June 2026:Vermilion Cliffs Notes
Series A season, buying GitHub stars, and SF AI Infra After Dark
Vermilion Cliffs Ventures is a pre-seed and seed fund investing in technical founders building the connective tissue infrastructure for AI: orchestration, security, runtime, identity, workflow, and the layers in between as we figure out how software gets rebuilt around AI. We're based in NYC and SF. Created by Ashley Smith, a career early-stage startup operator.
Summer is here and for Vermilion that means we’re headed to San Francisco for the AI Engineer World’s Fair. Join us at two key events: AI Infra After Dark co-hosted by Amplify and Deploy, Scale, Score World Cup Social co-hosted with DigitalOcean.
✨ Register for both events here.
Basecamp updates
What’s happening in the portfolio
💰 CopilotKit raises $27M Series A led by Glilot Capital, NFX, and SignalFire, with participation from Vermilion Cliffs Ventures, to build the Enterprise Agentic Frontend Stack for generative UI and agent-human collaboration (TechCrunch)
🚀 Confident releases an open-source harness for vibe coders building AI agents — purpose-built to verify whether agent code changes actually improve outcomes, after research showing 94% of users have no reliable way to evaluate coding-agent output
🚀 Atomic ships repository-native code intelligence for CLI and Agent Tools — semantic search, scoped code search, entity extraction, and source-grounded summaries
📈 Keycard named to Redpoint’s InfraRed 100, honoring 100 transformative companies in cloud infrastructure, plus the CB Insights AI 100 for building the identity and access foundation that lets enterprises deploy autonomous agents at scale
🚀 Starsling launches Runners, the world’s first self-driving CI service — a closed loop around frontier models delivering automated DevOps after 500,000 CI jobs in production
From the trail
The latest industry news, interviews, and forward-thinking considerations from Vermilion, founders, and investors in the field.
📰 Why open source at GTM is having a moment via Meghan Murphy of Vermilion
📰 Founders are buying GitHub stars and getting funded via Elena Marchetti of Awesome Agents
📰 Raising a Series A with Magid and Co’s Aaron Harris via Ashley Smith of Vermilion
Who’s hiring
Find the latest roles across engineering, marketing, and developer relations on the new Vermilion Careers page here
Upcoming events
Where Vermilion will be in the next month, look forward to seeing you in person 👋
🌠 AI Infra After Dark with Amplify + Vermilion Cliffs Ventures | SF
🚀 Deploy, Scale, Score with DigitalOcean + Vermilion AI Infra Social | SF