[Hiring] Customer Retention Specialist @Property Leads

Role Description

Property Leads is hiring a Retention Specialist to own our response to customers at risk of canceling. You'll personally handle high-stakes escalations, build the plans and playbooks that prevent churn, and coach Customer Success Managers to catch problems before they reach you.

Responsibilities

• Own retention for high-risk or high-value accounts: review health signals (usage, support history, payment activity, feedback), prioritize by risk and revenue exposure, and reach out proactively.
• Build account-specific save plans with clear actions, owners, and follow-up dates.
• Document every retention conversation and outcome.
• Serve as the escalation point for complex or sensitive cancellation risk: de-escalate, coordinate with Ops/Product/Billing/Sales to fix root causes, and close the loop with the customer.
• Coach CSMs on early pre-churn conversations: objection handling, discovery questions, call reviews, and set clear rules for when to escalate vs. handle directly.
• Turn churn patterns into playbooks, SOPs, and process fixes; partner with the Senior Manager of Customer Success on what's driving cancellations and what to change.
• Support expansion conversations on retained accounts, but only once the customer's core concern is actually resolved.

Qualifications

• 3–5+ years in Customer Success, Account Management, Retention, or a related B2B customer-facing function, with a track record of talking customers back from the ledge.
• Strong de-escalation, negotiation, and consultative communication skills.
• Experience coaching or training customer-facing teammates.
• Comfortable working in a CRM and turning account data into a plan of action.
• Nice to have: subscription/SaaS/lead-gen background, experience with real estate investors or small-business customers, building playbooks, and familiarity with churn/NRR metrics.

Requirements

• Fewer high-risk accounts churn, and CSMs handle early-stage risk without escalating.
• Every cancellation risk has a documented save attempt (no more silent losses).
• Retention improves without relying on giving credits or overpromising.
• Churn themes turn into concrete changes to onboarding, product, or process.

Benefits

• 401k, Medical, Vision, Dental.
• A fast, low-bureaucracy team where your work has direct, visible impact. No six layers between you and the outcome.