Head of Customer Experience

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 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.

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.

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.

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.

Drive AI & Automation

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

Examples include:

• AI-enabled customer support
• Intelligent ticket routing and case management
• Automated onboarding workflows
• Digital customer education
• Self-service knowledge management
• Customer health monitoring
• Predictive churn identification
• AI-enhanced productivity tools for customer-facing teams
• Automated journeys that guide customers toward activation, adoption, and expansion

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

Improve Customer Outcomes

Own and improve key customer metrics, including:

• Customer Retention
• Gross Revenue Retention (GRR)
• Customer Health
• Time to Value
• Product Adoption
• Customer Satisfaction (CSAT)
• Net Promoter Score (NPS)
• Support SLAs
• Resolution Time

Use customer insights and data to identify friction, improve onboarding, increase product adoption, and strengthen long-term customer relationships.

Partner Cross-Functionally

Serve as the voice of the customer across the business by partnering closely with:

• Product, Engineering, Sales, Marketing, Revenue Operations, Finance
• Translate customer feedback into actionable recommendations that influence product strategy, operational improvements, and customer experience initiatives.
• Partner with Product and Engineering to identify and address experience gaps within the product itself.
• Bring a holistic view of customer behavior, needs, and friction points to cross-functional planning and prioritization.

Build for Scale

• Develop scalable systems, processes, and operating models that support rapid company growth.
• Create dashboards, forecasting models, workforce planning, and operational KPIs that provide visibility into customer performance and organizational health.
• Connect customer behavior, product usage, support interactions, onboarding progress, and retention signals to identify opportunities for improvement.
• Build feedback loops that translate customer insights into improvements across people, processes, product, and technology.

Drive Holistic Customer Journey Optimization

• Map and measure key customer journeys to understand where customers experience friction, where they derive value, and where Roofr can proactively improve the experience.
• Prioritize journey improvements based on customer impact, business value, and scalability.
• Establish a culture of continuous experimentation and optimization, using data and customer feedback to test, learn, and improve the customer experience over time.

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.
• Experience owning or optimizing end-to-end customer journeys across multiple customer-facing functions and touchpoints.
• Proven ability to build scalable processes and high-performing teams in high-growth environments.
• Strong analytical and data-driven decision-making skills.
• Exceptional executive presence and cross-functional leadership.

Who You Are:

• Awareness that strategic clarity comes from a deep understanding of customers, products, teams and processes. You become decisive through deliberate learning and bring a growth mindset to every role.
• Experience scaling a Customer Experience organization and innovating to solve problems.
• Experience partnering closely with Product and Engineering to improve customer adoption and product usability.
• You think beyond individual functions and see the customer experience as one connected journey rather than a series of departmental handoffs.
• You naturally look for friction across the customer lifecycle and bring teams together to solve the underlying problem.
• You are deeply customer-centric and use a combination of qualitative feedback, behavioral data, and business metrics to understand what customers need and where the experience can improve.
• Familiarity with platforms such as Intercom, Gainsight, Salesforce, HubSpot, Gong, or similar customer technologies.
• Experience designing digital-first customer journeys and self-service customer experiences.
• Strong understanding of SaaS metrics including GRR, churn, customer health, adoption, and customer lifetime value.

Success in Your First 12 Months

• Establish a unified Customer Experience strategy across Support, Onboarding, and Retention.
• Map and establish a clear view of the end-to-end customer journey, including key moments that matter, friction points, and opportunities for optimization.
• Reduce customer effort by implementing AI-enabled support and automation.
• Improve onboarding efficiency and accelerate customer time-to-value.
• Increase product adoption and customer engagement.
• Improve customer retention and satisfaction metrics.
• Establish measurable customer journey KPIs and feedback loops that enable continuous optimization.
• Build scalable operating processes and dashboards that support Roofr's continued growth.
• Strengthen cross-functional partnerships that elevate the voice of the customer throughout the organization.

Compensation Band: $200-250k CAD