CEO Pamela Diaz Takes Chicago-Based MSP Entara to Next Level

In some respects, Pamela Diaz may seem an unlikely person to be the CEO of a highly regarded MSP. Diaz spent more than two decades working in finance, and not technology. She climbed her way up the chain of command at UBS, responsible for working directly with financial traders. By the time Diaz left the company, she was an executive director and global business manager for all of operations. Then she took on positions of head of global operations and interim CIO at a boutique equity investment firm. She said her leadership skills landed her both roles from the start.

And that’s when the unlikely became a reality.

As CIO, Diaz outsourced the firm’s IT work to YJT (You Just Trade), now known as Entara, a Chicago-based MSP that worked solely with traders. When she decided to leave her role at the investment firm, Diaz didn’t know exactly what she wanted to do next in her career. She had spent 26 years in the financial world and thought maybe it was time for a change. Entara’s then-CEO Linda Maclachlan got wind that Diaz was looking for something new. She immediately approached Diaz about her taking over as president of Entara.

“She just reached out to me and asked if I would be interested in running her firm. At first, I honestly thought she was kidding,” Diaz said.

Maclachlan was inspired by Diaz’s operational acumen. However, Diaz said she was nervous about the proposition.

“Over time I realized it was something that was scaring me because it was such a big change from what I was doing,” Diaz said. “What I know best is that if it scares you that’s the thing you should do.”

It’s been five years since Diaz took a leadership role at Entara, considered one of Chicago’s best places to work. This month she became the firm’s CEO.

In this Q&A with Channel Futures, Diaz discusses Entara’s unique hybrid MSP-MSSP business model, XSP, how the company addresses cybersecurity and accountability, and the role the channel will play for the future of her organization.

Channel Futures: Considering you didn’t have experience working within an MSP, what was the learning curve like going into this IT space at Entara?

Pamela Diaz: It was quite a learning curve. I spent a lot of time after hours digesting information. And I talked to my husband who works in IT about the inner workings of this technology space. It meant trying to understand the engineering side of it as well as the business side of it.

Knowing how to be an effective leader in IT doesn’t mean you need to know, for example, how to spin up a server, but you need to know what a server is. You must know the components and how it impacts the business.

CF: What has been the evolution of the company?

PD: Entara is in its 20^th year. It was founded by Linda Maclachlan, who is still the majority owner of Entara. She was CEO but now is the board chair. Low-latency trading firms were our real focus at first. When you have a trader who can’t trade, or an analyst that is trying to configure the next trade, and they don’t have their internet or can’t get something done … the immediacy to support those types of people helps you really step up your game. We knew from that aspect that if you can support the financial world as an MSP, you can support anybody.

As we evolved as a company, we became known across the spectrum in Chicago, not just in the financial industry. And that’s how we’ve continued to grow. When I came in, we really started to …