Vermilion Cliffs Ventures closes $25M second fund

Vermilion Cliffs Ventures announced the close of a $25 million Fund II on Wednesday, the second fund since operator-turned-investor Ashley Smith founded the firm in 2023. Smith runs it as one of the few solo women general partners in venture capital — the firm’s sole decision-maker rather than part of a multi-partner team. She told TechCrunch the fund will continue the firm’s existing thesis: backing technical founders building in AI infrastructure, security, and developer tools.

Raising the new fund took Smith around four months this year, with much of the capital coming from existing investors. Fund II’s average check size will run between $500,000 and $1 million, and the firm hopes to invest in at least 25 companies over the next two and a half years. It has already backed six companies from the new fund.

Vermilion Cliffs’ debut fund raised $13 million and backed 35 companies, including cybersecurity startup Keycard and AI infrastructure company CopilotKit — portfolio bets that track the same thesis Fund II continues: technical founders selling into developer and security buyers.

Smith’s approach to supporting those founders draws on her own background in marketing at Twilio, Facebook, GitHub, and GitLab. She said many early-stage firms position themselves mainly as help for raising the next round, but she wants to help founders earn that next round through go-to-market strategy. “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.”

Why it matters

A solo GP with an operating background in developer- and security-focused marketing gives technical founders a source of go-to-market help that’s harder to find from generalist early-stage firms — a gap Smith is betting Vermilion Cliffs’ next 25 investments can fill.