Not SpecifiedCompensation
Senior (5 to 8 years)Experience Level
Full TimeJob Type
UnknownVisa
Financial Services, Health Insurance, HealthcareIndustries

Position Overview

  • Location Type: [Not Specified]
  • Employment Type: [Not Specified]
  • Salary: [Not Specified]

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.

Responsibilities

  • 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.

Requirements

  • 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.

Company Information

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!

Skills

Financial Planning and Analysis
Budgeting
Forecasting
Financial Modeling
Strategic Planning
Internal Controls
Audit Preparedness
Investor Relations
Financial Reporting
Capital Allocation
Cash Flow Management
Scenario Planning
Risk Mitigation
Financial Infrastructure
Systems and Reporting Frameworks

Sidecar Health

Affordable health insurance with price transparency

About Sidecar Health

Sidecar Health provides health insurance plans that focus on affordability and transparency, including options compliant with the Affordable Care Act (ACA). The company allows members to see average cash prices for medical services upfront, helping them make informed decisions and avoid unexpected costs. Revenue is generated through member premiums, which cover medical expenses, while also benefiting from the difference between negotiated cash prices and premiums. Sidecar Health's goal is to empower members to take control of their healthcare expenses with straightforward and cost-effective insurance options.

El Segundo, CaliforniaHeadquarters
2018Year Founded
$319.1MTotal Funding
SERIES_DCompany Stage
Financial Services, HealthcareIndustries
201-500Employees

Benefits

Health Insurance
Dental Insurance
Vision Insurance
401(k) Retirement Plan
Paid Vacation
Paid Holidays
Stock Options
Company Equity

Risks

Increased competition from similar insurtech companies may erode market share.
Regulatory scrutiny on cash pay models could pose compliance challenges.
Economic downturns might reduce consumer spending on health insurance premiums.

Differentiation

Sidecar Health offers transparent pricing, empowering members with upfront healthcare cost information.
The company provides customizable plans, aligning with individual coverage needs and budgets.
Partnerships with institutions like Ohio State University enhance their fixed-price care model.

Upsides

Recent $165M Series D funding supports expansion and innovation in health insurance.
Partnership with Mark Cuban Cost Plus Drug Company lowers prescription drug costs for members.
ACA-compliant product line expansion increases market reach and consumer options.

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