Head of Customer Experience - Roofr

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.

Reporting to the Chief Operating Officer, the Head of Customer Experience will define and execute Roofr's post-sale customer strategy, leading the Customer Experience team.

This leader will be responsible for building a future-focused organization that leverages AI, automation, and digital-first experiences to accelerate customer time-to-value, improve retention, and deliver world-class customer experiences at scale.

What you’ll get to do:

Build the Future of Customer Experience

• Develop and execute Roofr's Customer Experience strategy aligned with our Product-Led Growth (PLG) and Product-Led Sales (PLS) models.
• Design a scalable customer journey that enables customers to achieve value quickly while creating a seamless experience across every customer touchpoint.
• Establish a customer-first culture focused on simplicity, speed, and measurable customer outcomes.
• Own the holistic customer experience across the post-sale lifecycle, identifying opportunities to improve the journey from onboarding through adoption, engagement, support, and retention.
• Create a consistent experience across digital, self-service, and human-assisted interactions.

Lead Customer Operations

Provide leadership and/or support across:

• Customer Support
• Onboarding & Customer Success (Interim)
• Customer Retention (Interim)
• Develop leaders, build organizational capability, establish operational rhythms, and create clear performance metrics that drive accountability and continuous improvement.

Drive AI & Automation

Champion the use of AI and automation to transform both the customer and employee experience, including AI-enabled support, automated onboarding workflows, predictive churn identification, and AI-enhanced productivity tools.

Improve Customer Outcomes

Own and improve key customer metrics, including Customer Retention, GRR, Time to Value, Product Adoption, CSAT, NPS, and Support SLAs.

Partner Cross-Functionally

Serve as the voice of the customer across the business by partnering closely with Product, Engineering, Sales, Marketing, Revenue Operations, and Finance.

What You’ll Bring to the Role:

• 10+ years of experience leading Customer Experience, Customer Success, Customer Operations, or Support organizations within a B2B SaaS company.
• 5+ years leading multiple customer-facing functions through managers and senior leaders.
• Experience supporting SMB customers in a Product-Led Growth (PLG) and/or Product-Led Sales (PLS) environment.
• Demonstrated success improving customer retention, customer satisfaction, and operational efficiency.
• Experience implementing AI and automation to improve customer outcomes and team productivity.
• Strong understanding of onboarding, customer support, customer lifecycle management, and digital customer engagement.
• Strong analytical and data-driven decision-making skills with exceptional executive presence.