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Technical Support Specialist

Flywire · Chicago, United States

Imported listingfull-time4 days ago

About The Role

Join our team as a Technical Support Specialist, where you will be the first line of support for our hospitality/e-commerce customers. You will handle inbound tickets, troubleshoot technical issues, and maintain high-quality communication with customers. This role requires strong organizational skills, experience in a customer-facing technical support role, and the ability to self-prioritize in a high-volume support environment.

  • Handle inbound tickets from intake to resolution using Zendesk, applying standard procedures to routine problems and escalating when appropriate.
  • Troubleshoot complex technical issues using logs, developer tools, DataDog, and internal tools, providing clear replication steps and documentation to escalate issues to Engineering.
  • Contribute to macros, Help Center articles, and internal documentation, and take ownership of escalated or pattern-based tickets, tracking them to resolution.
  • Strong organizational and time-management skills; comfortable with ticket queues, call logs, and daily targets
  • Experience using Zendesk, including Explore, Help Center, and custom views/macros
  • Experience with SOP creation is a plus
  • 2+ years in a customer-facing technical support role (B2B SaaS or eCommerce preferred)
  • Strong verbal and written communication skills; able to break down complex issues for technical and non-technical audiences
  • Rotate into the holiday or on-call support schedule as needed
  • Background in hospitality or hotel technology (e.g., PMS, eSign/ePay systems) is a plus
  • Demonstrated initiative in bug tracking, internal documentation, or team training support
  • Ability to self-prioritize in a high-volume support environment (600+ monthly solved tickets expected)
  • Participate in customer calls, screen shares, or trainings when escalations require higher-level communication
  • Familiarity with Jira, DataDog, browser developer tools, and analyzing logs or error messages

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