How ASG President Alice Song Channels Her Own Executive Experience as a Mentor to ASG CEOs

As Alpine Software Group (ASG) President, Alice Song helps vertical SaaS CEOs and their teams identify obstacles, receive resources and chart paths that accelerate growth. Her leadership is rooted in fostering a culture of inclusivity, and Song has found support in doing so alongside Alpine Investors’ PeopleFirst philosophy. In reflecting on her experiences with Alpine, Alpine-backed ASG and its companies, Song shares how embracing unexpected opportunities has catapulted her career and landed her in a role where she’s constantly learning.

I knew I wanted to go into business relatively early on. I was born in China and immigrated with my parents— both engineers— to the U.S. when I was 4 years old. Watching my parents build and run a small business sparked my desire to do the same when I grew up.

After I graduated from Yale, I spent five years working in finance, investment banking and private equity. I developed a love for sitting down with portfolio executives, talking strategy and working on new add-ons. I craved that team element and wanted to build something that felt like a different muscle from investing.

With this insight, I applied to the Stanford Graduate School of Business (GSB) with the goal of raising a search fund. I knew exactly what I wanted to get out of business school: to become the best possible leader. GSB had a lot of programs geared towards finding your authentic voice and leadership style. I took all the touchy-feely and leadership classes that I could.

I think GSB was the first time I really felt free to be myself and to put myself out there. I told my story authentically and people responded in a positive way. That experience made me much more comfortable in my own skin and that confidence makes me a better manager and leader.

Choosing Alpine

As I considered my next steps after business school, I heard so many great things about Alpine that I went through the interview process to learn more about its CEO-in-Training (CIT) program. Alpine’s community of CITs and peers really stood out to me and it felt like a community I could learn from.

The PeopleFirst aspect of Alpine also resonates with me. I like the idea that Alpine wants A-players and they welcome folks to bring their full selves to work. The entire firm and all the companies that they partner with go through PeopleFirst programming, focused on finding one’s passion and purpose. As a gay, Asian-American woman, I have often been “the other” in the groups I’m a part of, especially in finance. I value being able to bring my full self to work and I love working with a very diverse team. I hope to carry this kind of inclusive culture wherever I lead. I joined Alpine Software Group (ASG) in 2019 as a CIT and started searching for an executive role in an ASG company.

Embracing Unexpected Opportunities

At the time, Traject, then ASG MarTech, had an opening for a COO role and I decided to go for it. They were looking at a bunch of acquisitions and growing quickly.

Even before my first 90 days were up, then-CEO of Traject Steve Reardon let me know he was going to take a larger role back at ASG and asked if I wanted to become the next CEO of Traject. I knew it was the right choice for me and for the company. During my short tenure as COO, I had gotten to know our leadership team and trusted them completely. I knew that we would work well together and continue to grow the business.

Then after two and a half years at Traject— where I oversaw five add-on acquisitions, built an amazing leadership team and worked alongside two other CITs— Steve asked if I would come back to ASG to run mergers and acquisitions (M&A) and to serve as ASG President. I happily accepted. ASG was building out its investing team, focused on vertical SaaS businesses— acquiring both new verticals and add-ons for existing businesses. My focus became building out the M&A team and working on deals. I also acted as a mentor to many of ASG’s CEOs and leadership teams.

The Power of Hiring Well

At Traject, I saw the impact of hiring an A-Player versus a B-Player or even a C-Player, and I saw how hard it is to assess people during interviews. Alpine’s deep dive approach to interviews is incredibly helpful. I love trying to figure out what motivates somebody, what they really care about, and then how these values show up in their experiences, successes or failures. Framing the interview around motivations and following those questions helped us assess whether a person was a good fit. I went through the process myself when I was interviewing for Alpine and I found value in sitting on the other side and hearing the different responses. The process works.

When I came on as President at ASG, we noticed a lack of gender diversity in our recruiting pipeline for the M&A team, so we spent the first 15 minutes of our weekly hiring meetings trying to solve that challenge. We found that hearing directly from a female leader was one of the best ways to source strong female candidates, so I carved out time every week to personally connect with those I thought could be a good fit for the role. Our recruiter’s pitch was also very direct with female candidates, sharing that our M&A team was led by a woman and about ASG and Alpine’s commitment to diversity.

This intentionality worked. In 2022 and 2023 our intern class comprised 50/50 men and women, and our Analyst & Associate class was three men and two women. We’re also very thoughtful at ASG about spotlighting female CEOs and their work, as well as making sure that all voices are heard in any forum.

Doubling Down on Growth

In mid-2023, we decided to shift ASG’s focus. Alpine has spent the past two decades focused on creating a strong investing team; they already have the recruiting, training and development infrastructure. So, we decided that ASG would be best served by leaning on Alpine for M&A and doubling down on growth and operations. I’ll focus entirely on the President side of my role, which means I’ll sit on boards of ASG’s companies; lean into strategy, operations, and growth at ASG; and help mentor the more than 30 CEOs at ASG companies.

I have a lot of empathy for the CEOs and leadership teams who I work with; I was one of them not long ago. Knowing the challenges of the role inspires me to do whatever I can to help them and their businesses succeed. I’m excited to devote my time to it.

Looking Ahead: International Expansion and Organic Growth

This year, we want to scale our bright spots by taking the successful parts of what founders have built and amplifying them with our software, product and go-to-market know-how.

The thing about organic growth is that it’s a game of inches; there is no magic bullet. Our goal is to work with company leaders to create very clear plans— which will be different for every company— then support them in reaching each goal.

Part of that growth focus is making sure we have a terrific product, vision and roadmap. Then we’ll make sure we’re investing in talent to help execute the plan. Historically, we’ve often put the burden of that product visionary role or that product strategy role either with the CEO or with the CTO. We’ve realized that running the Product team is a huge job that needs a person entirely devoted to it.

We hired VP of Product for ASG Ron Yang earlier this year, and he’s very in-demand already. Every company wants to talk to him, and he’s currently running five searches for VPs or Head of Product within our portfolio. Besides growing our team, we’re also spending a lot more of our deal time on international markets. We think there’s a wealth of opportunity to buy software companies in places like the U.K., Germany, Australia, and New Zealand.

When I finished business school four years ago, I never expected to be a former CEO advising other CEOs. I never imagined I would have the chance to build out an investing team. My career path continues to exceed my expectations for learning and growth. I’m energized by my constant chances to lead and can’t wait to see what’s around the next corner.

Certain statements about Alpine made by portfolio company executives herein are intended to illustrate Alpine’s business relationship with such persons, including with respect to Alpine’s facilities as a business partner, rather than Alpine’s capabilities or expertise with respect to investment advisory services. Portfolio company executives were not compensated in connection with their participation, although they generally receive compensation and investment opportunities in connection with their portfolio company roles, and in certain cases are also owners of portfolio company securities and/or investors in Alpine-sponsored vehicles. Such compensation and investments subject participants to potential conflicts of interest in making the statements herein. Past performance not indicative of future results. Results may vary materially and adversely. Please see Alpine’s Terms of Use for additional disclaimers.