Customer Retention Representative

Roofr; Canada; Remote; CAD 55,000 - 75,000; Full time

Job summary

A dynamic technology startup in Canada is looking for a Retention Specialist who will focus on reducing churn and maximizing customer retention. You will engage high-volume customers, identify churn risks, and provide tailored solutions to keep customers engaged. The ideal candidate has 2+ years of experience in managing accounts and a strong skill set in objection handling and data-driven strategies. Join a company that values growth and innovation in a flexible, remote-first environment.

Benefits

Mandatory PTO during the first week of employment

1 Friday off per month

Flexible time off

80% employer paid benefits

Generous parental leave policy

Home office setup stipend

Internet and phone allowance

Qualifications

• 2+ years experience handling a high volume of accounts focused on retention.
• Experience in subscription-based business models with recurring revenue.
• Ability to think on your feet and keep customers engaged in real-time.

Responsibilities

• Engage and re-engage high-volume customers showing signs of churn.
• Identify churn risk factors and provide tailored solutions.
• Analyze churn data and seasonal trends to refine outreach strategies.

Skills

Objection-handling skills

Conversational selling skills

Data-driven mindset

Ability to multi-task

Collaboration skills

Tools

HubSpot

Salesforce

Gainsight

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.

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:

• 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
• 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!

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 ️

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 [e-mail] .

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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