Manny Medina’s New Venture: Revolutionizing AI Monetization

In a significant development for the tech industry, Manny Medina, the visionary co-founder and former CEO of Seattle-based sales powerhouse Outreach, has secured an impressive $21 million seed funding for his new startup, Paid. This London-based venture, launched earlier this year, addresses one of the most critical challenges facing the AI industry today: how companies can effectively monetize their AI agents. The substantial investment, which has already valued the company at over $100 million according to TechCrunch, signals strong confidence in both Medina’s leadership and the urgent market need for innovative AI billing solutions. As Medina articulated on LinkedIn, Paid is “building the infrastructure that lets SaaS companies break free from the seat-based trap and return to growth” – a mission that resonates deeply with companies struggling to adapt traditional software pricing models to the unique value proposition of AI agents.

The timing of Medina’s new venture couldn’t be more strategic, as he had previously explored the complexities of AI agent monetization in a business advice column for GeekWire. In his analysis, he highlighted the fundamental disconnect between conventional software-as-a-service pricing structures and the value delivery mechanisms of AI agents. This insight forms the foundation of Paid’s business model, which helps companies create pricing frameworks that align with how customers actually derive value from AI solutions. More than just a billing platform, Paid enables companies to modify their AI agent code to accommodate diverse pricing mechanisms, offering the flexibility that today’s rapidly evolving AI market demands. This approach addresses a critical pain point for technology companies attempting to capitalize on AI innovations while ensuring their pricing reflects true customer value – a balance that has proven elusive for many in the industry.

The impressive seed round was led by Lightspeed, with Alexander Schmitt, a partner at the firm, articulating their investment thesis in a blog post: “This investment also reflects our broader conviction about where AI value creation is heading: the next wave of AI value will come from infrastructure that operationalizes AI deployment at scale and application companies that harness the value created.” This perspective aligns perfectly with Paid’s mission to create the foundational infrastructure for AI monetization. The funding round also attracted participation from Bellevue, Washington-based FUSE, whose founding partner Kellan Carter emphasized Paid’s critical role in the evolving tech landscape, stating that “Paid is essential for AI native companies and SaaS companies to monetize and win in 2025.” Seattle-based Founders’ Co-op had previously invested in the company, further strengthening Paid’s connections to the vibrant Pacific Northwest tech ecosystem despite its London headquarters.

Medina’s transition to this new venture comes after a significant chapter in his career at Outreach, where he stepped down as CEO in September 2024 to become executive chairman before transitioning to his current role as a board member. Under his leadership, Outreach emerged as a transformative force in sales technology, helping companies optimize seller workflows and close more deals effectively. The company’s impressive growth trajectory included raising nearly $500 million in funding and achieving a remarkable $4.4 billion valuation following a $200 million investment round in 2021. While Outreach experienced rapid expansion during the pandemic, like many high-growth tech companies, it subsequently navigated challenges that necessitated multiple rounds of layoffs in recent years. The company is now under the leadership of CEO Abhijit Mitra, who joined Outreach in 2023 as its president of product and technology, bringing fresh perspective to the organization Medina helped build.

Medina’s entrepreneurial journey with Outreach began in 2014 when he co-founded the company alongside Wes Hather, Gordon Hempton, and Andrew Kinzer. This founding team created what would become one of Seattle’s most successful tech startups, demonstrating their collective vision and technical acumen. The paths of these co-founders have since diverged in interesting ways that showcase the dynamic nature of entrepreneurship. Hather and Hempton have focused their talents on construction software startup Specbook after exploring several venture ideas in recent years. Meanwhile, Kinzer has navigated both challenges and new opportunities, shutting down a smart fridge company before recently launching a new stealth startup according to his LinkedIn profile. These varied journeys highlight the resilience and adaptability that characterize successful entrepreneurs in the ever-changing technology landscape.

With Paid, Medina is tackling a problem that sits at the intersection of two major business trends: the explosive growth of AI applications and the evolution of software business models beyond traditional subscription approaches. The challenge is substantial – AI agents operate fundamentally differently from conventional software, often delivering value through transactions, outcomes, or usage patterns that don’t fit neatly into seat-based pricing structures. By building infrastructure that enables companies to align their monetization strategies with their unique AI value propositions, Paid is positioning itself as an essential layer in the emerging AI economy. The substantial seed funding and impressive early valuation suggest that investors see Medina’s new venture as addressing a mission-critical need for AI companies in 2025 and beyond. As AI continues to transform industries and create new categories of software, Paid’s approach to monetization could help unlock the next wave of innovation by ensuring that companies can sustainably capture the value they create through AI – a fitting next chapter for an entrepreneur who has already made his mark on the enterprise software landscape.