Sidecar Health

Senior Manager, Product Strategy and Operations

Remote

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

Position Overview

  • Location Type: Remote
  • Employment Type: Full-time
  • Salary: Not specified

Summary: Sidecar Health is seeking a Senior Manager, Product Strategy & Operations to lead high-impact, cross-functional initiatives. This role is ideal for someone with a consulting background who thrives in ambiguity and excels at both strategy and execution. You will work closely with senior leaders to identify opportunities, develop strategic recommendations, and translate ideas into actionable plans.

Responsibilities

  • Lead and own strategic, cross-functional initiatives from ideation through execution, with measurable business outcomes.
  • Partner with Product, Engineering, Finance, Legal, Operations, and Marketing to translate high-level priorities into detailed, actionable roadmaps.
  • Analyze performance data, product metrics, and market trends to develop insights and inform product and operational strategies.
  • Align stakeholders across functions and levels – including executive leadership – through clear communication, structured frameworks, and strong facilitation.
  • Build structure and drive momentum in highly ambiguous problem spaces, often without a playbook.
  • Develop and support long-term strategic planning and business reviews that scale with the company.
  • Identify, define, and lead initiatives that address gaps, remove inefficiencies, or unlock growth levers across the business.

Requirements

  • Experience: 3+ years in management consulting, business operations, product strategy, or similar roles (experience at firms like McKinsey, BCG, Bain strongly preferred).
  • Skills:
    • Strong analytical problem-solving skills with a bias for action and ability to turn insight into execution.
    • Exceptional written and verbal communication skills; proven ability to influence stakeholders at all levels.
    • Experience independently leading cross-functional projects in a high-growth, fast-paced environment.
    • Comfort working across technical and non-technical teams and navigating competing priorities.
    • Self-starter mindset with a track record of ownership, initiative, and delivering results without constant direction.

Company Information

Sidecar Health: Sidecar Health is redefining health insurance. Their mission is to make excellent healthcare affordable and attainable for everyone. They are committed to fixing a broken system and making it more personalized, affordable, and transparent.

Application Instructions

  • Not specified in the provided text.

Skills

Management Consulting
Business Operations
Product Strategy
Analytical Problem-Solving
Communication
Stakeholder Influence
Cross-Functional Project Leadership
Strategic Planning

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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