Technical Support Engineer

Flywire • Chicago, IL

26d • $68,838 - $98,340

About The Position

Flywire is seeking a highly motivated Technical Support Engineer II to support customers and cross-functional teams with daily support and operational tasks. The role supports Flywire’s Student Financial Services (SFS), eStore, and TPI products for clients across the U.S. and Canada. A key part of the position is proactively using AI tools, including Claude and Gemini, to automate workflows, maintain internal repositories, investigate issues, and streamline client communications.

The engineer manages customer and departmental tickets in accordance with service-level agreements, researches and isolates complex technical issues using web-based products and command-line tools, and develops accurate solutions. The role communicates technical issues clearly to customers and acts as an escalation bridge between clients and product and engineering teams. It also maintains AI skills and project repositories and the internal knowledge base, and uses AI to automate routine tasks, investigate client issues, prepare bug and product enhancement requests, and draft client communications.

Requirements

• 3–5 years of experience in technical support engineering.
• At least 3 years of hands-on experience with MySQL, Regular Expressions (Regex), and SaaS-based web applications.
• Proficiency using AI tools, specifically Claude, to optimize daily tasks and operational efficiency.
• B.S. degree in a science or engineering field.
• Outstanding verbal and written communication skills.
• Detail-oriented and highly organized, with the ability to multitask.
• Eagerness to learn new technologies and determination to find root causes.

Nice To Haves

• Master’s degree in a 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 tools.

Responsibilities

• Manage and resolve customer and departmental tickets efficiently while meeting quality standards and SLA requirements.
• Use web-based products and command-line tools to research and isolate complex support issues.
• Assess technical problems, propose accurate solutions to customers, and collaborate with development teams on long-term product enhancements.
• Communicate with customers by email or phone, translating complex technical issues into clear explanations suited to their technical level.
• Act as a liaison and escalation bridge between customers and product and engineering teams.
• Align technical support work with Flywire’s business domain, vision, mission, and strategy.
• Manage and maintain the TSE team’s AI Skills repository, TSE Project Repos, and internal knowledge base.
• Use AI tools to automate routine maintenance, investigate client issues, create bug and product enhancement requests, and draft professional client communications.

Benefits

• Competitive compensation.
• Employee Stock Purchase Plan (ESPP).
• Competitive time off.
• Wellbeing programs, including mental health and wellness programs and Yoga, Pilates, and HIIT classes.
• Talent and development programs, including Managers Taking Flight and OneFlywire Career Mobility.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level