Head of Member Experience

Summary

Join Sidecar Health as the Head of Member Experience and play a pivotal role in shaping and executing member and customer strategies. Reporting to the Co-founder/COO, you will drive satisfaction, loyalty, and advocacy by championing the member voice. Leveraging data and cross-functional collaboration, you'll enhance engagement, optimize processes, and partner with product teams to prioritize innovation. You will set the strategic vision, architect and optimize the end-to-end experience, drive cross-functional alignment and execution, generate insights and drive continuous improvement, and champion a member-centric culture. This leadership role requires extensive experience in customer/member experience strategy and execution, data analysis, and cross-functional team management within the healthcare industry.

Requirements

• 10+ years of experience leading customer/member experience strategy and execution, with a proven track record of driving measurable improvements in customer satisfaction, loyalty, and advocacy
• Demonstrated ability to build and execute multi-year strategic roadmaps aligned with business goals, balancing long-term vision with short-term execution
• Expertise in using data, analytics, and customer insights to drive decisions, measure outcomes, and continuously improve member satisfaction metrics (e.g., NPS, CSAT, customer retention rates)
• Experience designing and optimizing end-to-end customer/member journeys, including creating detailed service blueprints and process workflows to improve efficiency and reduce friction points
• Familiarity with CX tools, automation platforms, and analytics software (e.g., Salesforce, Zendesk, Qualtrics) to monitor and enhance the customer experience
• Strong ability to lead cross-functional initiatives, aligning teams across Product, Marketing, Sales, and Operations to deliver on member experience goals
• Proven success in driving cultural and operational change within an organization to prioritize customer-centric strategies
• Experience implementing scalable systems and processes that support rapid growth while maintaining high levels of member satisfaction
• Experience building, mentoring, and scaling high-performing teams focused on member success and experience
• Knowledge of healthcare regulations and compliance requirements to ensure all member experience initiatives meet industry standards

Responsibilities

• Define and drive both near-term and long-term member experience roadmaps aligned with business goals
• Ensure teams across the company integrate member experience priorities into their annual strategies and plans
• Anticipate evolving member needs and position Sidecar Health to exceed expectations
• Analyze current customer and member journeys, identifying opportunities for improvement with clear problem statements
• Design and iterate on ideal future-state member experiences, supported by robust service blueprints
• Lead cross-functional collaboration to prioritize impactful initiatives using data-driven insights
• Leverage emerging technologies and automation tools to enhance efficiency and innovation
• Socialize prioritized member experience initiatives across teams to ensure alignment and support
• Translate strategic insights into actionable roadmaps for cross-functional teams
• Partner closely with frontline teams (Marketing, Sales, Operations) to enable optimal member experiences through training, automation tools, and pilot programs
• Collaborate with Product teams to influence roadmap priorities and enhance features that directly improve member satisfaction
• Develop and deliver executional resources, including playbooks and guidelines, for seamless alignment across teams
• Establish and monitor KPIs to measure and optimize member experience
• Build robust tracking and reporting systems to validate strategies and inform decisions
• Create ongoing feedback loops to capture, analyze, and act on member insights
• Develop actionable dashboards and learning reports to surface key opportunities across the journey
• Serve as the "Voice of the Customer," ensuring member needs are central to decision-making
• Partner with the People Team to foster a culture of member-centricity within the employee experience
• Advocate for member-first initiatives at all levels of the organization

Benefits

• Competitive salary, bonus opportunity, and equity package
• Comprehensive Medical, Dental, and Vision benefits
• A 401k retirement plan
• Paid vacation and company holidays
• Opportunity to make an impact at a rapidly growing mission-driven company transforming healthcare in the U.S