[Remote] Director of Product Management at Sidecar Health

Remote

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Not SpecifiedCompensation

Senior (5 to 8 years), Expert & Leadership (9+ years)Experience Level

Full TimeJob Type

UnknownVisa

Healthcare, Health Insurance, TechnologyIndustries

Requirements

8+ years of product management experience, with at least 1-2 years managing or mentoring product managers
Demonstrated success owning consumer-facing product strategy and delivering seamless user experiences
Experience working with or building AI/ML-powered products, especially to streamline or personalize experiences
Strong collaboration skills across technical and non-technical teams
Comfort working in ambiguous, fast-moving environments with a bias for action
Excellent communication, storytelling, and documentation skills
Strong data and analytical mindset (including proficiency in SQL)
Bachelor's or Master’s in a relevant field
Bonus: experience in healthcare, insurance, or similarly complex, regulated industries

Responsibilities

Own the end-to-end product strategy and roadmap for key member-facing features and experiences
Lead a small team of product managers—providing guidance, mentorship, and alignment around goals and priorities
Translate member pain points, business needs, and operational challenges into scalable product solutions
Drive cross-functional collaboration with engineering, design, operations, member support, and compliance to bring products to life
Evaluate and integrate third-party solutions where appropriate, and lead build-vs-buy decisions
Define and track KPIs related to member engagement, product usage, and satisfaction to guide prioritization
Partner closely with marketing and member operations to ensure member awareness, adoption, and feedback loops
Champion an iterative, data-informed approach to product development with an emphasis on quality, accessibility, and ease of use
Ensure member-facing experiences remain compliant, secure, and in alignment with regulatory requirements

Skills

Key technologies and capabilities for this role

Product StrategyRoadmap PlanningTeam LeadershipMentorshipCross-Functional CollaborationBuild-vs-BuyKPIsAIMember EngagementHealthcare Product Management

Questions & Answers

Common questions about this position

What experience level is required for the Director of Product Management role?

The role requires 8+ years of product management experience, with at least 1-2 years managing or mentoring product managers.

What key skills are needed for this position?

Candidates need demonstrated success in consumer-facing product strategy, experience with AI/ML-powered products, strong collaboration skills, comfort in ambiguous environments, excellent communication, and a strong data mindset with SQL proficiency.

Is this a remote position or does it require office work?

This information is not specified in the job description.

What is the salary or compensation for this role?

This information is not specified in the job description.

What does the team structure look like for this role?

The Director will manage a small team of product managers, providing guidance, mentorship, and alignment around goals and priorities.

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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