FlexHired LogoFlexHired
Logo of Sidecar Health

Sidecar Health

Director of Product Management

Job Summary

The role involves leading claims automation initiatives and working with cross-functional teams to enhance the member experience. It requires a strategic product management background with hands-on experience in AI/ML products, system integrations, and data-driven systems. The candidate will define solutions, develop roadmaps, and oversee multi-phase projects to improve claims processing at scale. The position emphasizes collaboration, technical understanding, and driving value through innovative automation solutions within the healthcare insurance context.

Required Skills

Problem Solving
Data Analysis
Stakeholder Collaboration
Automation
Product Management
Technical Documentation
Agile Development
SCRUM
System Integration
AI/ML Technologies

Benefits

Paid Holidays
Equity
Retirement Plan
Bonus
Paid Vacation
Company Holidays
Medical, Dental, Vision Insurance

Job Description

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

With proven product-market fit, we are on a mission to scale and automate our claims processes and improve the member experience. Multiple sub-systems need to be automated and integrated with high accuracy and auditability through automation workflow, decision-making, tracking, and human-in-the-loop processes where necessary. We are seeking an experienced and strategic Director of Product Management with a strong background in AI technologies to work with senior technologists to co-create product strategy, define solutions, and execute large-scale, multi-phase initiatives that enable us to process claims at scale. This role is a critical partner that will help us execute today and plan for the future.

What You'll Do

  • Be the primary owner leading all claims automation initiatives, setting strategy, and leading execution
  • Partner with engineering, operations, business intelligence, finance, and legal to shape problems, opportunities, and strategies
  • Evaluate 3rd party vendors and technology platforms and perform build vs. buy analysis
  • Become an expert on our operational processes and map them to technology and software solutions
  • Define solutions and roadmaps with iterative development to incrementally drive value and de-risk big-bang releases
  • Identify and lead the development of AI/ML-powered solutions to gain efficiencies and scale in claims ingestion and normalization
  • Define and analyze quality metrics and use that information in roadmap prioritization
  • Define success KPIs and instrument processes to measure and report progress on goals
  • Ensure our system remains current and compliant with new insurance regulations, as well as integrate and support accounting and financial needs
  • Lead multi-phase, multi-team initiatives to execute and deliver on the strategic goals and solution implementation, launch, and optimization
  • Manage vendors and integrations as necessary
  • Set ambitious goals and hold yourself accountable

What You'll Bring

  • 8+ years of product management experience
  • Hands-on experience building or working closely with AI/ML products and platforms especially those used in automation, data normalization or decisioning
  • Experience with complex system integrations, evolutions, and modernizations
  • Experience in utilizing complex datasets to conceptualize, build, and launch large-scale data-driven systems
  • Strong SQL skills to self-serve your analysis and investigations
  • Ability to understand, map, and define data and system integrations, including accounting and compliance reporting
  • Ability to frame and add structure to chaotic/ambiguous situations and decisions
  • Comfort diving into uncharted territory and leading initiatives that involved AI-driven innovation
  • Ability to break large problems down into smaller parts that can be released incrementally for testing or delivering value early
  • Ability to absorb technical requirements and communicate them to broad and business audiences
  • Strong documentation, diagramming, and storytelling skills
  • Strong communication skills with the ability to simplify the complex
  • Strong analytical, troubleshooting, and problem-solving skills
  • Experience leading multi-phase, multi-team projects
  • Strong understanding of Agile development and Scrum methodology
  • Bachelor’s or master’s degree in computer science, data science, information systems, business administration, or a related field
  • Experience working in a fast-paced, growth-stage startup is a plus
  • Healthcare or Insurance experience is a plus

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 adopts a market-based approach to compensation, where base pay varies depending on location and is further influenced by job-related skills and experience. The current expected salary range for this position is $180,000 - $195,000.

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.

Interested in this job?

Application deadline: Open until filled

Logo of Sidecar Health

Sidecar Health

Looking for a new kind of health insurance? Sidecar Health offers transparent & affordable health insurance for individuals, and you can choose any doctor you like. Learn more.

See more jobs
Date PostedMay 23rd, 2025
Job TypeFull Time
LocationRemote
Salary$180,000 - $195,000
Exciting fully remote opportunity for a Director of Product Management at Sidecar Health. Offering $180,000 - $195,000 (full time). Explore more remote jobs on FlexHired!

Safe Remote Job Search Tips

Verify Employer Thoroughly

Research the company's identity thoroughly before applying. Check for a professional website with contacts, active social media, and LinkedIn profiles. Verify details across platforms and look for reviews on Glassdoor or Trustpilot to confirm legitimacy.

Never Pay to Get a Job

Legitimate employers never require payment for applications, training, background checks, or equipment. Always reject upfront payment requests or demands for bank details, even if they claim it's for purchasing necessary work gear on your behalf.

Safeguard Your Personal Information

Protect sensitive data like SSN, bank details, or ID copies. Share this only after accepting a formal, written job offer. Ensure it's submitted via a secure company system or portal, never through insecure channels like standard email attachments.

Scrutinize Communication & Interviews

Watch for communication red flags: poor grammar, generic emails (@gmail), vague details, or undue pressure. Be highly suspicious of interviews held only via text or chat apps; legitimate companies typically use video or phone calls.

Beware of Unrealistic Offers

If an offer's salary or benefits seem unrealistically high for the work involved, be cautious. Research standard pay for similar roles. Offers that appear 'too good to be true' are often scams designed to lure you into providing information or payment.

Insist on a Formal Contract

Always secure and review a formal, written job offer or employment contract before starting work or sharing final personal details. Ensure it clearly defines your role, compensation, key terms, and conditions to avoid misunderstandings or scams.

Related Jobs

Full Time
$150,000 - $185,000
Remote
Full Time
$160,000 - $190,000
Remote
Full Time
$180,000 - $220,000
San Francisco, CA, Washington, D.C., New York City, N.Y., Remote (USA)
Full Time
$160,000 - $210,000
Remote - US
Full Time
$152,150 - $179,000
New York, New York, United States; Remote; San Francisco, California, United States; Seattle, Washington, United States

Subscribe Newsletter

Never miss a remote job opportunity. Subscribe to our newsletter today and receive exclusive job alerts, career advice, and industry insights delivered straight to your inbox.