We are seeking a part-time Fractional Head of Customer Experience to establish and optimize CareMessage’s customer experience infrastructure, lifecycle standards, and operational rigor. This role will focus on building scalable systems that enable high-quality onboarding, engagement, health monitoring, and customer enablement across segments.
This role is infrastructure- and operations-focused. It will work closely with the Chief Customer Officer and manage the Sr. Manager of Professional Services and Customer Success functions to ensure Gainsight optimization, standardized playbooks, customer lifecycle clarity, and scalable outreach models are in place.
The focus is not on owning renewals or expansion revenue directly, but on strengthening the operational foundations that make retention, adoption, and customer health predictable and measurable.
CX Infrastructure & Gainsight Optimization
Audit and optimize Gainsight configuration, health scoring, workflows, and reporting.
Define and implement standardized lifecycle stages and engagement triggers.
Ensure consistent data hygiene and CX tooling adoption across teams.
Establish executive-level dashboards for customer, partner, and program health.
Playbooks & Lifecycle Design
Develop clear, repeatable playbooks for onboarding, success planning, outreach cadence, and risk management.
Define success plan templates and engagement standards for Strategic CSMs.
Clarify handoffs between Sales, Implementation, and Customer Success.
Standardize QBR frameworks and reporting structures.
Strategic CSM Enablement
Ensure Strategic Customer Success Managers have structured processes, documentation, and operating standards.
Define expectations for customer engagement, health monitoring, and proactive outreach.
Install scalable outreach models aligned to segment complexity.
Customer Programs & Advisory Infrastructure
Stand up and operationalize Customer Advisory Boards (CABs).
Define program structure, cadence, insight capture, and executive reporting loops.
Build training operational infrastructure (coordination, tracking, and integration into lifecycle).
Outreach & Scale Strategy
Develop scalable customer communication frameworks.
Define segmentation-based engagement strategies.
Recommend staffing models and engagement ratios aligned to ARR and customer complexity.
Leadership & Team Oversight
Manage and coach the Sr. Manager of Professional Services and Customer Experience.
Ensure alignment between Implementation, Technical Support, and Customer Success.
Drive execution of defined operating plans during the engagement period.
10–15+ years in Customer Experience, Customer Success, or CX Operations leadership.
Demonstrated experience implementing or optimizing Gainsight (or similar platforms) at scale.
Strong background in lifecycle design, health scoring frameworks, and playbook development.
Experience standing up CX infrastructure in SaaS or healthcare technology environments.
Ability to operate independently and deliver structured outputs within a defined contract window.
Experience working in startup, transformation, or fractional consulting environments preferred.
Alignment with CareMessage’s mission to advance health equity.
Recommended Experience
Healthcare SaaS or provider-facing technology experience.
Background in scaling Customer Success teams from early to growth stage.
Experience advising executive leadership on CX operating models.
Prior fractional or consulting leadership engagements.
Direct ownership of renewals or expansion revenue.
Long-term cultural leadership or team redesign beyond defined scope.
Deep involvement in product roadmap prioritization.
Daily account management or frontline CSM execution.
