Key Takeaways
- • Vermilion Cliffs Ventures closed a $25 million Fund II on July 8, 2026, marking solo GP Ashley Smith's second institutional fund raise since founding the firm in 2023.
- • Fund II will deploy capital via $500,000 to $1 million check sizes across at least 25 companies over 2.5 years, with six portfolio companies already backed; the fund targets AI infrastructure, security, and developer tools sectors.
- • Smith raised the $25 million in approximately four months with predominantly existing investor capital, reflecting institutional confidence in her operator-to-investor track record across Twilio, Facebook, GitHub, and GitLab.
- • Fund I ($13 million, 2023) backed 35 companies including cybersecurity startup Keycard and AI infrastructure platform CopilotKit, establishing a proven early-stage thesis focused on technical founders serving technical end-users.
- • Smith's strategy leverages go-to-market expertise for developer and security team sales, positioning the firm to help founders avoid costly market entry mistakes in highly specialized categories.
Summary
Vermilion Cliffs Ventures, the solo-GP venture firm founded by Ashley Smith in 2023, announced the close of a $25 million Fund II on Wednesday, July 8, 2026. Smith, one of a select cohort of female solo general partners operating independently in venture capital, raised the capital in approximately four months with substantial participation from existing Fund I investors, signaling institutional confidence in her investment thesis and operational execution.
Fund II will focus on early-stage companies building AI infrastructure, security solutions, and developer tools—verticals where technical founders serve technical users. The fund intends to deploy capital across at least 25 companies over a 2.5-year investment horizon, with check sizes ranging from $500,000 to $1 million. Six portfolio companies have already received commitments from Fund II, underscoring active deployment since fund inception.
Smith's investment approach is informed by operational experience across high-growth technology platforms. Her prior roles in marketing at Twilio, Facebook, GitHub, and GitLab provided direct exposure to go-to-market strategies in developer-focused and security-oriented segments. She has articulated a thesis centered on helping technical founders avoid costly mistakes in sales to developers and security teams—disciplines that require specialized expertise distinct from broader B2B sales motions. Smith stated that she aims to help founders "skip mistakes I've made or seen other founders make," positioning value-add mentorship as a core element of her fund strategy.
The firm's track record supports this positioning. Fund I, a $13 million debut vehicle, backed 35 companies including notable exits and growth-stage businesses such as cybersecurity startup Keycard and AI infrastructure company CopilotKit. The substantial portfolio construction (35 companies from a $13 million fund) reflects a micro-check strategy typical of operator-led seed funds with deep founder networks and operational insight. Fund II's slightly larger check size ($500K–$1M versus implied $370K average in Fund I) suggests a modest fund-size increase while maintaining the early-stage thesis and portfolio construction velocity.
Fund II will focus on early-stage companies building AI infrastructure, security solutions, and developer tools—verticals where technical founders serve technical users. The fund intends to deploy capital across at least 25 companies over a 2.5-year investment horizon, with check sizes ranging from $500,000 to $1 million. Six portfolio companies have already received commitments from Fund II, underscoring active deployment since fund inception.
Smith's investment approach is informed by operational experience across high-growth technology platforms. Her prior roles in marketing at Twilio, Facebook, GitHub, and GitLab provided direct exposure to go-to-market strategies in developer-focused and security-oriented segments. She has articulated a thesis centered on helping technical founders avoid costly mistakes in sales to developers and security teams—disciplines that require specialized expertise distinct from broader B2B sales motions. Smith stated that she aims to help founders "skip mistakes I've made or seen other founders make," positioning value-add mentorship as a core element of her fund strategy.
The firm's track record supports this positioning. Fund I, a $13 million debut vehicle, backed 35 companies including notable exits and growth-stage businesses such as cybersecurity startup Keycard and AI infrastructure company CopilotKit. The substantial portfolio construction (35 companies from a $13 million fund) reflects a micro-check strategy typical of operator-led seed funds with deep founder networks and operational insight. Fund II's slightly larger check size ($500K–$1M versus implied $370K average in Fund I) suggests a modest fund-size increase while maintaining the early-stage thesis and portfolio construction velocity.
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