Customer Retention Specialist (Remote)

Company: Roofr

Location: Remote

About Roofr:

Roofr is revolutionizing the roofing industry with its powerful, integrated CRM platform built specifically for roofing contractors. We started by developing essential tools like aerial roof measurements and digital proposals, but driven by customer feedback, we’ve created a comprehensive solution that helps roofers manage and scale their entire business – from sales and payments to material ordering and more. We’re a successful, fast-growing startup with strong financials, a fantastic remote-first culture, and a clear roadmap for continued innovation. Joining Roofr now offers significant growth opportunities, equity, and the chance to make a real impact.

The Role:

We are seeking a proactive and results-oriented Customer Retention Specialist to join our remote team. In this vital role, you will focus on minimizing customer churn and maximizing retention, particularly among our high-volume Product-Led Growth (PLG) subscribers who often experience seasonal usage patterns. Your primary goal will be to swiftly identify at-risk customers, effectively communicate the ongoing value of the Roofr platform, and secure their engagement before transitioning them to an Account Manager for deeper relationship building and strategic discussions.

Key Responsibilities:

• Proactively engage with high-volume PLG and Sales-Assisted customers exhibiting churn indicators or expressing intent to cancel.
• Quickly diagnose reasons for potential churn and offer tailored solutions and compelling value propositions in real-time conversations.
• Effectively handle objections and guide conversations to prevent immediate churn.
• Secure customer commitment for further discussion, facilitating smooth handoffs to Account Managers for demonstrations and long-term strategy alignment.
• Conduct targeted outreach to actively churning customers, creating urgency and reinforcing the benefits of remaining on the platform.
• Analyze churn data and seasonal trends to identify patterns and refine retention outreach strategies.
• Develop, track, and optimize retention playbooks to continuously improve customer lifecycle management.
• Collaborate effectively with Account Management, Implementation, and Support teams to ensure a cohesive and positive customer experience.

What You’ll Bring:

• Minimum 2 years of experience in a customer retention, account management, or customer success role, preferably handling a high volume of accounts.
• Proven ability in objection handling and engaging customers through effective conversational selling techniques.
• Strong critical thinking skills and the ability to adapt and respond effectively in real-time customer interactions.
• Experience working within a subscription-based or recurring revenue (SaaS) business model.
• A data-driven mindset with the ability to analyze trends, identify insights, and adapt strategies accordingly.
• Excellent organizational and multitasking skills to manage a dynamic portfolio of at-risk customers efficiently.
• Demonstrated ability to collaborate cross-functionally with Sales, Support, and Account Management teams.
• Proficiency with CRM software (e.g., HubSpot, Salesforce, Gainsight, or similar).

Bonus Points:

• Experience in the Roofing, Construction Technology, or related SaaS industries.

What We Offer:

Join Roofr and make a significant impact in a supportive, remote-first environment. We invest in our team’s growth and well-being with:

• Unique Time Off: Mandatory paid first week off to recharge before you start, one paid Friday off per month (“laundry days!”), a company-wide paid shutdown between Christmas and New Year’s, and flexible PTO.
• Comprehensive Benefits: 80% employer-paid health benefits, RRSP/401k matching program, and a generous parental leave policy.
• Remote Work Support: Home office setup stipend, plus internet and phone allowances.
• Growth & Culture: Ample learning and development opportunities, bi-annual company retreats (we pay for travel!), engaging team-building activities, a vibrant remote culture, and convenient weekly paydays.

Our Commitment to Diversity:

Roofr is proud to be an equal opportunity employer committed to diversity and inclusion. We celebrate individuality and encourage candidates of all backgrounds, experiences, and identities to apply. We believe that diverse perspectives make our product and culture stronger.

Important Security Notice:

Roofr takes applicant security seriously. We will never ask for payment, bank details, or personal financial information during the application process. All legitimate job postings are on our official career site (https://boards.greenhouse.io/roofr). Please be cautious of communications from [email address removed] email addresses, instant messaging platforms, or unsolicited calls regarding job offers.

Apply Now: https://job-boards.greenhouse.io/roofr/jobs/4548677005