Amanda Sayigh doesn’t shy away from a challenge. The COO of Alpine Investors-backed Innovative Systems set her sights on division one basketball at Dartmouth and achieved it, then spent four years in banking at Morgan Stanley before a stint at Apple. A search for community landed her at Stanford GSB which inspired a startup and led her to Alpine for a VP of M&A role at its portfolio company Escape Technology. Here, the mom of two shares what she’s learned about herself during her CEO-in-Training (CIT) to executive leadership journey, the magic of building alongside incredible people and why parenting is the ultimate c-suite preparation.

It doesn't matter your age, what you look like, who you are or where you come from; you roll up your sleeves. Your experience as a CIT goes from diving into the dirty work to sitting in a boardroom getting ready to sell the company.

The theme of my life has always been finding challenging things and doing them. Choosing to take a hard path set me up well for life as a CIT, and now for life as a working parent of two young kids. I believe that difficult tasks yield big returns, and I feel a sense of calmness now that I’ve faced challenges before and succeeded because of them.

Solving Puzzles and Finding Belonging

I discovered Alpine and the CIT program while at GSB, but before joining I co-founded a business in the recruiting space. Through that experience I learned the power of working with great people and that I’m best suited to growing companies from one to 100 instead of zero to one. I love building a team, building up others, architecting deals and negotiating. That plays out in operating, too. Managing teams is all about negotiations. “What do you want to do? Where do you want to be?” I view it as one big puzzle that can be solved, as long as you have the right pieces.

When my co-founder and I decided to shut down the startup, I met with the Alpine partners and we connected right away. I committed to becoming a CIT, unsure what my role would look like. In my first meeting with Ali Jenab, an Alpine CEO-in-Residence (CIR) and the CEO of Escape Technology, a company that provided enterprise resource planning software to K-12 schools, he told me he wanted to build a big, acquisitive EdTech business. We just clicked. I’ve always loved the thrill of the deal, so I signed on with him as VP of M&A and never looked back.

I had so much autonomy right away. Ali has 30 years’ experience, and my fellow CIT (Escape VP of Business Development Charlie Pratt) and I were fresh out of business school, but there was never hierarchy. Within a week, Ali asked me to become interim CFO as well, and I figured it out. We were a lean team and it was all hands on deck. That’s what I love about the CIT program. It doesn’t matter your age, what you look like, who you are or where you come from; you roll up your sleeves. Your experience as a CIT goes from diving into the dirty work to sitting in a boardroom getting ready to sell the company. You see and do everything from start to finish.

I had always aspired to be CEO. I wanted to realize my dream not only for myself, but also to become someone my children would look up to.

Pretty soon, we had acquired several education software businesses alongside Escape. We named the holding company Perennial EdTech. A year later, we were running the exit process. During the sale of Perennial, I was bombarded with questions in management meetings, and I enjoyed answering anything they threw at me. That’s when I realized that I had solved the puzzle. It took time and effort, but I knew I belonged.

After the sale, I stayed with Alpine as a principal focused on corporate development and investor relations, and I got to see the Alpine ecosystem from a new perspective. I then connected with April Smith through my network and hired her to lead investor relations and fundraising at Alpine. She brings a new level of expertise and rigor to the role.

Throwing Out the Plans

As for many others, the beginning of the pandemic in 2020 forced me to reevaluate my life and what I considered important. The difficult and premature birth of my first child at that time coupled with the fact that I was separated from my extended family for her first months of life gave me the additional opportunity to reflect on what I wanted for the future of my own growing family. I had always aspired to be CEO. I wanted to realize my dream not only for myself, but also to become someone my children would look up to— someone who faced challenges, persevered and achieved.

Amanda Sayigh with her daughter Colette and son Lucas.

A few weeks later, Ali called about joining him at Alpine’s newly acquired business, Innovative Systems, a South Dakota-based provider of enterprise software for rural telecom and broadband providers. I knew I wanted to get back to building and growing something alongside great people. I had a personal tie to the business because my parents live in rural Vermont where they don’t have reliable Wi-Fi, and I knew I could learn a lot at Innovative and from Ali, so I joined as chief financial officer and chief revenue officer. After a year, I was promoted to chief operating officer.

Winning Through People

At the end of the day, it’s all about the people. From day one, Ali and I (as well as Chief Revenue Officer Austin Monahan, another Alpine CIT) had to earn trust and work with the current team to make strategic changes. Over the past three years we’ve systematically converted our customer base to subscription. It’s been a huge success and we’ve had zero churn during the process.

I’ve also brought in new talent on the Finance, Corporate Development, and Customer Experience teams. I recruited my former colleague from Perennial EdTech, Robert Merii, to come work with me again, as our director of finance. I hired Brennan Smith to lead Corporate Development, and Enrique Olivas, Sr. as director of customer experience. They both have made tremendous impacts across our company. I’ve been able to put my Perennial EdTech learnings into action at Innovative Systems by up-leveling talent and building engaged teams.

I still dream of building a team and starting something, and I know I am so much better suited to be a CEO now that I’m a parent. I understand what matters, know the importance of making impactful decisions quickly and I see no option but to win. Failure wasn’t an option for me in April 2020 when I brought my daughter Colette home, and it’s not an option now. There are hundreds of biases against working parents, especially moms, but I view my need to juggle and prioritize as an advantage. I’m energized to build something both to provide for my family but also to show Colette and my son Lucas that both mom and dad can achieve anything.

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.
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