Ventures Associate - Enterprise & AI

Technical Associate

Plug and Play is one of the most active early-stage venture investors globally. Since 1998, we've backed 2,000+ startups including PayPal, Dropbox, SoundHound, and LendingClub and operate across 65+ locations and 20+ verticals. Our model combines venture investing with a global network of 550+ corporate partners to accelerate innovation and help startups scale.

We're expanding our Enterprise & AI Ventures team and hiring a technical Associate who can evaluate complex AI/enterprise software products and translate that diligence into clear investment decisions. You'll build theses, run structured technical + market diligence on early-stage companies, and work closely with enterprise partners to understand real buyer needs and validate startup solutions.

This role is ideal for someone with an engineering mindset who wants to operate at the intersection of AI systems, enterprise workflows, and venture investing.

What You'll Do

Investment, Sourcing & Thesis Development

• Build and refine investment theses across Enterprise AI and adjacent infrastructure (data, security, devtools, agentic systems).
• Source and evaluate early-stage companies through a mix of inbound, outbound, and ecosystem channels.
• Conduct technical diligence: architecture reviews, data infrastructure evaluation, and scalability analysis
• Track emerging technologies, competitive landscapes, and venture activity across your focus areas

Enterprise Partner Engagement

• Conduct structured interviews with corporate partners to understand technology gaps and innovation priorities
• Translate enterprise needs into actionable sourcing + diligence criteria.
• Facilitate introductions between startups/scaleups and corporate partners
• Support executive briefings, demo days, and enterprise matchmaking.

Technical Contributions

• Conduct structured product + architecture reviews (data flow, model approach, deployment model, integration pattern, scalability).
• Assess feasibility and differentiation: "is this real?", "what breaks at scale?", "what's defensible?"
• Engage in technical conversations with founders to assess team capabilities and product sophistication

Knowledge & Content

• Maintain market maps, startup databases, and competitive intelligence in your focus areas
• Produce research reports, investment memos, and market analyses for internal and external audiences
• Contribute to thought leadership through blog posts, whitepapers, or speaking engagements

About You

Ideal Requirements

• Strong technical foundation: CS/engineering background or equivalent experience shipping software.
• Comfort evaluating modern AI systems and data stacks (e.g., LLM apps, RAG, fine-tuning, evals, vector DBs, warehouses/ETL, observability).
• Ability to ask informed architecture/security questions and validate product claims
• Demonstrated analytical skills: can size markets and synthesize complex information
• Excellent written and verbal communicationable to explain technical concepts to non-technical audiences
• Genuine curiosity about startups, venture capital, and emerging technologies

Preferred

• Experience at a startup or a tech firm in product engineering, solutions engineering, ML engineering, security engineering, or technical PM
• Experience with technical content creation (blog posts, documentation, technical writing) or contributions to open source or side projects that show builder mentality

This is an opportunity to gain comprehensive venture capital experience while leveraging your technical background. You'll develop pattern recognition across hundreds of startups, build relationships with founders and enterprise executives, and gain exposure to deals from seed to high growth.