Top Tech Jobs & Startup Jobs in Chicago, IL

Own the Toast Delivery Services product roadmap, improving dispatch, order tracking, exception handling, refunds, and AI-assisted delivery operations. Partner with Guest, POS, Order Management, AI teams, restaurants, couriers, and external integration partners to deliver measurable outcomes for operators and guests. Shape real-time delivery experiences, proactive alerts, capacity matching, and trusted automation for restaurant delivery.

Manage and develop a team of 10–12 payroll tax care experts. Oversee productivity, quality, customer satisfaction, escalations, service levels, and tax case outcomes. Coach agents, provide subject matter expertise on payroll tax filing and recovery, monitor regulatory changes, deliver reporting and analytics, and collaborate with cross-functional teams on process improvements, support guidelines, and customer experience initiatives.

Define and evolve Toast’s consumer brand across product, marketing, and restaurant touchpoints. Build the visual and verbal identity system, expressive product design layer, motion, illustration, photography, and brand toolkits. Partner with product, engineering, marketing, and growth teams to deliver cohesive experiences across apps, campaigns, lifecycle communications, and physical restaurant interactions. Lead critiques, contribute hands-on execution, prototype in design tools or code, and ensure concepts reach polished, shipped results.

Lead Toast’s lending product strategy and roadmap, including Toast Capital and Easy Pay. Partner with engineering, design, data science, credit, legal, finance, marketing, and external financial partners to develop, launch, and optimize B2B financial products. Responsibilities include defining requirements, managing backlogs, facilitating agile ceremonies, building business cases, gathering customer feedback, and measuring product outcomes.

Lead cloud security strategy and hands-on execution across AWS environments. Own CNAPP and CSPM capabilities, improve IAM and container security, build infrastructure-as-code guardrails, conduct architecture reviews and threat modeling, support detection and incident response, and drive remediation programs. Establish a multi-year cloud security roadmap, influence engineering priorities, mentor teammates, and partner with platform, infrastructure, SOC, and product engineering teams.

Leads development of resilient, scalable features across Toast’s enterprise Sports and Entertainment platform, including backend, frontend, and POS systems. Responsibilities include designing, deploying, testing, monitoring, and maintaining production services; leading complex technical projects; collaborating with Product, Design, Customer Success, Sales, and other teams; mentoring engineers; and using AI tools to improve development productivity.

Serve as the technical lead for complex mid-market retail sales opportunities. Conduct discovery, deliver tailored demonstrations, design integrations and data flows, lead pilots and proofs of concept, complete technical RFPs and security reviews, and ensure effective implementation handoffs. Partner with Sales, Product, Partnerships, and Implementation while communicating customer needs, product gaps, and roadmap priorities. The role requires POS and retail operations knowledge, API fluency, strong communication, and willingness to travel up to 25%.

Build AI workflows, agents, and customer-facing web experiences that accelerate website production and improve conversion. The role involves optimizing Contentful-based processes, configuring chat, enrichment, voice AI, and personalization tools, running experiments, establishing AI guardrails, monitoring performance, and training marketing teams on reusable AI systems. Collaboration spans Web Platform, CRO, SEO, product marketing, legal, privacy, and brand teams.

Design and deliver Android system applications for Toast POS devices, including device policy enforcement, setup, firmware and app updates, background services, and fleet deployment. Lead technical design, cross-functional planning, Android and hardware upgrades, automated testing, production issue investigations, and staged rollouts. Mentor engineers and collaborate with product, hardware, QA, and software teams to build secure, reliable device-management systems.

Lead end-to-end development of reliable care-agent tooling and software services integrating contact-center platforms with backend systems. Own architecture, performance, security, production operations, and technical direction while partnering with product, care operations, QA, and engineering teams. Translate operational workflows into scalable solutions, mentor engineers, and improve tools using agent feedback, operational metrics, and AI-assisted development practices.