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Product | AI & ML | Healthcare

Alyssa Simpson Rochwerger

Alyssa Simpson Rochwerger is the CEO of Grounded Work, an AI strategy and implementation firm built by three senior operators who have actually shipped AI inside real companies — not theorized about it. She spent a decade closing the gap between “AI is interesting” and “AI is producing measurable value,” including leading a 120-person AI organization at Blue Shield of California
delivering $XX million of savings in first 6 weeks.
Alyssa Simpson Rochwerger

Areas of Expertise

AI strategy and prioritization
Help you figure out where AI is actually worth investing in your business, and where it isn’t — before you spend money finding out the hard way.

AI implementation and build
Move from strategy to shipped product. Grounded builds alongside you, AI-accelerated, with senior operators who’ve done it before.

Healthcare AI
Deep expertise in health system transformation, clinical operations, and the specific constraints (regulatory, organizational, political) that make healthcare AI hard.

AI product leadership coaching
For CPOs, VPs of Product, and founders navigating what it means to build an AI-native product org. Includes hiring, roadmap, and team structure.

Fractional CPO / executive advisory
Embedded product leadership for companies that need senior AI product judgment without a full-time hire.

PE portfolio AI assessments
Due diligence and value-creation roadmaps for private equity firms evaluating or accelerating AI across their portfolio companies.

GTM for AI products
Help founders and product leaders figure out how to position, message, and sell AI products to buyers who are skeptical and overwhelmed.

$ Retainer or Project based.

BOOK TIME WITH Alyssa

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highlights:

More About the Expert:

Alyssa is a product leader with 15+ years building AI at scale — as a Founding PM on IBM Watson, VP of Product at Figure Eight (data labeling), Interim VP at Blue Shield of California, and now CEO of Grounded Work. She has spent her career doing one thing: finding where AI is actually worth investing and making sure it gets built. Her work at Blue Shield is the clearest proof point — she built a 120-person AI organization that delivered $35M in measurable savings in four weeks.

Grounded Work is the firm she co-founded with Ben Kearns (former VP Engineering at DataStax, 20+ years of 0-to-1 systems across energy, life sciences, and robotics) and Keith Vertrees (former CPTO at Shift Technologies, former Director of Product at IBM). They diagnose where AI actually helps a business, then build it — working AI-accelerated, so engagements that once required 20-person teams now run with a handful of senior operators on compressed timelines at meaningfully lower cost.

Recent clients span healthcare (Particle Health, DaVita), legal, real estate, PE-backed portfolios, and early-stage startups. She’s also the author of Real World AI, creator of the AI for Product Managers course on Udacity, and was named to Modern Healthcare’s 40 Under 40 in 2025.

“Never doubt that a small group of thoughtful, committed, citizens can change the world. Indeed, it is the only thing that ever has.”― Margaret Mead
Alyssa Simpson Rochwerger
Product | AI & ML | Healthcare