Sales & Retention Specialist (Contractor Role)

About the Role

As the Retention, Onboarding & Outside Sales Lead, you own the commercial life of a premium student from the moment they buy to the moment they consider leaving. Our masteries run from $4,000 to $6,000 and higher, and three things decide whether that revenue stays: how honestly they were sold to, how well they were onboarded, and how well we handle the conversation when they ask for their money back.

This is an ownership role, not a caseload. You will run the retention conversations that matter, manage the external sales partners who bring students in, and treat onboarding as the stage that prevents refunds rather than the handoff before them. You will work AI-assisted every day, with call transcription, case summarisation and reporting handled by our tools so your attention goes to the conversations and the judgement calls.

You are expected to find why cases arrive, change the system that produces them, and prove the change worked. This role suits someone who wants a number they can move and the authority to move it.

Responsibilities

Retention & Loyalty

• Own the Number: Own the end-to-end retention process for premium programs, and own the retention rate and retained-value targets attached to it.
• Frontline Conversations: Run retention calls personally on high-value and complex cases, and set the script, standard and coaching for anyone covering the queue.
• Offer Ladder: Own what we offer, against which root cause and in what order, and revise it on evidence rather than instinct.
• Experimentation: Design and run structured retention experiments each quarter: state the hypothesis, define the sample, report the result, adopt or discard.
• Friction Removal: Identify and remove friction in the refund journey, with the authority to change intake, routing and tooling in consultation with CX and Tech.
• Win-Back: Own the re-engagement motion for churned students and convert the win-back list into future cohort revenue.

Onboarding & Customer Experience

• Onboarding Standard: Own onboarding as a measured stage, defining what a student should have done, understood and felt by the end of week one and week two.
• Early Warning: Build risk signals into onboarding so disengaging students are identified before they reach the refund form.
• Promise vs Delivery: Close the gap between what was sold and what is delivered, bringing divergence to Product and Marketing with evidence rather than anecdote.
• Escalated Support: Deliver empathetic, high-judgement support on escalated cases through Zendesk and email, resolving them without leaving customers waiting.
• Root Causes: Work cross-functionally with Product, Tech and Community to fix the causes behind recurring complaints, not just the instances.

Outside Sales & Agency Management

• Agency Ownership: Own the commercial relationship with external sales and appointment-setting agencies end to end: sourcing, benchmarking, interviewing, negotiating rates and commission, contracting and ongoing management.
• Performance Standards: Define and enforce the metrics agencies are held to, including connect rate, booked calls per hour, show rate and close rate on booked calls.
• Internal Benchmark: Maintain our own numbers against the same metrics, so we can judge whether an agency is an improvement or a cost.
• Sales Verification: Verify agency-claimed sales against our systems before they reach Finance, and own that reconciliation.
• Lead Supply: Own the lists that feed outside sales, including failed payments, abandoned checkouts and churned students, and report on what they convert.

Data, Reporting & Enablement

• Sales Enablement: Partner with internal and external closers on content training, objection handling, one-pagers, pricing clarity and QA of the booking flow.
• Data Integrity: Own the retention dataset. Offer made, refund reason, call outcome and case status are complete and accurate on close; this is a condition of the role, not an administrative extra.
• Reason Taxonomy: Maintain a refund-reason taxonomy specific enough to act on, keeping unclassified cases to a minimum.
• Leadership Reporting: Present retention, onboarding and outside sales performance to leadership monthly, in person, with your own analysis and recommendations.
• Product Feedback Loop: Turn churn reasons into named issues for Product and Marketing, with evidence and follow-through on whether anything changed.
• Living Documentation: Maintain the Retention DNA, call scripts and transcript library as working documents, not archives.

Technical Competencies

• Retention strategy: understanding of churn drivers, save offers, win-back mechanics and lifetime value in a high-ticket environment.
• Commercial management: ability to source, benchmark, negotiate with and hold external sales partners to performance standards.
• Sales strategy: conversion techniques, funnel optimisation, objection handling and customer decision psychology.
• Data fluency: able to build and interrogate a dataset, design a valid test, read the result honestly and act on it; confident in Airtable and Google Sheets.
• AI-assisted working: comfortable using AI daily for transcription, case analysis and reporting, and keen to push what it can take off your plate.
• CRM & tooling: proficiency with CRM platforms, ticketing systems (Zendesk) and scheduling tools.

Soft Competencies

• Ownership: treats the number as theirs, brings problems with a proposed answer attached, and does not wait to be asked.
• Customer-Centricity: deep empathy, sound judgement on sensitive cases, and the integrity to do right by the customer even when it costs a save.
• Sales Influence: clear, compelling communication that inspires action, with colleagues as readily as with customers.
• Commercial Backbone: comfortable holding an external partner, or an internal team, to a number.
• Problem Solving: goes after root causes rather than symptoms, and closes the loop on whether the fix worked.
• Calm at Volume: composed when case volume spikes around cohort launches and refund windows.

Experience

• 5+ years in retention, customer success or customer-facing sales, with at least two years owning a commercial outcome.
• Demonstrable track record of moving a retention, churn or conversion metric, with the numbers to show it.
• Experience managing agencies, contractors or vendors against performance standards.
• Experience designing and running structured tests rather than only executing a process.
• Experience with online learning platforms, high-ticket programmes and international customer bases.
• A strong personal interest in personal growth and development (familiarity with Mindvalley content is a distinct advantage).