At the end of each quarter, the team at Toronto-based Ripple Ventures faced a time-consuming challenge: gathering updates from numerous portfolio companies spread across various communication platforms, including emails, PDFs, and meeting notes. The arduous task required weeks of manual collating before investor reports could be finalized. However, this process has dramatically transformed, thanks to the firm’s internal AI system, Ripple OS, which now handles much of the workload in just a few hours.
According to managing partner Matt Cohen, Ripple OS constitutes a significant advancement in the operational dynamics of Ripple Ventures. The system, which the firm began developing seriously about a year ago, utilizes around 15 AI agents to perform numerous functions—ranging from market research and sourcing investment opportunities to recruiting talent and establishing connections between portfolio companies and potential customers or investors. The capabilities of Ripple OS allow the small, four-person team to execute tasks that would conventionally be managed by a workforce of about 100 employees, redefining the scale of their operations.
Cohen likens Ripple OS to having an exceptionally skilled team of executives—operating as a blend of COO, CFO, and CEO—effectively integrated into one application. This innovative platform signals to the venture capital (VC) industry a potential future characterized by lean teams empowered by advanced AI, enabling them to manage larger investment portfolios and compete with bigger firms.
Ripple’s embrace of AI technology comes amid a broader trend among Canadian tech investors who have recognized the transformative potential of AI—not only to streamline operations but also to identify and capitalize on emerging startups in a rapidly evolving landscape. While other venture capitalists might employ AI for minor tasks, Ripple has gone further, developing a cohesive, agent-driven system that permeates its workflow.
This system has caught the attention of outside investors, with inquiries about its potential for sale. However, Cohen has opted to maintain Ripple’s competitive edge by keeping the technology proprietary. The push toward building Ripple OS began around two years ago, inspired by the possibilities of AI. The turning point came when the firm hired Jay Lee, a former intern with experience from McKinsey, who proposed developing in-house systems to automate various operational tasks.
The initial implementation of Ripple OS focused on sourcing deals and conducting market research. The technology has since expanded its reach, integrated into daily workflows where team members can query the system via platforms like Slack or Notion. For example, employees can obtain specific details about investment opportunities, run financial models, and analyze investment performance with ease, significantly accelerating decision-making processes.
The system’s impact extends to portfolio companies as well. Mike Kim, co-founder and CEO of cybersecurity startup Mycroft, noted that since the implementation of Ripple OS, the VC firm has enhanced its ability to connect him with potential hires and industry contacts more efficiently, often producing results within minutes—a stark contrast to the prolonged timelines typical of other investors.
Despite Ripple’s advanced use of AI, it is not alone in the venture capital space. Other firms, such as Georgian, are also leveraging AI technologies for tasks like briefing startups and conducting financial analyses. However, barriers remain, including issues of trust in AI-driven outputs and the costs associated with implementing sophisticated systems.
Cohen articulated that Ripple’s relatively recent foundation has facilitated a more integrated approach to AI, lacking the constraints of legacy systems that older firms grapple with. Amid discussions about the future, industry experts caution against the tendency to indiscriminately apply AI across functions, emphasizing the importance of targeted deployment that genuinely enhances outcomes.
As Ripple continues to evolve, Cohen’s team has found themselves busier than ever, utilizing AI to not only streamline tasks but elevate productivity. “We’re running on fumes, but we’re getting way more work done in a way shorter time period,” he said, highlighting the promising yet demanding nature of operating in an AI-enhanced environment.
