Top Tech Jobs & Startup Jobs in Chicago, IL

Provides technical support for Flywire’s financial services and eStore products across the U.S. and Canada. Responsibilities include managing tickets within SLAs, troubleshooting web applications using MySQL, regex, command-line tools, and protocols, communicating solutions to clients, escalating issues to engineering, and maintaining AI-assisted knowledge repositories. The role also uses Claude, Gemini, and related tools to automate workflows, investigate issues, draft communications, and improve operational efficiency.

Provides first-line technical support for hospitality and e-commerce customers through email, web, and phone tickets. Responsibilities include troubleshooting platform, browser, network, payment, and log issues; resolving routine problems; escalating complex issues to Tier 2 and Engineering; documenting replication steps; maintaining knowledge articles and SOPs; and communicating clearly with customers. The role manages a high-volume queue, identifies bugs and workflow improvements, and may support customer calls, trainings, holiday coverage, or on-call rotations.

Develop and maintain full-stack billing and payments features using Java and related technologies. Build secure, scalable, testable code; write comprehensive unit tests; use AI-assisted development tools; collaborate with engineering and product stakeholders across global teams; and contribute to solutioning and technical decision-making.

Develop and maintain secure, scalable, testable features for Flywire’s billing and payments platform. This full-stack role involves Java application development, relational database work, automated testing, quality and performance assurance, and collaboration with engineering and product teams across global time zones. The engineer will also use AI-assisted development tools, navigate legacy systems, communicate with stakeholders, and contribute to solution design and problem-solving.

Own the strategy and multi-year roadmap for internal HCM and enterprise systems, including Workday. Partner with executives, translate business needs into product requirements, lead cross-functional delivery, govern product metrics, influence architecture and Agile practices, mentor Product Managers, and manage vendor relationships. The role drives scalable, secure enterprise platforms supporting global growth.

Lead technical strategy and roadmap for Go-To-Market platforms. Partner with stakeholders and engineering to translate requirements into user stories, manage product lifecycle, drive agile adoption, measure KPIs, and deliver platform capabilities that enable revenue growth and improve GTM experience.

Lead enterprise architecture strategy for a global payments platform. Establish architecture standards, modernize legacy systems, guide cloud-native and microservices adoption, mentor architects, enable governance, advise the CTO on technology investments, and drive platform scalability, security, and compliance across global engineering teams.

Lead strategy and roadmap for Treasury and finance enterprise systems; translate business needs into product requirements; drive cross-functional delivery, vendor relationships, architecture decisions, and metrics. Mentor product managers and partner with senior leaders to prioritize scalable, secure solutions supporting growth.

First-line technical support for hospitality/e-commerce customers: triage and resolve high-volume tickets via Zendesk, troubleshoot using logs/DataDog/browser dev tools, escalate with replication steps, write SOPs/knowledge articles, and collaborate with Tier-2 and Engineering to close issues.