About Landon Gray

I build software, help teams put AI to work, and think about how the pieces fit together.

I’m Director of AI & Infrastructure at DealMaker, where I work across engineering, AI strategy, and adoption. My background is in software consulting: understanding an unfamiliar business, finding the problem worth solving, and working with people to deliver something useful.

How I approach the work

I’m interested in systems thinking because a technical decision rarely stays technical. It changes how people work, what they can see, and who has to maintain the result. I try to understand those connections before choosing a tool.

That perspective carries into my AI work: build the system, make its behavior observable, and involve the people who know the domain in judging whether it works. My selected work includes production agents, evaluation workflows, and an internal AI tools program.

Building and sharing

I’m building Shinkiro to help people turn ideas into working software, and FoodieLog to remember and share food worth coming back to.

I write Landon Notes about software, systems, and what I’m learning. I also speak and teach, and founded the RubyAI community.

For the longer personal version, read my story. For what has my attention today, visit my now page.

Founder of the RubyAI community

I founded and run RubyAI, a community on X for engineers building AI applications in Ruby.

Everyone was building AI in Python. I set out to prove what Ruby could do, and to raise AI literacy across a community I care about.

Get in touch

I’m based in Rochester, New York. For an interesting conversation, a leadership opportunity, or a collaboration, email me with a little context. For a specific business decision, see advisory work.