Note: The job is a remote job and is open to candidates in USA. insightsoftware is a global provider of reporting, analytics, and performance management solutions that empower leaders from over 32,000 organizations. They are seeking a Digital Customer Success Manager to lead the strategy and execution of digital-first customer engagement initiatives, focusing on building and scaling programs that drive adoption, retention, and expansion across their customer base.
Responsibilities
- Design and execute automated customer journeys across the full lifecycle:
- 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
Skills
- 3-5 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
Benefits
- For non-sales roles, you may be eligible for a bonus.
- For sales roles, this range includes a commission target.
- Background checks are required for employment with insightsoftware, where permitted by country, state/province.
Company Overview
insightsoftware is the most comprehensive provider of solutions for the Office of the CFO. It was founded in 2018, and is headquartered in Raleigh, North Carolina, USA, with a workforce of 1001-5000 employees. Its website is https://www.insightsoftware.com.