How Aileen Alexander Is Leading The World’s Largest Woman-Founded Executive Search Firm

Aileen Alexander has spent her career moving between worlds where the stakes are high and the margin for error is small. Before leading DSG Global, she worked in international security and defense policy at the Department of Defense and the U.S. House of Representatives, served as a Captain in the U.S. Army, and later built a career advising companies on the leadership decisions that can shape their future.

Today, as CEO of DSG Global, Aileen brings that same focus to the boardroom. Her approach is grounded in a philosophy she developed early in her military career, which is “people first, mission always.” For Aileen, that means pairing empathy with performance, staying calm when the pace accelerates, and making sure teams understand not just what they are doing, but why.

That perspective also shapes how she thinks about leadership succession. Aileen and DSG Global’s founder, Judith, explored their different generations and leadership experiences in their book Deliberately Different. Their conversations reinforced one of Aileen’s central beliefs — the best successor isn’t necessarily someone who mirrors the person who came before them, but someone who shares the company’s values while bringing a different perspective to the role.

Now, as shifting expectations reshape the workplace, Aileen is watching the same evolution unfold in the boardroom. In an interview with Her Agenda, Aileen says the leaders who stand out are those who can look around the corner, communicate clearly, embrace technology, and think beyond traditional organizational silos.

Her Agenda:DSG Global was founded in 1974 by Judith at a time when women faced significant barriers in corporate leadership. What does it mean to you personally to steward that legacy today?

Aileen Alexander: So first of all, I’ve got to tell you about our founder, Judee. If you know her story, it’s pretty amazing. After founding the company in 1974, we had our 50th anniversary just a couple of years ago. I don’t know if you know, but we are the largest woman-founded executive search firm in the world.

We’re top 10 in the US and have received a lot of recognition with that, so it’s just pretty incredible what she launched and how she did it. It’s really about staying grounded in our values and really looking to have a positive impact in boardrooms and C-suites across industries and sectors. 

Coming into this role, I was drawn to our foundation, what our legacy means, but also the growth that we’ve had over the last five decades. And I think where we started, again, we remained sort of grounded on our values.  Our reach is coast to coast.

We’re also through an international alliance. We’re in 30 countries, 60 cities worldwide, which is great. We also very much engage locally in our community, philanthropically, which is what Judy’s always done.

I think in terms of how we sustain that legacy is by continuing to do all of that, but also staying nimble and entrepreneurial and always looking around the corner at the same time, because that’s what we’ve done the last five decades. 

Her Agenda:How do you honor a company’s history while ensuring it evolves to meet the demands of a rapidly changing business landscape?

Aileen Alexander: I think you stay focused and grounded. Again, I’ve mentioned values. I think your sort of values, your ethos, to me, that can stand the test of time and trends.

you start there. That’s number one. Number two, as a firm, we are in the people business. That’s about our people and our teams, right? So staying, maintaining that focus as well in terms of grounding. 

I think, again, if you look back over the last five decades, there’s always new ways of working, new technologies that are coming in, and always having that openness and that willingness to adapt and try new things while staying grounded on what we do on behalf of our clients. 

It’s part of our ethos, and it’s how we’ve operated over the years.

Her Agenda:The transition from Judith to you represents a rare women-to-women CEO succession. After looking it up, only about 1% of all CEO successions are women-to-women. What lessons can founders and future leaders learn from that experience?

Aileen Alexander:, I did have a predecessor before Judith, but really, she’s been an active founder for us.

We wrote a book called Deliberately Different. We published it last year, and we look back over the last 50 years, and as we talk about being from two different generations, I think that became a bit of a metaphor,

Like you said —  a transition from founder to CEO. I think the sort of lesson that we learned, I’ve got to give Judy a lot of this credit, is that you have to look at where the company is today. 

Sometimes there can be sort of a desire to look in the mirror and bring somebody in who is just like you. And Judy had the foresight to recognize that where the company was at this moment was bringing in somebody who, again, shared values, shared ways of operating, but a different type of leader. I think that’s one lesson.

I think the second is how important it is to really listen and learn from one another. Again, I reference the book here, but we didn’t know that it was going to turn into a conversation between the two of us, but the conversation and dialogue that ended up in text is exactly how we work. I think it’s a lesson in and of itself of listening, learning, and being open to differences in terms of ways of doing things.

Her Agenda:Speaking of your book, Deliberately Different, and talking about the two different generations, what surprised you most during those conversations?

Aileen Alexander: I don’t know if surprised is the right word. Across the five decades, what I learned is how important context is in terms of where you’re operating.

Understanding the environment in which you’re operating is important. Even though we each had different experiences, we had experiences in our lives that profoundly shaped who we are as leaders. One thing we have in common is that we both spent time in Washington, but Judy started in Washington, DC in her career. 

In the arena of power and political decision-making, I started my career in uniform and on active duty.

At those earlier stages in our careers, there were both profound things that were happening that just had really shaped us as leaders and the way we operate and how we brought that forward into business. 

I think it’s something that we were aware of, but we got deeper into as we were writing the book together on how those earlier experiences can have a profound impact.

Her Agenda:What does being deliberately different mean in leadership today?

Aileen Alexander: I think being deliberately different is being authentically who you are. It’s so important. I think in today’s work environment with your employees, with your customers, with all your various constituencies or stakeholders, it’s really important to be authentic to who you are and to embrace differences. 

For example, Judy is very open as an extrovert. She gets a lot of energy in a very extroverted way. 

I am an ambivert. An ambivert is someone who is between being an introvert and an extrovert. We need that downtime in terms of how we fill our energy tank. Those differences, that’s just one expression of what makes us different. Being deliberately different isn’t always looking for sameness.

Her Agenda:How did your experience in the US Army shape your leadership philosophy? Particularly, is your approach people-first, mission always?

Aileen Alexander: The people first, mission always philosophy is definitely my North Star. It is the inverse of the actual saying, but I learned pretty quickly as a second lieutenant that it does start with people in terms of accomplishing the mission or your strategic objectives and the like.

What that means for me is that leadership is about service. Again, to mission, to the people alongside you, it’s about the team. That has been my North Star.

A couple other things I learned early on, and this is at the beginning of my career, that I’ve used as just as a leader, the importance, and you learn this, and the importance of operating and communicating with clarity. It’s really important to ensure that your teams know what you’re doing, and where you’re going, and the why. 

We used to do something called the back brief. After you brief, you kind of hear back, and you can either emphasize what needs to be emphasized or force correct what needs to be a bit clearer, restated. 

Another thing, I happened to be on active duty during 9-11, and that, again, talking about earlier experiences also had a profound impact on me. I was really fortunate to work for, and be surrounded by leaders who really demonstrated what it means to be calm, and to ensure stability, and what felt like a very uncertain, very chaotic time. 

That’s something that, as I’ve gone forward in my career and today, when it can sometimes feel like the world is spinning on high octane, I’ve learned how important it is, in this seat and as a leader, to remain calm, have clarity, and keep your teams focused as well.

One thing that I’ve discovered that is really applicable to the business world is AAR. It stands for After Action Review. It’s having the discipline to hit the pause button, whether it’s after a project, or in our case, we’ll do an AAR with not only internally, but potentially with our clients, to really spend time to talk about what worked, what didn’t, how to adapt, where to adjust, and how to apply lessons learned, so you can be that much better the next time.

An AAR is really about embracing a learn-it-all, what I call a learn-it-all culture. I’m really grateful for that. I think it’s really important as a leader, too, to do that in front of your teams, because we’re all learning.

Her Agenda:What qualities do you believe women bring to leadership that are often overlooked or undervalued in traditional corporate environments?

Aileen Alexander: I don’t know that I frame it as overlooked, but I would just say to continue. I think what can start to happen is conversations and dialogue around what I’ll call the either-or. 

We’ll talk a lot about the human skills, and I intentionally call those the human skills. I know some have said soft skills, but I believe human skills are the hard skills. Those include operating with empathy, operating with intentionality in terms of how you communicate, especiall in multi-generational environments. There’s different modes and different channels of communicating and how important that is.

Caring for your people and ensuring that you have those cultures and those environments where all can be successful is really important. Those human skills, you can embrace those, practice those, get better at those, and you will drive performance. 

When it looks at the results orientation, the financial results, driving the business outcomes you’re seeking, you really can embrace and do both. So it’s not allowing those to be an either-or, but an and.

Her Agenda:Looking at the boardroom through both you and Judith’s perspectives, what do you think has changed the most? What do you think has remained remarkably the same?

Aileen Alexander: I think what we’ve seen in boardrooms today, particularly over the last three to five years, is that while they’ve always operated this way, the dial has really been turned up in terms of operating not just strategically, but with a very strong future orientation. So, really being intentional from a governance perspective and looking around the corner, whether that’s from a macroeconomic perspective, a geopolitical perspective, or a technology perspective. So I would say that’s one thing.

I think boards have also gotten really thoughtful about assessing their composition — the differences in terms of experiences and skills that are at the table — and being very intentional around that, again, from a succession perspective and what’s paramount to the company or organization achieving its strategy and strategic objectives. There’s a lot more discipline and rigor around that. It’s a lot less about, you know, “seat opens up, fill the seat,” and much more about being very forward-looking and thoughtful on that front.

You know, the archetypes we see in the boardroom continue to include sitting or former CEOs and P&L leaders, as well as CFOs. We’ve also seen more CHROs, given the importance of people operations and what that means for companies today, as well as technology leaders.

Her Agenda:As companies navigate different tech, such as AI, shifting workforce expectations, and increasing demands for more inclusive leadership, what characteristics will define board leaders and CEOs going forward?

Aileen Alexander: I think there are three things that we see that have stood the test of time and trends when it comes to CEOs, and I would say also directors. The first is being highly strategic — someone who can see the big picture and look around the corner.

The second is cultural fit. There’s a boardroom culture, just as you might have within your enterprise, and from a cultural perspective, being somebody who can communicate effectively is really important.

The third is embracing and being committed to driving performance and results. Those are still all key.

I think what we’ve seen, particularly in the last couple of years, is an increase in terms of competencies. At a minimum, it’s curiosity, but I would also say increasingly now it’s about rolling up your sleeves and embracing technology, digital and AI. It’s no longer siloed within the CTO realm. It impacts all of us, whether you’re a director, a CEO, a chief marketing officer, or a CFO. 

It’s being willing to embrace and learn, and in some places now experiment, with how to utilize different tools, technologies and automation as well.

I think the second is a competency that we’re hearing more and more about, which is what we call systems thinking. I think in the past we talked about the need to break down silos, but leaders who really operate in a systems-type of way and innately can sort of cut through departments — I think that’s definitely needed today as organizations look to innovate and drive performance.