Manager, Customer Success (Digital First/Mid-Market)

Posted Friday, March 27, 2026 at 4:00 AM We are seeking a Manager of Digital Customer Success and Enablement to lead and scale our customer education and digital customer success programs. This role will be responsible for building scalable strategies that drive product adoption, customer engagement, and long-term value realization across our customer base. The Manager will oversee our customer education initiatives, digital engagement strategy, and product-focused Customer Success SMEs, ensuring customers have the resources, knowledge, and guidance needed to successfully adopt and expand use of our product suite. This role partners closely with Customer Success, Marketing, Product, and Sales to design digital programs and enablement experiences that support customers at scale, particularly across SMB and mid-market segments, while complementing high-touch customer success engagement. Requirements Customer Education & Enablement Lead the strategy and execution of our customer education and training programs. Manage the customer enablement specialist responsible for developing and delivering training content and learning experiences. Develop scalable education programs including: On-demand learning Live and recorded training sessions Webinars and workshops Knowledge base content and documentation Ensure customers can quickly gain product proficiency and realize value across the product suite. Digital Customer Success Programs Define and implement a digital customer success strategy to support onboarding, adoption, engagement, and retention at scale. Build digital lifecycle programs that guide customers through key milestones in the customer journey. Design scalable touchpoints including: Automated campaigns In-app messaging and guidance Digital check-ins and product updates Monitor engagement metrics and continuously optimize programs to improve customer outcomes. Product Adoption & Customer Value Partner with Product and Customer Success teams to translate product capabilities into adoption programs and educational content. Drive awareness and usage of new features through targeted digital campaigns and training initiatives. Develop resources that help customers expand their use of the platform and achieve business outcomes. Product Subject Matter Experts Manage a team of product-focused CSMs or subject matter experts who support adoption and customer success across key products. Ensure SMEs contribute to: Customer education content Adoption programs Internal knowledge sharing Support for complex product use cases Partner with Product teams to ensure new releases are supported by clear customer guidance and enablement. Digital Campaigns & Cross-Functional Collaboration Collaborate with Marketing to develop targeted digital campaigns that drive product engagement and customer success outcomes. Work with Customer Success leadership to align digital programs with broader CS strategies. Partner with Sales and Product teams to ensure consistent messaging and enablement throughout the customer lifecycle. Customer Retention & Growth Develop scalable programs designed to improve retention and expansion within SMB and scaled customer segments. Identify adoption gaps or churn risk signals and implement proactive digital interventions. Use customer data and product insights to inform education and engagement strategies. Qualifications 5+ years of experience in Customer Success, Customer Education, Digital Customer Success, or Customer Experience roles Experience developing customer training or education programs Experience building or managing digital customer engagement programs Strong collaboration experience working with Marketing, Product, and Customer Success teams Data-driven approach to measuring customer engagement and adoption Experience managing customer enablement teams or product specialists Background in B2B SaaS or technology platforms Experience supporting SMB or scaled customer segment Familiarity with customer success, learning management, or product adoption platforms Success Metrics Success in this role will be measured by: Customer product adoption and engagement Participation and effectiveness of customer education programs Retention and expansion within SMB and scaled customer segments Digital program engagement (training completion, campaign performance, feature adoption) Reduction in time-to-value for new customers