We're looking for a sharp minded Escalations & Retention Specialist to own our highest-stakes customer moments — the ones where a customer is ready to walk. This is not a traditional customer service role. We need someone who thinks like a closer: someone who can de-escalate a frustrated customer, diagnose the real reason behind churn risk, and turn that conversation into a win — a saved customer, a repeat order, a restored relationship.
The ideal candidate has cut their teeth in a fast-paced, high-volume D2C environment where retention wasn't a KPI on a dashboard but a daily hustle — where they've had to think on their feet, negotiate outcomes, and genuinely win back customers who were ready to leave. If you know the difference between resolving a ticket and saving a customer, this role is for you.
Key Responsibilities
- Own and resolve escalated customer complaints end-to-end, acting as the final point of contact before a customer churns
- Proactively identify at-risk and high-value customers, and run structured win-back and retention plays to keep them
- Negotiate outcomes with customers (credits, offers, alternatives) within defined guardrails — balancing customer satisfaction with business economics
- Diagnose root causes behind escalations and repeat complaints, and drive fixes with internal teams rather than just closing tickets
- Build genuine rapport with customers across phone, email, and chat to convert detractors into loyal, repeat customers
- Track and report on save rates, churn drivers, escalation trends, and retention outcomes using CRM and support tools
- Partner cross-functionally with Support, Product, Ops, and Marketing to flag systemic issues and improve the end-to-end customer journey
- Continuously refine retention scripts, offers, and playbooks based on what's actually converting
- Maintain composure, professionalism, and a solutions-first mindset even in high-pressure, high-emotion conversations
What Sets You Apart
- 2–4 years of experience in a strong D2C / e-commerce business, ideally in a retention, escalations, or high-touch customer-facing role with clear ownership of save/win-back metrics
- A proven track record of winning back customers — not just closing tickets or following a script
- Strong negotiation and persuasion skills; comfortable making judgment calls in real time
- Sharp problem-solving instincts — you dig into why a customer is upset, how could this be impacting others, not just what they're upset about
- Data-driven approach: comfortable tracking save rates, churn metrics, and using data to justify decisions
- Excellent verbal and written communication skills, with the composure to handle high-emotion conversations
- Comfortable working with CRM/support tools and moving fast in a high-volume environment
- Experience in healthcare, pharmacy, SaaS, or e-commerce is a strong plus
- A completed graduation degree is mandatory
The annual compensation is based on a number of factors and may vary depending on job-related knowledge, skills, experience and alignment to the market.
We may use artificial intelligence (AI) tools to support certain aspects of our recruitment process, such as screening applications and reviewing resumes. These tools assist our hiring team and improve efficiency; however, they do not replace human evaluation. All final hiring decisions are made by our team. If you would like more information about how your data is processed, please contact us.
Pocketpills is committed to creating an accessible and inclusive organization. We are committed to providing barrier-free and accessible employment practices. Should you require accommodation through any stage of the recruitment process, please make them known when contacted and we will work with you to meet your needs.
