How I Got Promoted: Marques Stewart, VP of Technology at Achievement First

A couple of weeks ago, we launched a new podcast called SaaSOps Leaders With David Politis. Although the podcast has only been a thing for a short while, we’ve already noticed that the majority of our audience aspires to become an IT executive. And in a recent episode with Marques Stewart, vice president of technology at Achievement First, he briefly reflected on how he got promoted.

I walked away from the episode wanting to know more—and I figured that I wasn’t alone. So I asked Stewart for more of his time to hear about his career and ultimately what it took to become an executive. Here’s what he had to say.

Editor’s note: This conversation has been edited lightly for clarity.

When you began your career in IT, was it your goal to become an executive? Or did your career goals evolve over time?

No, at least not initially. I knew that because I have my master’s in information science, you can either become a librarian or you can help people understand how to use information to meet their goals. I just wanted to get into IT because I like troubleshooting and I’m good at it. I also knew that it wouldn’t be something that I’d get bored with over time.

When I started at Achievement First, there was the iPhone. When did that come out again?

I remember it was while I was still in college. So, 2006 or 2007.

Yeah, that sounds right. I had just left the Peace Corps the same year the first iPhone came out, and now look where we are in terms of technology. I just knew there was always going to be something new to learn and I wasn’t going to get stagnant in it. The goal was really just to get into IT and keep learning.

It wasn’t really until six or seven years ago that my former boss asked me, “Hey Marques, what’s your ultimate goal? Do you want to do break/fix IT work for your entire career or do you want to do something more than that?” At that time, I said, “You know what, I think I really want to become a CIO or CTO.” I didn’t necessarily know how to get there, but that really started resonating with me as I became more mature in my career.

When you made that decision, did you come up with a plan for how to get there? Did you change your approach to your job at the time? Was it a combination of the two?

It was a combination of all that. Achievement First had a mentorship program, so I signed up for that just to connect with people who were a little bit higher up than me, but not necessarily in IT. It’s very easy for technology folks to say, “As long as the lights are on, I’m doing my job and everything’s great.” But if you really want to go further, faster, and higher, you have to get outside of that. So talking with these folks was the first step in really doing that.

I wouldn’t say that I had a formal path to a VP role, but I knew it was important for me to start betting on myself. I knew that I needed to start looking for opportunities that would allow me to get outside of being the person who connected some wires or got a new school off the ground.

So I started looking for IT conferences to attend, certifications to start getting into, and communities to join. Over time, I started piecing all those things together and that became my path. But at the beginning, all I knew was that I needed to do something different than what I had been known for.

How did you balance your job at the time with all the extra things you were doing? My guess is that those upleveling activities are great, but you also have to remain a high performer.

Part of the process required me to lean on other people to help me out. I wasn’t necessarily giving them my work, but other folks have ambitions too. So one of the steps to achieving my career goals was to figure out if something I was working on represented a growth opportunity for someone else on the team. If so, I knew that was a great way to increase capacity for myself while also creating a career growth opportunity for someone else.

When I decided I wanted to be a CIO or CTO, I was an associate director or what other companies might call a junior director. I had to make a decision between adding more to my plate and passing it onto someone else who might be able to grow their skills through doing those things. If I had chosen the former, I ran the risk of “taking away” a great opportunity from someone who was more junior than I was. So it was mutually beneficial for me to start turning over the keys to certain initiatives and being a mentor to someone who was also looking to improve.

As I got more experienced in identifying learning opportunities for folks on my team, I was able to take on more of the extra things that benefitted me. What’s interesting is that the new skills and certifications that benefitted me also helped the organization. I’d go to a conference, for example, and get a great idea from one of my peers. You quickly realize that if you hadn’t attended the conference, you wouldn’t have been able to bring that idea back to your organization.

I’ve noticed this about software developers, but I also see it in many IT careers. Was people management something you had to just accept as a reality when you decided you wanted to be a CIO? Or have you always wanted to manage and mentor people?

I did not want to manage people when I first started. When you deal with technology, it tends to be binary. It either works or it doesn’t. If it halfway works, then there’s a halfway problem with it. There’s a logic to it. But humans are the greatest piece of technology ever invented because we’re so complex and we can go in multiple ways all at the same time.

I didn’t necessarily want to, but I knew I had to. That was the most natural growth path for me, especially in my organization, was to manage people. I started by managing one person at first, and then two, and now I manage a staff of like 15 people.

Oh, just a few people, right?

Just a few [Laughs].

When you go further in your career, people tell you to manage up. Not only do you need to manage the people who are “below” you, but you also need to manage up to your boss and tell them how you want to be managed.

In my environment, I also have to work with leaders at the 41 schools in our network. That’s 41 different personalities of directors or principals that we have to manage in some capacity and understand what each of those people needs from IT.

Wow. How did you learn to, well, manage all of those different personalities?

I really learned from the managers who came before me, including the person who hired me. She had a very outgoing personality, so she showed me how to connect with people on an empathetic level. Other managers that I had taught me how to balance the technical and relationship-building requirements of the job.

Ultimately, my fundamental philosophy has been to manage how I want to be managed. I want to be the type of manager that when somebody leaves, they say, “Hey, I’m moving on and I want a manager like Marques was.”

You don’t have to name names, but who were some of the folks who helped you get to where you are today?

One was a guy named Sam Torn. He manages a summer camp that I worked at for three summers. He showed me how to be the type of boss that cares about people, even if you have a staff of 20-something people. It’s important to know something about each person on your team. Sam showed me how to have a high standard while also showing folks that you care about them.

The other people are a woman named Laurie Bussmann, a guy named Jason Tavarez, and a guy named Anthony Nevico. All three of them have worked at Achievement First and they’re like the Mount Rushmore of IT. They built this organization. Each of them showed me how to be empathetic, not only to the people who you manage, but also to people who are coming to you with issues. It is very easy to fall into the stereotypical IT mindset where you assume that end users are being silly or just don’t know what they’re talking about. But the three of them showed me how to put myself in the other person’s shoes.

Each of these people has played a key role in not only my development as a manager/leader but also my vision of what a team should look like. I’m deeply grateful for the technical and emotional tools they gave me to be the best possible IT leader I can be.

On the other hand, what were some of the biggest challenges that you kind of came across along the way to becoming a VP?

One of the biggest challenges was transitioning from being the one who fixed things to being the person who thought about tier three, tier four, or policy creation issues. I’m really good at fixing things, but you can’t be as deep in the weeds when you get to a certain level. You have to take a step back and say, “There’s a problem over there, but what is the greater thing that we should be working towards as a team?” It took me around a year to make that transition.

Another mental challenge I had to get over was my “imposter syndrome” feelings. As I looked around the world of IT, I didn’t see a lot of folks who were people of color. When you don’t see a lot of people who look like you represented in a certain industry, it really makes one wonder, “Am I good enough for this position? Am I exceptional enough?” The answer was always undoubtedly yes, but that doesn’t make the “imposter syndrome” feel any less real. Thankfully, I got over that one very quickly or I might not have completed my journey to this VP position.

Do you ever miss being in the weeds and responding to tickets?

I did when I was dealing with our recent ransomware incident. I would have rolled up my sleeves, asked what I could do to help, and gone off and done it. Now I’m the one who has to tell people what to do and make a plan. There are definitely days when I miss it.

Most days, I’m excited about the position that I have because it’s allowing me to create the vision of IT that I’ve had in my head for the last five years.

Obviously, I’ve got to talk to my boss about that vision. But otherwise, there’s no one that I have to pass and say, “Can I do this?”

You’re a big part of the SaaSOps Community. How has that community and the SaaSOps framework impacted the vision of IT that you mentioned?

It impacted my strategy and approach well before I became VP. My organization has been around for over 20 years. During the early stages of its history, we built everything. But as you grow as an organization, you see how many resources that requires, including money, people, and time. The SaaSOps framework helped me embrace the idea of purchasing tools that met our needs and allowed us to work on the things we really needed to focus on.

The SaaSOps Community is where I learned about best-of-breed technology. I could build a help desk, but could I build the best help desk? Will I improve it over time? No, I won’t dedicate the time or the people to do that.

Our previous help desk system was on-premise and had its own server. When it came to patching it and keeping it up to date, none of us really wanted to do it. Zendesk was the first major piece of cloud technology that convinced us that we should just do it in the cloud. We are not going to spend the hours patching it or making new features but we could invest in a company/SaaS platform that would make that investment for us.

Do you have a couple of bits of advice that you’d offer to someone who aspires to get to a VP or CIO level someday?

I mentioned the first one on David’s podcast, but it’s really important to look for opportunities. We’re dealing with some weird after-effects on some laptops; on some machines, the microphones just don’t work, even though the drivers are fine. So someone on my team took it upon themselves to build a solution, test it, and bring it back to the team. It made my life easier because all I needed to do was recommend testing the fix on a few more computers.

I didn’t assign this task to that employee. But they saw that there was a need, came up with a good idea, and executed it. Looking for those types of opportunities is a great way to make yourself stand out.

The other thing that I would say is that if you really want to get to this position, look for opportunities outside of your normal bubble. Get to know people. As you become a director and a VP, get to know people not only within your organization but also especially outside of it. The most successful executives that I’ve seen have had connections outside of their own IT department that gave them great ideas that impacted their companies. Those ideas enable you to bring so much extra value to your organization that it almost feels like they’ve hired a brand new person.

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