Q&A with First Factory Chief Operating Officer Don Gregori

‘Fear impacts every decision that we make. The stress that we carry makes us less open to new ideas, and we pass that on to our employees. Leading ourselves and leading the company is the same project.’

Don Gregori’s journey to become chief operating officer for a multinational technology company began with earning a liberal arts degree.

“I have a fairly untraditional path into business leadership,” the Amherst resident says. “I graduated from Stony Brook University as a theater major and didn’t realize that there was so much about running a theater and plays — directing and managing people toward a unified effort — that really would play out in business later,” he says.

As chief operating officer for First Factory, Gregori manages a company that provides custom software development and consulting, currently for over 45 active clients.

“Everything from startups to S&P Global, really anything that you need from mobile development, cloud, AI, project management, product design,” he says. “We kind of do it all.”

Before joining First Factory, Gregori spent 18 years with Kaplan Test Prep, a company that provides test preparation, practice tests and private tutoring for standardized college admission tests. His work helping the company transition from brick-and-mortar centers to online informs his leadership vision.

“We moved 800 people at about 130-plus centers to remote work. That was really the point where understanding different management skills came into play for managing a remote workforce,” says Gregori, adding the company also had to find new tools to adapt.

With the rise of multinational companies and remote working, it’s not surprising that Gregori lives in New Hampshire but works for a company that is based in New York with just five people in the U.S. and has major operations in Costa Rica, where its subsidiary employs 160 people.

In June, Gregori released “The Emergent Leader,” a book that shares his vision of management in the modern era. He recently appeared as a guest on NH Business Review’s “Down to Business” podcast, from which this article was adapted.

Q. What brought you to Amherst, New Hampshire?

A. I’m originally from New York. I met my wife in New York 12 years ago. She’s originally from New Hampshire. When we moved to Florida, we really didn’t want two homes. But with COVID and people not traveling, and some family and friends here and children being born, we figured we needed to get back here for a bit. I did also miss hiking. Florida’s pretty flat. We bought this house in Amherst sight unseen as we were actually in an Airbnb in Georgia having evacuated from a hurricane in Florida. We wound up liking this so much that we sold the Florida house and have been up here full-time for 2½ years.

Q. Why did you choose to write “The Emergent Leader” as a book?

A. I never really thought of myself as a writer. I have a background in theater, so I think I’m more of a storyteller. I see things visually and in pictures. I don’t have an advanced degree. I don’t have an MBA. Every year for the first at least 12 years at Kaplan, I had a new job. I would kind of get promoted into something else and would have to learn a whole new set of skills, whether it was academics and delivering courses and training and legal and compliance and procurement, and facility management and contract negotiations. Every time I was getting a new opportunity, I needed to reach out to someone in something to learn about how to handle that.

I had a different perspective than what to me seemed to be this cadre of MBA graduates at Kaplan. It’s an education company; you need higher education pedigree for a lot of it. I was like, why do I differ in perspective from them? And why am I doing something differently and being successful? When I wasn’t successful? That was an easy question to answer.

I went to magazines like Fast Company and Inc. magazine, and even Wired back then, and was pulling these really tight articles about people’s experiences and perspectives. And I’d read a 17-page Harvard Business article, and I’m like, I could say this in three paragraphs. I don’t have the time or the luxury, and that’s also just not me.

I jotted some notes down for myself. And then as I managed people — and I’ve managed hundreds and hundreds of full-timers over the years — I found myself repeating some of these wisdoms and analogies to my employees.

At this point in life, I was reflecting back on building a company. Even though we’ve been in business at First Factory for 26-plus years, every day feels like a startup. As an agency, you respond to every client differently. You respond to the headwinds differently.

I said, is there a book that covers brand building strategy, innovation, efficiency, career development and stress management for a leader? Whether it’s at a brand-new company or you’re growing a company, or you’re a leader at an inflection point, which I think many of us are with AI.

What is a desk reference that I would go back to? With clear, concise and hopefully a little bit irreverent and fun anecdotes to say, “This is my takeaway, and here’s my take-action, and I can try that today. And next month I’m going to be in a different position. I can review that again and have a different outcome.” That’s why I wrote it.