Sales and Retention Specialist

This is a fully remote position, open to applicants in Costa Rica.

📋 Description

• Take charge of the complete retention process for premium programs, ensuring retention rate and retained-value targets are met.

• Conduct retention calls for high-value and complex cases personally, while developing scripts, standards, and coaching for queue coverage.

• Create and update save-offer ladders based on identified root causes and supporting evidence.

• Design and implement structured quarterly retention experiments.

• Identify and eliminate friction in the refund process by modifying intake, routing, and tools in collaboration with CX and Tech teams.

• Oversee re-engagement and win-back initiatives for students who have churned.

• Establish and assess onboarding standards for the first two weeks of student engagement.

• Integrate early-warning risk signals into the onboarding process.

• Bridge the gaps between sales commitments and actual delivery, escalating findings to Product and Marketing teams.

• Resolve escalated customer issues through Zendesk and email communications.

• Collaborate with Product, Tech, and Community teams to tackle root causes of recurring complaints.

• Manage external sales and appointment-setting agencies, including sourcing, benchmarking, interviewing, negotiating rates and commissions, and ongoing oversight.

• Define and enforce performance metrics for agencies, including connect rate, booked calls per hour, show rate, and close rate.

• Maintain internal benchmarks against agency performance metrics.

• Verify sales reported by agencies against company systems and reconcile results prior to Finance processing.

• Manage lead lists comprising failed payments, abandoned checkouts, and churned students, while reporting on conversion performance.

• Support sales enablement through the creation of training content, objection handling strategies, one-pagers, pricing clarity, and booking-flow quality assurance.

• Keep accurate records of retention data, refund-reason taxonomy, scripts, transcript library, and Retention DNA documentation.

• Present retention, onboarding, and outside sales performance, along with analysis and recommendations to leadership on a monthly basis in person.

• Transform reasons for churn into actionable insights for Product and Marketing and follow up on the outcomes.

⛳️ Requirements

• Minimum of 5 years of experience in retention, customer success, or customer-facing sales roles.

• At least 2 years of experience owning a commercial outcome.

• Proven track record of improving retention, churn, or conversion metrics, demonstrating measurable results.

• Experience in managing agencies, contractors, or vendors against established performance standards.

• Proven ability to design and execute structured tests.

• Familiarity with online learning platforms, high-ticket programs, and international customer bases.

• Strong insight into churn drivers, save offers, win-back strategies, and lifetime value in a high-ticket context.

• Capability to source, benchmark, negotiate with, and manage external sales partners.

• Knowledge of conversion techniques, funnel optimization, objection handling, and customer decision psychology.

• Proficient in building and analyzing datasets, designing valid tests, interpreting results, and acting on findings.

• Comfortable using Airtable and Google Sheets.

• Proficient with AI tools for daily tasks such as transcription, case analysis, and reporting.

• Experienced with CRM platforms, Zendesk, and scheduling tools.

• Strong personal interest in personal growth and development.

• Familiarity with Mindvalley content is an added advantage.

🏝️ Benefits

• Equal opportunity employer dedicated to fostering a diverse and inclusive workplace.

• Access to AI-assisted tools for transcription, case summarization, and reporting.