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.
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.
Sidecar Health Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Sidecar Health and has not been reviewed or approved by Sidecar Health.
-
Fair & Transparent Compensation — Compensation in tech and product roles is described as market‑aligned and competitive. Feedback suggests many in these functions feel total pay stacks up well against peers.
-
Healthcare Strength — Employer‑paid major‑medical coverage for employees and family is highlighted, positioning health benefits as a strong component of total rewards. Feedback suggests low denial rates, added navigation tools, and center‑of‑excellence partnerships reinforce the plan’s practical value.
-
Equity Value & Accessibility — Total rewards are presented to include stock options and bonuses in addition to salary. Feedback suggests these elements can meaningfully enhance perceived upside beyond base pay.
Sidecar Health Insights
Similar Jobs
What We Do
Sidecar Health is changing the health industry with modern, common-sense health insurance that finally gives consumers control over costs and choices. We are a passionate group of people-people on a mission to make quality healthcare affordable and accessible for everyone.
Why Work With Us
Being a growth-stage distributed startup, transparent and asynchronous communication is critical. We'll provide you with the resources and tools you need, and regularly seek your feedback through quarterly engagement pulses on what is or isn't working well.
Gallery
