Who's Winning Enterprise AI + The New Way to Close Deals

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Week of May 11, 2026 – May 17, 2026

Hey SaaStr AI Community: Who's pulling ahead in enterprise AI adoption? Is discounting dead in the age of AI-driven deployments? And why is your API probably not agent-friendly enough? Plus, a closer look at the week's most actionable founder lessons. - Jason & Amelia

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Salesforce

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Who's Winning Enterprise AI Now: Claude Up 128%, Gemini Up 48%, OpenAI Down 8%, Grok Still A Rounding Error

OpenAI is still the enterprise AI leader, but for the first time, it’s losing ground. Claude adoption is up 128%, and Google’s Gemini is making big moves. The coding assistant market is driving the shift, and multi-model strategies are becoming the new standard. Who’s winning, and why?

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Stop Discounting. Start Deploying. The New Way to Close Deals in B2B + AI.

Discounting to close deals? That’s yesterday’s playbook. The best AI-native B2B companies are deploying instead of discounting, collapsing time-to-value and letting the product sell itself. Deployments create momentum, and they’re redefining how deals get done.

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This edition of SaaStr AI Weekly is sponsored in part by Wistia

Over 13 million videos analyzed. Too many insights to count.

Wondering what a “good” play rate even is? Or how to use AI so you stay on budget? Cue: Wistia’s 2026 State of Video Report. Wistia analyzed over 13 million videos from over 1,000 marketers to surface the trends and benchmarks your video strategy needs.

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Yes, SaaStr AI Annual 2026 Crushed It. But We Had to Rebuild Our Entire Customer Base for AI.

SaaStr AI Annual 2026 was our best at least since 2022, and in many ways, a refounding of the events as part of the refounding of SaaStr AI itself for the age of AI Agents in B2B. Everyone building AI agents together. Bigger and far, far better energy than 2023-2025.

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This edition of SaaStr AI Weekly is sponsored in part by Salesforce

Build your startup to outlast the competition

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We're Hiring a Human Marketing Exec to Report to 10K, Our AI VP Marketing. Could You Report to an AI?

We're hiring a hands-on, driven human marketing exec who loves AI and loves running campaigns. To report directly to our AI VP Marketing, 10K.
We're hiring for a Director of Digital Marketing. 6 figure salary. Mostly remote. And … you'll be reporting to 10K, our AI VP of Marketing.

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The #1 Way to Win as a GTM Exec in the Age of AI: Be a True Product Guru. Know Your Space 10x Better Than Any Customer.

It's not enough to be a "people person" anymore. Not even close. Here's a test I want every sales leader to try right now: Upload your company's pitch deck, product documentation, and competitive battlecards to Claude or ChatGPT. Then ask it hard questions—the kind your best prospects ask.

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Let's Watch

Video of the Week: Video of the Week

Our AI is Hiring! Would You Work for One? And Are Autonomous Agents ... Safe? The Agents #005

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Listen to the Latest

The Official SaaStr Podcast

SaaStr 853: SaaStr 853: The Agents #004: Tragedy Apps, Too Many AI SDRs, and Why Your Next Hire Should Report to an Agent

SaaStr 852: SaaStr 852: The Agents #003, Our Agent Now Runs Campaigns on Weekends, Plus Why We Pay More for Salesforce Than Ever Before

SaaStr 851: SaaStr 851: The Agents, Episode 002. Managing 20+ AI Agents: Lazy Agents, Stealth Churn & the Death of 60% Solutions

Apple Podcasts · Spotify · Google Podcasts

@JasonLK on X

Tweets of the Week

Imagine you are a Director, Product at a large SaaS company

You make say $185k base, $50k bonus, pull $50k-$100k in RSUs (less now because stock is down). It's ... fine.

Your CEO tells you everyone has to work much harder because of "AI". Gotta "go, go, go"

Would you?

107 likes · 1 retweets · May 10

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I've been doing this long enough to know there is no karma

Folks do awful things and do just fine

But I've also been doing this long enough to know if you are really, really good to a lot of people

A few will really surprise you down the road and pay it back many times over

92 likes · 4 retweets · May 10

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Can’t do much better that Figma’s last quarter. Beat. Raise. Accelerate:

1/ $1.3B ARR Growing 46% YoY.
2/ 38% → 40% → 46% growth acceleration
3/ Stock pops

But even with all that … still trades at < 10x ARR

The SaaSpocolypse is over. But that doesn’t mean it’s easy. https://t.co/Us3HB9yyJZ

71 likes · 3 retweets · May 15

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