Client Support Specialist at Flywire — Chicago, USA | Base Career | Base Career

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Client Support Specialist

Flywire

Chicago, USA

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Full Job Posting

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.
What You’ll Do
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.
Here's What We'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.
Strong organizational and time-management skills; comfortable with ticket queues, call logs, and daily targets.
Background in hospitality or hotel technology (e.g., PMS, eSign/ePay systems) is a plus.
Experience with SOP creation is a plus.
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.
Tools You’ll Use
Zendesk (tickets, macros, views, Explore)
Jira (bug tickets) and Confluence (SOPs/KB)
Browser developer tools; basic log review
DataDog and internal monitoring dashboards
PDF conversion tools and hospitality SaaS platforms
Submit today and get started!
We are excited to get to know you! Throughout our process you can expect to meet different FlyMates including the Hiring Manager and other Flymates. Your Talent Acquisition Partner will walk you through the steps and be your “go-to” person for questions.
Flywire is an equal opportunity employer and follows a policy of administering all employment decisions and personnel actions without regard to race, color, religion, sex, pregnancy, gender identity, national origin, age, ancestry, physical or mental disability, sexual orientation, genetic disposition or carrier status, veteran status, or any other category protected under applicable national, federal, state or local law.
The US base salary range for this full-time position is $45,000 - $60,000 and benefits. Our salary ranges are determined by role, position level, and location. The range displayed on this job posting reflects the minimum and maximum target for new hire salaries for the position across all US locations. Within the range, individual pay is determined by work location and several other factors, including job-related skills, experience, relevant education and training.
#LI-Hybrid
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. We use our Flywire Advantage - the combination of our next-gen payments platform, proprietary payment network and vertical specific software, to help our clients get paid, and help their customers pay with ease - no matter where they are in the world.
What more do we need to truly be unstoppable? Perhaps, that is you!
Who we are: Flywire is a global payments enablement and software company, founded more than a decade ago to solve high-stakes, high-value payments in higher education. We’ve since scaled into new regions and industry verticals and expanded our product offerings to deliver meaningful value to our clients around the world.
Today we support more than 5,100 clients across the global education, healthcare, travel & B2B industries, with diverse payment methods across 240 countries & territories and more than 140 currencies.
With over 1,200 global FlyMates, representing more than 40 nationalities, and in 12 offices world-wide, we’re looking for FlyMates to join the next stage of our journey as we continue to grow.

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.
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.
Background in hospitality or hotel technology (e.g., PMS, eSign/ePay systems) is a plus.
Experience with SOP creation is a plus.
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.
Zendesk (tickets, macros, views, Explore)
Jira (bug tickets) and Confluence (SOPs/KB)
Browser developer tools; basic log review
DataDog and internal monitoring dashboards
PDF conversion tools and hospitality SaaS platforms

Client Support Specialist

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