Alyssa Simpson Rochwerger

CEO of Grounded Work

Alyssa Simpson Rochwerger is chief executive of Grounded Work, an AI strategy and implementation firm. Her expert profile at MoralesHR says she co-founded it with Ben Kearns and Keith Vertrees and that the firm identifies where AI can help a business and then builds it using small teams of senior operators working with AI-accelerated methods.^[1]

Her company profile lists clients in healthcare, including Particle Health and DaVita, as well as legal, real estate, private-equity portfolios and early-stage startups. Services include AI strategy, AI implementation, healthcare AI, product-leadership coaching, fractional chief product officer work, AI assessments for private-equity portfolios and go-to-market support for AI products, on retainer or project terms. These descriptions come from a speaker-bureau profile rather than an independent source, and no other coverage of the firm was found.^[1]

Early career: IBM Watson

Rochwerger's conference biographies describe her as a product leader focused on hard problems for everyday users, and say she has taken products from concept to large-scale returns at both startups and large enterprises. Her machine-learning career began at IBM's Watson group, where she was a director of product and, according to the Author Hour interview about her book, shaped business strategy for computer vision products. MoralesHR calls her a founding product manager on Watson.^[1][2][4]

Figure Eight and Appen

She became vice president of product at Figure Eight, a data-labeling company that was later acquired by Appen. After the acquisition, a speaker biography lists her as Appen's vice president of AI and data, a role described as covering go-to-market pricing and packaging for its platform and offerings. She describes herself as a customer-driven product leader focused on building products that produce large-scale return in new markets.^[2][3]

Healthcare: Blue Shield of California

Her conference biography says she left the AI industry to work on improving healthcare through technology and joined Blue Shield of California as director of product, leading the digital member experience organization. The more recent MoralesHR profile describes her as interim vice president at Blue Shield, leading an AI organization of about 120 people. That page gives conflicting savings figures for the work, so none is reproduced here.^[1][2]

Real World AI

Rochwerger co-wrote Real World AI: A Practical Guide for Responsible Machine Learning with Wilson Pang, who was Appen's chief technology officer. It appeared in early 2021. On the Author Hour podcast the two said the book draws on lessons from many AI projects and more than a hundred real-world examples, and is written in plain language for business leaders who are not technical and for technical staff who need to work with business partners.^[4]

Topics covered include deciding whether a problem needs AI at all, defining a narrow problem backed by good data, building diverse teams, planning for deployment and monitoring, choosing between building and buying, and understanding how unintended bias enters systems. The book closes with an AI-readiness quiz built on a five-level maturity framework: planning, experimentation, stabilization, scaling and transformation. Kirkus Reviews called it a thorough primer on managing AI projects in business, praising its worksheets and real-world examples.^[4][5]

Teaching, recognition and background

MoralesHR says she created the AI for Product Managers course on Udacity and was named to Modern Healthcare's 40 Under 40 list in 2025. She was born and raised in San Francisco and holds a bachelor's degree in American Studies from Trinity College, according to her conference biographies.^[1][2][3]

A note on her current role

The Executive List row shows her as chief revenue officer at Figure AI. Her most recent biography describes her as CEO of Grounded Work, which is the title used here.^[1]

Why she matters

Rochwerger has worked on the data, product and deployment sides of applied AI, at an IBM research-driven business, a data-labeling vendor and a large health insurer. The advice in her book, to start from a narrow problem, check that good data exists and plan for maintenance, is aimed at the gap between AI demonstrations and working systems, and her current firm is built around the same idea.^[4][5]

On The Executive List

Alyssa Simpson Rochwerger is ranked No. 42 on The Executive List (October 2026) in the Chief Revenue Officers discipline. She is listed as Chief Revenue Officer at Figure AI; no source we could find confirms that role, and her current role appears to be CEO of Grounded Work. The ranking reflects The Executive Review's own editorial Trending Score; it is not an outside award, and placement on the list is never sold. View the October 2026 edition.