Head of Member Experience
Sidecar Health is redefining health insurance. Our mission is to make excellent healthcare affordable and attainable for everyone. We know that to accomplish this lofty mission, we need driven people who will make things happen.
The passionate people who make up Sidecar Health’s team come from all over, with backgrounds as tech leaders, policy makers, healthcare professionals, and beyond. And they all have one thing in common—the desire to fix a broken system and make it more personalized, affordable, and transparent.
If you want to use your talents to transform healthcare in the United States, come join us!
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
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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
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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
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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
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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
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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
Sidecar Health is an Equal Opportunity employer committed to building a diverse team. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status or disability status.
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