Sidecar Health is redefining health insurance. Our mission is to make excellent healthcare affordable and attainable 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 Vice President of Finance, you’ll play a critical role in shaping the financial strategy and operational foundation of Sidecar Health as we scale. You’ll lead all aspects of FP&A, partner closely with senior leadership, and help guide the company through key milestones — including potential IPO readiness and capital planning. This is a highly visible role with significant impact on our long-term growth, financial discipline, and organizational success.
What You’ll Do
- Lead the company’s Financial Planning, Reporting & Analysis (FP&A) function, including annual budgeting, monthly forecasting, long-term strategic planning, and advanced financial modeling
- Partner with the CFO, Controller, and Executive Leadership Team to develop and execute financial strategies that fuel company growth and drive operational efficiency
- Play a key leadership role in IPO readiness, including S-1 preparation, internal controls development, audit preparedness, and investor-facing financial materials
- Build and scale a high-performing finance team, ensuring operational excellence, cross-functional alignment, and a strong internal control environment
- Serve as a thought partner to functional leaders, providing financial insights that shape business strategy, support decision-making, and optimize capital deployment
- Lead the development of scalable financial infrastructure, systems, and reporting frameworks to support a high-growth, potentially public company
- Oversee capital allocation, cash flow management, scenario planning, and financial risk mitigation strategies
- Ensure accurate and timely financial reporting in compliance with GAAP and other relevant standards
- Support fundraising and investor relations efforts, including financial due diligence and board communications
- Foster a culture of transparency, accountability, and continuous improvement across the finance organization
What You’ll Bring
- 10+ years of progressive finance experience, including at least 5 years in a senior leadership role within a growth-stage or public company
- Proven experience leading FP&A and financial strategy, including taking a company through a successful IPO or public filing process
- Track record of capital raising through private equity, venture capital, or public markets
- Deep understanding of corporate finance, FP&A, healthcare financial metrics, and public company readiness
- Demonstrated success building and leading high-performing teams in fast-paced, evolving environments
- Exceptional communication and executive presence — able to influence at the highest levels of the organization and communicate financial strategy clearly
- Hands-on, strategic thinker with a strong bias for action and problem-solving mindset
- Experience with financial systems implementation and process optimization
What You'll Get
- Competitive salary, bonus opportunity, 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.
Skills Required
- 10+ years of progressive finance experience
- At least 5 years in a senior leadership role within a growth-stage or public company
- Experience leading FP&A and financial strategy
- Experience taking a company through a successful IPO or public filing process
- Track record of capital raising through private equity, venture capital, or public markets
- Deep understanding of corporate finance, FP&A, healthcare financial metrics, and public company readiness
- Success building and leading high-performing teams in fast-paced environments
- Exceptional communication and executive presence
- Strategic thinking, hands-on approach, bias for action, and problem-solving ability
- Experience with financial systems implementation and process optimization
Sidecar Health Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Sidecar Health and has not been reviewed or approved by Sidecar Health.
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Fair & Transparent Compensation — Compensation in tech and product roles is described as market‑aligned and competitive. Feedback suggests many in these functions feel total pay stacks up well against peers.
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Healthcare Strength — Employer‑paid major‑medical coverage for employees and family is highlighted, positioning health benefits as a strong component of total rewards. Feedback suggests low denial rates, added navigation tools, and center‑of‑excellence partnerships reinforce the plan’s practical value.
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Equity Value & Accessibility — Total rewards are presented to include stock options and bonuses in addition to salary. Feedback suggests these elements can meaningfully enhance perceived upside beyond base pay.
Sidecar Health Insights
What We Do
Sidecar Health is changing the health industry with modern, common-sense health insurance that finally gives consumers control over costs and choices. We are a passionate group of people-people on a mission to make quality healthcare affordable and accessible for everyone.
Why Work With Us
Being a growth-stage distributed startup, transparent and asynchronous communication is critical. We'll provide you with the resources and tools you need, and regularly seek your feedback through quarterly engagement pulses on what is or isn't working well.
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