AI-Driven Technical Support Engineer II (FinTech SaaS)

Flywire; Illinois; On-site; USD 81,000 - 101,000; Full time

Job summary

Flywire is seeking a Technical Support Engineer II to work directly with customers across the U.S. and Canada, supporting Student Financial Services, eStore, and TPI products.

The role emphasizes proactive use of Claude and Gemini for automating workflows, maintaining knowledge bases, and collaborating with product and engineering to drive improvements. If you are detail-oriented, love solving complex problems, and have 3–5 years in tech support, we want to hear from you.

Qualifications

• 3–5 years of technical support engineering experience.
• 3+ years hands-on experience with MySQL, Regex, and SaaS-based web applications.
• Proficiency with AI tools, specifically Claude, to optimize tasks.
• B.S. degree in a science or engineering field.
• Outstanding verbal and written communication skills.

Responsibilities

• Ticket Management: manage and resolve customer tickets to SLA.
• Deep Research: work with web-based products and command-line tools to isolate issues.
• Issue Resolution: propose solutions and collaborate with Dev for long-term enhancements.
• Client Communication: explain complex issues clearly via email or phone.
• AI & Knowledge Management: maintain AI repositories and draft client communications.

Skills

MySQL

Regex

SaaS

AI tools Claude

Communication

Java

Education

BS in Science/Engineering

Master's degree (preferred)

Tools

Zendesk

Jira

Confluence

Looker

Job description

Flywire is seeking a Technical Support Engineer II to work directly with customers across the U.S. and Canada, supporting Student Financial Services, eStore, and TPI products.

The role emphasizes proactive use of Claude and Gemini for automating workflows, maintaining knowledge bases, and collaborating with product and engineering to drive improvements. If you are detail-oriented, love solving complex problems, and have 3–5 years in tech support, we want to hear from you.