Customer Retention Representative, Contract

At Roofr, we’re obsessed with our customers. We constantly gather feedback to shape, prioritize, and launch the products they truly need. That’s what makes Roofr’s CRM special. We started by building essential sales tools like aerial roof measurements and digital sales proposals. But when our customers asked for a simple, affordable way to manage and scale their entire businesses, we listened. So, we created a CRM that connects these solutions—along with payments, material ordering, and more—into a seamless, powerful platform. With a clear roadmap ahead, we’re excited to continue expanding and leading the market with innovative products. We have an amazing culture, strong financials, and best-in-class company metrics. It’s an exciting time to be part of an extraordinary startup that is already successful, yet still early enough to offer its team significant growth, equity, and the opportunity to make a real impact. This position is for an existing vacancy. We are looking for a Contract Retention Specialist for 12 months to reduce churn and maximize customer retention, with a primary focus on 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 reengaging at-risk customers often by leveraging cross-functional resources such as personalized demos with Account Managers or guided onboarding through Implementation Specialists to reconnect them with the tools and support they need to succeed. What You’ll Get to Do: Engage and re-engage customers across all segments who show signs of churn Quickly identify churn risk factors and provide tailored solutions Reach out to actively churning customers and create urgency to keep them on the platform Deliver compelling, real-time value propositions to prevent immediate churn Hook customers into a conversation long enough to explore their concerns, identify the right retention strategies, and connect them with the resources or team members best suited to help them succeed Conduct discovery conversations to surface recurring pain points and product feedback, sharing insights cross-functionally to inform improvements 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 What You’ll Bring to the Role: 2+ years of 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 multitask 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 Compensation Range: $65,000.00 - $75,000.00 + 25% variable CAD Our compensation ranges are built using multiple market benchmarks and reflect both the scope of the role and current market data. While many hires fall within the beginning to midpoint of the band to allow for growth over time, we tailor offers based on each candidate’s experience, seniority, and demonstrated impact. 🏠 What we offer (US + Canada) When you join our team, you’re not just accepting a job. You’re making a career move. Here’s how we’ll support you in doing some of the most impactful work of your career: 🏝️ Vacation/Paid Time Off: 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 shutdo ... (truncated, view full listing at source)