VC Deal Tracker: a16z, Sequoia & YC — Issue #1 (May 1–June 11, 2026)

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

Interconnected data network representing AI compute and model infrastructure — AI and infrastructure deals dominated May–June 2026 by disclosed dollar volume. 1

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

Hacker at keyboard representing autonomous penetration testing and AI-powered security — Sequoia-backed XBOW closed the window's largest standalone cybersecurity round. 10

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.