Payments Operations Specialist

Flight Schedule Pro • Overland Park, KS

9h • $50,000 - $70,000

About The Position

Flight Schedule Pro is the world’s leading flight school management software, trusted by 1,300+ operators worldwide — including top training academies that produce pilots for major airlines like United, Delta, and British Airways. With 16,000+ instructors and 12,000+ aircraft, Flight Schedule Pro provides cutting-edge tools to optimize operations, enhance student retention, and drive revenue growth.
As an AI-forward company, we are transforming aviation operations and reimagining the pilot journey. We’re embedding AI deeply into our platforms—not as an add-on, but as a driving force behind smarter training, safer flying, and more efficient operations. Our commitment to innovation means we’re building tools and experiences that haven’t existed before, and we’re looking for curious, innovative minds to help us lead the way.
Now part of the Flight Schedule Pro ecosystem, LogTen Pilot Logbook simplifies and perfects pilot log management. With over 300,000 downloads, LogTen is the most used, trusted, and awarded flight logging app ever created. We’re now pushing the boundaries of what’s possible with AI-powered logging, delivering proactive, predictive insights to help pilots and organizations unlock new levels of efficiency and safety.
This role will be a critical contributor within the Fintech team, focused primarily on our Payments offering. Payments is a major strategic priority for Pilotbase and a highly valued offering by our customers. As we continue to scale our embedded payments capabilities and reach, this role sits at the center of that growth. This role focuses on ensuring our payments ecosystem operates smoothly, efficiently, and at scale. As adoption accelerates and our customer base expands, we’re looking for someone who can help drive faster onboarding, stronger engagement, and a seamless payments experience across the platform.
This position is highly cross-functional and collaborative, working closely with customer experience, implementation, support, product, and external partners. The ideal candidate thrives in dynamic environments, builds deep subject-matter expertise in payments, and serves as connective tissue across teams to remove friction, surface insights, and improve outcomes. Ultimately, this role acts as the “oil in the engine,” helping customers ramp quickly on payments while enabling the broader organization to move faster and smarter as we grow.

Requirements

• 2+ years of experience in fintech, payments, customer success, sales operations, or a related customer-facing role
• Great attention to detail
• Proven ability to work cross-functionally and drive outcomes in fast-paced, high-growth environments
• Strong communication and problem-solving skills, with a customer-first mindset and being a data driven decision maker
• Usage of AI tools to improve efficiency and outcomes

Nice To Haves

• Familiarity with fintech or payments platforms, including onboarding flows, payment processing, or partner integrations
• Background or exposure to the aviation industry or aviation software (experience working with flight schools or aviation operations is a plus)
• Experience with a fast paced, high growth company

Responsibilities

• Optimize Payments Funnel:
• Partner with Implementation to accelerate onboarding and drive faster adoption of payments and fintech products
• Build strong relationships with customer stakeholders to remove blockers and move accounts through the payments funnel
• Collaborate with Customer Success to grow processing volume among existing high-adoption customers
• Act as a trusted advisor and subject-matter expert on fintech and payments offerings
• Handle Customer Support & Internal Operational Needs:
• Support customers—especially strategic accounts—by troubleshooting issues that impact payments adoption or volume
• Work closely with GTM leaders across Fintech, Sales, Customer Success, and Marketing to drive data-informed decisions that improve performance and customer visibility
• Become Payments Partner Subject Matter Experts
• Serve as the primary liaison between Support, Customer Success, and our payments partner
• Develop deep expertise in the payments partner portal to support both internal teams and customers
• Own best practices and documentation for customer billing and payments workflows, and enable internal teams to effectively sell and support payments

Benefits

• Full benefits package (Medical, Dental, Vision, Short-Term Disability, Life Insurance, 401(k) plan)
• Equity Appreciation Plan
• Flexible Time Off policy
• Seven (7) company-wide paid holidays + two (2) floating holidays
• Two (2) wellness days
• Employee Assistance Program
• Professional Development Stipend
• Home Office Stipend

What This Job Offers

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