Executive Spotlight: Alyssa Simpson Rochwerger, Founder and CEO of Grounded Work (2027)
Alyssa Simpson Rochwerger is the Founder and CEO of Grounded Work, an operator-led AI services firm. That is the title on Grounded Work's own website, which was read on October 31, 2026. Some directories describe her as a co-founder, and the site lists two other founders, Ben Kearns as CTO and Keith Vertrees as COO.
She is a product leader who built AI products at IBM Watson, Figure Eight and Appen, then moved into healthcare at Blue Shield of California before starting Grounded Work. She also co-wrote the book Real World AI.
This page uses only public professional information from Grounded Work's website, speaker bios and a 2018 news item, all read on October 31, 2026. Company figures are company-reported. No freely licensed photo of her was found, so the hero image is the company logo.
Current role and company
Grounded Work describes itself as providing operator-led AI services. Its homepage says it helps companies find where AI is worth investing, build the operating model to make it work, and ship products that generate real value. The site's footer says Grounded Work is part of Consult Koala LLC. The pages read do not state when the firm was founded.
- Title (Grounded Work website)Founder, CEO.
- Fellow founders (same page)Ben Kearns, Founder, CTO; Keith Vertrees, Founder, COO.
- Her listed focus (About page)AI Product & GTM Operator.
- Offerings (company site)Advisory tracks, Ground Truth technical audits and Grounded Health.
Career path
- Trinity College. Speaker bios say she holds a BA in American Studies from Trinity College; a 2024 conference bio adds Phi Beta Kappa and Presidential Scholar.
- IBM Watson. Her conference and speaker bios place her in IBM's Watson group, and Grounded Work's site lists IBM Watson first among the places she built AI products.
- Figure Eight, 2018. Finovate reported on May 22, 2018 that Figure Eight, the data-labeling company formerly called CrowdFlower, hired her as VP of Product. A speaker bio says Figure Eight was later acquired by Appen.
- Appen. A speaker page lists her as VP, AI & Data at Appen, leading go-to-market pricing and packaging for the platform.
- Blue Shield of California. A 2024 conference bio lists her as Senior Director of Member Digital Experience. A third-party expert profile says she was also Interim VP leading a 120-person AI organization there.
- Grounded Work. She now leads Grounded Work, alongside two co-founders, according to the company's website.
What she is known for
- Real World AI. She co-wrote Real World AI: A Practical Guide for Responsible Machine Learning with Wilson Pang. Grounded Work's site quotes Kirkus Reviews calling it "as comprehensive as it is detailed".
- AI inside a health insurer. Grounded Work's homepage says she was part of a 120-person AI organization at Blue Shield of California that delivered $35M in savings in four weeks. This is the company's own claim; the page does not say how savings were measured.
- Speaking. The site's proof page lists the O'Reilly Artificial Intelligence Conference (2018), an NVIDIA GTC enterprise AI panel (2023), a Hakkoda healthcare and life sciences summit (2025) and Snowflake Summit (2025).
- Recognition and teaching. A third-party expert profile says she was named to Modern Healthcare's 40 Under 40 in 2025 and created an AI for Product Managers course on Udacity. Her 2024 conference bio also mentions a patent in data processing and support for Girls Who Code.
Leadership style and philosophy
The sources read here do not include a long interview with her, so this section relies on how Grounded Work describes its own approach on its website. It is written in the firm's voice, not as direct quotes from her.
- Results over decks. The homepage promises stuff people will actually use, "without the hype and without the powerpoint slides".
- Learning from AI that did not work. The homepage says she has been inside organizations where AI worked and where it did not, which is why she started the firm.
- People first. The About page says the hardest problems are human, and that the firm believes AI should make people more effective, not more replaceable.
- Start small. The services page says most engagements start with one track and expand only if the work earns it; its Find It track is pitched as a two-to-three-week assessment.
Key numbers about Grounded Work (company-reported)
The firm is private and publishes few metrics. These are claims from its own website, read October 31, 2026, with no audit.
- Blue Shield AI organization120 people; $35M in savings in four weeks (as described on the homepage).
- Co-founder Keith Vertrees, prior role125 deployed agents and 26 enterprise deals in four months.
- Co-founder Ben Kearns, experience20+ years and 15+ patents.
- Find It assessment lengthTwo to three weeks.
- Grounded Health statusBeta, for self-insured employers' claims data.
What to watch next
Worth tracking: whether Grounded Health moves out of beta, what case studies the firm publishes, and how it describes results as it grows.
Questions people ask
Who is Alyssa Simpson Rochwerger?
She is the Founder and CEO of Grounded Work, an AI services firm, and a co-author of Real World AI. She previously held product roles at IBM Watson, Figure Eight, Appen and Blue Shield of California.
Is she a founder or co-founder of Grounded Work?
Grounded Work's website lists her as Founder, CEO, alongside Ben Kearns (Founder, CTO) and Keith Vertrees (Founder, COO). Another profile says the firm was co-founded by the three.
What does Grounded Work do?
Its site describes operator-led AI services: finding where AI is worth investing, building an operating model, and shipping products. It also offers Ground Truth technical audits and Grounded Health, a beta claims-data service for self-insured employers.
What did she do before Grounded Work?
Speaker bios and the company site list IBM Watson, Figure Eight, Appen and Blue Shield of California, where a 2024 bio gives her title as Senior Director of Member Digital Experience.
Did she write a book?
Yes. She co-wrote Real World AI: A Practical Guide for Responsible Machine Learning, which Grounded Work's site says Kirkus Reviews called "as comprehensive as it is detailed".
Sources
- Grounded Work: Home · Title, co-founders, Blue Shield claim, offerings
- Grounded Work: About · Role descriptions, beliefs, parent company
- Grounded Work: Services · Tracks and standalone offerings
- Grounded Work: Grounded Health · Beta status, benefits cost statement
- Grounded Work: Ground Truth · Technical audit offering
- Grounded Work: Proof · Book, review quote, appearances
- MoralesHR: expert profile · Third-party profile: Interim VP, 40 Under 40, Udacity
- Missouri State Public Affairs Conference 2024: presenter bio · Blue Shield title, education, patent
- HCCA: speaker page · Career roles
- Chatbot Summit: speaker page · Appen role
- Finovate: Figure Eight rebrand (May 22, 2018) · Figure Eight VP of Product hire
Facts were read from the linked pages on October 31, 2026. Several pages were read through a fetch tool that returns summaries, so check each detail on the original page before quoting it. LinkedIn and Modern Healthcare could not be fetched. Company figures are the company's own. Photo: Missouri State University Public Affairs Conference presenter page. This page is an independent profile and is not affiliated with Grounded Work or Alyssa Simpson Rochwerger.
Top photo: Missouri State University Public Affairs Conference (https://publicaffairs.missouristate.edu/2024/presenter-bio.aspx?PresenterID=2010)