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.

• 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.

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