Director of Customer Experience at caremessage

Who We’re Looking For We are hiring a Director of Customer Experience (L4) to own the quality, consistency, and effectiveness of the CareMessage experience across customers, partners, and grant-funded programs. This role is responsible for ensuring that customers and ecosystem partners are successfully onboarded, engaged, supported, and enabled to realize value from the platform, with a strong focus on adoption, time to value, and long-term health. This is a senior people-management and systems-leadership role. The Director of Customer Experience leads multiple customer-facing functions and programs, including Professional Services, Customer Success across segments, Workforce Enablement, Partner Success, and core CX infrastructure such as Gainsight, CareMessage Academy, and Customer Advisory Boards. While this role does not own renewals or expansion revenue, it plays a critical role in supporting Net Revenue Retention and philanthropic accountability by ensuring customers, partners, and grant-funded programs are healthy, engaged, and meeting their intended outcomes. Equally important: we need a leader who will help CareMessage scale its CX function non-linearly—growing our ability to serve more customers per team member through thoughtful use of digital engagement, AI-augmented workflows, and scalable enablement infrastructure. The best modern CX leaders are building systems where AI handles routine interactions and surfaces insights, freeing human team members to focus on high-impact, relationship-driven moments. We expect this person to bring that mindset to CareMessage. This role partners closely with Revenue (Sales & Partnerships), Product, Engineering, Design, Product Marketing, Clinical, Strategy, and Philanthropy and reports into the CEO. Who You Are You are, first and foremost, an exceptional people manager and leader. You know how to build, coach, and hold teams accountable in ways that produce 1+1=3 outcomes. 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 rigor directly influence customer health, partner success, and retention. You are comfortable managing both people managers and individual contributors and know how to create clarity, consistency, and accountability across diverse customer and partner segments. You genuinely love our customers—the safety-net clinics, FQHCs, free and charitable clinics, Tribal Health organizations, and partner networks—and the patients they serve. You are deeply motivated by health equity and believe technology should close gaps in access, outcomes, and social drivers of health. You understand that the organizations we serve are often resource-constrained, 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 maintain and deepen key strategic partnerships where CareMessage is highly penetrated, including Primary Care Associations, Clinically Integrated Networks, Accountable Care Organizations, and regional networks—particularly in geographies where healthcare disparities are most concentrated. You see 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-led 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 the Professional Services, Customer Success, Workforce Success, and Customer Enablement functions. • Coach and develop managers and ICs, setting clear expectations, priorities, and performance standards that drive accountability and growth. • Build a culture of accountability, empathy, and continuous operational improvement across all customer- and partner-facing teams. • Design onboarding, ramp, and ongoing training for team members that enables scalable, consistent delivery. • Drive execution of departmental operating plans, translating company and CX priorities into clear goals, sequencing, and accountability. • Lead and support iteration of organizational policies on recruiting, hiring, and onboarding with attention to diversity, equity, inclusion, accessibility, and belonging. • Conduct skip-level 1:1s and ensure consistent feedback and performance review practices across the department. II. Customer & Partner Experience Strategy • Own the end-to-end experience across customers and ecosystem partners, ensuring a consistent, high-quality journey from onboarding through renewal. • Define and maintain lifecycle standards for customers and partners, including onboarding, engagement cadence, success planning, and health monitoring. • Ensure a consistent, high-quality experience across FQHCs, Free and Charitable Clinics, Tribal Health organizations, and partner-led networks. • Visit customers, partners, and regional networks and attend relevant industry conferences and convenings to maintain direct, firsthand understanding of the customer and partner experience. • Partner with Sales to support Net Revenue Retention through strong customer and partner health, readiness, and engagement. III. Scalable CX & AI-Augmented Operations • Drive non-linear scaling of the CX function: grow 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 customer lifecycle—from automated health scoring and risk detection to digital onboarding sequences and proactive outreach. • Design engagement models that blend high-touch, low-touch, and digital-led motions appropriate to customer segment, maturity, and complexity. • Build repeatable processes and playbooks that drive consistently strong customer experience at scale, in alignment with CareMessage’s product-driven approach. IV. Strategic Partnerships & Systems Change • Maintain strategic partnerships in high-penetration CareMessage states, including Primary Care Associations (PCAs), Clinically Integrated Networks (CINs), Accountable Care Organizations (ACOs), and regional health networks. • Ensure partners are enabled to effectively support their 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 experience for grant-funded and regionally coordinated programs, ensuring commitments, milestones, and outcomes are met. V. Customer Programs & Enablement • Own and evolve CareMessage Academy, ensuring scalable, role-appropriate training and enablement for customers and partners. • Collaborate with Product Marketing and Strategy to support adoption campaigns, education, and value storytelling. • Ensure customer- and partner-facing teams are equipped with clear playbooks, tools, and best practices. VI. Customer Experience Infrastructure, Insights & Reporting • Own the 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 consistently used across teams. • Regularly report on customer health, partner health, and grant-funded program health to executive leadership. • Synthesize insights from customer visits, partner engagements, and conferences into actionable recommendations that inform CX standards and cross-functional priorities. Performance Indicators (KPIs) • Customer and partner engagement metrics • Time to Value (TTV) • Customer and Partner Health Score trends • 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 track record as a people manager who develops high-performing teams, manages managers, and drives accountability and growth across cross-functional customer- or partner-facing teams. • Strong background in customer and partner lifecycle design, enablement, and health measurement. • Experience implementing or operating CX platforms such as Gainsight, including health scoring, playbook automation, and digital engagement. • Demonstrated ability to scale CX operations—growing 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. • Deep alignment with CareMessage’s mission to advance health equity. • Comfort with regular travel to maintain firsthand relationships with customers, 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 working with ecosystem partners such as FQHCs, Primary Care Associations, Clinically Integrated Networks, ACOs, or similar networks. • Familiarity with nonprofit, safety-net, or hybrid revenue models. • Experience applying AI and automation to customer success workflows (e.g., AI-powered health scoring, automated playbooks, digital-led onboarding) and data analytics tools (e.g. Metabase, Looker, etc.) • 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 • Master CareMessage’s product portfolio, customer segments, partner ecosystems, roadmap, and user workflows. • Conduct initial customer and partner interviews across key segments; build relationships with customers, partners, and internal stakeholders. • Learn CareMessage’s customer success motion, pricing models, 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 state of AI and digital engagement maturity across CX workflows. 90 Days • Fully own customer outcomes and customer operations. • Establish 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, TTV, and health indicators. • Identify and begin implementing the first AI/digital engagement pilot (e.g., automated onboarding sequences, AI-assisted health scoring) etc. 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. • Establish durable feedback loops with Product, Marketing, Clinical, Sales, Strategy, and Philanthropy. • Show measurable progress on non-linear scaling: improved customers-per-team-member ratio through digital and AI-augmented workflows. • Influence annual planning inputs with data-driven CX and partnership insights. • Operate as the clear owner of customer, partner, and program experience health across the organization. Note: If you don’t meet every qualification listed (especially if you come from an under-represented background) but have held senior or director-level customer experience, customer success, or services leadership roles in the past, we strongly encourage you to apply. We believe in equal work for equal pay. All team members performing the same role at the same level are paid the same, regardless of geographic location.