Senior Payments Support Specialist

Summary

Join Raintree Systems as a Senior Payments Support Specialist and become a subject matter expert in payment systems, methods, and regulations. You will resolve complex payment issues, support escalations, and drive improvements in payments processes. This fully remote role (in designated states) requires managing and optimizing Payment Facilitation operations, troubleshooting challenges, and collaborating with internal and external teams. You will analyze trends, recommend process improvements, ensure compliance, mentor junior staff, and contribute to quarterly reporting. The ideal candidate possesses strong analytical and problem-solving skills, excellent communication skills, and experience in merchant services and SaaS organizations. This role offers the opportunity to make a significant impact on the future of therapy technology.

Requirements

• 5+ years Merchant Services experience preferably in payments operations/support roles within fintech, banking, or e-commerce
• Experience working in a SaaS organizations with a focus on integrated payments
• Experience collaborating positively across disciplines: Marketing, Support, Sales, Product, Customer Success
• In-depth understanding of the payments industry - systems, transaction lifecycle, and financial compliance
• Experience working with payment gateways, processors (e.g., Stripe, Adyen, Worldpay), and banking APIs
• Strong analytical and problem-solving skills; able to interpret large data sets and spot anomalies
• Excellent written and verbal communication skills
• Proficiency with support and ticketing systems (e.g., Zendesk, Salesforce)
• Ability to manage multiple priorities in a fast-paced, high-growth environment
• Travel up to 25% of time
• Well-developed verbal, listening and phone communication skills
• Good written communication skills with the ability to write routine correspondence
• Highly organized and comfortable being accountable to achieving successful outcomes
• Ability to communicate effectively with clients, peers and leadership
• Accountable
• Demonstrates relationship building skills both internally and externally
• Strong organizational skills and ability to execute manual detailed tasks
• Strong customer service focus and commitment
• Ability to establish and maintain effective working relationships within the team and across teams
• Ability to work well with diverse personalities
• Tactful, mature and flexible

Responsibilities

• Serve as a point of escalation for complex or high-impact payment issues (e.g., failed transactions, chargebacks, fraud disputes, reconciliation errors)
• Provide advanced support for a variety of payment methods including credit/debit cards, ACH, wire transfers, e-wallets, and real-time payment networks
• Act as a point of contact for 3rd party vendors who support the PayFac solution (RT Payments)
• Partner with banks, payment processors, and third-party vendors to investigate and resolve payment anomalies
• Analyze trends and recurring issues in payment operations; recommend and help implement process or system improvements
• Assist in onboarding and support of enterprise clients or partners with complex payment needs
• Ensure compliance with relevant financial regulations (e.g., PCI DSS, AML, PSD2) and internal risk policies
• Document and update internal knowledge base with advanced troubleshooting steps and best practices
• Mentor and support junior support staff; lead by example in customer communication and issue resolution
• Participate in cross-functional initiatives with Product, Engineering, and Risk to improve payment flows and support scalability
• Monitor performance metrics (e.g., resolution time, CSAT, error rate) and contribute to quarterly reporting
• Report to leadership on operational health, total transaction volume, account utilization, and more
• Work with internal teams on developing & expanding PayFac performance analytics
• Monitor individual account revenue to ensure that merchant fee structures are correctly set
• Work with legal to ensure payment offerings, systems, and associated policies are in compliance with all applicable laws and regulations
• Actively monitor the Raintree Payment pipeline to track progress and goals
• Champion customer feedback to improve the payment offering (as applicable)
• Facilitate cross-team coordination to ensure a positive customer experience. This includes the sales process, merchant application / implementation / training as well as ongoing account needs
• Stay apprised of general industry trends

Preferred Qualifications

• A degree in Accounting / Finance / Economics or equivalent experience is preferred
• Familiarity with tools like SQL, Excel, or Looker is a plus