise restaurant rollouts. Translate business requirements into scalable designs, validate integrations during pilots, oversee rollout integrity, produce handoff documentation, manage technical risk and escalations, and coordinate cross-functional teams from pre-sale through post-live stabilization.

Provide multi-channel customer support for payroll tax accounts: research and resolve tax notices, coordinate with tax agencies and internal teams, reconcile liabilities, assist with TPA and POA setups, and contribute to recurring filings and process improvements.

Founding Retail BDR for Toast90: build prospect lists and perform high-volume outreach (80+ activities/day) to convenience stores, grocery and bottle shops; qualify leads, schedule meetings for Account Executives, use Salesforce to track activity, partner on sales strategy, and position the Toast Retail solution against competitors.

Design and implement Kotlin backend services and end-to-end systems for Toast POS device management. Lead technical designs, estimations, performance optimization, cross-team collaboration, and software quality practices including modern testing and observability. Mentor peers and drive product roadmap alignment with product, hardware, and QA stakeholders.

Design, build, deploy, and operate a high-concurrency, resilient configuration and publishing platform. Lead cross-team projects, set technical direction, improve engineering productivity, optimize performance, and maintain end-to-end ownership of distributed systems at scale.

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.

As a Staff Software Engineer, you will define technical strategy for Drive-Thru solutions, standardize Android practices, and ensure seamless integration between mobile clients and backend services while mentoring peers.

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.

Develop and deliver production-ready web experiences for marketing using React, Gatsby, and Tailwind. Build API integrations, maintain a lightweight codebase and design-system components, ensure accessibility, performance, SEO, and multi-region support, participate in code reviews, and help shape tooling and best practices across the team.

Lead strategy and execution for enterprise and mid-market GTM across multi-unit restaurant brands. Drive C-suite engagements, modernize sales motions, scale AI-powered forecasting, partner with Product/Engineering, and represent Toast in industry forums to win large, complex contracts.