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
Vendor acknowledgment vs. order verification
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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How it’s delivered
One connector. Every tool.
Your tools live on one connection to your AI system. Setup happens once and takes about a minute per person. Everyone gets their own login, and everyone sees only what their role allows. The owner, the sales manager, and the newest customer service rep run the same connector with different permissions inside it. New tools and updates deploy instantly. No installs. No rollouts.
Subscribe to your tools, or own them outright. Every tool comes both ways: a setup fee with a monthly license, or built for you and bought out. Owned tools run in accounts your company controls. Subscribers can buy out anytime.
Even the reporting is built in. Pull your team’s usage report any time. Who is using which tools, for which jobs, how often.
Training is built in. Every tool carries its own instructions. Ask it how it works and it walks your team through it in conversation, on their own projects, not a sample file. No training meetings needed.
On safety. Some tools look things up. Those are exact. Others interpret: reading a vendor quote, sorting line items, making a judgment call. Those come with verification and confidence thresholds. Anything the AI is not sure of gets flagged for a person to review.
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.