Digital Customer Success Manager

insightsoftware is a global provider of reporting, analytics, and performance management solutions. They are seeking a Digital Customer Success Manager to lead digital-first customer engagement initiatives, focusing on building and scaling programs that drive adoption, retention, and expansion across their customer base.

Responsibilities:

• Build and optimize onboarding sequences that accelerate time-to-value across multiple product families
• Develop adoption campaigns triggered by telemetry and usage data to drive feature engagement
• Create retention and expansion campaigns targeting specific customer segments and behaviors
• Design win-back flows for at-risk and dormant customers
• Continuously analyze campaign performance metrics and iterate based on data
• Build playbooks and automation workflows in Totango (or similar CS platforms)
• Integrate campaigns across email, in-app messaging, community, and other digital channels
• Coordinate with cross-functional teams (Product, Marketing, Support, Sales) to ensure message consistency
• Establish KPIs including reach, engagement, conversion, and business impact (NRR, GRR, churn reduction)
• Define what customer problems AI agents should solve and how they should delight customers
• Design the customer experience for AI-powered email responses, proactive outreach, and intelligent recommendations
• Map customer touchpoints where AI intervention creates value vs. where human CSMs are essential
• Establish success criteria, KPIs, and measurement frameworks for AI agent performance
• Create the strategic roadmap for phased rollout across customer segments and product families
• Partner with IT and AI Ops teams to translate customer experience requirements into technical specifications
• Work with data engineering to identify required data sources, triggers, and integration points
• Test pilot programs with select customer cohorts and gather feedback to refine the approach
• Document use cases, expected outcomes, and customer journey maps that guide technical development
• Stay current on AI developments in customer success and evaluate emerging capabilities
• Design in-app messaging strategies leveraging WalkMe or similar digital adoption platforms
• Develop contextual tooltips, smart tips, feature announcements, and value prompts
• Implement in-app NPS and feedback collection to measure customer sentiment in real-time
• Create webinar promotion banners and welcome shoutouts that drive engagement
• Partner with Product and UX teams to ensure in-app experiences align with product roadmap

Requirements:

• 5+ years in digital customer success, customer marketing, or marketing automation in B2B SaaS
• Proven track record designing and executing lifecycle campaigns at scale (1,000+ customers)
• Deep hands-on experience with customer success platforms (Totango, Gainsight, ChurnZero, or similar)
• Strong technical aptitude with ability to learn complex software products quickly
• Experience integrating multiple systems (CRM, CS platforms, marketing automation, data warehouses)
• Data-driven decision maker who uses analytics to drive program optimization
• Ability to build customer segmentation strategies and personalized journeys
• Experience tracking leading and lagging indicators (reach KPIs, effect KPIs, ROI KPIs)
• Comfortable working with telemetry data, health scores, and behavioral triggers
• Strong project management skills with ability to manage multiple initiatives simultaneously
• Strategic thinker who can envision how AI can delight customers and solve real problems
• Ability to translate customer needs into requirements that technical teams can build
• Understanding of what AI agents can and can't do—where automation adds value vs. where humans are essential
• Experience partnering with technical teams (IT, Engineering, Data) to bring customer-facing solutions to life
• Curiosity about AI developments in customer success with ability to evaluate and apply new capabilities
• Excellent written communication skills—you'll be crafting customer-facing campaigns
• Cross-functional influencer who can build bridges with Product, Engineering, Marketing, Sales, and Support
• Ability to navigate ambiguity and drive projects forward without perfect information
• Comfortable presenting strategy and results to senior leadership
• Experience in a multi-product SaaS environment with diverse customer base
• Background in product-led growth or digital-first companies
• Familiarity with digital adoption platforms (WalkMe, Pendo, Appcues)
• Customer success or customer marketing experience in AI/ML product companies
• Marketing automation platform expertise (Pardot, Marketo, HubSpot)
• Experience designing customer experiences that blend automation with human touchpoints