Technical Support Engineer

Flywire; Chicago (IL); Hybrid; USD 69,000 - 98,000; Full time

Benefits offered by this job

Competitive compensation

Stock Purchase Plan (ESPP)

Wellbeing programs

Career development

Job summary

Flywire is seeking a Technical Support Engineer II to support customers across the U.S. and Canada, delivering expert technical help for SFS, eStore, and TPI products. You will manage tickets, perform deep research, and collaborate with product and engineering teams.

The role emphasizes using AI tools like Claude to automate tasks, maintain knowledge bases, and craft clear client communications. A BS in science or engineering and 3–5 years in SaaS support are required; hybrid work from Chicago

Qualifications

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

Responsibilities

• Ticket management: handle and resolve customer tickets to SLA.
• Deep research: investigate issues using web apps and command-line tools.
• Issue resolution: propose solutions and coordinate with product/engineering teams.
• Client communication: clearly explain technical issues to customers at their level.
• AI & knowledge management: maintain AI repositories and draft client communications.

Skills

MySQL

Regular Expressions

SaaS Web Apps

AI Tools Claude

Communication

Education

BS in science or engineering

Master's degree (plus)

Tools

Zendesk

Jira

Confluence

SumoLogic

Looker

Job description

## Technical Support EngineerApply: Hybrid: Chicago, IL: Full time: Posted Today: JR-1032**Are you ready to trade your job for a journey? Become a FlyMate!** Passion, excitement & global collaboration are all core to what it means to be a FlyMate. At Flywire, we’re on a mission to deliver the world’s most important and complex payments. We use our Flywire Advantage - the combination of our next-gen payments platform, proprietary payment network and vertical specific software, to help our clients get paid, and help their customers pay with ease - no matter where they are in the world. What more do we need to truly be unstoppable? Perhaps, that is you! **Who we are:**Flywire is a global payments enablement and software company, founded more than a decade ago to solve high-stakes, high-value payments. We’ve scaled into new regions and industry verticals and expanded our product offerings to deliver meaningful value to our clients around the world. Today we support more than 5,100 clients across the global education, healthcare, travel & B2B industries, with diverse payment methods across 240 countries & territories and more than 140 currencies. With over 1,400+ global FlyMates, representing more than 40 nationalities, and in 15 offices world-wide, we’re looking for FlyMates to join the next stage of our journey as we continue to grow. **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:****Technical Support & Troubleshooting*** **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. **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 **What We Offer:**Competitive compensationEmployee Stock Purchase Plan (ESPP)Competitive time offWork with brilliant people globally Learn more about their journeys by checking out #InsideFlywire on social mediaWellbeing Programs (Mental Health, Wellness, Yoga/Pilates/HIIT Classes) with Global FlyMatesBe a meaningful part in our success - every FlyMate makes an impactGreat Talent & Development Programs (Managers Taking Flight – for new or aspiring managers, OneFlywire Career Mobility) **Submit today and get started!** We are excited to get to know you! Throughout our process you can expect to meet with different FlyMates including the Hiring Manager, Peers on the team, the VP of the department, and a skills assessment. Your Talent Acquisition Partner will walk you through the steps and be your “go-to” person for any 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 base salary for this position is:$68,838-$98,340 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.