Retention Specialist

Raleigh, United States | Posted on 02/11/2026

• Salary $60,000 + performance bonus ($70,000-$75,000 OTE)
• State/Province North Carolina
• Country United States

Pay Bright 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.

• 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

• 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

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

• Full-time (40 hours per week)
• Monday–Friday, with occasional weekend hours as needed
• Candidates in the Raleigh, NC area will be expected to…