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 

Sidecar Health is looking for a People Operations & Employee Experience Coordinator to join a small, high-impact People team reporting directly to the Chief People Officer. This is not a task-executor role - it is a builder role for someone early in their career who wants to own culture and connection programs, sharpen processes, and help shape what it feels like to work at Sidecar Health. If you have seen best-in-class People practices at a tech company and want to bring those instincts somewhere they will matter immediately, please read on! 

What You'll Do 

• Serve as a primary point of contact for employee questions and requests, triaging the shared People inbox and resolving issues quickly and accurately 
• Partner with the CPO and existing People Operations team member to maintain HR systems, ensure data accuracy, and support onboarding and offboarding logistics 
• Build and manage our employee engagement programs, virtual connection rituals, and company events that build culture across a distributed workforce 
• Audit the end-to-end onboarding process, map every manual step and friction point, and present a concrete improvement plan that incorporates AI and automation opportunities 

What you will grow into 

• Own and continuously iterate on company-wide culture and engagement initiatives — from recurring employee rituals to in-person offsites and leadership meetings — so that connection and belonging are a core part of our culture 
• Drive process design and optimization across People Operations, identifying opportunities to leverage AI and automation to reduce manual work and improve the employee experience at every touchpoint 
• Provide polished executive support — scheduling, coordination, and professional communications — for senior leadership while remaining primarily anchored in People Operations and culture-building rather than administration 

What You'll Bring 

• 1–2+ years in a People or HR function at a technology company, where you absorbed what great employee experience looks like in practice 
• A track record of designing or improving processes independently — not just following them — including comfort using AI or automation to eliminate manual work 
• Exceptional written and verbal communication skills, polished enough to work directly with senior executives and clear enough to connect with employees across every level 
• A self-starter mindset: you identify gaps, propose solutions, and take ownership without waiting to be asked 
• Genuine enthusiasm for building culture and human connection, especially in a distributed or remote-first environment 

Nice to have 

• Experience at a remote-first or distributed tech company where you have built virtual connection programs or engagement rituals from scratch 
• Exposure to program management frameworks or tools that help you track and deliver cross-functional initiatives 
• Familiarity with People Operations platforms and HRIS tools used in high-growth tech environments 
• A track record of introducing new people programs or culture initiatives rather than simply maintaining inherited ones 

What You'll Get 

• Competitive salary, annual bonus opportunity, and an equity package 
• Medical coverage from day one, with 100% of the premium paid by Sidecar for you and your dependents. Choose an HSA-eligible plan or a $0 deductible plan 
• Dental and vision with 100% of your premium covered, and 80% covered for your dependents 
• A 401(k) retirement plan 
• Paid vacation, company holidays, and paid parental leave 
• The opportunity to make an impact at a rapidly growing, mission-driven company transforming healthcare in the U.S.