Client Relationship & Retention Specialist

Location: Canada; United States; United Kingdom; South Africa We are looking for a Client Relationship & Retention Specialist to take ownership of complex customer situations where there is a risk of disengagement, cancellation, refund, or loss of trust. This is a high-accountability, client-facing role requiring strong judgment, confident phone communication, commercial awareness, and the ability to remain calm and effective in difficult situations. You will investigate the full customer journey, identify the true cause of an issue, and work directly with customers to help them regain confidence and move forward. This means looking beyond the immediate complaint to understand what is actually driving the customer’s concern, whether that is a practical, technical, delivery, expectation, or mindset blocker. You will be expected to troubleshoot appropriate issues directly, coordinate across internal teams when additional action is required, and maintain ownership of the customer relationship through resolution. This is not passive customer support or an aggressive refund-prevention role. It is a high-trust, consultative role for someone who can combine strong call control and influence with genuine curiosity, empathy, and problem-solving. Success requires the ability to build trust quickly, lead challenging conversations confidently, diagnose problems accurately, and help customers move toward a constructive next step without pressure, manipulation, or unsupported promises. THE COMPANY A multi-8-figure ARR business with 200+ team members, bootstrapped and profitable. The company launches and scales information and software products on a marketing and sales engine refined across a dozen product launches and $100M+ in ad spend. This seat sits within our client operations team and plays an important role in strengthening customer relationships, resolving complex issues, improving retention, and protecting long-term customer value. WHAT YOU WILL DO Take ownership of at-risk customer cases involving dissatisfaction, disengagement, cancellation, refund concerns, or loss of confidence Contact assigned customers quickly by telephone and use SMS and email when appropriate Review the customer’s complete journey before making contact to understand the history, context, and potential issues Speak directly with customers by phone and build trust quickly, even when emotions are high Diagnose practical, technical, delivery, expectation, or mindset blockers and identify the true root cause of the issue Troubleshoot appropriate issues directly and coordinate additional support when required Lead calm, confident resolution and de-escalation conversations Separate the immediate complaint from the underlying issue and determine the most appropriate path forward Help customers reframe unhelpful conclusions without dismissing legitimate concerns Reconnect customers with their original goals and help establish a clear recovery plan and next action Correct misunderstandings clearly and respectfully without becoming defensive or argumentative Use strong conversational influence and judgment to help restore customer confidence without applying pressure or making unsupported promises Make sound judgment calls while balancing customer experience, commercial considerations, and the facts of each case Coordinate with Onboarding, Tech, Delivery, Sales, Finance, and other teams when additional action is required Maintain ownership of the customer relationship while internal work is being completed rather than simply passing the customer between departments Use approved support options or concessions when appropriate and justified Escalate continued refund requests or complex cases through the appropriate process Keep customers informed while outstanding issues are being resolved Maintain clear and accurate records of conversations, decisions, commitments, actions, and outcomes Identify recurring causes of disengagement, dissatisfaction, and refunds and recommend practical improvements to prevent them in the future Requirements Previous experience in consultative or high-ticket sales/closing, Customer Retention, Customer Success, Account Management, Escalations, Complaints, Dispute Resolution, Service Recovery, or a similarly high-touch client-facing role Strong conversational influence and call control, with the ability to confidently lead a customer toward a constructive next step Strong ability to build rapport with frustrated, disappointed, uncertain, or skeptical customers Comfortable leading difficult and emotionally charged conversations Able to listen carefully while remaining confident enough to challenge an unhelpful conclusion when appropriate Able to recognize legitimate customer or company-side issues rather than treating every concern as a mindset problem Persuasive without relying on pressure, manipulation, or unsupported promises Strong investigative and problem-solving skills with the ability to identify root causes rather than simply addressing surface-level issues Comfortable troubleshooting practical issues and coordinating with other teams when additional expertise is required Good commercial judgment and an understanding of customer value, retention, and financial impact Strong organisation, attention to detail, and written documentation skills Comfortable taking personal ownership of a customer issue and driving it toward resolution across multiple teams Able to manage multiple complex customer cases and priorities at the same time High level of integrity and sound judgment when determining the appropriate next step Reliable, resilient, coachable, and willing to review calls and feedback to continuously improve Benefits Full-time opportunity Independent Contractor Agreement $6,000–$8,000 USD monthly base, depending on experience Additional monthly performance incentive based on results Fully remote Opportunity to grow into broader Client Operations, Customer Success, senior, or team-lead responsibilities