[Hiring] Customer Retention Representative @Roofr

Role Description

We are looking for a Retention Specialist to reduce churn and maximize customer retention, with a primary focus on high-volume PLG subscribers who frequently churn and return due to seasonal demand changes. You will be responsible for quickly identifying customer pain points, articulating the full value of Roofr’s platform, and ensuring that at-risk customers stay engaged long enough to be reconnected with an Account Manager for a deeper conversation.

• Engage and re-engage high-volume PLG and Sales Assisted customers who show signs of churn
• Quickly identify churn risk factors and provide tailored solutions
• Deliver compelling, real-time value propositions to prevent immediate churn
• Hook customers into a conversation long enough to transition them to an Account Manager demo
• Reach out to actively churning customers and create urgency to keep them on the platform
• Analyze churn data and seasonal trends to refine outreach strategies
• Collaborate with Account Management & Implementation & Support teams to ensure seamless retention efforts
• Track and optimize retention playbooks for improving customer lifecycle management

Qualifications

• 2+ years experience handling a high volume of accounts with a focus on retention
• Strong objection-handling and conversational selling skills
• Ability to think on your feet and keep customers engaged in real-time
• Experience in subscription-based business models with recurring revenue
• A data-driven mindset—able to identify trends and react quickly
• Ability to multi-task and manage a large volume of at-risk customers
• Strong collaboration skills with Account Managers, Sales, and Support teams
• Proficiency in CRM tools (HubSpot, Salesforce, Gainsight, or equivalent)
• Roofing, SaaS, or construction tech experience is a plus

Benefits

• 1st week of employment is mandatory PTO
• 1 Friday off per month (laundry days)
• Company wide paid shutdown for the week between Christmas and New Years
• Flexible time off
• 80% employer-paid benefits in the U.S. and 100% employer-paid premiums for Extended Healthcare and Dental in Canada
• RRSP/401k match
• Generous Parental Leave policy
• Annual company retreat with great team building activities
• Ample learning and development opportunities
• Home office setup stipend
• Internet and phone allowance
• Remote first culture
• Weekly Friday paydays