PeakSpan’s B2B Finance Automation Landscape

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.

Justin joined PeakSpan Capital in 2022 and has made investments across the firm’s Digital Health, FinTech & Payments, and Customer Experience Management themes. Today, he leads PeakSpan’s Digital Health practice and co-leads the firm’s FinTech & Payments coverage. Prior to joining PeakSpan, Justin invested in early- and growth-stage businesses across healthcare, insurtech, and vertical software at AXA Venture Partners. Justin started his career as an investment banker at Houlihan Lokey, where he worked on M&A and private financing transactions in software and tech-enabled services. Justin graduated with honors from the University of Pennsylvania, where he earned a B.A. in Political Science. Outside of work, he enjoys playing tennis, hiking national parks with his brothers, and rooting for the New York Knicks.

Chase joined PeakSpan Capital in 2021 and has since worked closely with 10+ growth-stage software and technology businesses in the PeakSpan portfolio. Prior to joining PeakSpan, Chase was an investment banker at Houlihan Lokey, where he advised on M&A and private financing transactions across software, internet, FinTech, and tech-enabled services. Chase holds a B.A. in Economics from Middlebury College, where he graduated Magna Cum Laude and with departmental honors while also serving as a member of the men’s lacrosse team. In his free time, Chase enjoys international travel, exercise, cheering on Washington D.C. sports teams, and trying new restaurants in New York City.

Cassie grew up in New Jersey and is currently based in New York. She graduated Summa Cum Laude from the University of Michigan’s Ross School of Business (Go Blue), where she received her BBA and a minor in Entrepreneurship. Before joining PeakSpan, Cassie worked at multiple startups, which gave her a firsthand view into the challenges and pace of building a company from the ground up. Over the past several years, she has worked closely with founders as an investor, advisor, and board observer. Today, Cassie is a board observer at Routefusion, Boostly, Finally, and Sales Layer.