Head of Customer Experience

About the role

Reporting to the Chief Operating Officer, the Head of Customer Experience will define and execute Roofr's post-sale customer strategy, leading Customer Experience team. This leader will build 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. Success in this role requires an operator who can balance strategy and tactical execution to build high-performing teams, optimize processes, and partner cross-functionally with Product, Engineering, Sales, Marketing, and Revenue Operations to continuously optimize the end-to-end customer journey and create a cohesive experience across every customer touchpoint. The Head of Customer Experience will own the end-to-end customer lifecycle, ensuring that every interaction reinforces Roofr's commitment to simplicity, speed, and measurable outcomes. This position is critical for translating product-led growth into a scalable, customer-obsessed support model that drives long-term loyalty and expansion. The leader will establish a customer-first culture that prioritizes clarity, efficiency, and data-driven decision-making across all post-sale interactions.

Key facts

What you'll do

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.

Provide leadership and/or support across Customer Support, Onboarding (Interim), and Customer Retention (Interim).

Develop leaders, build organizational capability, establish operational rhythms, and create clear performance metrics that drive accountability and continuous improvement.

Connect these functions into a cohesive Customer Experience organization, breaking down operational silos and ensuring customers experience a consistent journey regardless of how or where they engage with Roofr.

Champion the use of AI and automation to transform both the customer and employee experience.

Implement AI-enabled customer support, intelligent ticket routing and case management, and automated onboarding workflows.

Drive digital customer education and self-service knowledge management initiatives that reduce friction and increase product adoption.

Utilize customer health monitoring and predictive churn identification to proactively address risks and opportunities.

Leverage AI-enhanced productivity tools for customer-facing teams and automated journeys that guide customers toward activation, adoption, and expansion.

Continuously evaluate emerging technologies that improve efficiency while maintaining a high-quality customer experience.

Own and improve key customer metrics, including Customer Retention, Gross Revenue Retention (GRR), Customer Health, Time to Value, Product Adoption, and Customer Satisfaction.

Collaborate cross-functionally with Product, Engineering, Sales, Marketing, and Revenue Operations to identify bottlenecks, align on goals, and optimize the end-to-end customer journey.

Establish clear processes and documentation to ensure consistency, scalability, and repeatability across customer touchpoints.

Champion data-driven decision-making by tracking and analyzing customer behavior, feedback, and operational performance.

Foster a culture of experimentation and continuous learning within the Customer Experience organization.

Communicate progress, insights, and learnings to executive leadership on a regular cadence to inform strategic decisions.

Requirements

Demonstrated experience in leading Customer Experience or Customer Operations in a SaaS or subscription-based business.

Strong background in developing and executing customer strategies that align with product-led growth and sales motions.

Proven ability to build, lead, and scale high-performing customer-facing teams, including support, onboarding, and success.

Exceptional skills in process optimization, operational rigor, and the ability to turn complex problems into simple, scalable solutions.

Deep understanding of the customer journey and the ability to design end-to-end experiences that drive adoption, retention, and expansion.

Experience leveraging AI, automation, and data tools to improve customer outcomes and operational efficiency.

Strong collaboration skills with the ability to influence cross-functional stakeholders and align teams around shared customer-centric goals.

Excellent communication, presentation, and storytelling abilities with the capacity to translate complex concepts into clear, actionable insights.

Nice to have

Experience with CRM, billing, and revenue systems that integrate with product usage data.

Background in applying behavioral science principles to customer experience design.

Familiarity with roofing, construction, or home improvement verticals is a plus given Roofr's market focus.

Experience managing customer outcomes in a fast-paced, high-growth startup environment.

Practical notes

This role is full-time.

Candidates must be eligible to work in Canada without sponsorship.

No visa sponsorship is available for this position.

The position is for an existing vacancy with an immediate start expectation.