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Salary: CAD 200,000 - 250,000 / annual
Roofr is a B2B SaaS CRM platform serving the roofing and home services industry. The company has built essential sales tools (aerial roof measurements, digital proposals) and is expanding into a comprehensive platform connecting payments, material ordering, and business management. Roofr is well-funded, profitable, and growing rapidly.
Reporting to the Chief Operating Officer, you will define and execute Roofr's post-sale customer strategy and lead the Customer Experience organization. This is a strategic and operational role requiring someone who can balance vision with execution, build high-performing teams, and optimize the entire customer journey from onboarding through retention.
Key Responsibilities:
**Build the Future of Customer Experience:** 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 that enables rapid time-to-value. Establish a customer-first culture focused on simplicity and measurable outcomes. Own the holistic post-sale lifecycle—onboarding, adoption, engagement, support, and retention. Create consistent experiences across digital, self-service, and human-assisted interactions.
**Lead Customer Operations:** Provide leadership across Customer Support, Onboarding & Customer Success (interim), and Customer Retention (interim). Develop leaders, establish operational rhythms, and create clear performance metrics. Connect these functions into a cohesive organization, breaking down silos so customers experience a consistent journey.
**Drive AI & Automation:** Champion AI and automation to transform customer and employee experiences. Examples include AI-enabled support, intelligent ticket routing, automated onboarding workflows, digital customer education, self-service knowledge management, customer health monitoring, predictive churn identification, and automated journeys guiding customers toward activation and expansion.
**Improve Customer Outcomes:** Own and improve key metrics including retention, Gross Revenue Retention (GRR), customer health, time-to-value, product adoption, CSAT, NPS, support SLAs, and resolution time. Use customer insights and data to identify friction and strengthen relationships.
**Partner Cross-Functionally:** Serve as the voice of the customer across Product, Engineering, Sales, Marketing, Revenue Operations, and Finance. Translate customer feedback into actionable recommendations influencing product strategy and operational improvements.
**Build for Scale:** Develop scalable systems, processes, and operating models supporting rapid growth. Create dashboards, forecasting models, workforce planning, and operational KPIs. Build feedback loops translating customer insights into improvements across people, processes, product, and technology.
**Drive Holistic Customer Journey Optimization:** Map and measure key customer journeys to identify friction and value. Prioritize improvements based on customer impact and business value. Establish a culture of continuous experimentation using data and feedback.
Success in your first 12 months includes: establishing a unified Customer Experience strategy; mapping the end-to-end customer journey; reducing customer effort through AI and automation; improving onboarding efficiency and time-to-value; increasing product adoption and engagement; improving retention and satisfaction metrics; establishing measurable KPIs and feedback loops; building scalable operating processes and dashboards; and strengthening cross-functional partnerships.
Requirements:
- 10+ years leading Customer Experience, Customer Success, Customer Operations, or Support organizations within B2B SaaS
- 5+ years leading multiple customer-facing functions through managers and senior leaders
- Experience supporting SMB customers in PLG and/or PLS environments
- Demonstrated success improving customer retention, 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 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 experiences
- Strong understanding of SaaS metrics including GRR, churn, customer health, adoption, and customer lifetime value
