Retention Specialist

PayBright is a leading merchant services provider focused entirely on supporting agents and ISOs nationwide. Our business is built on relationships — with our partners, merchants, and internal teams — and we believe operational excellence is one of our greatest competitive advantages. We operate with an agent-first philosophy, work relentlessly to support our merchants, and approach problems with professionalism, calm judgment, and long-term thinking. As we continue to scale, the complexity and risk profile of escalations has increased, and we are investing in senior operational talent to support that growth. The Retention Specialist is responsible for turning “no” into “yes” by identifying merchant objections, developing creative solutions, and successfully retaining or reactivating accounts that are at risk of cancellation or already closed. This role is highly consultative and outcome-driven, requiring persistence, strong objection-resolution skills, and the ability to translate merchant feedback and data insights into tailored save strategies. The Retention Specialist proactively engages merchants to preserve revenue, strengthen relationships, and reduce overall churn. This role may be open to remote candidates in select states; however, candidates based in or near Raleigh, NC will be strongly prioritized. Key Responsibilities Own merchant retention and winback outcomes by converting cancellations and objections into retained, active accounts Proactively identify at-risk merchants and initiate outreach before cancellation occurs Lead winback efforts for closed merchant accounts by diagnosing root causes of churn and presenting tailored solutions Conduct high-volume outreach via phone, email, and follow-ups to engage merchants, uncover objections, and negotiate retention outcomes Analyze account data and merchant history to inform save strategies and prioritize outreach efforts Develop and execute creative retention approaches aligned to merchant needs, pricing concerns, service issues, or operational challenges Partner with Operations, Support, and Leadership to resolve systemic issues impacting churn and retention Provide structured feedback to leadership on product, pricing, process, or service gaps affecting merchant satisfaction Track, measure, and report on retention, churn, and winback performance, including revenue recovered and save rates Maintain accurate documentation, notes, and disposition tracking in CRM and internal systems Required Education & Experience Bachelor's Degree 5+ years of experience in high-stakes customer service or retention Demonstrated success in reducing churn or recovering lost revenue Experience in payments or merchant services is strongly preferred; candidates with relevant experience in SaaS or other service- or relationship-based B2B industries will also be considered Experience with merchant statements, processing fees/pricing models, chargebacks/disputes, ACH rejects, equipment programs, and gateway/POS setups is a plus Required Skills & Abilities Expert-level objection handling, negotiation, and retention save techniques Excellent verbal and written communication skills, including the ability to clearly explain complex billing and processing topics Consultative, solutions-oriented approach to merchant conversations Proven ability to build trust quickly and manage high-stakes, high-emotion retention scenarios Proactive mindset with a record of solving potential problems before they emerge Strong analytical skills with the ability to interpret data and translate insights into action Strong account management and relationship-building skills Results-driven mindset with focus on measurable retention outcomes Ability to work independently while collaborating cross-functionally Proficiency with CRM systems, reporting tools, and structured documentation Schedule & Location Full-time (40 hours per week) Monday–Friday, with occasional weekend hours as needed Candidates in the Raleigh, NC area will be expected to work in the office at least four days per week Full-time remote candidates will be considered in Arizona, Florida, Georgia, Indiana, Kentucky, North Carolina, Pennsylvania, or Texas Benefits Medical insurance Dental insurance Vision insurance Paid time off Paid holidays 401(k) retirement plan with company match Company Culture At PayBright, we pride ourselves on honesty, tenacity, and reliability—values that guide everything we do. We hold ourselves to the highest standards, with a strong emphasis on clear, consistent communication and a relentless focus on execution. We’re driven by a passion for quality, with our success built on persistence, integrity, and a shared commitment to doing things the right way—delivering exceptional service and maintaining excellence across the board. Equal Opportunity Statement PayBright provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state, or local laws. Pay: From $60,000.00 per year Benefits: 401(k) 401(k) matching Dental insurance Health insurance Paid time off Parental leave Referral program Vision insurance Work Location: Hybrid remote in Raleigh, NC 27612