Sidecar Health is redefining health insurance. Our mission is to make excellent healthcare affordable and accessible 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

We're seeking for a Director of Quality and Continuous Improvement who can lead from both ends of the strategy-to-execution spectrum. The role is structured around two distinct functions: (1) overhauling how we approach quality assurance, leveraging AI and speech analytics to shift from manual, sample-based review to continuous, intelligent insights; and (2) converting those signals into action across the organization — whether through training, documentation and SOPs, or broader cross-functional process improvement.

The right person for this role thrives in both the strategic and tactical – presenting quality trends and risks to executive leadership while rolling up their sleeves to drive improvement initiatives from insight to implementation understanding what “good” looks like and how to build the systems, tools, and team to get there.

Key Responsibilities

Quality Strategy & AI Evolution (40%)

• Own the Quality evolution roadmap, including the transition from manual, sample-based evaluation to AI-powered scoring, automated coverage, and always-on quality insights
• Leverage AI, speech analytics, and interaction data to surface actionable coaching and process improvement opportunities
• Design and maintain quality scorecards, evaluation criteria, and calibration standards – leading sessions calibration sessions to ensure consistency across evaluators and time
• Perform deep-dive analysis on quality trends, complaints, and outliers, generating executive-level reports with actionable insights

Converting Insight into Action (30%)

• Design feedback loops connecting quality insight to action – whether that’s coaching, training updates, documentation changes, workflow updates, or technology needs
• Conduct structured root cause analysis on critical failures, escalations, and member complaint trends
• Build business cases for improvement initiatives with clear ROI projections and measurable impact
• Pilot and test new processes, workflows, and member interaction scripts before scaling; create and maintain SOPs and documentation standards

Team and Stakeholder Leadership (30%)

• Partner with the Member Services leadership team to define and execute a multi-year Quality Assurance and Continuous Improvement strategy aligned to company growth objectives
• Build, lead, and develop a team of QA analysts and continuous improvement practitioners including certification pathways, analyst development tracks, and Green/Black Belt mentorship
• Represent operational excellence in cross-functional forums, present findings, risks, and recommendations to executive leadership
• Champion a continuous improvement culture across Member Services, partnering with Operations, Technology, Product, Training, and Compliance on integrated initiatives
• Ensure compliance with healthcare regulations (HIPAA, CMS, state requirements), partner with Legal and Compliance teams on audit readiness, and lead corrective action plans

Required Qualifications

• 8-10 years of progressive experience in process excellence, quality management, or operational improvement, with 3-5 years in leadership roles
• Bachelor’s degree in business administration, Operations Management, Healthcare Administration, or related field
• Demonstrated application of methodology in a contact center or healthcare services environment
• Direct experience with quality monitoring, scorecards, contact center analytics, and coaching leaders with documented performance outcomes
• Hands-on experience directing or implementing AI-powered quality tools, speech analytics platforms, or automated scoring systems
• Demonstrated ability to translate quality analytics into business recommendations for executive audiences
• Understanding of healthcare regulations: HIPAA, ACA, CMS, and state insurance compliance requirements
• Strong executive presence with excellent facilitation, coaching, and communication skills across all organizational levels
• Analytical mindset with experience in statistical analysis and converting data into actionable operational decisions
• Bias toward action, rapid iteration, and an entrepreneurial approach to problem-solving

Preferred Qualifications

• Lean Six Sigma Green Belt or Black Belt strongly preferred
• Additional certifications in COPC, Project Management (PMP), or Change Management
• Experience in high-growth healthcare technology or insurtech with contact center operations background
• Familiarity with Genesys Cloud, or CRM-integrated quality tools

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 adopts a market-based approach to compensation, where base pay varies depending on location and is further influenced by job-related skills and experience.