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Client Success Specialist

Remote / Online - Candidates ideally in
Chicago, Cook County, Illinois, 60290, USA
Listing for: Flywire
Remote/Work from Home position
Listed on 2026-02-28
Job specializations:
  • Customer Service/HelpDesk
    Technical Support
  • IT/Tech
    Technical Support
Salary/Wage Range or Industry Benchmark: 65000 - 80000 USD Yearly USD 65000.00 80000.00 YEAR
Job Description & How to Apply Below

Are you ready to trade your job for a journey? Become a Fly Mate!

Passion, excitement & global collaboration are all core to what it means to be a Fly Mate. 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 4,800 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 Fly Mates, representing more than 40 nationalities, and in 12 offices world-wide, we’re looking for Fly Mates to join the next stage of our journey as we continue to grow.

The Opportunity

Flywire acquired Sertifi in early 2025 and has aggressive plans to integrate Sertifi into the existing Flywire environment. We need a self-motivated and highly driven Client Success Specialist to work closely with our customers as we upgrade them to the combined system. The individual will play a critical role in Flywire’s most important project of 2026, ensuring an understanding of specific customer workflows, navigating the customer side updates, maintaining adoption through change, and working closely with the product and development team to ensure all customers needs are met.

This role seamlessly transitions into an ongoing Client Success specialist role in the future.

Key Responsibilities
  • Oversee customer upgrade projects to the combined system as new features become available. Key responsibilities include managing change, promoting continued or increased adoption, and providing necessary education to ensure strong account health throughout the transition.
  • Educate clients of the self-service tools and other key features not being used that could benefit the customer and realize additional value
  • Use Customer Success Software (Churn Zero) to apply account specific messaging that leads to engagement and positive change
  • Collaborate with Enterprise CSM’s to strategize and understand the brand requirements for the upgraded Flywire system.
  • Host brand or property specific webinars to foster a community of understanding, account growth and overall adoption of Sertifi
  • Develop an in-depth knowledge of all Sertifi products and services; maintain product expertise across our platform
  • Establish high-level of personal credibility and build strong relationships to improve customer health
  • Deliver high-impact training, establish custom workflows, and provide white-glove onboarding via web conferencing.
  • Collaborate cross-functionally with Sales, Product, Engineering, and Support teams to resolve issues and unlock growth opportunities.
  • Actively manage customer interactions via Salesforce, Churn Zero, and Zendesk while delivering clear, actionable insights to internal stakeholders.
  • Target Property Management Groups to partner on designing an adoption and education plan for their portfolio of hotels using Sertifi ensuring strong account health
  • Identify opportunities for account growth and work with the account owner to expand/upsell
  • Work on ad hoc customer set up and adoption projects as needed
Here’s what we’re looking for
  • 3–5 years of experience in customer success, implementation, or enterprise onboarding in a SaaS environment.
  • 2–3 years of experience in the hospitality industry, ideally working with hotels, travel technology platforms, or related verticals.
  • Demonstrated success managing complex customer projects and drive customer outcomes independently.
  • Strong knowledge of Salesforce and customer success software (e.g., Churn Zero).
  • Exceptional…
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