Spend Matters welcomes this guest post from Jack Freeman, Principal at PeakSpan Capital who is a growth-stage software investor.
We take a highly thematic approach to investing at PeakSpan. As a group, we’ve looked at business software exclusively for the past 20+ years. Within business software, each investment professional at PeakSpan can only pursue 3-4 themes at any point in time. Taking the supply chain market and the procurement market in tandem — our team is probably spending about 50% of our time in the space.
The direct procurement segment is fascinating to us for one primary reason: The stakes are higher.
Nothing against saving dollars on office supplies, but is there anything more strategic than optimizing the spend and supply chain surrounding your core product or service?
We set out with this thesis in 2016, and five years in are sad to report: The market is not as robust as we thought (for clarity, that’s defined as the number of scale-up firms targeting direct procurement specifically).
Indirect procurement is an extremely well-defined category with players attacking various segments, various customer verticals, various categories of indirect spend and even specializing for specific nodes in the source-to-pay value chain. Rarely however, do you find players positioned as “direct procurement software platforms.”
Optimizing your communication/engagement and spend with direct materials suppliers is central to supply chain optimization.Jack Freeman, Principal at PeakSpan Capital
Why is that?
We arrived at the realization years ago that “direct procurement” is really just “supply chain.” Optimizing your communication/engagement and spend with direct materials suppliers is central to supply chain optimization. After accepting this, we then began to unpack what software platforms are best positioned to add the most value to manufacturers’ supply chains in this space, regardless of how they are positioned.
Direct procurement software platforms automate all or a portion of the source-to-pay value chain surrounding an enterprise’s direct costs.
Relative to the market awareness/voice for indirect procurement, we see a gap in the direct procurement software market. This may be a “real” gap and could be for a specific reason (too nuanced, too complex, not enough start-up founders arrived at this mission, etc.). However, the more likely scenario is a lack of category definition, unclear product positioning and a softer market voice.
Over the years, we have started to identify and come across players who clearly fit the “direct procurement software” space and were surprised to find a wide variance in how these various subsegments described the value prop and market. Nonetheless, we see ample opportunity in the long term for software platforms to automate the direct procurement supply chain.
We’re unsure that “direct procurement” will ever be spoken about as a defined category, but nonetheless it continues to be a top area of interest given the strategic nature of the function it serves. Spoiler alert, it’s only becoming more mission critical!
Below are a few ways we’ve looked at the market:
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.