The median check size keeps climbing. The round count does not.
Mid-May 2026 deal flow reflects a venture market that has structurally bifurcated. Capital is pooling at the top — larger rounds for companies with clear revenue or strategic leverage — while early-stage deal volume stays compressed. Eight notable rounds from this week's deal flow, totaling over $4.4B.
Notable Rounds: May 12, 2026
| Company | Amount | Stage | Sector | Lead Investor |
|---|---|---|---|---|
| Safe Superintelligence (SSI) | $2B | Series B | AI Safety | Andreessen Horowitz |
| Skydio | $800M | Series F | Defense Drones | a16z / Tiger Global |
| Runway ML | $308M | Series D | AI Video / Creative | General Atlantic |
| Ramp | $300M | Series D | Fintech / Enterprise | Thrive Capital |
| Glean | $260M | Series F | Enterprise AI Search | Kleiner Perkins |
| Cognition AI | $175M | Series C | AI Dev Tools | Founders Fund |
| Vanta | $150M | Series D | Security Automation | Sequoia Capital |
| Nuro | $400M | Series E | Autonomous Delivery | Tiger Global |
Deal Flow Patterns
AI safety is now a standalone VC category — SSI's $2B round is the clearest signal that investors are treating it as infrastructure, not research
Defense drones are institutionalizing: Skydio's Series F is backed by crossover funds, not just defense specialists, marking a maturation of the category
Enterprise AI with measurable ROI (Glean, Vanta) is pulling growth-stage checks that would have gone into SaaS in 2020–2022
Creative AI (Runway) is outpacing most B2B peers on valuation multiples — Hollywood and media budgets are starting to flow in at scale
What to Watch
SSI trajectory
Safe Superintelligence has operated in near-total silence since founding. A $2B round signals either a major product milestone or a race to lock up frontier AI talent before competitors.
Skydio's DoD pipeline
The drone market is bifurcating into commercial and defense. Skydio's Series F is explicitly defense-oriented — watch for contract announcements with Army or Air Force programs in Q3.
Ramp vs. Brex endgame
Ramp's Series D at this size suggests IPO prep is underway. The fintech market can support one dominant corporate card platform — this round may be the last before a public filing.
Creative AI monetization
Runway's $308M round is a bet that media companies will pay enterprise-level contracts for AI-generated content. Whether studios adopt or fight the technology will determine if this valuation holds.
Track startup funding benchmarks on the Funding 2025 dashboard. For VC fundraise data, see VC Fundraises 2026 at Value Add VC.