Technical Support Engineer II

Flywire

Confirmed live yesterday High trust
Hybrid

Quick summary

Work type
Hybrid
Location
Chicago, IL
Salary
$81,000–$101,000 / yr
Posted
7 days ago
Freshness
Confirmed live yesterday

Market check

Salary context

Below market

How this pay compares to similar roles

Similar $134k
This role $91k
$71k most similar roles pay here $176k

This role pays less than 94% of similar roles. Most pay $113,925–$154,100 — the shaded band above. At the midpoint, this role pays about $91k versus about $134k for comparable roles.

Based on 240 similar postings.

Employer

About Flywire

Flywire is a global payments enablement and software company specializing in high-stakes, complex payment verticals including education, healthcare, travel, and B2B, processing international payments across 240 countries. Industry: Financial Technology & Global Payments

Flywire currently has 22 open roles on FindRole.

Listed pay typically runs $81,000–$101,000 across 11 roles with salary data.

Most-posted roles

View all roles at Flywire

At a glance

TL;DR · Technical Support Engineer II

The Technical Support Engineer II joins the support team to manage daily operations for Student Financial Services, eStore, and TPI products across North America. This role involves managing and resolving customer tickets within strict SLA requirements while performing deep research using web-based products and command-line tools to isolate complex issues. The engineer serves as a critical liaison between customers and engineering teams, translating technical problems into clear communications. A core component of the position is leveraging AI tools like Claude and Gemini to automate workflows, maintain internal knowledge bases, and streamline investigations. Required skills include experience with MySQL, Regular Expressions, and SaaS web applications. The role utilizes technologies such as Java, HTTP/SFTP protocols, Zendesk, Jira, Confluence, SumoLogic, and Looker to solve technical challenges within the global payments and fintech domain.

What you'll do

  • Manage and resolve customer and internal tickets while strictly adhering to SLA requirements.
  • Research and isolate complex technical issues using web-based products and command-line tools.
  • Translate complex technical problems into clear, easy-to-understand explanations for customers via email or phone.
  • Serve as a mediator between customers and product/engineering teams to resolve escalated issues.
  • Utilize AI tools like Claude and Gemini to automate routine workflows and investigate client issues.
  • Maintain internal knowledge bases, project repositories, and AI skill databases.
  • Create bug reports and product enhancement requests for the development team based on technical investigations.

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 tasks and operational efficiency.
  • Bachelor's degree in a science or engineering field.
  • Outstanding verbal and written communication skills.
  • Experience in higher education, Student Financial Services (SFS), FinTech, or the payments industry is preferred.
  • Familiarity with industry-standard logging, analytics, and ticketing tooling is preferred.
  • A master's degree in a science or engineering field is preferred.

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