Sidecar Health is a healthcare technology company focused on delivering transparent, cash-pay insurance plans. The organization employs roughly 160 people and has added about 25 new team members while 14 employees departed, resulting in steady net growth. This hiring activity points to ongoing investment in both product development and customer-facing roles as the insurer scales its offering.
Sales and Support is the largest group at Sidecar Health with 39 employees, closely followed by Engineering at 38; together they account for nearly half of the workforce. Marketing and Product contribute another 25 employees, reflecting the company’s emphasis on market education and user experience. Finance & Administration and Business Management collectively employ 29 professionals, supporting compliance and strategic planning. Lean teams in Operations, Human Resources, IT, Legal, and other functions round out the staff, ensuring the business runs smoothly without significant overhead.
Sidecar Health’s talent base is distributed across the United States, with its largest in-office presence in Los Angeles at 29 employees. Additional hubs include Salt Lake City, Columbus, and San Francisco, each maintaining single-digit to low-teens headcounts. Smaller clusters operate in Seattle, Dallas–Fort Worth, Boston, Miami–Fort Lauderdale, and Chicago. A sizable contingent of about 87 employees works from other or fully remote locations, underscoring the company’s flexible, distributed work model.