Director of Implementation

As the Director of Implementation & Retention, you will oversee Account Set-up (Builds), Implementation, Onboarding, Retention, Customer Education and Customer Insights. You'll be responsible for designing and scaling processes, playbooks, and strategies that ensure customers achieve measurable value quickly and continue to grow with us. This is a hands-on leadership role where you'll both build the foundation for Customer Success at scale and directly coach and develop a growing team.

• Leadership & Strategy
• Define and execute the vision, strategy, and operating model for the success across Builds, Implementation, Onboarding, Retention, Customer Education and Customer Insights functions.
• Build, mentor, and inspire a high-performing CS team while fostering a customer-centric culture.
• Partner closely with Growth, Product, Sales, Support, Partnerships and Marketing to align on customer journey, feedback loops, and GTM strategy.
• Account Set-up (Builds)
• Manage the Build Manager, responsible for Offshore Shift Leads, and Offshore Builders.
• Ensure accurate and scalable execution of customer account setup, account optimization and data migration.
• Expand Builder responsibilities to support growth in new products, increased self-serve demand, and migration work.
• Maintain round-the-clock coverage through offshore teams and shift leads.
• Implementation & Onboarding
• Oversee Managers of Customer Onboarding (Greenfield, Brownfield, and Field) and Implementation Specialists, ensuring consistent, high-quality onboarding experiences across all customer segments.
• Design scalable onboarding frameworks to reduce time-to-value and set customers up for long-term success.
• Create and refine implementation playbooks that not only drive adoption but also surface upsell and cross-sell opportunities as customers expand their usage.
• Customer Education
• Oversee Customer Education; training programs, persona-based enablement, virtual and in-person onboarding, and scaling Roofr Academy content.
• Ensure adoption across self-serve and sales-assisted customers through structured education programs that support both admins and end-users.
• Retention & Growth
• Establish metrics, processes, and playbooks to increase retention and reduce churn.
• Develop and optimize health scoring models to identify risks and opportunities across the customer base.
• Build proactive retention strategies, including customer engagement and success planning.
• Design churn-save playbooks that systematically identify at-risk accounts, outline intervention strategies, and generate pipeline for upsells, cross-sells, and increased adoption.
• Operations & Scale
• Translate customer insights into actionable initiatives across Product, Marketing, and Revenue.
• Build systems, processes and playbooks that support customer success across self-serve, sales assisted and sales lead customers at scale.
• Define key success metrics and provide executive-level reporting on onboarding & implementation, adoption, retention, education, customer insights and customer experience.
• Standardize playbooks and best practices across all CS functions.
• Drive operational planning for headcount, ramp time, and resource allocation based on subscription growth.

• 8 years of Customer Success experience, with at least 3 years leading CS teams in B2B SaaS with both self-serve and sales-assisted motions.
• Proven track record scaling CS organizations in early-stage to growth-stage startups.
• Strong background in PLG environments, with experience aligning CS motions to both self-serve and sales-assisted journeys.
• Excellent leadership, coaching, and people-development skills.
• Highly operational, with proven ability to build scalable systems, playbooks, and processes that enable consistent execution across teams.
• Strong analytical mindset with the ability to translate data into strategy & decisions.
• Exceptional cross-functional collaboration skills, especially with Product, Sales, and Marketing.
• Passionate about delivering an outstanding customer experience and building long-term relationships.
• Aptitude for quickly learning and adapting to new technologies, tools, and systems.
• Exceptional communication skills, with the ability to distill complex concepts into clear, actionable narratives for diverse audiences.

We are only accepting candidate who reside in Canada at this time.