Customer Retention Representative

Summary

Join Roofr as a Retention Specialist and focus on reducing churn and maximizing customer retention for high-volume PLG subscribers. You will identify customer pain points, articulate the value of Roofr's platform, and keep at-risk customers engaged. Responsibilities include engaging with churning customers, delivering value propositions, and collaborating with other teams. You will analyze churn data, refine outreach strategies, and optimize retention playbooks. The ideal candidate has 2+ years of experience handling high-volume accounts with a focus on retention, strong objection-handling and conversational selling skills, and experience with subscription-based business models. Roofr offers various benefits, including paid time off, flexible time off, employer-paid benefits, RRSP/401k match, parental leave, retreats, learning and development opportunities, and a remote-first culture.

Requirements

• 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)

Responsibilities

• 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

Preferred Qualifications

Roofing, SaaS, or construction tech experience is a plus

Benefits

• 1st week of employment is mandatory PTO! Start your journey with Roofr by decompressing and recharging - we will see you in week 2!
• 1 Friday off per month (we call those our laundry days!)
• Company wide paid shutdown for the week between Christmas and New Years
• Flexible time off
• 80% employer paid benefits
• RRSP/401k match
• Generous Parental Leave policy
• We host 2 retreats per year and great team building activities
• Ample learning and development opportunities to continue growing your career
• Home office setup stipend
• Internet and phone allowance
• Remote first culture
• Weekly Friday paydays!