About Kevin

I’m Kevin Olivieri – a technology and operations leader who builds systems that help organizations work better. For the past 25+ years, I’ve been sitting at the intersection of people, process, and technology, figuring out how to make complex things feel simple.

I serve as Chief Technology & Operations Officer at Allen & Gerritsen, an independent advertising agency in Boston. I lead the systems, teams, and strategy that keep the place running – infrastructure, security, AI adoption, workflow automation, web and digital development, and the platforms our creative and strategy teams rely on every day. My job is to make sure none of that gets in the way of the actual work.

What I care about most is the gap between how organizations could operate and how they actually do. That gap is almost never a technology problem. It’s a design problem – workflows built for a different moment, tools that don’t talk to each other, processes that made sense once and nobody questioned since. I get interested in those gaps. Then I build something to close them.

Some of what I’ve built recently: an AI-powered knowledge base that replaced a firehose of onboarding information with something people actually use, a proposal automation system that cut RFP turnaround time significantly, and an off-boarding workflow that turned a compliance risk into a self-driving process. You can read about those on the Projects page.

I also write about this stuff – AI in the workplace, responsible automation, and the human side of technology decisions. The blog is called Droppings, which felt right.

When I’m not troubleshooting systems or chasing a better workflow, you’ll find me on the water, at a BC game, or with my family and our sweet-natured, adventurous dog who has opinions about everything.
If any of this sounds like a conversation worth having, let’s connect.