Customer Retention Representative, Contract at Roofr

Job Description

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 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

🤝 Perks:

We host an annual company retreat with 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. Bring your real, unfiltered self, we promise we will too.

And don’t worry, a real, live human is behind every part of our process. Every application is reviewed by a real person, and you’ll always speak with real humans throughout the interview process. No bots, just good people ☺️

⚠️ Important Notice

We’ve been made aware of an individual impersonating Roofr using a fraudulent domain: roofrr.com (note the extra “r”). 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. All our legitimate job postings can be found on our official career site. Please be cautious of job offers that come from non-company email addresses, instant messaging platforms, or unsolicited calls.

To ensure your application is legitimate, please apply directly through our official careers page: https://roofr.com/careers.

If you receive any suspicious messages or have questions, reach out to us at talent@roofr.com.

Your safety and security are important to us — thank you for your vigilance!

Roofr is proud to be an equal opportunity employer. We are committed to equal employment opportunity in the workplace regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or veteran status.

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