The Next New Thing “I make $4.5 million implementing AI”
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Apr 23, 2026 Jon Cheney, founder who scaled an AI services and software company from $400 to $4.5M ARR. He talks about building fast with Replit, turning prototypes into paid offers, and using AI to interview and plan businesses. He explains a fractional Chief AI Officer model for recurring revenue, moving from services to productized agents, and the tool stack that powers it all.
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Sell A Fractional CAIO To Create Recurring Revenue
- Convert training engagements into recurring revenue by selling a fractional Chief AI Officer (CAIO) retainer.
- Jon priced ongoing CAIO services at ~$15,000/month and immediately closed clients who wanted continuous strategy, building, and accountability.
Use The STE Framework For CAIO Engagements
- Structure ongoing services into three buckets: Strategy, Transformation, and Education (STE) to cover planning, building, and upskilling.
- Jon uses STE to sell CAIO work: CEO strategy calls, building throwaway software, and hands-on training to change company behavior.
Built Jenna Agent To Scale And Stick Clients
- Jon built an internal agent named Jenna (GenAIPI) on secure NVIDIA/OpenAI infra to automate client work and make offerings sticky.
- Jenna runs clients' operations, connects tools, and uncovers new patterns; Jon trains customized Jenna instances per client during onboarding.