Ashley Smith Raises $25 Million for Second Vermilion Cliffs Fund

Smith secured the new capital in just four months, leaning heavily on her existing investor base. The firm plans to write checks ranging from $500,000 to $1 million, targeting at least 25 new startups over the next 30 months. This follows a successful debut fund, where Smith deployed $13 million across 35 companies, including notable bets like Keycard and CopilotKit.

Beyond capital, the firm differentiates itself by focusing on the specific challenges of selling to technical audiences. Drawing from her tenure at companies like Twilio, Facebook, GitHub, and GitLab, Smith provides hands-on guidance for go-to-market execution. By helping founders navigate the complexities of selling to developers and security teams, she intends to help them bypass the costly trial-and-error process that often stalls early-stage ventures.