Ashley Smith Launches $25M Second Venture Fund to Invest in AI and Cybersecurity Startups.

Vermilion Cliffs Ventures announced on Wednesday that it has successfully closed its second investment fund, raising $25 million to continue backing early-stage technology startups. The venture firm was founded in 2023 by Ashley Smith, an operator-turned-investor who is among the relatively small number of solo female general partners in the venture capital industry. Smith said the new fund will continue the firm’s focus on supporting highly technical founders, particularly those developing products in AI infrastructure, cybersecurity, and developer tools.

According to Smith, the fundraising process took approximately four months to complete this year, with a large share of the capital coming from existing limited partners who had previously invested in the firm. Through Fund II, Vermilion Cliffs Ventures expects to write initial cheques ranging from $500,000 to $1 million. The firm plans to invest in at least 25 startups over the next two and a half years and has already completed investments in six companies.

The new fund follows the firm’s first $13 million debut fund, which invested in 35 startups. Among those portfolio companies are cybersecurity startup Keycard and AI infrastructure company CopilotKit, both of which have become notable examples of the firm’s investment strategy.

Smith explained that while many early-stage venture firms primarily help founders secure their next round of financing, her own background allows her to provide practical support beyond fundraising. Having previously worked in marketing leadership roles at Twilio, Facebook, GitHub, and GitLab, she aims to help startup founders develop effective go-to-market strategies that position their businesses for long-term success.

She said that selling products to developers and security teams requires a specialised approach, adding that many founders only learn those lessons through costly trial and error. By sharing the experience she has gained throughout her career, Smith hopes to help entrepreneurs avoid common mistakes and accelerate their path to building successful companies.