Sales & Retention Specialist

Accountabilities: Own the end-to-end retention process for premium programs, including retention rates and retained-value targets. Personally lead high-value and complex retention conversations while defining scripts, standards, and coaching approaches for other team members. Develop and refine retention offers based on customer needs, root causes, and performance data. Design and run structured quarterly retention experiments, clearly defining hypotheses, samples, results, and next actions. Identify friction in the refund journey and work with relevant teams to improve intake, routing, processes, and tooling. Lead win-back initiatives for churned customers and convert re-engagement opportunities into future revenue. Define onboarding standards and measurable expectations for what customers should accomplish, understand, and experience during their first one to two weeks. Establish early-warning signals to identify disengagement before customers reach the refund stage. Identify gaps between sales promises and customer delivery, providing evidence-based feedback to Product and Marketing. Handle escalated customer cases through ticketing and email channels with empathy, sound judgement, and timely resolution. Manage relationships with external sales and appointment-setting agencies, covering sourcing, benchmarking, interviews, negotiations, contracts, and ongoing performance management. Define and monitor agency performance metrics, including connect rate, booked calls per hour, show rate, and close rate. Verify agency-reported sales against internal systems and manage the reconciliation process before results reach Finance. Manage lead lists for external sales, including failed payments, abandoned checkouts, and churned customers, and monitor conversion performance. Support sales enablement through training content, objection handling, one-pagers, pricing clarity, and booking-flow quality assurance. Maintain accurate retention data, including offers, refund reasons, call outcomes, and case statuses. Present retention, onboarding, and external sales performance to leadership with clear analysis and actionable recommendations. Translate recurring churn and customer feedback into specific issues for Product and Marketing, following through on whether improvements deliver results. Maintain working documentation such as retention playbooks, call scripts, and transcript libraries. Requirements: 5+ years of experience in retention, customer success, customer-facing sales, or a related commercial role, including at least 2 years owning a measurable commercial outcome. Demonstrated success improving a retention, churn, conversion, or comparable business metric, supported by measurable results. Experience managing agencies, contractors, vendors, or other external partners against defined performance standards. Experience designing and running structured experiments rather than simply executing established processes. Strong understanding of retention strategy, including churn drivers, save offers, win-back approaches, and customer lifetime value in a high-value or premium environment. Strong commercial and sales skills, including funnel optimization, objection handling, conversion techniques, and understanding of customer decision-making. Strong data fluency, with the ability to build and interrogate datasets, design valid tests, interpret results, and translate findings into action. Confidence using tools such as Airtable and Google Sheets, along with CRM, ticketing, and scheduling platforms such as Zendesk. Comfortable using AI tools for transcription, case analysis, reporting, and workflow optimization. Strong customer empathy, sound judgement, and integrity when handling sensitive customer situations. Excellent communication and influencing skills, with the ability to motivate customers, colleagues, and external partners. Strong ownership mentality, commercial discipline, and willingness to take responsibility for measurable outcomes. A proactive, root-cause-oriented approach to problem solving, with a focus on closing the loop and validating whether changes worked. Ability to remain calm and effective when customer and case volumes increase around launches or refund periods. Experience with online learning platforms, premium programs, or international customer bases is advantageous. A genuine interest in personal growth and development is valued; familiarity with personal-development content is a plus. Benefits: High-ownership role with direct influence over customer experience, retention, sales performance, and revenue. Opportunity to work across retention, onboarding, customer experience, sales operations, and external partner management. AI-assisted working environment designed to reduce administrative work and enable greater focus on high-value activities. Opportunity to collaborate cross-functionally with Product, Marketing, Technology, Community, and Customer Experience teams. Exposure to an international customer base and premium digital learning programs. Strong opportunity for professional growth through ownership of measurable commercial outcomes. Inclusive and diverse working environment with equal opportunity for qualified candidates. Opportunity to contribute to continuous experimentation and process improvement across the customer lifecycle.