From databases to Dynamics to AI — in one 37-year run
Ray started as a database consultant working with his father in the late 1980s. What followed was nearly four decades moving through CRM, Microsoft Dynamics, and — for the final chapter of his Sikich career — leading the firm's approach to artificial intelligence. RayViation AI will be where that experience keeps working next: teaching, advising, speaking, and exploring what comes next — launching January 2027.
1988/89 - Information Managers -> Softbite International
2002 - Softbite joins ICS becomes Sikich
2020s - Takes on AI strategy
Then, as now
Paradox Informant, 1991 — reviewing a Softbite seminar. I was the instructor. Every tool on that page is gone now; the part about the questions still holds.
Why "rayViation"
A good friend of mine is a commercial pilot who also owns a small plane. For years we joked about going into business together, me doing the AI side, him doing the flying. RayAI and aviation. We even landed on a name for the joint venture we never started: rayViation.ai.
That stayed a running joke until an unexpected loss at the firm, followed by a wave of partners retiring, had me looking hard at what came next. Almost all of them moved on to something completely different, which makes sense. The skills that got them started had mostly been replaced by managing, long before they stopped working. I realized I didn't want that. I still love learning the next thing; I've spent my career being the one who raises a hand when something new shows up, and staying hands-on with it rather than climbing away from the work itself.
"AI, at its core, is about navigation and orientation: helping people find their bearings in something unfamiliar and get where they're trying to go.”
No chartering of planes yet. But the goal's the same one my friend and I joked about: help people navigate this AI world and arrive safely.
Tray tables up, seatbelts fastened. We're ready for takeoff.