Leadership Profile: Partner Jake Brodsky

Jake Brodsky first joined Alpine Investors to learn the skills needed to start his own business. He only expected to stay for a year. Today, over eight years later, he leads Alpine’s sourcing team and was named partner in January. Here, he reflects on the entrepreneurial values and culture that kept him here, the importance of supporting people, and why he’s energized by his and Alpine’s future.

I was raised by two entrepreneurs. My dad was a doctor, running his own independent practice, and my mom ran a consulting business focused within healthcare on hospital administration. I grew up in a household that valued creativity, innovation, competition and the entrepreneurial spirit. We prioritized academics and sports for what they could teach about setting goals, working hard and expecting success as a result.

In undergrad, I studied business with a concentration in finance and entrepreneurship at the University of Southern California. I took a class as a junior where you got to hear the stories of successful entrepreneurs, which further sparked my interest. Over the next summer, I set out to start a business around a household cold-brewing coffee machine. A portion of the population suffers from acid reflux and can’t have regular hot-brewed coffee because it’s too acidic. Cold brewing solves that problem. However, cold-brewing typically takes 24 hours, and your average person doesn’t have quite that much patience. While it might sound like a no-brainer idea today, cold-brew coffee was not what it is now— few of the large or small coffee chains offered the product. It was an unlikely business for me to start as I didn’t drink coffee at the time nor was I skilled at building machines, but I loved the angle of solving a problem for a population that wasn’t able to access something that almost everyone else could. It didn’t hurt that I felt like I was working in the “healthcare” field, following my mom and dad’s footsteps. To this day, I love looking at Alpine companies in the healthcare space or those focused on supporting under-served populations.

Needless to say, the business didn’t perform like my 20-year-old self thought it would. My professor and advisor at the time told me she saw potential in me and said, “You can be an entrepreneur one day— you just need to learn some building blocks, starting with sales.” So, after college I looked for the biggest company I could find with the best sales training program. That’s how I found Oracle. My role there put me in the Bay Area and taught me how to prospect, build relationships, and close, a skillset that I still use today. It was an excellent foundation.

Entrepreneurial Goals

After a year at Oracle, Alpine’s team reached out to me about their plan to build out a sourcing function. I was entertaining a move at that time anyway, planning to leave Oracle to move back to LA to start a company of my own. I knew little about private equity except that even to be asked to interview with my background was atypical. But then I learned more about Alpine’s approach and thought joining the sourcing team could be a perfect learning opportunity.

I thought working for Alpine for a year could teach me everything I needed to know about making a business successful enough that someone would want to buy it, imagining it’d be a small step on my journey. I also thought joining a team that had yet to be formed would satisfy my entrepreneurial drive. While I had a lot to gain from joining Alpine, the decision came down to how Alpine talked about people, culture and values. All of the partners specifically embodied values of family and kindness, and were determined to win, but never at the cost of people or relationships. That culture was so different from the little I knew about the private equity industry. I joined and knew quickly that I would likely stay for a long time.

I was motivated at Alpine by how much responsibility the team gave me almost right away, more than I was ready for at times. Partners Mark Strauch and Billy Maguy were incredible mentors and always gave me chances to push myself. About a year and a half into my time at the firm, we wanted to figure out a creative way to put more capital into software. So I found myself working on this entrepreneurial project that soon became Alpine Software Group (ASG), a platform for acquiring vertically-oriented SaaS companies that would benefit from operating in highly specialized niches. I co-founded ASG along with Mark and Billy, and became its head of M&A. I was 25 years-old at the time.

Building Diverse Experiences

Our first office at ASG was opened in Walnut Creek and we jokingly named it the “Death Box” because there were no windows. We fit two or three people into a couple of 100-square-foot rooms. Jamie Linden joined as CFO and spent more time within the space than anyone else. Through those first few years at ASG, I got the opportunity to develop a more diverse skill set, not because I was qualified, but because that’s what ASG needed. Scrappiness and entrepreneurial spirit quickly became core values of ASG, along with our desire to win— later these values would go up on the walls of our much nicer office as “Will to win, win with love.” That experience allowed me to expand my skill set from sourcing, to executing the entirety of the investment lifecycle, to board leadership.

As ASG grew and the team expanded, we started to realize that ASG’s true potential was significantly larger than our original design. Alpine supported ASG and pushed us to think bigger, and then bigger again. This manifested itself not just in the number of deals we sought to do— surpassing the 50th acquisition milestone earlier this year, but also in how we leveraged some of Alpine’s programs.

One thing I’m particularly proud of from my time at ASG was our approach to the CEO-in-Training (CIT) program. At the time, Alpine had created this program to place top MBA students from great schools in their companies at a VP level or reporting directly to a CEO. They gave promising young leaders the chance to learn the ropes hands-on, with the goal of becoming CEOs one day.

I’m proud of the role that ASG played in helping to not only grow that program, but to provide growth opportunities for so many individuals within it. That impact really hits home when we go through a company exit and take a pause to celebrate the life-changing accomplishment with the management team. I love building relationships with individuals, so to have dinner with Soumya Nettimi, Colin Li and the ASG Leadership Team after we completed the sale of Paradigm was one of the best moments of my career.

Leading Larger Teams

In September 2020, I rejoined Alpine’s software team. Then in January 2022, I took over leadership of the sourcing function. Leading it was a job I thought I was prepared for, until I realized it was another opportunity that Alpine gave me to rise to the occasion. While I had experience managing small teams and winning individual deals as a deal lead, I had never managed such a large team and built strategies to deploy capital in a multi-billion dollar fund. That’s what keeps me at Alpine. I don’t have to go anywhere else to scratch that entrepreneurial itch. I love the fact that my job looks different every day. I get to work with unbelievably smart people, and now as a leader, I get to impact people.

That’s what keeps me at Alpine. I don’t have to go anywhere else to scratch that entrepreneurial itch. I love the fact that my job looks different every day. I get to work with unbelievably smart people, and now as a leader, I get to impact people.

As a sourcing team, we’re tasked with finding great investments for Alpine and its portfolio companies. We’re the first step in a very long M&A process. We source through a variety of channels, either working through intermediaries that bring us deals they are representing for sale or sourcing directly where we build relationships with founders for when they’re ready to sell.

At Alpine, we’re creating opportunities for people to build a diverse, yet specialized skillset so that they can be the best people and professionals in whatever areas they choose. There is not one set career path that defines success here. Some people started on my path and became CEOs. Some decided to go back to business school or change industries. Some have grown within sourcing and are leading teams and channels of their own. My goal as a partner is to empower our people to build the skills they need to grow into someone they couldn’t have imagined when they were 22 and fresh out of college. I was the first hire on the fully dedicated sourcing team back in 2015, so I’ve appreciated the opportunity to train and develop others, as Matt Picciano, the original leader of the sourcing function, did for me.

At Alpine, we’re creating opportunities for people to build a diverse, yet specialized skillset so that they can be the best people and professionals in whatever areas they choose.

I also love the pressure our team puts on ourselves to hit a new record of deals closed every single year. It’s wonderful to get to invest in people and see those people exceed expectations, resulting in our ability to continue to build Alpine into a private equity group that breaks the mold. If we didn’t have those results, we wouldn’t be able to devote so many resources to hiring and career growth. I love that we can be a PeopleFirst firm without sacrificing results.

To me, becoming a partner means taking a moment to pause and reflect on what I’ve accomplished over the past eight years. It’s a recognition for the value I’ve contributed, Alpine’s innovations, and also recognition for the potential of what I still have left to contribute. I view the Alpine partnership as a team. We each contribute skills that are complementary to others in the room, and we learn a lot from each other. We place a lot of trust in one another to create something greater than anything any one of us could create on our own. I bring an ability to find investment opportunities and look at them in creative ways. Co-founding ASG is one example of that, and another is helping found Elevation, our Salt Lake City-based office that focuses on direct sourcing.

I view the Alpine partnership as a team. We each contribute skills that are complementary to others in the room, and we learn a lot from each other.

With my path, I hope to inspire those just joining Alpine that they too can choose a path and make it happen. Even without a traditional background, through hard work and an amazing team, you can exceed your expectations for yourself. The people of Alpine are what make this place special and make it successful.