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.