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.

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:

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
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!

At Roofr, we celebrate individuality and uniqueness. Roofr is proud to be an equal opportunity employer. We are committed to building an organization that empowers inclusion and diversity. We encourage candidates and employees to be true to themselves and express all aspects of their identities. We believe that the convergence of fresh perspectives and experiences from all walks of life is what makes our product and culture so great. We do not discriminate against employees based on race, color, religion, sex, national origin, gender identity or expression, age, disability, pregnancy (including childbirth, breastfeeding, or related medical condition), genetic information, protected military or veteran status, sexual orientation, or any other characteristic protected by applicable federal, state or local laws.

IMPORTANT NOTICE: Our company takes the security and privacy of job applicants very seriously. We will never ask for payment, bank details, or personal financial information as part of the application process.

Customer Retention Representative