Sidecar Health

Director of Account Management

8+ years in Account Management or Customer Success in insurance/healthcare; 4+ years in leadership; strong relationships with employer groups and brokers; systems thinker; excellent communicator; East Coast location preferred.

Head of Enterprise Sales

10+ years in health insurance or benefits sales with jumbo/national groups; proven enterprise client wins; strong broker/consultant network; excellent communication and negotiation; Bachelor's degree.

Lead Product Designer

Lead product designer with 7+ years of experience; responsible for end-to-end member and provider experiences, design system governance, and cross-functional leadership.

Senior Actuarial Analyst

Actuarial Analyst

4+ years actuarial experience; BS in Mathematics/Actuarial Science/Statistics/Economics; strong Excel; SQL/R/Python; interest in AI/ML; pursuing ASA; strong communication; balance accuracy with speed.

Senior AI Engineer

5+ years software engineering; production AI/ML experience; strong Python/TypeScript; experience with OpenAI/AWS Bedrock; LangChain/LangSmith/LlamaIndex; cloud infrastructure (AWS)

Regional Sales Manager, Large Group Plans (Dallas)

Regional Sales Manager

4+ years sales experience in healthcare/benefits; bachelor’s degree; proven ability to generate new opportunities; strong relationship-building; willing to travel up to 40% within Georgia.

Regional Sales Manager, Large Group Plans (Houston)

4+ years of sales in healthcare or related fields; Bachelor's degree; proven ability to generate new opportunities; strong relationship-building; willing to travel up to 40% within Texas.

Lead Product Manager

5+ years in product management, focus on search or data analytics, SQL, Agile/Scrum, strong UX sense.

Title	Location	Date
Director of Account Management Full Time · 8+ YOE United States · Remote	United States Remote	Apr 15, 2026
Head of Enterprise Sales Full Time · 10+ YOE United States · Remote	United States Remote	Mar 30, 2026
Lead Product Designer Full Time · $160K-$180K · 7+ YOE United States · Remote	United States Remote	Mar 6, 2026
Senior Actuarial Analyst Full Time · $110K-$130K · 4+ YOE United States · Remote	United States Remote	Feb 19, 2026
Senior AI Engineer Full Time · 5+ YOE United States · Remote	United States Remote	Feb 13, 2026
Regional Sales Manager, Large Group Plans (Dallas) Full Time · 4+ YOE United States · Remote	United States Remote	Jan 26, 2026
Regional Sales Manager, Large Group Plans (Houston) Full Time · 4+ YOE Houston, Texas, United States · Remote	Houston, Texas, United States Remote	Jan 26, 2026
Lead Product Manager Full Time · $160K-$180K · 5+ YOE United States · Remote	United States Remote	Nov 12, 2024

Activities	Health insurance provisionMedical payment processingPrice transparency softwareHealth benefit administrationDigital health platform
Headquarters	US
Industries	InsuranceHealth Care
Name	Sidecar Health
Employees	258
Type	Private
Tagline	Offers transparent health insurance plans and instant provider payment tools.
Founded	2,018
Website	sidecarhealth.com
Latest Funding Round	Series D
Latest Funding Year	2,024
Latest Funding Amount	165,000,000
Latest Investors	Koch Disruptive Technologies

Sidecar Health

About Sidecar Health