Technical Support Specialist — SaaS & Escalations

Flywire; Chicago, Northern (IL, KY); Hybrid; USD 45,000 - 60,000; Full time

Job summary

Flywire is seeking a Technical Support Specialist to be the first line of support for hospitality/e-commerce customers. You will triage tickets, answer product questions, and document steps for the next team, building technical support skills and maintaining high-quality customer communication.

In this role you’ll use Zendesk and other tools to resolve issues, contribute to knowledge bases, and collaborate with Escalations, Tier-2, and Engineering.

Qualifications

• 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.
• Strong verbal and written communication; 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).
• Demonstrated initiative in bug tracking, internal documentation, or team training support.
• Background in hospitality or hotel technology is a plus.

Responsibilities

• Handle inbound tickets (email/web/phone) from intake to resolution using Zendesk.
• Apply standard procedures to routine problems; elevate when appropriate.
• 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 technical issues using logs, developer tools, DataDog, and internal tools.
• Provide clear replication steps, screen recordings, or documentation to elevate issues to Engineering.
• Translate technical findings into simple, actionable updates for customers and internal stakeholders.
• Assist in writing SOPs and contributing to knowledge base articles and internal documentation.
• Take ownership of escalated or pattern-based tickets and track them to resolution.
• Identify bugs or process inefficiencies and work with the team to improve the overall support workflow.

Skills

Communication

Time management

Organizational skills

Customer-facing

Self-prioritization

Initiative

Tools

Zendesk

Jira

Confluence

DataDog

PDF conversion

Job description

Flywire is seeking a Technical Support Specialist to be the first line of support for hospitality/e-commerce customers. You will triage tickets, answer product questions, and document steps for the next team, building technical support skills and maintaining high-quality customer communication.

In this role you’ll use Zendesk and other tools to resolve issues, contribute to knowledge bases, and collaborate with Escalations, Tier-2, and Engineering.