Retention Specialist

About Client

Our client is a rapidly growing, data-driven company that provides high-quality, motivated seller leads to real estate investors and is expanding into the home services market. The company has played a role in a significant portion of off-market home sales over the past year and operates with a fast-paced, low-bureaucracy culture where results matter. Their customers are running real businesses on the leads they receive, so when an issue comes up, the goal isn't simply to respond — it's to understand the problem, solve it quickly, and build a relationship that keeps the customer successful.

Job Summary

We're looking for a Retention Specialist who can step in when an important customer is at risk of leaving and turn the situation around. You'll work directly with high-value and high-risk accounts, understand what's driving their concerns, and create practical plans to resolve the issues and earn their continued business. You'll also help Customer Success Managers become better at identifying and addressing problems before they turn into cancellations. This is a highly visible role where you'll have a direct impact on customer satisfaction, retention, and recurring revenue — with the opportunity to turn what you learn from customers into better processes, playbooks, and company-wide improvements.

What We Offer

• Base Salary: $70k - $90k

• Performance Bonus, On-Target Earnings (OTE): $120k - $150k

• Comprehensive paid training and onboarding

• Employer-paid Medical, Dental, and Vision insurance

• 401(k) with company match

• Fully remote position with long-term growth opportunities

• Performance bonuses tied to customer retention, revenue protection, account expansion, and customer satisfaction

• Opportunity to make a direct impact on company growth and recurring revenue

• Work alongside a collaborative, high-performing leadership team

• Career advancement opportunities within a rapidly growing organization

Essential Duties & Responsibilities

• Own retention efforts for high-risk and high-value customer accounts, using account health, usage, support history, payment activity, and customer feedback to identify and prioritize risk.

• Proactively reach out to customers showing signs of dissatisfaction or potential cancellation before the relationship is lost.

• Develop account-specific retention plans that clearly outline the problem, required actions, responsible parties, and follow-up timeline.

• Act as the primary escalation point for complex, sensitive, or high-value cancellation situations.

• De-escalate challenging customer conversations while maintaining a consultative, solutions-focused approach.

• Work cross-functionally with Operations, Product, Billing, Sales, and Customer Success to identify and resolve the underlying causes of customer issues.

• Document retention conversations, action plans, outcomes, and customer feedback accurately in the CRM.

• Coach Customer Success Managers on handling early-stage churn risk, including objection handling, discovery, and knowing when an issue requires escalation.

• Identify recurring reasons for cancellations and turn those insights into retention playbooks, SOPs, and improvements to the customer experience.

• Identify expansion opportunities within retained accounts once the customer's core concerns have been fully addressed and the relationship is healthy.

Qualifications

• 3–5+ years of experience in Customer Success, Account Management, Retention, or another B2B customer-facing role.

• Proven ability to successfully retain customers who are considering canceling or leaving.

• Strong de-escalation, negotiation, and consultative communication skills.

• Comfortable having difficult conversations and addressing customer concerns directly and professionally.

• Experience coaching, mentoring, or training customer-facing team members.

• Strong problem-solving skills with the ability to identify root causes rather than simply address symptoms.

• Comfortable working in a CRM and using customer/account data to determine priorities and build action plans.

• Strong organizational skills and the ability to manage multiple high-priority accounts and follow-ups simultaneously.

• Experience building or improving playbooks, SOPs, workflows, or customer-facing processes is a plus.

• Experience with subscription/SaaS, lead generation, real estate investors, small-business customers, or familiarity with churn and NRR metrics is a plus.