My Two Cents

Glean Reaches $300 Million ARR, Citing Surging Enterprise Demand

Ken Yeung — Fri, 29 May 2026 03:50:18 +0000

Credit: Ken Yeung/Microsoft Copilot

" data-image-caption="

Credit: Ken Yeung/Microsoft Copilot

" data-large-file="https://i0.wp.com/thelettertwo.com/wp-content/uploads/2026/05/glean-neon-sign-aws-reinvent-2024-kenyeung-960x540-1.jpg?fit=960%2C540&ssl=1" />

Glean has reached $300 million in annual recurring revenue (ARR), the company said Thursday, an amount that tripled in just 15 months. It attributes the growth to stronger enterprise data context, broader departmental deployment, and higher-than-average user engagement. This milestone signals that Glean is holding its ground, even as enterprise software vendors like Slack, Dropbox, […]

CoreWeave Wants Enterprises to Ship Agents First and Fix Them Later

Ken Yeung — Thu, 28 May 2026 21:40:51 +0000

Credit: ChatGPT

" data-image-caption="

Credit: ChatGPT

" data-large-file="https://i0.wp.com/thelettertwo.com/wp-content/uploads/2026/05/chatgpt-futuristic-data-center-corridor-960x540-1.jpg?fit=960%2C540&ssl=1" />

Building reliable AI agents has traditionally meant doing most of the hard work before anyone uses them. Developers run lengthy offline evaluations against labeled datasets, measure performance across quality, accuracy, cost, and style benchmarks, make improvements, and repeat the cycle until the numbers look acceptable. Only then does the agent get deployed to users. CoreWeave […]

Asana Buys StackAI to Close the Gap Between Work Management and Enterprise Execution

Ken Yeung — Thu, 28 May 2026 20:03:00 +0000

Credit: StackAI/screenshot

" data-image-caption="

Credit: StackAI/screenshot

" data-large-file="https://i0.wp.com/thelettertwo.com/wp-content/uploads/2026/05/asana-stackai-enterprise-no-code-agent-platform-960x540-1.jpg?fit=960%2C540&ssl=1" />

As Asana positions itself as the “operating system for human-agent teams,” it has faced a real vulnerability: its agents couldn’t execute work end-to-end across the enterprise systems where business actually runs. That changes today with the company announcing the acquisition of StackAI, a no-code platform that lets enterprises build and deploy AI agents across critical […]

ServiceNow University Is Growing Fast. Now Comes the Hard Part.

Ken Yeung — Sun, 24 May 2026 22:11:55 +0000

ServiceNow CEO Bill McDermott unveils the company’s new learning and development platform, ServiceNow University, during the Knowledge conference in Las Vegas, Nevada, on May 6, 2025. Photo credit: Ken Yeung

" data-image-caption="

" data-large-file="https://i0.wp.com/thelettertwo.com/wp-content/uploads/2025/05/servicenow-university-knowledge-2025-02-kenyeung-1920x1080-1.jpg?fit=1024%2C576&ssl=1" />

Walking through the Venetian Convention and Expo Center in Las Vegas on a Wednesday afternoon in May, I navigate through the crowds and vendor booths before arriving at a section called the “Playground.” It’s here where I find Jayney Howson, ServiceNow’s chief learning officer. This wasn’t our first meeting: In 2025, we spoke on the […]

Google Rebuilt Search Around AI. Don’t Throw Away Your SEO Playbook.

Ken Yeung — Fri, 22 May 2026 22:21:06 +0000

Google’s AI-powered Search overhaul, unveiled at I/O 2026, is accelerating the push for marketers to rethink SEO and embrace AEO. Credit: OpenAI ChatGPT

" data-image-caption="

Google’s AI-powered Search overhaul, unveiled at I/O 2026, is accelerating the push for marketers to rethink SEO and embrace AEO. Credit: OpenAI ChatGPT

" data-large-file="https://i0.wp.com/thelettertwo.com/wp-content/uploads/2026/05/ai-economy-so-you-think-you-can-seo-chatgpt-1920x1080-1.jpg?fit=1024%2C576&ssl=1" />

IN THIS ISSUE: Google didn’t just update Search at I/O this week. It rebuilt it around AI, with consequences for every marketer who has spent years optimizing for a SERP that no longer looks the same. This issue examines what the shift from SEO to Answer Engine Optimization actually means for businesses trying to stay […]

Docusign Wants Its AI to Know Your Contracts Better Than You Do

Ken Yeung — Thu, 21 May 2026 12:00:00 +0000

Credit: Microsoft Copilot

" data-image-caption="

Credit: Microsoft Copilot

" data-large-file="https://i0.wp.com/thelettertwo.com/wp-content/uploads/2026/05/agreements-contracts-microsoft-copilot-960x540-1.jpg?fit=960%2C540&ssl=1" />

Docusign made its intentions clear two years ago when it pivoted beyond e-signatures into the Intelligent Agreement Management space. Now, it’s ready to show what that actually looks like in an AI agent world. At its Momentum conference on Thursday, the company announced that its AI engine for agreements, Iris, is expanding into agents along […]

OpenClaw Agents Were Built for Users. EnterpriseClaw Rebuilds Them for the Enterprise.

Ken Yeung — Tue, 19 May 2026 22:18:05 +0000

An AI-generated image of a cartoon crustacean leader in a corporate boardroom holding a gavel and security badge. Credit: Microsoft Copilot

" data-image-caption="

An AI-generated image of a cartoon crustacean leader in a corporate boardroom holding a gavel and security badge. Credit: Microsoft Copilot

" data-large-file="https://i0.wp.com/thelettertwo.com/wp-content/uploads/2026/05/cartoon-lobster-boardroom-enterpriseclaw-badge-microsoft-copilot-960x540-1.jpg?fit=960%2C540&ssl=1" />

AI agents are getting more capable by the day, pushed forward by computer-use frameworks like OpenClaw and its variants. Enterprise adoption should be accelerating—and it would be if not for the security and governance issues: No one wants an agent wiping out an entire database in nine seconds without permission. On Tuesday, Automation Anywhere unveiled […]

‘The Era of the Chatbot Is Over’: Zendesk Makes Its Case for the Autonomous Service Workforce

Ken Yeung — Tue, 19 May 2026 15:00:00 +0000

Zendesk CEO Tom Eggemeier at the company’s 2025 Relate conference. Credit: Ken Yeung

" data-image-caption="

Zendesk CEO Tom Eggemeier at the company’s 2025 Relate conference. Credit: Ken Yeung

" data-large-file="https://i0.wp.com/thelettertwo.com/wp-content/uploads/2026/05/zendesk-ceo-tom-eggemeier-kenyeung-960x540-1.jpg?fit=960%2C540&ssl=1" />

Zendesk spent years building software to manage customer service tickets. Now, its attention has turned to building an AI workforce that resolves them. It’s a “fundamental reset” of its platform, one where deflection-based bots are replaced by specialized AI agents that operate across all channels. At this year’s Relate conference, Zendesk is unveiling autonomous AI […]

8 in 10 Workers Are Still Doing AI’s Job for It

Ken Yeung — Fri, 15 May 2026 19:51:03 +0000

IN THIS ISSUE: New Workday research reveals that most employees are still spending their days manually bridging broken systems, even as AI adoption spreads. Then, a new Gallup survey finds most Americans don’t want AI data centers in their backyards, putting a number on the public resistance threatening the industry’s $700 billion infrastructure push. The […]

ServiceNow and Nvidia Want to Make Desktop AI Agents Safe Enough for the Enterprise

Ken Yeung — Thu, 14 May 2026 03:45:17 +0000

Credit: ServiceNow

" data-image-caption="

Credit: ServiceNow

" data-large-file="https://i0.wp.com/thelettertwo.com/wp-content/uploads/2026/05/servicenow-nvidia-partnership-logos-960x540-1.jpg?fit=960%2C540&ssl=1" />

For years, enterprises have struggled to govern AI where it actually runs, across clouds, tools, and now, increasingly, the desktops where employees do their work. ServiceNow thinks it has an answer, and it’s building the solution with Nvidia. Project Arc is the result: an enterprise desktop agent designed to bring autonomous capabilities seen in tools […]