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.

• 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.

• 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, ticketin