Vermilion Cliffs Ventures Fund II has closed at $25 million, giving Ashley Smith fresh capital to back technical founders building in AI infrastructure, security, and developer tools from her base in New York.
Smith founded the firm in 2023 after a career in marketing at companies including Twilio, Facebook, GitHub, and GitLab. She runs it as a solo general partner, a structure that remains uncommon in venture capital and rarer still for women.
The raise took roughly four months, with much of the capital coming from existing investors who backed her debut fund.
Vermilion Cliffs Ventures Fund II: The Mechanics
The firm plans to write cheques of between $500,000 and $1 million, targeting at least 25 companies over the next two and a half years. Six portfolio companies have already been backed under the new fund.
Fund II follows a $13 million debut fund that invested in 35 companies. Among the graduates of that first portfolio are the cybersecurity startup Keycard and CopilotKit, an AI infrastructure company that has since raised a total of $27 million: a $6.5 million seed round followed by a $20.5 million Series A led by Andreessen Horowitz, with participation from Lakestar and executives from OpenAI.
CopilotKit was founded by Israeli brothers Atai Barkai and Uli Barkai and builds open-source infrastructure for AI agent-based applications. Its AG-UI open standard has been adopted by Google, Microsoft, Amazon, and Oracle, as well as leading AI libraries. The company employs 25 people at a development centre in Israel.
The Operator Edge Smith Is Selling
The thesis is not just sector focus. Smith’s pitch to founders centres on what she saw repeatedly in her years selling developer products: that getting a technical product in front of engineering and security buyers is a discipline most founders learn painfully late.
‘Selling to developers and security teams is its own discipline, and most founders learn it the expensive way with time,’ she said. ‘I try to help them skip mistakes I’ve made or seen other founders make.’
That experience, accumulated across four companies with developer-facing products, shapes how Vermilion Cliffs Ventures positions itself relative to other early-stage investors. Many seed funds focus on helping portfolio companies raise the next round; Smith’s value proposition is the go-to-market work that makes the next round worth raising.
Vermilion Cliffs Ventures Fund II will test whether that argument holds at scale. The first fund deployed $13 million across 35 companies, a high-volume approach that produced at least one portfolio company, CopilotKit, now attracting institutional capital and big-tech adoption. The second fund’s tighter cheque range and 25-company target implies a more selective pace, though still broader than most institutional seed funds.
The watch point will be how many of those 25 companies convert early go-to-market support into the kind of growth that attracts a Series A: the metric that will define whether Fund II justifies a third.
