---
title: 'VP of Strategic Accounts at Sidecar Health'
canonical: 'https://feeny.ai/job/vp-of-strategic-accounts-sidecar-health-remote-dx7xv2b9sj0n'
type: 'job'
last_seen: '2026-10-15'
---

# VP of Strategic Accounts at Sidecar Health

- **Company:** Sidecar Health
- **Location:** Remote
- **Work type:** remote
- **Posted:** 2026-03-30
- **Last confirmed live:** 2026-10-15
- **Apply:** https://job-boards.greenhouse.io/sidecarhealth/jobs/5840363004

## Job 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!

## About the Role

Sidecar Health is transforming how employers and their members experience healthcare — through transparent cash pricing, no provider networks, and meaningful cost savings. As we accelerate our enterprise growth, we are looking for a VP of Strategic Accounts to lead that charge. Reporting directly to the Market President of National and Strategic Accounts, this individual will own our enterprise sales strategy and execution at a pivotal moment for the company, with a pipeline of national accounts already in active evaluation.

## What You'll Do

- Develop and execute a comprehensive enterprise sales strategy to drive new business growth
- Set and achieve ambitious revenue targets, with a focus on net-new client acquisition
- Identify and pursue opportunities within jumbo and national employer groups
- Build and scale a repeatable, high-performing sales process
- Build and maintain strong relationships with brokers, consultants, and enterprise employer clients
- Partner with clients to understand their unique needs and work with internal teams to tailor solutions accordingly
- Serve as a trusted advisor on health plan solutions and benefits strategy
- Stay informed about industry trends, competitor offerings, and regulatory changes
- Collaborate with product and marketing teams to refine offerings based on market feedback and client insights
- Partner with finance, operations, and member experience teams to ensure seamless client onboarding and ongoing support
- Provide input on pricing strategies, service enhancements, and value propositions

## What You'll Bring

- 10+ years of experience in health insurance or employee benefits sales, with a strong focus on jumbo/national employer groups
- Proven track record of securing enterprise clients and driving significant revenue growth
- Strong network within the broker/consultant community and with benefits leaders at large organizations
- Exceptional communication, negotiation, and relationship-building skills
- Deep understanding of health plan products, self-funded and ASO models, and benefits administration
- Strategic thinker with the ability to balance long-term vision and short-term execution
- Experience in a high-growth, entrepreneurial environment is a plus
- Bachelor's degree required

## What You'll Get

- Competitive salary, uncapped incentive bonus, and equity package
- Comprehensive Medical, Dental, and Vision benefits
- 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.

Sidecar Health is an Equal Opportunity employer committed to building a diverse team. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status or disability status.

## About Sidecar Health

## Company Overview
- **One-liner**: Sidecar Health is a health insurance company that provides ACA-compliant, employer-sponsored major medical plans with transparent pricing and no provider networks.
- **Entity Type**: Private (Series D)
- **Headquarters**: Manhattan Beach, California, USA
- **Founded**: 2018
- **Founders**: Patrick Quigley (CEO) and Veronica Osetinsky (COO)

## Core Business
- **Primary industry**: Health Insurance / Healthcare Technology
- **Target customers**: B2B — Large employers (fully insured and self-funded/ASO groups); previously served individuals
- **Mission**: To make quality healthcare affordable and accessible for all by bringing price transparency and consumer choice to health insurance

## Products & Services
- **Sidecar Health Employer Plans**: ACA-compliant major medical coverage for large employers. The model provides members with transparent, upfront pricing on care, allows them to shop for services, and shares savings when they choose lower-cost providers. Members keep 50% of the difference between the plan’s typical local cost and what they actually spend. The company covers members in 46 states and partners with employers across 50 industries. Plans are available as fully insured and administrative services only (ASO) for self-funded employers. [sidecarhealth.com](https://www.sidecarhealth.com/)

## Market Standing
- **Valuation**: Not publicly disclosed
- **Key Metric – Total Funding**: $328M (across 4 rounds)
- **Annual Revenue**: $50M (estimated, per LinkedIn data) [linkedin.com](https://www.linkedin.com/company/sidecarhealth)
- **Notable Investors**: Koch Disruptive Technologies (led Series D), Drive Capital (led Series C), Cathay Innovation (led Series B), GreatPoint Ventures, Morpheus Ventures [linkedin.com](https://www.linkedin.com/company/sidecarhealth)
- **Notable Advisors/Board Members**: Anne Wojcicki (CEO & Co-Founder, 23andMe), Andrew Liveris (President, Brisbane 2032 Olympic Committee), The Honorable David J. Shulkin, M.D. (Former Secretary of Veterans Affairs), Adam Stavisky (Former Walmart SVP, US Benefits) [sidecarhealth.com](https://www.sidecarhealth.com/about-us)
- **Growth Signals**: Headcount grew 18.7% YoY to 202 employees; active job postings surged 466.7% monthly and 1600% quarterly; expanded large group employer plans from Ohio to Georgia (2023) and Florida (2024); launched ASO capabilities for self-funded national employers in 2025. [linkedin.com](https://www.linkedin.com/company/sidecarhealth)

## Competitive Advantages
- **No provider networks**: Members can see any doctor or use any facility, removing the limitations of traditional narrow networks.
- **Transparent pricing engine**: The company shows guaranteed, local costs for care upfront, enabling members to shop and compare.
- **Shared savings model**: A behavioral economics approach that incentivizes members to be cost-conscious, which the company claims lowers overall costs for the entire group.
- **Carrier ownership**: Sidecar Health established its own insurance carrier (Sidecar Health Insurance Company) in 2021, allowing it to underwrite its own products and control the full insurance stack.
- **High claims approval rate**: The company reports approving over 99% of claims. [linkedin.com](https://www.linkedin.com/company/sidecarhealth)

## Strategic Focus
- **Shift to employer market**: After proving the model with individual plans, the company pivoted exclusively to employer-sponsored coverage, targeting large national employers.
- **Geographic expansion**: After launching in Ohio, the company expanded to Georgia and Florida, with a stated goal of covering members in 46 states.
- **Product breadth**: Offering both fully insured and ASO (self-funded) plans to capture different segments of the large employer market.
- **AI investment**: Actively hiring a Lead Product Manager, AI, signaling an investment in AI-powered capabilities. [job-boards.greenhouse.io](https://job-boards.greenhouse.io/sidecarhealth)

## Why Work Here
- **Mission-driven work**: The company is explicitly focused on fixing a broken healthcare system, which attracts talent from tech, policy, and healthcare backgrounds.
- **Remote-first culture**: All current open positions (engineering, product, marketing, sales, member care) are listed as remote. [job-boards.greenhouse.io](https://job-boards.greenhouse.io/sidecarhealth)
- **Strong ratings**: 4.2/5.0 on LinkedIn (117 reviews), with Culture rated 4.4 and Career rated 4.1. [linkedin.com](https://www.linkedin.com/company/sidecarhealth)
- **Growth trajectory**: With a recent $165M Series D, rapid job posting growth, and a headcount expansion of nearly 19% YoY, the company is in a scaling phase — offering advancement opportunities.
- **Diverse team composition**: Team members come from backgrounds as tech leaders, policymakers, and healthcare professionals. The company is an Equal Opportunity employer. [job-boards.greenhouse.io](https://job-boards.greenhouse.io/sidecarhealth)
- **Open roles (as of mid-2026)**: 17 active job postings including Senior Software Engineer (Backend/Full Stack), VP of Marketing, VP of Strategic Accounts, Director of Account Management, Lead Product Manager (AI), and more. [linkedin.com](https://www.linkedin.com/company/sidecarhealth)

## Sources
1. [sidecarhealth.com - About Us](https://www.sidecarhealth.com/about-us)
2. [sidecarhealth.com - Homepage](https://www.sidecarhealth.com/)
3. [job-boards.greenhouse.io - Sidecar Health Careers](https://job-boards.greenhouse.io/sidecarhealth)
4. [linkedin.com - Sidecar Health Company Profile](https://www.linkedin.com/company/sidecarhealth)

## Other roles at Sidecar Health

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- [Staff Software Engineer, Full Stack (Member Benefits)](https://feeny.ai/job/staff-software-engineer-full-stack-member-benefits-sidecar-health-remote-jed2cz2vjnqa)
- [Lead Product Manager, Claims Automation](https://feeny.ai/job/lead-product-manager-claims-automation-sidecar-health-remote-gekn6t8k2qvg)
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