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Technical Support Engineer II

Flywire - Chicago, IL, USA - Hybrid - posted 2026-09-18

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Salary: USD 81,000 - 101,000 / annual

Flywire is seeking a Technical Support Engineer II to provide technical support and operational excellence for its Student Financial Services (SFS), eStore, and TPI products serving clients across the U.S. and Canada. This role combines hands-on customer support with innovative use of AI tools to streamline workflows and enhance efficiency. You will manage customer and departmental support tickets while maintaining strict SLA compliance, conduct deep technical research using web-based products and command-line tools, and collaborate with development teams on product enhancements. A key differentiator of this role is proactively leveraging AI tools such as Claude and Gemini as a smart personal assistant to automate day-to-day workflows, maintain internal repositories, assist with issue investigations, and streamline client communications. Key responsibilities include: - Efficiently managing and resolving customer tickets to the highest quality standards while adhering to SLA requirements - Conducting hands-on research and troubleshooting of complex technical issues - Communicating clearly with customers via email or phone, translating complex technical concepts into accessible explanations tailored to the client's technical level - Serving as an effective liaison and escalation bridge between customers and product/engineering teams - Maintaining the TSE team's AI Skills repository, project repositories, and internal knowledge base - Utilizing AI tools to automate routine maintenance tasks, investigate client issues, create bug reports and product enhancement requests, and draft professional client communications - Aligning technical support goals with Flywire's broader business vision and strategy Flywire is a global payments enablement and software company supporting over 5,300 clients across education, healthcare, travel, and B2B industries, with operations in 15 offices worldwide and a team of 1,400+ employees representing 40+ nationalities. 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 strong eagerness to learn new technologies and drive to find root causes PREFERRED QUALIFICATIONS: - Master's degree in a respective science or engineering field - Experience in higher education, Student Financial Services (SFS), FinTech, or the payments industry - Familiarity with industry-standard logging, analytics, and ticketing tooling (Zendesk, Jira, Confluence, SumoLogic, Looker) TECHNOLOGIES & TOOLS: MySQL, Java, SaaS Web Applications, HTTP/SFTP Protocols, Claude Code, Google Gemini, Notebook LM, Zendesk, Jira, Confluence, SumoLogic, Looker.

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