AI Automation Lead

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Glasswing Ventures is a first-capital-in venture capital firm dedicated to building the future of enterprise and security through AI and Frontier Technology. The firm combines deep domain expertise, decades of building, operating, and investing experience, and the guidance of world-class advisory councils to identify and partner with exceptional founders at their earliest stages and help them scale. The firm is committed to backing the AI-native and Frontier Tech platforms and products that will transform markets, establish new categories, and power the next generation of enduring global companies.

Visit Glasswing Ventures for more information.

As we build our next generation of internal AI capabilities to enhance how we source and evaluate investment opportunities and support portfolio companies, we are seeking an AI Automation Lead who can bridge the gap between investment strategy and applied AI development. This role combines hands‑on technical execution with strategic problem solving, working closely with the firm’s partners and investment professionals to identify high‑impact use cases and build intelligent workflows that improve decision‑making and operational efficiency.

This is a full‑time, in‑person role based in our Boston office.

You will be responsible for designing and implementing automation systems and AI‑enabled tools that directly support our investment process, from deal sourcing and due diligence to portfolio monitoring and investor communications. This role requires both technical fluency and business intuition, as you will shape how the firm applies AI to its most critical internal processes.

• Partner with the investment team and operations staff to identify repetitive, manual, or insight‑driven workflows that can be automated or enhanced using AI.
• Identify the most promising areas for predictive modeling.
• Translate business objectives such as sourcing, research, and diligence into clear technical specifications.
• Prioritize projects based on ROI, feasibility, and strategic value to the firm.

• Develop machine learning models that extract signals from both structured and unstructured data to help predict successful investments. Collect, aggregate & clean data from disparate public and private databases and continuously improve predictive performance.
• Develop AI agents that can conduct and summarize research and assist in preparing internal reports or memos.
• Build, maintain, and scale automation workflows using n8n, LLM APIs, and integrations with systems including our CRM, Notion, Slack, and internal data sources.
• Manage API connections, prompt engineering, and data transformations required to make workflows reliable and useful.

• Rapidly prototype new tools such as investment research bots, portfolio dashboards, and internal chat assistants.
• Collect feedback from team members to refine outputs, user experience, and workflow design.
• Set up data science pipeline to train and test predictive ML models.
• Create lightweight internal documentation and training materials.
• Maintain the security and privacy of the firm’s confidential data.

• Act as the primary liaison between the investment team and technical contributors such as Dev Ops engineers.
• Work with Dev Ops engineers to ensure secure and scalable deployment of automation tools on AWS.
• Communicate progress, risks, and opportunities clearly to firm leadership.
• Help establish technical standards and a roadmap for future AI initiatives.

• 3 to 7 years of experience in software engineering, machine learning and data science, or applied AI.
• Good knowledge of core ML and deep learning algorithms and experience with libraries such as Scikit-learn, Tensor Flow, and Keras. Strong Python skills, preferably in the context of ML and data science. Experience with experimental practice and hypothesis testing.
• Hands‑on experience with workflow automation tools such as n8n, Zapier, Lang Chain, or similar frameworks.
• Familiarity with large…