Customer Retention Representative

About Roofr

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.

Role Overview: Retention Specialist

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.

What You’ll Get to Do

• 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

What You’ll Bring to the Role

• 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

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 shutdown for the week between Christmas and New Years
• Flexible time off

Benefits & Financial

• 80% employer paid benefits
• RRSP/401k match
• Generous Parental Leave policy

Perks

• 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!

AI Notice

At Roofr, we’re big fans of AI. It helps us write job descriptions that don’t put you to sleep, takes notes during interviews so we can actually listen, and even helps us track down awesome humans like you.

Feel free to use AI to prep, research, or get pumped up for your interview (we see you, ChatGPT power users 👀). But when it’s time to chat, we’d love to meet you, not your AI alter ego.