Backed by 500 Global.
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.
What they're looking for
- 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
- 5+ years in retention, customer success or customer-facing sales, with at least two years owning a commercial outcome
More about this 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
Own the Number: Own the end-to-end retention process for premium programs, and own the retention rate and retained-value targets attached to...
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