Most companies are past needing convincing about AI. They want to know what to do next.
Rather than chasing shiny objects or stacking one-off automations, the approach is holistic: safe company-wide access, connected systems, real training, and tools your team uses every day. The AI champions who surface are the ones who expedite adoption and find better ways to work.
Some of what I’ve built and shipped:
Connected ERP, CRM, and communication systems to Claude
An internal AI teammate in Teams
Quote to SIF conversion tool
Interactive warehouse map
Automated order health sweeps
Packaged company skills
A prompt library for designers
Team training and champion programs
What we can build
When everything is buildable, the skill isn’t building. It’s knowing what to build, where to start, and why.
I get asked all the time: “Can we do X?” These days the answer is almost always yes. The real question is what to build. That takes knowing where your people need the most help and where you want to go (your knowledge), judgment about what’s feasible and what it will actually deliver (where I come in), and a decision about which of the near endless opportunities to prioritize.
This is how I think about adoption. Most companies I speak to are in Tiers 1 or 2: adopting tools rather than adapting them to the business, which is where the real value lies. Below, some of what I’ve built at each tier.
Adoption tiers
TIER 1 · INDIVIDUALS
Employees using AI, self-directed, on personal accounts.
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TIER 2 · TEAMS
The company adopts a managed team plan, promotes training and usage, and starts using the features of the chosen platform.
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TIER 3 · SYSTEMS
Moving beyond out-of-the-box AI to custom connections and tool building.
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TIER 4 · PROCESSES
Redesigning how the work happens, not speeding up how it used to happen.
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Why dealers first
I’ve spent the last year focused entirely on implementing, integrating, evaluating, and building AI tools in the dealership world. Those skills and that knowledge transfer directly to other dealers, at a fraction of the cost and time it would take to build internally.
Today is the worst AI is ever going to be. If you’re feeling behind or want to get ahead of your competition, schedule a time to talk.
I’m happy to show you everything I’ve built.¹
If you want to talk, email me: jack@dealerside.ai. Tell me where you are and where you want to be.
¹ “What Our ERP Knew That We Didn’t.” LinkedIn, June 10, 2026.