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Middleburg Earns 2025 Great Place to Work® Certification: What It Means for Our Team and Investors

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Ali Edelstein

Senior VP, People & Culture

October 07, 2025

A Q&A with Senior Vice President of People and Culture, Ali Edelstein.

Can you share a bit about your role at Middleburg?

Ali: I've been with the company a little over two years, and I'm the Senior Vice President of People and Culture. In this capacity, I lead our culture team to manage, improve, and enhance the entire life cycle of our team members. So, everything from org design to workforce planning, through talent attraction and recruitment, sourcing and selection, onboarding, team development, and retention—that whole cycle.

Since the start of your tenure, what changes have you seen in team culture at Middleburg? Are there specific initiatives that you've been driving?

Ali: Since I joined, we've grown tremendously. When I joined, we had about 170 employees, and now we have about 250 employees. So, that has been really exciting and energizing.

However, with growth, challenges inevitably arise. For example, how do you focus on retaining, supporting, nurturing, and cultivating the culture? And I would say one positive thing that I've witnessed here, and hopefully been able to help influence and impact, is keeping the culture at the forefront. You could have the best-laid business plans, but if you're not paying attention to the people and the culture—the underlying foundation—that can really upend any growth plans or plans for expansion, and the business as a whole.

Is that an idea that has organizational buy-in?

Ali: What really impressed me when I joined Middleburg was the strength of the culture. It was essential for me, knowing that we were going to grow, to pay attention to the culture and keep it healthy. Growing from a small company to a mid-sized company can be a challenging transition. What I kept hearing from leadership was that we definitely have to pay attention to that, we have to be intentional. It's really the invisible glue or architecture that holds the company together and allows us to meet the strategies that we've set out for ourselves. Our culture was already strong when I arrived, and it was clear that we needed to nurture and grow it further, ensuring it remained alive as we expanded.

What is the significance of getting certified as a Great Place to Work?

Ali: Oh, it's huge. I was really excited to participate in that program because the way you get certified as a Great Place to Work is by surveying your employees or your team members. The badge is, in fact, a reflection of the team's sentiments.

One significant benefit of participating in a program like this is the opportunity to receive feedback from your team members. That's invaluable to me as I lead the people and culture team, because I want to hear from everybody — I want to get a real pulse on the current state of the culture, the workplace, the environment, and employee engagement. And second, it's always wonderful when team members feel heard and know that they have a vehicle or a tool to share their feelings, opportunities for improvement, and what they love about working here.

So, it's a two-fold benefit: we gain an employee listening strategy as part of participating in this certification program, and we also get a real pulse on employee engagement levels. Additionally, you receive outstanding recognition of who we are and validation that we are a great place to work. We can promote and celebrate that, using it to attract top talent.

Reading through that feedback, what were some of the themes and trends that resulted in Middleburg earning a Great Place to Work certification?

Ali: One of the things that we're really proud of is that 92% of employees say that management trusts people to do a good job without watching over their shoulders. How empowering and freeing is that? I think that when you feel you have the courage, autonomy, and trust to make decisions and do your job, that's an excellent environment to be in.

Another standout is that 92% percent of Middleburg employees believe that management is honest and ethical in its business practices. And 92% say, ‘when I look at what we accomplish, I feel a sense of pride.’

Additionally, some of the engagement scores are incredible: 'I can be myself around here.’ That's one theme that I think is a fundamental aspect of our culture: people can be their true, authentic selves, and it's a genuinely kind place to be. Over 90% of our team members said, ‘I want to work here for a long time.’ And over 90% of our team members said, ‘I'm proud to tell others I work here.’ Those are some of the major themes that emerged from the survey.

After analyzing the survey results, are there specific initiatives that you have planned for Middleburg team members, things that you're excited about moving forward?

Ali: One key aspect is that we'll focus on celebrating our wins through recognition and communicating with our team members. That goes hand-in-hand with nurturing and investing in our culture, because as we grow, it becomes harder to stay connected. We're currently developing a new employee recognition platform that will enable us to acknowledge milestones, anniversaries, and significant work achievements with high-fives, applause, and celebrations.

How do you cast a vision for Middleburg in such a way that team members really feel like they're part of the story?

Ali: One initiative that we rolled out was hosting quarterly town halls. We always begin with a state of the business from Chris, our CEO, who shares our vision, progress, and accomplishments. He also reminds folks of where we're going and where we're growing. And I think that has really helped. All employees are invited, and it's crucial to hear from the top about our progress and feel a part of it, knowing you've contributed to moving the needle forward. And then think about how you can contribute — no matter what role you're in or what level you're at — to the vision and growth. That is always motivating, empowering, and inspiring.

It's interesting that as you describe team culture, you're not focusing on perks but on intrinsic value, with people feeling heard and valued. Has that been intentional on your end?

Ali: It's not just about perks and rewards, though they're essential. What truly makes a workplace great is creating an environment where people feel valued, can make an impact, and are part of something bigger. At Middleburg, we have that.

People want to feel heard, seen, supported, and inspired. They want to know they're contributing to something meaningful. I believe the most valuable benefit of all is being in an environment where you can do your best work.

What do you think the significance is of earning the Great Place to Work Certification for Middleburg's prospective employees and investors?

Ali: When you're thinking about investing in a company or a fund, there's an element of trust there — you want to trust that group. Part of what fuels trust is competence, capabilities, and delivering on what we say we will do. That's why we're looking to attract the best and the brightest. Earning a Great Place to Work certification helps us attract the right talent and demonstrates to our investors that we can be trusted. So, there's trust on the investor side, and then the trust has to be present on the culture side as well, at an internal level.