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

As a Data Entry Specialist, you will play a key role in ensuring the accuracy, completeness, and integrity of our operational data. You will enter information across multiple systems to support claims, member services, and business operations. Your attention to detail and commitment to quality will help ensure the data that powers our business is reliable and actionable. This role is ideal for someone who thrives in a fast-paced environment, enjoys organization and accuracy, and takes pride in getting the details right.

Job Responsibilities

• Enter and verify data: Accurately input claim, member, and operational information into internal proprietary systems

• Maintain data integrity: Regularly review and validate data for accuracy, completeness, and consistency

• Manage workload effectively: Prioritize tasks to meet daily, weekly, and monthly data entry targets

• Identify and correct errors: Detect discrepancies and work with team members or leadership to resolve issues quickly 

• Ensure compliance: Adhere strictly to confidentiality, compliance, and data security guidelines (e.g., HIPAA)

• Contribute to process improvements: Provide feedback on workflow efficiency and opportunities to automate or simplify tasks

• Collaborate with team members: Share knowledge, support peers, and help maintain a positive, team-oriented work environment

Job Requirements

• 1–3 years of experience in data entry, administrative support, healthcare operations, or a high-volume production environment (preferred)

• Demonstrated ability to meet measurable productivity and accuracy standards. 

• Member-first mindset, recognizing that claim accuracy, turnaround time, and responsible ownership directly affect members’ access to care and financial wellbeing. 

• Strong attention to detail with the ability to maintain accuracy while working at pace. 

• Comfort working in environments where performance metrics are monitored and reviewed regularly. 

• Dependable, self-motivated, and able to work independently in a remote environment while maintaining consistent output. 

• High level of discretion and professionalism when handling sensitive information. 

Why You'll Love Working at Sidecar Health

At Sidecar Health, you will be part of a mission-driven company redefining health insurance and building a more transparent, member-first experience. The work you do directly impacts our members’ access to care and financial wellbeing.

You will collaborate with a supportive, high-performing team that values accountability, ownership, and continuous improvement. We believe in developing our people and creating clear pathways for growth across data operations, claims, and analytics.

 What You'll Get

• Competitive hourly compensation and equity opportunities
• Medical, Dental, and Vision benefits with no waiting period
• Paid vacation and company holidays
• Company-provided IT equipment (laptop, monitors)
• Ongoing opportunities for professional development and career advancement

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. The current expected hourly rate for this position is $19.00 - $22.00.