Perspectives

PeakSpan’s Payments Infrastructure Landscape

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Jack Freeman

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Justin Kelly

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Chase Goree

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Cassie Alexe

August 9, 2022

The payments stack is a complex and evolving system as the various domains of payment (e.g., B2B, cross-border, C2B, P2P) require tailored infrastructure for digitizing transactions. The B2B realm is among the most archaic in terms of payments digitization, still largely dominated by paper checks due to the complexity that accompanies the business payment lifecycle — from purchase order/invoice to AR/AP. Beyond the technology that simplifies B2B payments, there is also a wide array of embedded financial products that integrate into a business’s existing infrastructure to streamline access to financial services, thereby enhancing the customer experience and eliminating friction across multiple systems of record. Notably, we have highlighted PFACs that allows businesses to accept card payments as sub-merchants under the umbrella of the PayFac’s master merchant ID and Banking-as-a-Service vendors that allow non-bank businesses to offer banking services (e.g. checking accounts, debit cards, and loans) directly within their products. These are just two of many sub-categories of embedded financial products that have come to the forefront of the B2B universe.

Cross-border payments are conducted mostly through expensive and slow wire transfers, underscoring speed, transparency, and high fee structures as pain points for innovators to address. Blockchain-based payments have also emerged as a cheaper, faster, and more flexible alternative for many vendors in the cross-border remittance space to facilitate payments overseas (particularly in countries with less developed banking infrastructure).

On the other hand, the C2B space is hyper-competitive and has witnessed widespread technology adoption that increases customer conversion and retention, while also eliminating friction at the point of sale. Specifically, vertical SaaS vendors have focused on C2B payments as a previously commoditized revenue stream that they can “earn the right” to via a slick, easy to use, and sticky platform experience. These vendors are the ideal customer profile (“ICP”) of the aforementioned embedded finance providers in the B2B space, cutting across embedded credit, embedded payroll, and embedded procurement.

Finally, P2P and blockchain-based payments are the industry’s poster child for innovation. While the benefits of decentralized protocols have been widely substantiated, it will be interesting to track the vendors that prioritize i) the most seamless and integrated infrastructure for on-ramping/off-ramping between fiat and cryptocurrency and ii) transaction security and fraud identification to prevent illicit activity from corrupting the benefits of blockchain networks.

With payments at the forefront of all consumer and business workflows, infrastructure modernization has quickly become table-stakes for those trying to optimize productivity and offer a truly differentiated payments experience.

About Jack Freeman

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.

About Justin Kelly

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.

About Chase Goree

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.

About Cassie Alexe

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.

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