Sidecar Health
Senior Manager, Product Strategy and Operations
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
We’re hiring a Senior Manager, Product Strategy & Operations to lead high-impact, cross-functional initiatives that drive strategic decision-making and execution at Sidecar Health. This is a high-visibility role ideal for someone with a consulting background who thrives in ambiguity, brings structure to complex problems, and is equally comfortable in strategy and execution. You’ll work closely with senior leaders across Product, Operations, and Go-to-Market functions to identify key opportunities, develop strategic recommendations, and turn ideas into actionable plans. If you're scrappy, analytical, and energized by fast-paced environments, this role offers the chance to drive critical company-wide initiatives from day one.
What You'll Do
- 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
What You'll Bring
- 3+ years in management consulting, business operations, product strategy, or similar roles (experience at firms like McKinsey, BCG, Bain strongly preferred)
- 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
- Healthtech or insurance experience is a plus, but not required
- Bachelor’s degree required; MBA or advanced degree is a bonus
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.
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.
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