Sr. Director, CX Digital Engagement

About the Role

Impact you will make

• Champion the customer onboarding journey, ensuring every new customer achieves rapid, measurable success and value realization.
• Develop and execute strategies that optimize the sale-to-adoption process, minimizing friction and accelerating adoption of core product capabilities.
• Own the definition, tracking, and continuous improvement of key metrics: onboarding completion rates, adoption rates, time-to-first value, and customer value realization.
• Lead the sourcing, aggregation, and analysis of operational reporting for onboarding and adoption KPIs, driving data-driven decisions and continuous improvement.
• Build and communicate a compelling vision for customer success, aligning cross-functional teams to deliver a unified, high-impact digital onboarding and engagement experience.

What you will do

• Customer Onboarding & Success
  • Lead the strategy and execution of customer onboarding programs, including digital onboarding flows, in-app guidance, and proactive onboarding communications.
  • Partner with cross-functional teams to ensure seamless handoffs and clear accountability for customer outcomes from sale through adoption.
  • Develop and implement frameworks for measuring onboarding effectiveness, adoption rates, and value realization, regularly reporting insights and recommendations to executive leadership.
• Customer Education & LMS Ownership
  • Oversee the Customer Academy, including curriculum development, role-based learning paths, certifications, and training content, with a focus on accelerating onboarding and driving adoption.
  • Ensure educational resources are tightly aligned with onboarding milestones and product adoption goals.
• Digital Content & Knowledge Strategy
  • Own customer-facing content architecture, ensuring all resources (knowledge base, help docs, product guides, videos) support onboarding, drive adoption, and are easily discoverable.
  • Implement unified content governance and versioning to maintain accuracy and relevance.
• Customer Communications & Lifecycle Messaging
  • Lead proactive and event-based communications (product releases, feature announcements, adoption campaigns, etc.) that support onboarding and ongoing engagement.
  • Build templates, SLAs, and guidelines to ensure consistent, high-quality communications that drive customer action.
• Digital Adoption & In-App Experience
  • Own the strategy and execution of in-app experiences (Walk Me, Gainsight PX, etc.) to deliver onboarding walkthroughs, nudges, and guidance that improve feature adoption and reduce time-to-value.
  • Continuously optimize in-app flows based on data and customer feedback.
• Data, Insights & Optimization
  • Establish and manage measurement frameworks for onboarding, adoption, content performance, and customer outcomes.
  • Translate analytics into actionable improvements across onboarding journeys, content, and in-app experiences.
  • Regularly present performance insights and recommendations to executive leadership.
• Cross-Functional Leadership
  • Collaborate with cross-functional leaders to coordinate onboarding, content, messaging, and digital programs.
  • Establish operating rhythms, intake processes, governance structures, and shared execution frameworks.
  • Lead a high-performing team of content strategists, instructional designers, LMS admins, and digital adoption managers.

What you will bring

• Bachelor's degree in business management, Business Intelligence, or related field.
• 10+ years in Customer Education, Customer Experience, Digital Engagement, Product Enablement, or similar SaaS roles.
• 5+ years managing multi-disciplinary teams (content, education, digital platforms).
• Proven success scaling digital customer programs at a mid-market SaaS or enterprise software company.
• Strong understanding of product education, onboarding, release communications, knowledge systems, and in-app adoption technologies.
• Demonstrated ability to create measurable improvements in onboarding, adoption, and customer satisfaction.
• Excellent communication, leadership, and cross-functional collaboration skills.
• Experience building dashboards, KPIs, and insights for executive audiences.

About Fin Thrive

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Fin Thrive's Core Values and Expectations

• Demonstrate integrity and ethics in day-to-day tasks and decision making, adhere to Fin Thrive's core values of being Customer-Centric, Agile, Reliable and Engaged, operate effectively in the Fin Thrive environment and the environment of the work group, maintain a focus on self-development and seek out continuous…