Sidecar Health

• Serve as the primary liaison for existing groups, maintaining positive relationships, and driving group satisfaction and retention • Attend virtual and in-person client meetings across Florida to build relationships with groups, conduct education meetings, and provide enrollment support • Lead renewal discussions, including negotiating terms and pricing to drive retention while balancing business objectives and client needs • Proactively identify potential obstacles to group success and collaborate with internal teams to develop strategic solutions • Collaborate closely with internal teams to ensure seamless implementation and optimize the group experience • Oversee resolution of escalated issues by responding swiftly and managing client inquiries, concerns, and requests • Be a part of a cutting-edge, fast-growing team

• Lead product strategy and execution for AI-powered member experiences • Define how and where AI capabilities should be applied across the member journey • Own product roadmaps for AI-driven features • Design human-in-the-loop workflows and fallback experiences • Define evaluation frameworks for AI product quality • Drive discovery and ideation for new AI-powered capabilities • Use data, experimentation, and user insights to measure AI feature performance • Partner with engineering and data science to scope AI initiatives • Lead a cross-functional pod of engineers, designers, and data scientists • Stay current on the rapidly evolving AI landscape

• Own end-to-end B2B demand generation strategy — from awareness through pipeline creation — across broker, consultant, and employer segments • Design and operate a content-driven ABM engine that targets high-value accounts with precision and scale • Build and manage a full ABM tech stack including intent data, account scoring, personalization, and orchestration tools • Partner closely with Sales and SDR leadership to ensure marketing programs translate directly into pipeline and revenue • Lead paid media strategy and execution across digital display, SEM, CTV, LinkedIn, and programmatic • Manage multimillion-dollar media budgets with a focus on measurable pipeline contribution and CAC efficiency • Continuously optimize channel mix and creative based on performance data • Develop a content strategy that supports every stage of the buyer journey — from first touch to close — with assets built for broker, Regional Sales Manager (RSM), and employer audiences • Build and own SDR sequences and marketing nurture programs that keep prospects engaged across long sales cycles • Own website strategy and optimization, including conversion rate improvement and intent-signal activation • Champion the use of modern AI tools across the function — from content production to campaign optimization to intent signal analysis • Maintain and evolve the marketing tech stack to ensure the team is operating with best-in-class tools and workflows • Lead and develop a high-performing marketing team that executes across channels with speed and accountability • Define team structure, role scope, and future hiring needs as the company scales • Report to the CMO; partner closely with Sales, Product, and Operations leadership.

• Build & Lead a High-Performance Claims Operation • Lead and scale a multidisciplinary Claims Operations team — spanning claims adjudication, quality, operations, and clinical — to drive accurate, timely claims processing and an exceptional member experience • Foster a culture of metrics-driven continuous improvement, accountability, and high performance across all Claims functions • Develop future leaders within the team and build the bench for a growing, complex operation • Drive AI, Automation, and Operational Transformation • Identify, prioritize, and lead automation that meaningfully increases end-to-end auto-adjudication rate, reduces claims processing time, and improves quality / accuracy • Partner with Product and Engineering to shape the roadmap for claims technology — acting as a strategic voice, not just an operator • Lead change management efforts as the team adopts new tools, workflows, and ways of working • Build and maintain governance structures that support scalable, compliant, and data-informed operations • Own Claims Strategy & Business Outcomes • Align claims operations with Sidecar Health's broader business objectives — including continued growth, sustainable MLR, and an obsessive focus on member experience • Drive payment accuracy, fraud prevention, and claims spend optimization through proactive stakeholder management and cross-functional initiatives • Translate operational data into strategic insights and recommendations for senior leadership • Mitigate operational and regulatory risk while maintaining full compliance with healthcare regulations • Own budget development and resource allocation, ensuring alignment with organizational priorities

• Visit clients onsite across Ohio and support members in navigating their Sidecar Health plans • Act as in-person support for client groups and members after enrollment • Assist our Account Management team in identifying and establishing relationships • Work in a traditional member care capacity, answering calls, responding to web chats and/or emails • Provide excellent customer service in a timely and positive manner • Build rapport and maintain positive relationships with existing members

• Own the end-to-end new hire onboarding experience for assigned operations teams — program design, content creation, classroom delivery, nesting coordination, job shadowing, and floor readiness evaluation • Design and facilitate ongoing refresher, upskilling, and process change training as business needs evolve • Build and maintain all training materials for assigned teams — e-learning modules, facilitator guides, presentations, knowledge checks, role-play scenarios, and assessments • Own operations-specific knowledge content within the knowledge management system, ensuring accuracy and alignment with current policies, workflows, and product changes • Assess the training and knowledge impact of operational and product changes as they come through, and proactively develop or update materials to support those changes • Manage all program logistics independently: LMS administration, scheduling, roster management, Zoom coordination, and SME preparation and briefing • Coordinate SME and supervisor involvement in training programs — providing clear direction and session context so their contributions are set up for impact • Evaluate training effectiveness through assessment data, QA results, nesting observations, and supervisor feedback — and act on gaps proactively • Develop and maintain coverage plans and program documentation so training continuity is never dependent on a single person's availability • Collaborate with the broader Enablement team on knowledge management, L&D initiatives, and operational content projects • Use AI-assisted tools to develop content efficiently, with full accountability for review and quality of all outputs.

Role Description Our Member Care team is at the forefront of our business. Their role is easily the most important: supporting our members on their healthcare journeys. We're growing our team and looking for warm, passionate people to join us and help deliver the best experience in healthcare. Your job will be to help our members - to answer their questions, help them solve problems, and ensure they have access to the care they need. As a startup, there is no shortage of opportunities, responsibilities, and growth! You'll work alongside a dynamic team that is disrupting the healthcare industry and having a positive and meaningful impact on our members' lives every day. Job Responsibilities - Handle inbound calls and chat boxes from our members in regard to Sidecar Health’s products and services - Provide excellent customer service in a timely and positive manner - Build rapport and maintain positive relationships with existing members to understand their needs and ensure a memorable member experience - Handle issues and complaints where appropriate - Maintain policies and standard operation procedures Qualifications - Education: High school diploma or equivalent required; bachelor’s degree preferred - Bilingual in English and Spanish (preferred) - Experience in healthcare or insurance (preferred) Requirements - Adaptable and resilient - you thrive in a fast-moving, ever-changing startup environment - People-first communicator - you listen with empathy, connect easily, and meet members where they are - Clear and confident in both written and spoken communication, with the ability to answer questions in the moment - Detail-oriented problem solver - you spot the small things and think creatively to help members navigate their plans - Available for one or more of these shifts options (Eastern Standard Time): - Monday–Friday: 10:00 AM – 6:30 PM - Monday–Friday: 11:00 AM – 7:30 PM - Monday–Friday: 11:30 AM – 8:00 PM - Monday–Friday: 8:00 AM - 12:00 PM and 4:00 PM - 8:00 PM - Saturday–Sunday: 9:00 AM – 5:00 PM and Monday–Wednesday: 10:30 AM -7:00 PM (Off Thursday & Friday) Benefits - Competitive hourly wage ($19.00) - Fully paid Sidecar Health medical, dental, and vision - coverage for you and your whole family, on us - 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. Company Description 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!

• Design and own high-throughput, distributed data pipelines and platform infrastructure from concept through production • Decompose large, ambiguous initiatives into structured, executable plans that the team can move on in parallel • Write production-grade Python — strongly typed, well-structured, and built to last — not scripts or notebooks • Optimize SQL at scale: query tuning, data modeling, and understanding execution plans • Architect across boundaries — defining contracts between frontend, backend services, and infrastructure • Be a technical resource and mentor for junior engineers, and partner directly with leadership on roadmap and technical decisions • Instrument systems for observability — knowing what to monitor, not just how to read a dashboard

• Design, build, and own scalable backend services and APIs that handle complex healthcare data and workflows • Optimize database queries and data models to ensure system performance and reliability at scale • Evaluate and articulate technical tradeoffs across system design, performance, and maintainability • Integrate AI tools and agentic coding patterns into backend workflows where they add real value • Write clean, well-tested, production-grade code with a high bar for quality • Partner with product, data, and cross-functional stakeholders to translate requirements into robust technical solutions • Contribute to engineering standards through code reviews, technical discussion, and better defaults

• Build and ship full-stack features end-to-end, from backend APIs to polished member-facing UI • Design scalable systems and make deliberate architectural tradeoffs between performance, maintainability, and speed to ship • Integrate AI tools and LLM APIs into product workflows where they add real value • Write clean, well-tested, production-grade code with a high bar for quality • Partner with product, design, and stakeholders across the business to translate requirements into great software • Contribute to engineering standards through code reviews, technical discussion, and better defaults