Vermilion Cliffs Ventures

Vermilion Cliffs Ventures Research Investment Thesis Vermilion Cliffs Ventures is a pre-seed and seed-stage fund built for the next generation of developer-led companies. Founded by Ashley Smith, a former CMO and operator with exits at Twilio, Parse, GitHub, and GitLab, the fund backs technical founders building developer tools, infrastructure, AI products, and security primitives. The core thesis is that the best category-defining software won't be born in pitch decks — it'll be hacked together by deeply technical founders who understand the problem they're solving. Vermilion is founder-first and operator-founded. The team brings hands-on GTM experience at the greatest developer companies of the last decade. They offer more than capital: practical help with go-to-market strategy, hiring the first marketing lead, writing the launch post, and turning early customers into champions. Sector Focus Vermilion invests in developer tools and infrastructure, enterprise software, AI/ML applications, and security. The portfolio reflects a strong emphasis on: Developer Tooling: Products used by engineers — workflows, APIs, infrastructure, CLI tools Enterprise AI: AI applications targeting enterprise workflows and automation Security: Application security, zero-trust, developer-native security primitives AI Infrastructure: Platforms for building, evaluating, and deploying AI products Robotics: Selective investments in robotics and automation They explicitly avoid non-technical founding teams and consumer social plays. Stage Focus Vermilion focuses exclusively on pre-seed and seed: Pre-Seed: First institutional check, often before product-market fit Seed: Early product, initial customers or strong signals They describe themselves as 'often the first yes' and prefer to be the first institutional investor in a company. They do not require revenue — conviction, clarity, and curiosity are the key criteria. Check Size Vermilion writes $200K–$500K checks. This is explicitly stated on their website. This positions them squarely at the earliest institutional stage. Lead Tendency Vermilion is a first-check, first-yes investor. Based on their positioning and portfolio founder testimonials, they typically lead or co-lead at pre-seed, and participate at seed. They describe themselves as operators who help founders 'figure out GTM' from day one. Recent Activity The fund's portfolio page states this is 'Vermilion's first fund.' The portfolio includes 30+ companies across developer tooling, AI, enterprise software, and security. Notable recent companies include Atomic (atomic.dev, developer tooling), Staris (staris.tech, security/AI), Colimit (colimit.ai), and Wallfacer (wallfacer.ai). Three notable exits/acquisitions are already in the portfolio: Argilla (acquired by Hugging Face), Sequin (acquired by Notion), and Delight (acquired by Simpro Group). Portfolio Highlights Exits: Argilla (argilla.io) — AI data labeling platform, acquired by Hugging Face Sequin (sequinstream.com) — Database sync platform, acquired by Notion Delight (delightapp.io) — Acquired by Simpro Group Active Portfolio: Catio (catio.tech) — Architecture management and planning; CEO Boris Bogatin cites Vermilion as 'high-trust investor' with deep PLG expertise CopilotKit (copilotkit.ai) — AI copilot infrastructure for developers Confident AI (confident-ai.com) — AI evaluation and testing platform Freeplay (freeplay.ai) — LLM testing and evaluation Cognee (cognee.ai) — AI memory and knowledge infrastructure ERSC (ersc.io) — Application security; CEO Adam Cecchetti: 'Ashley and Vermilion immediately got it. They shared our vision for the future.' Keycard (keycard.sh) — Security tooling Staris (staris.tech) — Security and AI Red Barn Robotics (redbarnrobotics.com) — Robotics Radiant Ops (radiantops.com) — AI operations Toolflow (toolflow.ai) — AI workflow automation Mach9 (mach9.ai) — AI platform Lemma (uselemma.ai) — AI tooling Gulp (gulp.ai) — AI developer tools Sutro (sutro.xyz) — AI/developer tools Starsling (starsling.dev) — Developer tooling Formalstack (formalstack.com) — Enterprise/developer tooling Hyper (hyper.video) — AI video Clarify (getclarify.ai) — AI developer tooling Atomic (atomic.dev) — Developer tooling Baz (baz.co) — Developer tooling Fiveonefour (fiveonefour.com) — Developer tooling Tillion (tillion.ai) — AI TaData (tadata.com) — AI/developer tools n0.computer (n0.computer) — Developer tooling Colimit (colimit.ai) — Developer tooling/AI Wallfacer (wallfacer.ai) — AI Team Ashley Smith — Founder, General Partner Ashley is an operator-turned-investor with a career spanning the most influential developer companies of the past two decades. She served as CMO at Twilio, Parse, GitHub, and GitLab, building GTM from zero to IPO multiple times. She brings strong opinions on PLG motions and developer-led go-to-market to every portfolio company. Founder of Vermilion Cliffs Ventures. Meghan Murphy — Chief of Staff, Head of Platform Meghan works across fund operations, portfolio GTM support, and partnerships. She specializes in helping early-stage technical teams cut through noise, launch well, and build systems that scale. Key resource for portfolio companies on launch strategy and early GTM execution. Decision Process Vermilion appears to be a solo GP fund (Ashley Smith as Founder/GP) with a small team. Decision-making is likely concentrated with Ashley, with advisor input. They describe making fast commitments: portfolio CEO Adam Cecchetti notes 'We were quick to commit. They were quick to execute with us.' Founder Preferences Vermilion backs 'product-first founders' — engineers, designers, and product-obsessed builders with a point of view. They don't require revenue, but look for conviction, clarity, and curiosity. They specifically call out preference for technical founders who deeply understand the problem they're solving. Background in developer tooling, AI infrastructure, or security is a strong fit. Geographic Focus Not explicitly stated. Given Ashley Smith's background at Twilio, GitHub, GitLab, and Parse (all SF Bay Area), and the general tech community context, the primary focus is likely US with Bay Area roots. No geographic restrictions are mentioned on their website. Blog / Changelog Vermilion runs an active Substack called 'Vermilion Cliff Notes' covering developer tooling, AI infrastructure, and go-to-market topics. Recent posts include pieces on SEO vs AIO/GEO in technical search, open source and AI agents, and operator-to-investor journeys.