Stepping Stone

About Stepping Stone

We believe executive judgment is the most under-distributed asset in business.

Most companies can't afford the executives they need. Most executives have judgment they can't reuse. Stepping Stone exists to close both gaps — turning experience into a curated, AI-accessible advisory layer.

C-suitedecades of operating judgmentAI opsenterprise AI transformationstructured knowledge modulecaptured · structured · cited

Our story

A father-son team that's seen both sides.

Stepping Stone was started by a father and son working from opposite ends of the same problem. One had spent decades inside the C-suite watching judgment evaporate into single meetings and consulting decks. The other had spent the post-2022 years inside a healthcare operator's AI transformation, watching the cost of expertise scale faster than the supply of experts.

We built Stepping Stone because the obvious next move in AI isn't more chatbots — it's better grounding. The companies who win the next decade won't be the ones with the most AI tokens. They'll be the ones who turn the right human judgment into the right durable, queryable, attributable asset.

Where we are

Early, on purpose.

  1. Early 2025

    Concept validated

    First Numotion engagement confirms the core thesis: structured executive frameworks accelerate AI transformation more than raw model access ever will.

  2. Mid 2025

    First commercial agreement

    Stepping Stone Advisors signs its first commercial services agreement, anchoring the platform's go-to-market with a real mid-market operator.

  3. 2026

    Platform v1 in build

    Founding contributor cohort onboarded. AI Transformation knowledge bank in development. First customer pilots beginning.

Founders

Built by operators.

Bob Barbieri

Co-founder & Chairman

Nashville Metro · Harvard Business School · CMA

Bob is a multi-time CEO who has built and led companies across cloud infrastructure, technology services, and consulting. He currently serves as CEO of NexQloud, a distributed cloud computing platform focused on grid-efficient AI infrastructure. He brings a Harvard MBA, the Certified Management Accountant credential, and operating experience spanning Palo Alto, Atlanta, Nashville, and Los Angeles. At Stepping Stone he sets product vision, leads the contributor network, and brings four decades of executive judgment to the platform's founding knowledge bank.

Robby Barbieri

Co-founder & CEO

Nashville · Vanderbilt University BA '13, MSF '14

Robby leads AI at Numotion, the country's largest provider of complex mobility solutions, where he has spent the past several years building enterprise AI capabilities. A Minnesota native and Vanderbilt graduate, he is the founder of Music City Wheels, a Tennessee nonprofit serving people with disabilities, and was the lead advocate behind the TennCare for Working Individuals with Disabilities Act, which passed the Tennessee legislature unanimously in April 2024. He brings to Stepping Stone an unusual triangulation of perspectives: a real operator running AI inside a national healthcare company, a finance background, and lived experience that informs how he thinks about access, dependency, and what it means to make expert judgment available to the people who need it.

Recognition

Selected mentions.

Vanderbilt University News

From Anger to Advocacy: Robby Barbieri, BA'13, MSF'14 — coverage of the TennCare disability advocacy effort and Robby's path to founding Stepping Stone (May 2025).

Read coverage ↗

Get in touch

Want to talk?

If you're an operator who wants to contribute, a company exploring a pilot, or a press contact — we read every message.

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