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
1 day ago
Freshness
Confirmed live yesterday

Market check

Salary context

Below market

How this pay compares to similar roles

Similar $133k
This role $91k
$70k most similar roles pay here $182k

This role pays less than 94% of similar roles. Most pay $113,925–$152,150 — the shaded band above. At the midpoint, this role pays about $91k versus about $133k 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 18 open roles on FindRole.

Listed pay typically runs $81,000–$101,000 across 9 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 a team providing support for Student Financial Services, eStore, and TPI products across the U.S. and Canada. This role involves managing and resolving customer and departmental tickets while ensuring strict adherence to SLA requirements. You will perform deep research using web-based products and command-line tools to isolate complex issues, translate technical problems into clear explanations for clients, and serve as a bridge between customers and engineering teams. A core component of the role is leveraging AI tools like Claude and Gemini to automate workflows, maintain internal repositories, and streamline communications. Required skills include experience with MySQL, Regular Expressions, and SaaS web applications. The technical stack includes Java, HTTP/SFTP protocols, Zendesk, Jira, Confluence, SumoLogic, and Looker to solve complex problems within the payments industry.

What you'll do

  • Manage and resolve customer and internal tickets while meeting strict 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.
  • Act 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 boost operational efficiency.
  • B.S. degree in a science or engineering field.
  • Outstanding verbal and written communication skills.
  • A master's degree in a respective science or engineering field (preferred).
  • Experience in higher education, Student Financial Services (SFS), FinTech, or the payments industry (preferred).
  • Familiarity with industry-standard logging, analytics, and ticketing tooling (preferred).

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