Glasswing Ventures
Investment Associate
Pre-Seed & Seed · AI-Native · Enterprise & Cybersecurity
Boston Office · Full-Time · Reports to Partner / Managing Director
About Glasswing Ventures
Glasswing Ventures is a first-capital-in venture capital firm building the future of enterprise and security through AI and frontier technology. Founded in 2016 in Boston, Glasswing has made over 70 investments, acting as the first institutional investor in more than 90% of its portfolio companies. The firm closed Fund III in November 2025 with over $200 million in capital commitments. With an extraordinary team, a 70-member advisory council, and deep ties to top-tier AI research universities, Glasswing is widely recognized as the venture firm that understands AI best, delivering a curated Trust Network that accelerates founder growth and category creation.
About the Role
AI is rewriting the rules of enterprise and cybersecurity, and Glasswing is writing the first checks into the founders making it happen. We are investing at the earliest stage during the most significant technology shift in a generation, and we are looking for an Investment Associate who wants to be at the center of it.
You will have a seat at the table. Glasswing just closed Fund III with over $200 million in capital commitments, and you will be deploying that capital alongside our Partners from day one. The companies you back in this role could define how enterprises operate and stay secure for the next decade. You will work directly with Partners on every deal, not behind layers of hierarchy. You will tap into our 70-member advisory council of former CTOs, CISOs, and operators from the world’s leading technology companies. And with 70+ portfolio companies already in the Glasswing network, you will build real operating experience alongside the founders you help fund.
If you thrive at the frontier of technology, are energized by big ideas, and want a front-row seat to the next wave of category-defining companies, this is the role.
Key Responsibilities
- Hunt for the next wave of cutting-edge AI-native startups through founder outreach, ecosystem immersion, and deep market intelligence
- Be the first to spot disruptive technologies: conduct hands-on due diligence across market sizing, competitive dynamics, product differentiation, and founder-market fit
- Craft compelling investment memos and deal narratives that bring bold ideas to life for the partnership
- Build conviction through data: develop models that stress-test unit economics, growth trajectories, and paths to market dominance
- Own and evolve sector theses at the intersection of AI, enterprise software, and cybersecurity, shaping where the fund places its biggest bets
- Roll up your sleeves with portfolio founders: help them navigate product-market fit, GTM strategy, hiring, and follow-on fundraising
- Be the face of the firm at the most exciting events in tech: demo days, hackathons, conferences, founder meetups, and accelerator showcases
Glasswing Ventures is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.
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- Build and nurture a world-class network of founders, operators, and co-investors that keeps our deal flow pipeline ahead of the market
Qualifications
Required
- Bachelor’s degree from a top institution in engineering, computer science, data science, or physics.
- 2+ years of experience in product management, sales, or account executive roles at large technology companies or very high-growth startups. We value builders who’ve been in the trenches with customers.
- Strong analytical skills with the ability to evaluate startup metrics, unit economics, and market opportunities.
- Demonstrated interest in and knowledge of AI-native technologies, enterprise software, and cybersecurity ecosystems.
- Excellent written and verbal communication skills, with the ability to synthesize complex topics into clear, compelling narratives.
- Self-starter mentality with comfort operating in a fast-paced, lean team environment. Preferred
- MBA from a top-tier institution.
- Technical background or familiarity with AI/ML infrastructure, cybersecurity, or enterprise software development preferred.
- Existing relationships within the startup and venture ecosystem preferred. • Prior experience evaluating early-stage pre-seed and seed technology companies.
Glasswing Culture
We are named after a butterfly with transparent wings. We lead with honesty, openness, and candor. We hustle like a startup because we are one. Lean team, outsized impact.
We are first capital in because we believe before the crowd does.
We are a flat team of builders. Low ego, high impact. Everyone rolls up their sleeves. We do good and do well. Impact and returns are not in conflict.
We are all different, and that is exactly why we win. We build trust first. Everything else follows.
How to Apply
Interested candidates should submit a resume and a brief investment memo, market map, or sector thesis. Show us how you think. We encourage applications from candidates with diverse backgrounds and perspectives.
Email your resume to: apply@glasswing.vc
Glasswing Ventures is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.
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