Technical engineer Jobs in Chicago, IL

Are you ready to trade your job for a journey? Become a FlyMate!

Passion, excitement & global collaboration are all core to what it means to be a FlyMate. At Flywire, we’re on a mission to deliver the world’s most important and complex payments. We use our Flywire Advantage - the combination of our next-gen payments platform, proprietary payment network and vertical specific software, to help our clients get paid, and help their customers pay with ease - no matter where they are in the world.

What more do we need to truly be unstoppable? Perhaps, that is you!

Who we are:
Flywire is a global payments enablement and software company, founded more than a decade ago to solve high-stakes, high-value payments in higher education. We’ve since scaled into new regions and industry verticals and expanded our product offerings to deliver meaningful value to our clients around the world.

Today we support more than 5,100 clients across the global education, healthcare, travel & B2B industries, with diverse payment methods across 240 countries & territories and more than 140 currencies.

With over 1,200 global FlyMates, representing more than 40 nationalities, and in 12 offices world-wide, we’re looking for FlyMates to join the next stage of our journey as we continue to grow.

The Opportunity

We are seeking a highly motivated and talented Technical Support Engineer II to work directly with customers and cross-functional teams on daily support and operational tasks. In this role, you will support Flywire’s Student Financial Services (SFS), eStore, and TPI products for our clients across the U.S. and Canada.

A unique and critical aspect of this role is proactively leveraging AI tools (such as Claude and Gemini) as a smart personal assistant to automate day-to-day TSE workflows, maintain internal repositories, assist with issue investigations, and streamline client communications.

Key Responsibilities:

Technical Support & Troubleshooting

• Ticket Management: Manage and resolve customer and departmental tickets efficiently, ensuring the highest quality standards while strictly adhering to SLA requirements.
• Deep Research: Work hands-on with web-based products and command-line tools to thoroughly research and isolate complex support issues.
• Issue Resolution: Logically assess technical problems, propose accurate solutions to customers, and collaborate with development teams on long-term product enhancements.

Communication & Collaboration

• Client Communication: Communicate clearly, concisely, and confidently with customers via email or phone, translating highly complex technical issues into easy-to-understand explanations based on the client’s technical level.
• Cross-Functional Liaison: Serve as a highly effective mediator and escalation bridge between customers and the product/engineering teams.
• Business Alignment: Align technical support goals with Flywire’s broader business domain, vision, mission, and strategy to deliver on both short- and long-term goals.

AI & Knowledge Management

• AI Repository Maintenance: Manage and maintain the TSE team's AI Skills repository, TSE Project Repos, and internal knowledge base.
• AI Automation: Utilize AI tools to automate routine maintenance tasks, investigate client issues, create bug/product enhancement requests for dev teams, and draft effective, professional client communications.

Here’s What We’re Looking For:

• 3-5 years of experience in technical support engineering.
• 3+ years of hands-on experience with MySQL, Regular Expressions (Regex), and SaaS-based web applications.
• Proficiency in leveraging AI tools - specifically Claude - to optimize day-to-day tasks and boost operational efficiency.
• B.S. degree in a science or engineering field.
• Outstanding verbal and written communication skills.
• Detail-oriented, highly organized multitasker with a strong eagerness to learn new technologies and a drive to go above and beyond to find root causes.

Preferred Qualifications:

• A master's degree in a respective science or engineering field is a plus.
• Experience in higher education, Student Financial Services (SFS), FinTech, or the payments industry.
• Familiarity with industry-standard logging, analytics, and ticketing tooling.

Technologies & Tools We Use:

• Core Technologies: MySQL, Java, SaaS Web Applications, HTTP/SFTP Protocols
• AI Assistants: Claude Code, Google Gemini, Notebook LM
• Operations & Tooling: Zendesk, Jira, Confluence, SumoLogic, Looker