About HealthCare.com
HealthCare.com is one of America's fastest-growing insurtechs — and we're on a mission that actually matters. We've combined advanced technology and data science to build smarter, more personalized health insurance products that cut through the confusion and put the right coverage in the hands of the people who need it. Less guesswork. Better decisions. Real outcomes.
We've helped millions of Americans find the right plan, raised over $200M, and built proprietary technology that's rewriting the rules of an entire industry.
If you're ready to do the most meaningful work of your career alongside a team that's genuinely fired up about it — welcome home.
About The Role
We are seeking a highly technical and pragmatic Senior Applied AI / Data Scientist to help scale AI-enabled systems, analytics workflows, and internal data applications across the organization.
This is not a traditional research-focused data science role. The ideal candidate is someone who can bridge business problems, analytics, engineering, and modern AI tooling to rapidly prototype and operationalize high-impact solutions.
What You'll Do
You will work closely with Data Engineering, Analytics, Product, and business stakeholders to:
Build AI-assisted workflows and internal tooling
Prototype and productionize LLM-enabled applications
Develop scalable analytics and decision-support systems
Improve self-service data access safely and responsibly
Reduce operational burden through automation and intelligent systems
Help evolve internal governance and semantic consistency practices
The environment is fast-moving, ambiguous, and highly collaborative. Success in this role requires strong systems thinking, ownership mentality, technical versatility, and the ability to operate independently with limited oversight.
Working at HealthCare.com
Great work deserves great rewards. Here's what's waiting for you:
Health insurance that actually makes sense — Florida Blue PPO or HSA plan, and we put money in your HSA ($2K for you, $4K if you’ve got a family). You’re literally in the business of healthcare. You deserve good coverage.
Dental & vision — Delta Dental, Aetna, or Guardian for your teeth. Aetna/VSP for your eyes. We’ve got your whole face covered.
401(k) with a match — contribute 6%, we kick in 3%. Eligible upon hire. Your future self will thank you.
PTO that respects your life — 15 days a year to start, rolls over, and you don’t have to beg for it. Plus paid holidays, because obviously.
8 weeks paid parental leave — new baby, new adoption, new chapter. Take the time. We mean it.
Free EAP — confidential support for life’s messier moments. Mental health, legal questions, financial stress — covered, no cost, no judgment.
Life & AD&D insurance — company-paid, because we’ve got your back.
Working Advantage — free access to exclusive discounts on Disney, Six Flags, NFL tickets, hotels, streaming, dining, and hundreds more. Work hard, play harder.
Our Commitment
At HealthCare.com, we believe a diverse and inclusive team makes us stronger — and better at serving the people who rely on us. We’re committed to recruiting, developing, and retaining talent from a wide range of backgrounds and to building a workplace where everyone can do their best work.
HealthCare.com is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.
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5+ years of experience in Data Science, Analytics Engineering, Applied AI, ML Engineering, or related technical roles
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Strong Python and SQL skills
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Experience building production-facing data or AI systems
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Experience working with LLMs, AI tooling, orchestration frameworks, RAG systems, or AI-enabled workflows
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Ability to independently scope and execute ambiguous technical projects
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Strong communication skills with technical and non-technical stakeholders
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Experience working in cloud-based data environments
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Strong systems thinking and debugging ability
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Comfortable operating in fast-moving and evolving environments
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Experience with Snowflake, Airflow, dbt, AWS, or modern analytics stacks
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Experience with vector databases, embeddings, semantic search, or knowledge systems
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Exposure to healthcare, fintech, marketplace, or other regulated/sensitive data domains.
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Experience building internal tooling or developer productivity systems
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Startup or high-growth company experience
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Experience working across Data Engineering and Analytics functions
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Experience evaluating AI governance, safety, or operationalization concerns