Hybrid AI-Driven 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

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.