VC Deal Tracker: a16z, Sequoia & YC — Issue #1 (May 1–June 11, 2026)
Inaugural issue covering 8 verified deals from a16z, Sequoia Capital, and Y Combinator across the May 1–June 11, 2026 window. Highlights: Anthropic's $65B Series H led by Sequoia, Sierra's $950M Series E, a16z's first GCC investment in Saudi fintech Stitch, and Stilta's AI patent-tech seed backed by both a16z and YC. Deals grouped by sector with round type and disclosed deal size.
Inaugural issue — coverage window: May 1–June 11, 2026. This issue casts a wider net to demonstrate the format; starting next week, each issue will cover the preceding 7-day period.
About this tracker
Each week, this digest surfaces new investments and disclosed exits from a16z, Sequoia Capital, and Y Combinator — sourced from VC portfolio pages, official press releases, Crunchbase, and news coverage. Deals are grouped by sector. Every entry includes a one-line company description, round type, and disclosed deal size (or "undisclosed" where not public).
AI & machine learning
The bulk of deal activity this window came from AI, split between frontier model companies drawing multi-billion-dollar cheques and narrower application-layer bets.
| Company | VC | Round | Amount | One-line description |
|---|---|---|---|---|
| Anthropic | Sequoia (co-lead) | Series H | $65B | Developer of the Claude family of AI models, deployed across enterprise and consumer workloads. |
| Sierra | Sequoia (participant) | Series E | $950M | AI agent platform for enterprise customer service, co-founded by Bret Taylor and Clay Bavor. |
| Standard Intelligence | Sequoia (co-lead) | Series A | $75M | Early-stage research lab building next-generation foundation models; six-person founding team. |
| Stilta | a16z (lead) + YC | Seed | $10.5M | AI-powered patent litigation platform that reasons across 180M patents and 250M scientific publications. |
Anthropic — $65B Series H (May 28, 2026). The round was led by Altimeter Capital, Dragoneer, Greenoaks, and Sequoia Capital, placing a $965 billion post-money valuation on the company. Sequoia partner Alfred Lin described Claude as "building the bridge between where enterprise AI stands today and where it's headed." Run-rate revenue had crossed $47 billion at the time of the announcement, according to Anthropic's own disclosure. 2
Sierra — $950M Series E (May 4, 2026). Led by Tiger Global Management and GV, with Sequoia, Benchmark, and Greenoaks participating. The round brought Sierra's post-money valuation to $15.8 billion. The company raised $350M eight months prior, making the accelerated return to market notable. 3
Standard Intelligence — $75M Series A (May 9–10, 2026). Co-led by Sequoia Capital and Spark Capital at a $425M pre-money valuation. Angels included Andrej Karpathy and investor Stanley Druckenmiller. 4
Stilta — $10.5M Seed (June 3, 2026). a16z led the round alongside participation from Y Combinator and founders from Sana, Legora, OpenAI, Lovable, and Listen Labs. The Stockholm- and New York-based startup uses agentic AI to enforce, defend, and commercialize patents. 5
Fintech
| Company | VC | Round | Amount | One-line description |
|---|---|---|---|---|
| Stitch | a16z (lead) | Series A | $25M | Financial operating system for modern financial institutions, based in Riyadh, Saudi Arabia. |
| Airwallex | Sequoia (participant) | Series G | $330M | Global payments and treasury platform with $1.3B ARR as of April 2026. |
Stitch — $25M Series A (May 14, 2026). Andreessen Horowitz led the round — its first investment in the GCC region — bringing Stitch's total raised to $35M. Existing investors Arbor Ventures and COTU also participated. The Riyadh-based company had processed over $5B in transaction volume through its infrastructure stack at the time of announcement. 7
Airwallex — $330M Series G (December 2025, reported into this window). Sequoia participated in the round alongside five other institutional investors. The company's ARR reached an estimated $1.3B as of April 2026, per Sacra research, with payment volume accelerating across APAC and Europe. 8
Infrastructure & developer tools
| Company | VC | Round | Amount | One-line description |
|---|---|---|---|---|
| Endra | a16z (lead) | Series A | $50M | AI platform for building design and construction documentation automation, based in Stockholm. |
Endra — $50M Series A (June 1, 2026). Andreessen Horowitz led, with Notion Capital and Norrsken VC co-investing. The round brings total funding to $75M. The company applies AI to the pre-construction documentation process — a segment the company describes as typically the most labor-intensive stage before a shovel hits the ground. 9
Cybersecurity
| Company | VC | Round | Amount | One-line description |
|---|---|---|---|---|
| XBOW | Sequoia (participant) | Series C | $120M | Autonomous AI-powered penetration testing platform that mimics real hacker behavior. |
XBOW — $120M Series C (May 6, 2026). Sequoia participated in the round alongside other institutional investors. Total funding reached $150M at close. The company subsequently added a $35M Series C extension (May 8, 2026), bringing total Series C capital to $155M and total funding above $270M. 11
Deal summary
| Sector | Total disclosed | Deals tracked |
|---|---|---|
| AI & machine learning | ~$67.0B | 4 |
| Fintech | ~$355M | 2 |
| Infrastructure | $50M | 1 |
| Cybersecurity | $120M | 1 |
Anthropic's $65B round dominates the aggregate. Stripping it out, the remaining eight disclosed deals total approximately $2.0B across the May 1–June 11, 2026 window.
Sources: Anthropic official press release; Tracxn company profiles for Sierra and Airwallex; aifundingtracker.com for Standard Intelligence; DLA Piper press release for Stilta; BusinessWire for Stitch; Bricks & Bytes for Endra; Tryfundable for XBOW. Deal data drawn from public announcements only — undisclosed valuations and unannounced investments are excluded.
References
- 1Pixabay – networking data center (CC0)
pixabay.com
- 2Anthropic Series H press release
anthropic.com
- 3Sierra funding profile – Tracxn
tracxn.com
- 4AI Startup Funding News – Standard Intelligence
aifundingtracker.com
- 5DLA Piper advises a16z on Stilta seed round
dlapiper.com
- 6TechCrunch venture coverage
techcrunch.com
- 7Stitch $25M Series A press release
businesswire.com
- 8Airwallex funding data – Tracxn
tracxn.com
- 9Bricks & Bytes – a16z invests in Endra
bricks-bytes.com
- 10Pixabay – cyber hacker photo (CC0)
pixabay.com
- 11XBOW Series C – Tryfundable
tryfundable.ai
This story was produced automatically by a channel. One sentence is all it takes for Neodrop to keep producing for you.