Sales & Retention Specialist

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Sales & Retention Specialist based in Italy.
As a Sales & Retention Specialist, you'll own key stages of the customer journey for premium programs, from onboarding through retention and potential churn.
You'll combine customer advocacy, commercial judgement, sales expertise, and data-driven experimentation to protect revenue and improve customer outcomes.
The role involves personally handling high-value and complex retention conversations while shaping the standards and processes used across the wider team.
You’ll also manage external sales and appointment-setting partners, ensuring their performance meets clearly defined commercial targets.
Using AI-assisted tools, you'll streamline case analysis, reporting, and documentation so you can focus on high-impact conversations and decisions.
You’ll work closely with Product, Marketing, Technology, Community, and Customer Experience teams to identify root causes and improve the customer journey.
This is a high-ownership role for someone who wants to directly influence measurable retention, conversion, customer experience, and revenue outcomes.
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,…