Freestyle Capital leads investment in a new AI platform for managing the thousands of third-party tools, services, and contractors powering today’s businesses

San Francisco, CA – May 13, 2025; Stackpack, the first intelligent Vendor Stack Management platform helping companies regain control over their growing network of third-party vendors, has raised $6.3 million. Freestyle Capital led the investment, with additional participation from Elefund, Upside Partnership, Nomad Ventures, Layout Ventures, MSIV Fund and strategic angels from Intuit, Workday, Affirm, Snapdocs and xAI.

Modern businesses are powered by a vast web of third-party providers — AI tools, SaaS platforms, contractors, and managed services. Yet most teams still manage these critical partnerships with spreadsheets, scattered documents, and crossed fingers. Stackpack is changing that.

Founded in 2023 by Sara Wyman, a veteran of Etsy and Affirm, Stackpack emerged from firsthand experience with the chaos and cost of unmanaged vendors. Wyman saw how missed renewals, redundant tools, and growing compliance risks could quietly drain budgets and introduce operational risk — and recognized that the vendors powering a business were as essential to its success as its internal team.

With Stackpack, finance and IT teams get a single source of truth for all third-party vendors – automatically surfacing renewal dates, contract owners, shadow IT, compliance gaps, and savings opportunities. The platform uses AI to not only uncover blind spots, but also acts on behalf of customers as an agent to ensure nothing falls through the cracks. Ultimately, Stackpack turns vendor sprawl into strategic advantage.

“The majority of companies aren’t managing the entities that power them,” said Sara Wyman, founder of Stackpack. “Companies think of themselves as ‘people-first’ – but today they’re ‘vendor-first’. There are typically 6x more vendors than employees at the average U.S. company, and that number is quickly increasing. And there isn’t a system to manage that shift.”

The early team behind Stackpack includes early leaders from PayPal, eBay, Adobe, Asana, Twilio, and Google — operators uniquely positioned to build a networked platform and scale it from early stage to market leadership.

Stackpack enters the market at a critical moment: Over $475 billion is spent annually on third-party software and services in the U.S. alone, with an estimated 25% of it going unused. Payroll budgets are shifting to outsourced contractors and AI expense. Compliance risks are multiplying as third-party vendors handle sensitive data. A lack of transparency in renewal dates and pricing are wrecking budgets and forecasts. Today’s finance and IT teams need real-time visibility, automated guardrails, and tighter controls more than ever, and Stackpack is building the platform for this new era.

“Every vendor decision today carries financial, legal, and privacy implications — it’s a C-suite concern,” said Dave Samuel, General Partner at Freestyle Capital. “You wouldn’t manage employees or customers in spreadsheets, so why are we still doing that for vendors? Stackpack is automating the entire vendor lifecycle – from discovery and evaluation to renewals – bringing visibility, control, and strategic oversight to every stage. With this foundation in place, they’re uniquely positioned to connect buyers and sellers in smarter, more transparent partnerships.”

Just months after launch, Stackpack is already managing over 10,500 vendors and $510 million in spend across more than 50 customers, including Every Man Jack, Rho, Density, HouseRx, Fexa, and ZeroEyes.

For finance leaders, the value is simple and provides the ultimate financial insurance. “The CFO is on the hook when something gets missed. Stackpack means we don’t have to cross our fingers every quarter,” said Brandon Lee, Accounting Manager at BizzyCar. At Stride Health, Controller Arthur Wei articulated the problem clearly: “Vendor buying is decentralized – but it comes back to the finance team to manage financial health and reporting.”

Alongside its core Stack Management platform, Stackpack is now expanding beyond visibility with a second product: Requests & Approvals, currently in beta. Designed as a lightweight, affordable alternative to platforms like Zip and Coupa, it gives teams a faster way to evaluate and approve vendor requests. Over time, Stackpack also plans to help customers discover and evaluate new partners.

Looking ahead, Stackpack’s mission is to help companies connect with the right partners, at the right time, on the right terms – transforming vendor management into a strategic capability. “This isn’t just a finance problem,” said Wyman. “It’s a foundational shift. We not only need to be the eyes and ears to help companies reduce cost and risk, but also find the right tools for their budget and size. Managing your vendors and

partners should be as strategic as managing your talent – vendor ecosystems are the next major competitive edge.”

About Stackpack

Stackpack is the first AI-native platform built to manage the accelerating costs, risks, and complexity of third-party vendors, AI tools, and contractors. It gives finance and IT teams a single source of truth to control spend, manage renewals, and reduce compliance risk across the entire vendor lifecycle. As external ecosystems grow, Stackpack turns vendor chaos into strategic clarity. For more information please visit: https://www.stackpack.ai/ or follow via LinkedIn

About Freestyle

Freestyle Capital is an early-stage venture capital firm managing over $565 million in assets with investments in 150+ technology companies, including a few notable names like Airtable, Intercom, Patreon, and BetterUp. Founded in 2009, Freestyle was one of the first firms to specialize exclusively in seed-stage investing, uniquely led by founders turned VCs. To learn more about Freestyle, please visit http://freestyle.vc

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