Customer Support Specialist

Flywire•Chicago, IL

11d•Hybrid

About The Position

The CS1 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.

Requirements

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.
Strong organizational and time-management skills; comfortable with ticket queues, call logs, and daily targets.

Nice To Haves

Background in hospitality or hotel technology (e.g., PMS, eSign/ePay systems) is a plus.
Experience with SOP creation is a plus.

Responsibilities

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 escalate 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.
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.
Participate in customer calls, screen shares, or trainings when escalations require higher-level communication.
Rotate into the holiday or on-call support schedule as needed.