Vermilion Cliffs Ventures
Venture capitalActively deployingNew York · Pre-Seed–Seed · 2 people tracked
Investment thesis
Vermilion Cliffs Ventures invests early in technical founders who are rebuilding the development stack for the agent era. Operator-founded and led by investors with hands-on go-to-market and product-led growth experience at leading developer companies, the fund backs early-stage, category-defining products in AI infrastructure, security, and developer tools. Beyond capital, Vermilion offers practical, founder-first support to help builders scale from the earliest days of their business.
Source: firm website, verified Aug 3, 2026.
Team · 2 people
from the firm's website.jpeg)
What they invest in
from 11 of 30 portfolio companiesAI & Machine Learning ×9Developer Tools ×9Enterprise Software ×8SaaS ×3Data & Infrastructure ×2Advanced Manufacturing ×1AgTech ×1Cloud Computing ×1
HQs:United States×9
Investments · 30 tracked
founders shown can be your intro pathBy year:2025 · 12024 · 12023 · 24 dated
PartnerAshley Smith· solo GP
Carpesa, Valencia
Albert Morro Vall(Director)James Alcorn(Director)Francisco de Asis Aranda Montes(Executive Officer, Director)Daniel Vila Suero(Executive Officer, Director, Promoter)Paco Nathan(Director)
BoardHadley Harris(Director)
PartnerAshley Smith· solo GP
PartnerAshley Smith· solo GP
PartnerAshley Smith· solo GP
PartnerAshley Smith· solo GP
PartnerAshley Smith· solo GP
PartnerAshley Smith· solo GP
Catio builds an "Architecture IDE," a control plane for engineering teams to make and evolve software architecture decisions, evaluate trade-offs, and generate decision-grade specifications.
AI & Machine LearningDeveloper ToolsEnterprise SoftwarePalo Alto, US
Boris Bogatin(Executive Officer, Director, Promoter)
BoardRaju Rishi(Director)
PartnerAshley Smith· solo GP
PartnerAshley Smith· solo GP
Brooklyn, US
Larry Wayne Diehl, Jr.(Executive Officer, Director)
BoardJesse Robbins(Director)
PartnerAshley Smith· solo GP
Confident AI is a platform for evaluating, monitoring, and governing AI systems in production.
AI & Machine LearningDeveloper ToolsEnterprise SoftwareSan Francisco, US
Jeffrey Ip(CEO & Cofounder)inKritin Vongthongsri(Co-Founder)in
PartnerAshley Smith· solo GP
PartnerAshley Smith· solo GP
PartnerAshley Smith· solo GP
PartnerAshley Smith· solo GP
Freeplay provides a platform for software product development teams to build and maintain generative AI products using best practices in experimentation, iteration, and data management.
AI & Machine LearningDeveloper ToolsEnterprise Software
PartnerAshley Smith· solo GP
Osmosis is a reinforcement fine-tuning platform that provides reinforcement learning infrastructure to help developers build and deploy AI agents that improve from experience.
AI & Machine LearningData & InfrastructureDeveloper ToolsEnterprise Software
PartnerAshley Smith· solo GP
PartnerAshley Smith· solo GP
PartnerAshley Smith· solo GP
Lemma provides production monitoring and observability for AI agents, surfacing failures, aggregating issues, and enabling quick resolution through integrated alerts and context-sharing tools.
AI & Machine LearningDeveloper ToolsEnterprise SoftwareSan Francisco, US
Jerry Zhang(Founder)inCole Gawin(Founder)in
PartnerAshley Smith· solo GP
Mach9 builds automated feature-extraction software for transportation, telecom, and construction industries, enabling rapid extraction and mapping of large-scale infrastructure projects.
AI & Machine LearningConstruction TechData & InfrastructureDeveloper ToolsEnterprise SoftwareSan Francisco, US
Alexander Baikovitz(Founder)inHaowen Shi(Founder)inMichael Mong(Cofounder)Zachary Sussman(Cofounder)
PartnerAshley Smith· solo GP
Brooklyn, US
Brendan O'Brien(Executive Officer, Director, Promoter)
PartnerAshley Smith· solo GP
PartnerAshley Smith· solo GP
Red Barn Robotics develops autonomous weeding robots for farms to eliminate intra-row weeds without human intervention, reducing labor costs and protecting soil health.
Advanced ManufacturingAgTechHardwareRoboticsSeattle, US
Adam Iseman(Founder)inIlya Kelner(Founder)inAlex Neff(Founder)in
PartnerAshley Smith· solo GP
PartnerAshley Smith· solo GP
StarSling builds AI-native continuous integration for GitHub Actions, providing fast runners and agents that analyze workflows, logs, and telemetry to automatically open pull requests optimizing CI pipelines.
AI & Machine LearningDeveloper ToolsEnterprise SoftwareSaaSSan Francisco, US
Yonas Beshawred(Co-founder & CEO)inDaniel Worku(Co-founder & CTO)in
PartnerAshley Smith· solo GP
Sutro provides a backend infrastructure platform that enables developers to define and deploy production-grade backends through a domain-specific language called SLang.
Cloud ComputingDeveloper Tools
PartnerAshley Smith· solo GP
Tadata is an AI agent platform that integrates into Slack to automate research and repetitive work by connecting to business tools like CRM, marketing, and ops systems.
AI & Machine LearningEnterprise SoftwareSaaS
PartnerAshley Smith· solo GP
CopilotKit provides an open-source framework and protocol (AG-UI) for developers to build and embed AI agents with rich, interactive user interfaces directly into applications, including web, Slack, and Teams.
AI & Machine LearningDeveloper ToolsSaaSIssaquah, US
Atai Barkai(CEO)
PartnerAshley Smith· solo GP
PartnerAshley Smith· solo GP
Exits · 1
IPOs and acquisitions across the tracked portfolio<UNKNOWN>acq. by Hugging Face
Portfolio news
latest coverage across their companiesStarSling · ycombinator.com · Jun 29, 2026
Mach9 · ycombinator.com · Mar 30, 2026
Lemma · ycombinator.com · Nov 5, 2025
Red Barn Robotics · agfundernews.com · Oct 23, 2025
Confident AI · confident-ai.com · Mar 19, 2025
Frequently asked questions
- What stage does Vermilion Cliffs Ventures invest at?
- Vermilion Cliffs Ventures invests at the Pre-Seed, Seed stages.
- What is Vermilion Cliffs Ventures's typical check size?
- Vermilion Cliffs Ventures typically writes checks of $200K – $500K.
- What sectors does Vermilion Cliffs Ventures focus on?
- Vermilion Cliffs Ventures focuses on AI & Machine Learning, Cybersecurity, Data & Infrastructure, Developer Tools.
- Where is Vermilion Cliffs Ventures located?
- Vermilion Cliffs Ventures is headquartered in New York, US.
Media · Podcasts & interviews
featuring the team#29 Ashley Smith, GP & Founder, Vermilion Cliffs Ventures
Zight · Ashley Smith
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