Startups · AI

Client Support Specialist

FlyWire · Chicago, IL · On-site

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About FlyWire

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. Backed by Techstars.

About the role

The Client Support Specialist role is the first line of support for our hospitality/e-commerce customers, triaging tickets, solving product questions, and documenting steps for the next team when needed. This role focuses on building technical support skills, using standard procedures to solve routine issues, and maintaining consistent, high-quality communication with customers.

What they're looking for

  • 2+ years in a customer-facing technical support role (B2B SaaS or eCommerce preferred)
  • Experience using Zendesk, including Explore, Help Center, and custom views/macros
  • Familiarity with Jira, DataDog, browser developer tools, and analyzing logs or error messages
  • Strong verbal and written communication skills, able to break down complex issues for technical and non-technical audiences
  • Ability to self-prioritize in a high-volume support environment (600+ monthly solved tickets expected)
  • Demonstrated initiative in bug tracking, internal documentation, or team training support
More about this role

The Client Support Specialist role is the first line of support for our hospitality/e-commerce customers, triaging tickets, solving product questions, and documenting steps for the next team when needed. This role focuses on building technical support skills, using standard procedures to solve routine issues, and maintaining consistent, high-quality communication with customers.

  • Handle inbound tickets (email/web/phone) from intake to resolution using Zendesk.
  • Apply standard procedures to routine problems; escalate when appropriate.
  • Troubleshoot by reproducing steps, reviewing screenshots/logs, and isolating variables (browser, network, payment gateway, etc.).
  • Support common use cases such as PDF conversion and basic platform navigation.
  • Maintain quality responses while averaging ~25 solved tickets per day (≈575–600/month).
  • Contribute to macros, Help Center articles, and internal documentation.
  • Partner with Escalations/Tier-2 and Engineering on escalated issues.
  • Provide proactive updates to customers and ensure clear handoffs.
  • Respond to a high volume of customer tickets, calls, and emails with empathy, professionalism, and efficiency.
  • Troubleshoot complex...

Read the full posting on FlyWire's site ↗

Relationship Mgmt, Travel

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