Client Success Specialist

Flywire • Chicago, IL

3h • $65,000 - $80,000 • Hybrid

About The Position

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.

Requirements

• 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., ChurnZero).
• Exceptional communication skills, with the ability to engage audiences ranging from end users to C-level executives.

Nice To Haves

• Strategic thinker with strong analytical and problem-solving skills.
• High attention to detail, time management, and organizational skills.
• Empathetic, resourceful, and highly collaborative.
• Comfortable working in a fast-paced, remote-first environment.

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 (ChurnZero) 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, ChurnZero, 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

Benefits

• Competitive compensation, including Restricted Stock Units
• Employee Stock Purchase Plan (ESPP)
• Flying Start - Our immersive Global Induction Program (Meet our Execs & Global Teams)
• Work with brilliant people that will keep you on your toes, learn more about their journeys by checking out #InsideFlywire on social media
• Dynamic & Global Team (we have been collaborating virtually for years!)
• Wellbeing Programs (Mental Health, Wellness, Yoga/Pilates/HIIT Classes) with Global FlyMates
• Competitive time off including FlyBetter Days to volunteer in your community and Digital Disconnect Days!
• Great Talent & Development Programs (Managers Taking Flight – for new or aspiring managers!)

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed