Jason Alexander has never been someone who sits still for long. After two decades building BANKW Staffing into one of NH’s most recognized staffing firms, the Manchester entrepreneur sold his interest and pivoted into artificial intelligence.
This winter, Alexander, along with a partner, launched ChiefAI, a business management and AI advisory firm aimed at helping small and mid-sized organizations cut through the noise around AI and put it to work. The company is young, but works with roughly 30 contracted consultants, and has operations in Central and South America for complex development work.
“Starting ChiefAI was a little bit of a leap of faith,” Alexander admits. “When I decided I was going to do it, I wasn’t 100% sure what it would look like. But I just knew I wanted to be on this AI train.”
The spark came after Alexander, who has spoken openly about focusing his attention in the past, used Claude AI as an editorial partner to write and publish a 550-page techno-political thriller—something he’d always dreamed of doing but never thought possible. That experience, he says, changed everything. The book became proof of concept for what happens when a curious, driven mind stops treating AI as a novelty and starts treating it as a collaborator.
That philosophy drives ChiefAI’s approach, and Alexander says it sets his firm apart in a crowded market. ChiefAI begins every engagement with a deep dive into a company’s workflows, goals, and existing tools before recommending anything new.
“Most people who are paying 20 bucks a month for ChatGPT don’t know what it can actually do,” he says. His team works to maximize what clients already have before customizing their AI tools.
ChiefAI also brings something uncommon to the table. The firm contracts with a network of attorneys specializing in artificial intelligence, intellectual property, and technology law to help organizations establish governance frameworks, policy documentation, and responsible AI practices.