Technical Support Engineer II

Flywire; Chicago (IL); Hybrid; USD 81,000 - 101,000; Full time

Job summary

Flywire is seeking a Technical Support Engineer II to directly assist customers and cross-functional teams across the U.S. and Canada. The role emphasizes proactive use of AI tools to automate tasks, maintain AI repositories, and streamline client communications.

You will manage tickets, perform deep research, and propose durable product improvements, while communicating effectively with clients and internal teams to achieve business goals.

Qualifications

• 3–5 years of experience in technical support engineering.
• 3+ years hands-on with MySQL, Regex, and SaaS-based web applications.
• Proficiency in leveraging AI tools (Claude) to optimize tasks and efficiency.
• B.S. degree in a science or engineering field.
• Outstanding verbal and written communication skills.
• Detail-oriented, organized multitasker eager to learn new technologies.

Responsibilities

• Manage and resolve customer and departmental tickets in line with SLA.
• Research complex issues using web-based products and command-line tools.
• Assess technical problems, propose solutions, and collaborate with development for improvements.
• Communicate clearly with customers via email or phone, translating technical issues to lay terms.
• Liaise between customers and product/engineering teams; align support goals with business strategy.
• Maintain TSE AI Skills repository and automations; draft bug/feature requests as needed.

Skills

MySQL

Regex

SaaS

Education

B.S. in science or engineering

Tools

Zendesk

Jira

Confluence

SumoLogic

Looker

Job description

Job Description

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:

• 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.

Qualifications:

Qualifications

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

Additional Information

We are excited to get to know you! Throughout our process you can expect to meet different FlyMates including the Hiring Manager and other Flymates. Your Talent Acquisition Partner will walk you through the steps and be your “go-to” person for questions.

Flywire is an equal opportunity employer and follows a policy of administering all employment decisions and personnel actions without regard to race, color, religion, sex, pregnancy, gender identity, national origin, age, ancestry, physical or mental disability, sexual orientation, genetic disposition or carrier status, veteran status, or any other category protected under applicable national, federal, state or local law.

The US base salary range for this full-time position is $81,000 - $101,000 and benefits. Our salary ranges are determined by role, position level, and location. The range displayed on this job posting reflects the minimum and maximum target for new hire salaries for the position across all US locations. Within the range, individual pay is determined by work location and several other factors, including job-related skills, experience, relevant education and training.

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