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 the Customer Experience team. This leader will build a future-focused organization leveraging AI, automation, and digital-first experiences to accelerate customer time-to-value, improve retention, and deliver world-class customer experiences at scale. Success requires balancing 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.

Responsibilities

• Develop and execute Roofr's Customer Experience strategy aligned with Product-Led Growth (PLG) and Product-Led Sales (PLS) models.
• Design a scalable customer journey enabling customers to achieve value quickly while creating a seamless experience across every 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 & Customer Success (Interim), and Customer Retention (Interim).
• Develop leaders, build organizational capability, establish operational rhythms, and create clear performance metrics driving accountability and continuous improvement.
• Connect customer-facing functions into a cohesive Customer Experience organization, breaking down operational silos.
• Champion the use of AI and automation to transform both customer and employee experiences, including:
  • 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 guiding customers toward activation, adoption, and expansion
• Continuously evaluate emerging technologies improving efficiency while maintaining high-quality customer experiences.
• 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.
• Serve as the voice of the customer across the business by partnering closely with Product, Engineering, Sales, Marketing, Revenue Operations, and Finance.
• Translate customer feedback into actionable recommendations influencing product strategy, operational improvements, and customer experience initiatives.
• Partner with Product and Engineering to identify and address experience gaps within the product.
• Develop scalable systems, processes, and operating models supporting rapid company growth.
• Create dashboards, forecasting models, workforce planning, and operational KPIs providing visibility into customer performance and organizational health.
• Connect customer behavior, product usage, support interactions, onboarding progress, and retention signals to identify improvement opportunities.
• Build feedback loops translating customer insights into improvements across people, processes, product, and technology.
• Map and measure key customer journeys to understand friction points, value derivation, and proactive improvement opportunities.
• Prioritize journey improvements based on customer impact, business value, and scalability.
• Establish a culture of continuous experimentation and optimization using data and customer feedback.

Requirements

• 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.
• 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.

Qualifications

• Awareness that strategic clarity comes from deep understanding of customers, products, teams, and processes; decisive through deliberate learning with a growth mindset.
• 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.
• Ability to think beyond individual functions, seeing the customer experience as one connected journey rather than departmental handoffs.
• Natural inclination to identify friction across the customer lifecycle and bring teams together to solve underlying problems.
• Deeply customer-centric, using qualitative feedback, behavioral data, and business metrics to understand customer needs and improve experiences.

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, friction points, and optimization opportunities.
• 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 enabling continuous optimization.
• Build scalable operating processes and dashboards supporting Roofr's continued growth.
• Strengthen cross-functional partnerships elevating the voice of the customer throughout the organization.

Benefits

• 1st week of employment is mandatory PTO to decompress and recharge.
• 1 Friday off per month (laundry days).
• Company-wide paid shutdown for the week between Christmas and New Years.
• Flexible time off.
• 80% employer-paid benefits in the U.S. and 100% employer-paid premiums for Extended Healthcare and Dental in Canada.
• RRSP/401k match.
• Generous Parental Leave policy.
• Annual company retreat with team-building activities.
• Ample learning and development opportunities.
• Home office setup stipend.
• Internet and phone allowance.
• Remote-first culture.
• Weekly Friday paydays.

Pay

Compensation ranges are built using multiple market benchmarks and reflect both the scope of the role and current market data. Offers are tailored based on each candidate’s experience, seniority, and demonstrated impact, with many hires falling within the beginning to midpoint of the band to allow for growth over time.