Sierra

Applications

Sierra passed $400 million in ARR, bought Anon, and signed Guardian Life for a million dental calls a year

Guardian Life pays Sierra per finished outcome for about a million dental calls a year, so Sierra bought the browser layer that lets agents finish the paperwork. The budget those calls and 2,000 staff came out of belonged to per-seat and per-head vendors: HCLTech, RingCentral, 8x8 and Salesforce's legacy stack.

November 6, 2026 · 2 min read

Applications

Klaviyo helped design the protocol that could let AI agents bypass its emails; insiders sold $200 million

Sierra and Meta's draft Personal Agent Protocol would let consumers' AI agents buy, return and rebook directly with brands, past the marketing messages Klaviyo sells. Klaviyo joined the design table as insiders net-sold $199.9 million of its stock over 12 months.

October 12, 2026 · 3 min read

Platforms

Cloudflare blocked 13.47% of AI bot requests in Q3, up from 5.98%; vendors sell agents the way in

Cloudflare's September 15 default change flipped agent access into a paid privilege, and the Q3 denial numbers already show it. The quiet winner may be the bypass vendors selling agents a way over the wall.

October 9, 2026 · 3 min read

Secondary market

Sierra passed $400 million in ARR, bought Anon, and signed Guardian Life for a million dental calls a year

Klaviyo helped design the protocol that could let AI agents bypass its emails; insiders sold $200 million

Cloudflare blocked 13.47% of AI bot requests in Q3, up from 5.98%; vendors sell agents the way in

ServiceNow fell 26.9%: its $1.7 billion AI target is arriving as services, not subscriptions

Environmental groups ask to unwind Kinder Morgan's $5.2 billion pipelines as it pitches a $1.3 billion one

Shopify just pointed every AI agent at its own cash register