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Retention Specialist

United States - Remote

Imagine being a healthcare provider whose sole mission is to focus on delivering high-quality patient outcomes, but with the knowledge that you need to constantly document your compliance with key healthcare regulations along the way. Now imagine tasking someone with a limited compliance background to manage that, with looming risks of audits, breaches and fines hanging over your practice. Compliancy Group’s vision is to deliver stress-relieving, tech-enabled services and software to the healthcare community that create stronger trust between patients and providers. We’re on a mission to support small and midsized medical practices as they work to comply with critical, ongoing healthcare compliance requirements.

To support this mission, Compliancy Group is looking for a highly motivated and customer-obsessed Retention Specialist (Full Time, Remote, USA) to join our Customer Success team. This role plays a critical part in reducing churn, strengthening client relationships, and supporting our customers throughout their compliance journey. You'll work closely with Customer Success Managers, Sales, and Support to proactively identify at-risk clients and implement strategies to retain and re-engage them.

Key Responsibilities:

  • Retention Focused Execution - Own and manage a portfolio of clients (700-1200 SMB customers). Identify retention risks, develop and execute retention strategies tailored to their needs.
  • Own the End-to-End Renewal Process -  Manage the full lifecycle of subscription renewals for your assigned book of business, including preparing renewal agreements and addressing questions related to pricing, terms, or billing.
  • Contract & Billing Support -  Respond to customer inquiries related to billing discrepancies, contract terms, and payment timelines, ensuring a smooth renewal experience.
  • Collaborate cross-functionally by partnering with Finance, Support, Product, and Customer Success team to ensure smooth renewals, handle cancellation requests, and resolve underlying issues driving potential churn.
  • Customer Communication at Scale - Use a 1:Many approach to provide renewal reminders, education, and support through campaigns (usage drop-offs, service satisfaction, etc), email sequences, webinars, light touch outreach (email, phone, video). Understand client concerns, reinforce value, and propose appropriate solutions or service enhancements.
  • Identify trends in client feedback and partner with Product and Support teams to drive improvements.
  • Data Hygiene & CRM accuracy - Keep Hubspot and other and other internal systems up to date with accurate customer, contract, customer interactions, touch points, and renewal information.
  • Track and report on retention KPIs - Contribute to the ongoing evolution of our retention playbooks.
  • Operational Efficiency -  Continuously improve and streamline renewal workflows to handle high volume efficiently while maintaining a high standard of customer service.
  • Cross-Team Collaboration - Partner with Finance, Support, Product , and Customer Success teams to resolve renewal blockers and ensure alignment.

Qualifications:

  • 2+ years of experience in a customer-facing role (Retention, Customer Success, Account Management, or Sales), ideally within SaaS or healthcare industries.
  • Excellent communication and interpersonal skills; able to listen with empathy and influence decisions with tact and professionalism.
  • Strong problem-solving skills with the ability to navigate complex client situations.
  • Experience with CRM tools (e.g., Salesforce, HubSpot) and customer success platforms (e.g., Gainsight, ChurnZero) is a plus.
  • Comfort working in a fast-paced, collaborative environment with evolving processes.
  • A proactive, positive mindset and genuine passion for helping customers succeed.

Equal Employment Opportunity is a fundamental principle at Compliancy Group, where employment is based upon personal capabilities and qualifications without discrimination based on race, color, religion, sex, age, national origin, disability, sexual orientation, or any other protected characteristic as established by law.

Job Type: Full-time, Remote

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