Director Customer Experience Leadership

last updated May 15, 2026 19:09 UTC

CareMessage

HQ: Remote

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We are hiring a Director of Customer Experience (L4) to ensure the CareMessage experience is high-quality, consistent, and effective for customers, partners, and grant-funded programs. This role is responsible for making sure customers and ecosystem partners are successfully onboarded, engaged, supported, and able to realize value from the platform—prioritizing adoption, time to value, and long-term program health.

This is a senior leadership role combining people management and systems leadership. The Director of Customer Experience leads multiple customer-facing teams and programs, including Professional Services, Customer Success across segments, Workforce Enablement, Partner Success, and core customer experience infrastructure such as Gainsight, CareMessage Academy, and Customer Advisory Boards. While this role does not own renewals or expansion revenue, it is critical to supporting Net Revenue Retention and philanthropic accountability by ensuring customers, partners, and grant-funded programs remain healthy, engaged, and achieve intended outcomes.

Just as important, we need a leader who can scale CareMessage’s customer experience function in a non-linear way—serving more customers per team member through smart digital engagement, AI-augmented workflows, and scalable enablement infrastructure. The best modern CX leaders build systems where AI handles routine interactions and surfaces insights, freeing humans to focus on high-impact, relationship-driven moments. We expect this mindset to guide how you lead at CareMessage.

This role works closely with Revenue (Sales and Partnerships), Product, Engineering, Design, Product Marketing, Clinical, Strategy, and Philanthropy, and reports directly to the CEO.

You are an exceptional people leader and manager. You know how to build, coach, and hold teams accountable in ways that create meaningful results beyond individual contributions. You think in systems, standards, operations, and outcomes—not just individual accounts. You have experience leading customer-facing teams and understand how onboarding quality, engagement, enablement, and lifecycle discipline directly affect customer health, partner success, and retention. You can manage both people managers and individual contributors, creating clarity, consistency, and accountability across diverse customer and partner segments.

You genuinely care about our customers—safety-net clinics, FQHCs, free and charitable clinics, Tribal Health organizations, and partner networks—and about the patients they serve. You are deeply motivated by health equity and believe technology should reduce gaps in access, outcomes, and the social drivers of health. You understand many of the organizations we serve face resource constraints, and you bring empathy, patience, and creativity to helping them succeed.

You think broadly about CareMessage’s role in systems change. You are able to build and deepen key strategic partnerships in states where CareMessage has strong reach, including Primary Care Associations, Clinically Integrated Networks, Accountable Care Organizations, and regional networks—especially in areas where healthcare disparities are most concentrated. You view these partnerships not as transactional relationships, but as opportunities to advance population health and reduce inequity at scale.

You bring a structured, data-driven approach to customer and partner experience, with strong instincts around adoption, time to value, and program health. You are forward-thinking about how AI and digital-first customer success can increase team leverage and improve outcomes. You collaborate easily across Product, Marketing, Clinical, Sales, Strategy, and Philanthropy, translating customer and partner signals into actionable insights and improvements. You are energized by building durable programs and infrastructure that scale impact in mission-driven environments.

Key Responsibilities

I. People Leadership & Team Development
– Directly manage and develop Professional Services, Customer Success, Workforce Success, and Customer Enablement functions.
– Coach and develop managers and individual contributors by setting clear expectations, priorities, and performance standards.
– Build a culture of accountability, empathy, and continuous operational improvement across all customer- and partner-facing teams.
– Design onboarding, ramp, and ongoing training that supports scalable, consistent delivery.
– Drive execution of departmental operating plans by translating company and CX priorities into clear goals, sequencing, and accountability.
– Lead and improve recruiting, hiring, and onboarding policies with attention to diversity, equity, inclusion, accessibility, and belonging.
– Run skip-level one-on-ones and ensure consistent feedback and performance review practices across the department.

II. Customer & Partner Experience Strategy
– Own the end-to-end customer and ecosystem partner experience, ensuring a consistent, high-quality journey from onboarding through renewal.
– Define and maintain lifecycle standards, including onboarding, engagement cadence, success planning, and health monitoring.
– Ensure consistent, high-quality experiences across FQHCs, Free and Charitable Clinics, Tribal Health organizations, and partner-led networks.
– Visit customers, partners, and regional networks, and attend relevant industry conferences to maintain firsthand understanding.
– Partner with Sales to support Net Revenue Retention by driving strong customer and partner health, readiness, and engagement.

III. Scalable CX & AI-Augmented Operations
– Scale the CX function non-linearly by increasing the number of customers served per team member through digital engagement, automation, and AI-augmented workflows.
– Identify and implement AI and automation opportunities across the lifecycle, from automated health scoring and risk detection to digital onboarding sequences and proactive outreach.
– Build engagement models that combine high-touch, low-touch, and digital-led approaches based on customer segment, maturity, and complexity.
– Create repeatable processes and playbooks that deliver consistently strong experiences at scale, aligned with CareMessage’s product-led approach.

IV. Strategic Partnerships & Systems Change
– Maintain strategic partnerships in high-penetration CareMessage regions, including Primary Care Associations, Clinically Integrated Networks, Accountable Care Organizations, and regional health networks.
– Ensure partners are enabled to effectively support downstream clinics and member organizations.
– Collaborate with Strategy, Sales, and Product to align partner engagement models and track partner adoption, engagement, and health.
– Oversee customer and partner experiences for grant-funded and regionally coordinated programs, ensuring commitments, milestones, and outcomes are met.

V. Customer Programs & Enablement
– Own and continuously improve CareMessage Academy to ensure scalable, role-appropriate training for customers and partners.
– Partner with Product Marketing and Strategy to support adoption campaigns, education, and value storytelling.
– Ensure customer- and partner-facing teams have clear playbooks, tools, and best practices.

VI. Customer Experience Infrastructure, Insights & Reporting
– Own successful adoption and ongoing use of Gainsight across the organization.
– Define and monitor customer, partner, and program health frameworks, including engagement, adoption, risk signals, and lifecycle milestones.
– Ensure customer and partner data is accurate, actionable, and used consistently across teams.
– Regularly report on customer health, partner health, and grant-funded program health to executive leadership.
– Turn insights from customer visits, partner engagements, and conferences into recommendations that inform CX standards and cross-functional priorities.

Performance Indicators (KPIs)
– Customer and partner engagement metrics
– Time to Value (TTV)
– Trends in customer and partner health scores
– Customers served per CX team member (scalability ratio)
– CSAT, NPS, and qualitative feedback
– Gainsight adoption and data quality
– Grant-funded program milestone and outcome attainment
– Team engagement, retention, and development metrics

Requirements
– 8–12+ years of experience in Customer Experience, Customer Success, Partner Success, Professional Services, or related roles.
– Proven success as a people manager who develops strong teams, manages managers, and drives accountability and growth across cross-functional customer- or partner-facing groups.
– Strong background in lifecycle design, enablement, and health measurement for customers and partners.
– Experience implementing or operating CX platforms such as Gainsight, including health scoring, playbook automation, and digital engagement.
– Demonstrated ability to scale CX operations by increasing customer coverage without proportional headcount growth through process design, digital engagement, and automation.
– Experience overseeing multi-stakeholder or grant-funded programs with milestone-based accountability.
– Ability to lead through influence and partnership in complex organizations.
– Strong alignment with CareMessage’s mission to advance health equity.
– Willingness to travel regularly to maintain firsthand relationships with customers and partners and the broader safety-net ecosystem (typically 1–2 trips per month for a few days each).

Recommended Experiences
– Healthcare technology, SaaS, or regulated markets experience.
– Experience working with ecosystem partners such as FQHCs, Primary Care Associations, Clinically Integrated Networks, ACOs, or similar organizations.
– Familiarity with nonprofit, safety-net, or hybrid revenue models.
– Experience applying AI and automation to customer success workflows (e.g., AI health scoring, automated playbooks, digital-led onboarding) and using data analytics tools (e.g., Metabase, Looker).
– Background in scaling or transformation-stage organizations.
– Multiple years of CS management experience in a remote-first environment.

30 / 90 / 180 Day Objectives

30 Days
– Learn CareMessage’s product portfolio, customer segments, partner ecosystems, roadmap, and key user workflows.
– Conduct initial interviews with customers and partners across key segments and build relationships with external and internal stakeholders.
– Understand CareMessage’s customer success approach, pricing model, subsidy mechanics, and contract standards.
– Review customer, partner, and program health metrics, Gainsight usage, onboarding flows, and engagement models.
– Establish operating cadence with team members and cross-functional partners.
– Assess the current maturity of AI and digital engagement across CX workflows.

90 Days
– Fully own customer outcomes and customer operations.
– Set clear CX and partner success standards across onboarding, engagement, and success planning.
– Improve consistency and adoption of Gainsight across customer- and partner-facing teams.
– Strengthen CareMessage Academy programming for customers and partners.
– Launch or refine Customer Advisory Boards and partner feedback loops.
– Deliver early improvements in engagement, time to value, and health indicators.
– Identify and begin implementing the first AI/digital engagement pilot (e.g., automated onboarding sequences, AI-assisted health scoring).

180 Days
– Demonstrate measurable improvements in customer and partner engagement, CSAT, TTV, and health scores.
– Institutionalize scalable CX, partner success, and grant program oversight processes.
– Build durable feedback loops with Product, Marketing, Clinical, Sales, Strategy, and Philanthropy.
– Show progress on non-linear scaling by improving customers per team member through digital and AI-augmented workflows.
– Influence annual planning inputs using data-driven CX and partnership insights.
– Operate as the clear owner of customer, partner, and program experience health across the organization.

Compensation
– This is a Director-level (L4) role, equivalent to a senior people leader who has progressively increased responsibility across customer experience, customer success, or services leadership—driving greater ownership, influence, and impact on teams, systems, and customer outcomes.
– Starting base salary is $172,189 per year (50th percentile). If expectations are met, compensation automatically increases to the 65th percentile ($198,476/year) at six months.
– No variable compensation or bonus is included. Because the Director of Customer Experience does not own the Net Revenue Retention target, compensation is base salary only.

Note: If you do not meet every listed qualification (especially if your background is under-represented), but you have held senior or director-level roles in customer experience, customer success, or services leadership, we strongly encourage you to apply.

We believe in equal pay for equal work. Team members in the same role and level are paid the same regardless of geographic location.

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