Customer Retention Specialist

Retention Specialist

REMOTE | US

About Us

Property Leads delivers high-quality, motivated seller leads to real estate investors, and we're expanding into home services. We're a quiet but mighty start-up company that participated in 50% of off-market home sales in the last 12 months. We move fast, we're data-driven, and we care about results. 

Our customers are investors running real businesses on the leads we sell them, so when something goes wrong for them, it matters– and fixing it well, fast, is how we grow. If you just want to check the box on responding to a ticket, text, or email without actually solving the problem, this isn't the place. If you want to own real customer relationships, get to the root of their problems, and solve them quickly, it is.

Role

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.

Requirements

• 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.

Results

• 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.