Technical Support Engineer II

Flywire•Chicago, IL

11d•$81,000 - $101,000•Hybrid

About The Position

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.

Requirements

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.

Nice To Haves

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.

Responsibilities

Manage and resolve customer and departmental tickets efficiently, ensuring the highest quality standards while strictly adhering to SLA requirements.
Work hands-on with web-based products and command-line tools to thoroughly research and isolate complex support issues.
Logically assess technical problems, propose accurate solutions to customers, and collaborate with development teams on long-term product enhancements.
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.
Serve as a highly effective mediator and escalation bridge between customers and the product/engineering teams.
Align technical support goals with Flywire’s broader business domain, vision, mission, and strategy to deliver on both short- and long-term goals.
Manage and maintain the TSE team's AI Skills repository, TSE Project Repos, and internal knowledge base.
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.