About the Role 

The Head of Member Experience will play a pivotal role in shaping and executing our member and customer strategies. Reporting directly to our Co-founder/COO, this leader will drive satisfaction, loyalty, and advocacy by championing the voice of our members and customers. Leveraging data, insights, and cross-functional collaboration, they’ll enhance engagement, optimize processes, and partner with product teams to prioritize innovation aligned with member sentiment and business objectives.

What You’ll Do 

• Set the Strategic Vision for the Sidecar Health Experience:

  • 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

• Architect and Optimize the End-to-End Experience:

  • 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

• Drive Cross-Functional Alignment and Execution:

  • 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

• Generate Insights and Drive Continuous Improvement:

  • 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

• Champion a Member-Centric Culture Across the Organization:

  • 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
    
    

What You’ll Bring 

• 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

What You'll Get

• 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