Q&A with Haley Van Cleve on Her Journey from Associate to VP

When Haley Van Cleve joined Alpine, she was fresh out of Princeton—with a computer science degree and zero experience in finance. But in the five years since, she’s gone from analyst to associate, and now VP. Below, Haley describes the responsibility she was given right away, the power of mentorship, and how rapid growth and constant challenges continue to motivate her as she plans her next steps.

Tell me about your path to Alpine.

I never expected to be in private equity; all through high school and into college I was dead-set on working in health care research, and I did a bunch of internships in that field. But I decided that before graduation, I should make sure there wasn’t something else I wanted to do. So I did an investment banking internship at Goldman, and that opened my eyes to a whole world I hadn’t been exposed to. Around that same time, a classmate who had interned at Alpine put me in touch with them, and I started talking with Graham,   about an investing role. I really had no idea what private equity was—in one interview, I asked the difference between revenue and profit! It’s a testament to Alpine’s commitment to hiring for attributes, rather than experience, that I’m here at all.

I felt like the company was on an exciting journey, and it seemed like a place where I could grow and really learn the nuances of investing. But I think the most compelling part was the people side of Alpine—understanding not just how to build and run great businesses, but how to be a leader. That was different from a lot of other roles in the finance world. So I decided to take the leap and move out to California; I joined the day after graduation.

What surprised you most in those early days?

Even though I knew coming in that Alpine puts a lot of emphasis on early empowerment, it was still surprising to see that in practice. Everyone contributes from the start, and everyone on the deal team is in on all of the conversations. I will never forget—on day one, I joined a deal review meeting, which is where we go over potential deals and decide where to spend time and where to pass. I sat down with my notepad, ready to listen and learn, but about 30 seconds in, Billy turned to me and said, “What do you think?” What I was really thinking was, “I started a few hours ago! I have no idea.” But I quickly learned that it’s standard practice at Alpine to go around the horn in reverse order of tenure.

By the end of that first week, I had joined a management meeting with sellers of a business; I’d been on calls with bankers; I’d attended a board meeting for a portfolio company and been encouraged to ask questions and challenge assumptions. Diving right in really forced me to start seeing myself as an investor and form my own independent ideas. And it’s not just lip service. Over the years, there have been several times when the CEOs and partners all think we should pass on something, but we explore it because an analyst makes a compelling argument. And in some cases, those deals have ultimately closed.

What was it like to climb those learning curves as a new member of the team?

At times it was like drinking from a firehose. I was on a deal on my second day, when I barely understood what that meant. But you learn, and you always have a great support system. It’s a combination of upfront classroom time and experiential learning—we do something called “modeling day,” for example, where you’re given data on a company and told to spend the day building the model. Since I didn’t know any accounting when I joined, that was intimidating. But you’re paired with a mentor, and you can basically sit next to them and just ask questions all day. I spent a lot of my first several months in that mode—on a whiteboard in a conference room, talking through the formulas in every Excel file, really getting a crash course in the full context of a deal.

And that support can go as far as you like; Alpine is very much an environment where if you want to take on more, you can, and you’ll have mentorship along the way. That’s allowed me to keep the learning curve really steep, and do more, earlier, than I could have at other firms.

What have you learned so far?

 There’s so much! I’ve had the opportunity to close more than two dozen deals now in five years, and I’ve learned from every one of them. I think one key lesson was the importance of seeing the big picture before you get too far in the weeds—making sure you understand the “why” first, then digging into the nitty gritty. That’s a quality you see in the most successful folks on our team, including our partners—they know how to fly at the right level, at the right time.

I’ve also learned a lot from the feedback loop of sitting on company boards. Investing isn’t just closing a deal and moving on to the next; it’s being with a business for the long haul. You’ve made projections about what will happen, but what actually does? What’s easy; what’s hard; what did you miss? Getting to work with our CEOs, CFOs, and other operators, and hearing how they see the business, has been invaluable. I learn from every conversation.

What’s been difficult about your work at Alpine?

I’m 27 years old, so I’m often talking with founders who have been in the industry longer than I’ve been alive, and building credibility can be a challenge. Here at Alpine, empowering people early in their career is the norm, but there are plenty of places where that’s not the case. I’ve even struggled with that mindset myself. I remember early on, Danny and I were set to meet with a team in the Midwest about a possible acquisition, and the weather was terrible; my flight made it, but his didn’t. I assumed at first that we’d have to cancel. They were expecting an experienced partner, not me! But to Danny’s credit, that never crossed his mind. I ended up taking that first meeting solo, and ultimately we closed the deal.

I’ve found effort makes up for a lot. As the saying goes, “People don’t care how much you know until they know how much you care.” Sometimes it also helps to acknowledge the obvious: I’m young, and at Alpine, we give young people the ball.

What are you most proud of?

 One thing is the way we’ve been able to grow some of our platforms, including behavioral health and hospitality tech. It’s so rewarding to see something that started as five slides in an investment committee meeting a few years ago grow into a living, breathing organization, with six businesses and hundreds of employees all working toward a common mission.

I’m also proud of Alpine’s own journey. When I joined, we looked very different in terms of both fund size and team size; it’s crazy to think that back then, we were all in one room. But the transformation has never felt like something that was happening to me, which I think is a stark difference between Alpine and some larger institutions. Everyone has a voice in our strategy and future. We’re all part of shaping the firm into what we want it to become.

But the transformation has never felt like something that was happening to me, which I think is a stark difference between Alpine and some larger institutions. Everyone has a voice in our strategy and future. We’re all part of shaping the firm into what we want it to become.

And even as we’ve grown, it feels like we’ve been able to stay true to that culture. With every new person we hire, after a few weeks on the job, we’re always thinking, “How did we ever survive without them?” That’s pretty special.

How are you excited to grow going forward?

One thing I’m continuing to work on is the relationship-building aspect of my work. Coming in, I thought it would be about my analysis skills—and of course, the numbers are important. But so much of a successful partnership is about understanding the people. Founders have many options when they’re selling their businesses, and it’s critical that we build trust with them and that they know our values are aligned. You have to create the space for transparency, too. It’s amazing how many times what’s presented up front is different from what you hear if you just ask someone directly what they actually want. Truly understanding each stakeholder and what they’re solving for is what allows us to create outcomes that everyone is excited about.

In general, I think the learning curve I came here to climb more than four years ago still hasn’t plateaued. But it’s about tackling one thing at a time, layering in skills as you go, whether it’s how to engage with a founder and pitch Alpine, or how to handle negotiations and difficult conversations that come up during diligence. I feel like each day is a nice mix of the things I’m good at and the new challenges I want to explore.

How are you excited for Alpine to grow?

For me, it’s about the impact we have. One of our objectives is to be a great private equity firm. The other is to be a force for good; to use our capital and influence to drive meaningful, sustainable change that truly improves lives, including the tens of thousands of employees across our companies. Those two goals aren’t in tension—in fact, part of what makes us good investors is understanding that in order to build a great business, you first have to build a great team. When I joined, I thought I’d spend a few years learning the finance skill set, then go apply it somewhere where I could have a more direct impact. But I’ve realized I can do that right here.

Note: Since publication, Haley was promoted to Partner at Alpine Investors in January 2024.