Hey, I'm Jon.
Before Pfeiffer Digital I spent my career on the operator side of software — leading partnerships and customer success at StellarAlgo (a data platform for pro sports teams, working with clubs across the NBA, MLB and NHL) and OwnBackup, and running customer success and sales at Quicket Solutions. I learned what makes software actually get used inside a business: it has to fit the systems people already run, and someone has to own it after launch. That's how Pfeiffer Digital works.
I played Division I baseball at UW-Milwaukee and am based in Oconomowoc.
Pfeiffer Digital is a Wisconsin AI automation company based in Oconomowoc, building custom AI voice agents, website chatbots, and back-office document automation for service businesses — HVAC and the trades, property management, and professional services. Founded by Jon Pfeiffer, Pfeiffer Digital builds and runs these systems rather than handing over a roadmap.
My Background
Before Pfeiffer Digital I spent my career on the operator side of software — leading partnerships and customer success at StellarAlgo and OwnBackup, and running customer success and sales at Quicket Solutions.
At StellarAlgo, a data platform for pro sports teams, I worked with clubs across the NBA, MLB and NHL. I learned that software only creates value when it fits the systems people already run and someone owns it after launch.
I played Division I baseball at UW-Milwaukee. Today, I live and work in Oconomowoc.
Built by an operator who spent his career making software stick inside real businesses.
How I Work
Direct Access
No account managers or ticket systems. You work directly with me on every project.
Fast Results
Most builds go live in 2–4 weeks.
Wisconsin-Based
I live and work right here. I understand local business challenges firsthand.
No BS Pricing
Transparent quotes with no hidden fees. You know exactly what you're paying for.
Ready to Get Started?
Let's chat about your business and see how AI automation can help you grow.