Jack Freeman: Partner at PeakSpan

Jack Freeman

Partner

In their words:

I have developed a deep appreciation for the term “owner-operator.” Operators work, think, and act differently. Everything matters.

Sector Expertise

Investments

About:

Jack has worked with growth-stage technology businesses his whole career and has partnered with over 25 portfolio companies at PeakSpan. He currently leads PeakSpan’s FinTech and Supply Chain investment themes. Jack was named to GrowthCap’s Top 40 Under 40 Growth Investors List in 2025. Prior to joining PeakSpan, Jack worked at Stackpop, an early-stage startup, where he helped build a SaaS spend management platform that enabled CTOs and IT teams to buy and manage internet infrastructure. After Stackpop was disrupted by AWS, Jack joined Macquarie Capital, where he spent three years executing software M&A and capital markets transactions for technology businesses. Jack holds a B.A. in Economics from Middlebury College. Prior to Middlebury, he played Division I soccer at Seton Hall University and for the New York Red Bulls U-23 team. Jack lives in Larchmont, NY, with his wife and two dogs, Willow and Leeuwen. Once a year, Jack captains a team in a charity bike ride to the Hamptons to support his brother’s autism program, Quest, where he has raised over $100K. Since retiring from collegiate soccer, Jack has become an avid endurance athlete, completing five of the “Big Six” World Marathon Majors (London remaining), an Ironman, and a 50-mile ultramarathon. He is currently focused on improving his marathon time from 2:32:30 to sub-2:30.

What makes you excited to come to work each day at this stage of your career?

The messy middle. Working with scale-ups in the emerging growth stage presents unique challenges and opportunities each year. There is no single playbook or right answer. For this reason, it is critically important to partner with the right entrepreneurs. It is only through strong, collaborative partnerships, combined with grit and creativity, that we can lock arms with CEOs and management teams to overcome obstacles and navigate the messy middle of scaling B2B technology companies from <$10M to $50M+ in ARR. Tackling these challenges alongside our entrepreneurs and rolling up our sleeves to solve problems is, without question, the most rewarding part of the job.

What’s a project or moment at PeakSpan where your involvement changed a company’s trajectory?

In 2017, we hired Andrew Bartusiak as PeakSpan’s first-ever summer analyst. Today, Andrew is a walking, talking case study of what it means to be a PeakSpanner. He set the archetype for the eight subsequent summer analyst classes, from which we have hired fourteen full-time teammates. Our experience working with Andrew prompted us to build what we believe is one of the most competitive and rewarding summer analyst programs in growth equity. Talent is our most precious asset, and PeakSpan is the most talent-dense organization I have ever had the privilege of being a part of. Thank you, Andrew.

Before PeakSpan, what did you learn the hard way that you now bring into every partnership?

There is no such thing as failure in sports (link). I have had the privilege of playing sports my entire life, including at a Division I school and for the New York Red Bulls. For the most part, I lost (a lot). For a competitor, failure is hard to process. It may have taken ten years of competition, but it eventually clicked: failure is only possible if you give in. This lesson translates directly to growth-stage investing partnerships. The path from $0 to $50M in ARR includes more roadblocks, setbacks, and perceived “failures” than most people appreciate. Understanding this reality helps reinforce the long-term perspective and resilience required for success in growth-stage software.

What personal experience most shaped how you work with founders today?

After joining PeakSpan in its early years and having previously operated as a founding employee, I developed a deep appreciation for the term “owner-operator.” Operators work, think, and act differently. Everything matters. For the right people, scale-ups are among the most rewarding professional journeys; conversely, those who are a poor fit stand out quickly. When working with founders, I implicitly understand the stakes, the attention to detail, and the level of care required. This perspective informs my entire approach to every interaction.

Personal side: