Customer Retention Representative, Contract

Roofr

6d•$65,000 - $75,000•Remote

About The Position

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.

Requirements

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)

Nice To Haves

Roofing, SaaS, or construction tech experience is a plus

Responsibilities

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

Benefits

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
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!