Technical Support Specialist

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

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 5,300 clients across the global education, healthcare, travel & B2B industries, with diverse payment methods across 240 countries & territories and more than 140 currencies.

With over 1,400 global FlyMates, representing more than 40 nationalities, and in 15 offices world-wide, we’re looking for FlyMates to join the next stage of our journey as we continue to grow.

The Opportunity

The Technical 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 You’ll Do

• 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.

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.
• 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)
• DataDog and internal monitoring dashboards
• PDF conversion tools and hospitality SaaS platforms

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. Your Talent Acquisition Partner can share more about the specific salary range for your preferred location during the hiring process.