Eric Jackson Is Short Salesforce And Other Software Stocks: Inside 'AI Paradox' Market Hack

Hedge fund manager Eric Jackson, best known for his ultra-bullish call on Opendoor Technologies Inc. (NASDAQ:OPEN), is taking a bearish stance on SaaS stocks and he's betting against some of the biggest names. 

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SaaS Shorts

In a post shared on X, Jackson revealed he's short Salesforce Inc. (NYSE:CRM), Asana Inc. (NYSE:ASAN), Five9 Inc. (NASDAQ:FIVN), DocuSign Inc. (NASDAQ:DOCU) and Atlassian Corp. (NASDAQ:TEAM) — all high-profile software-as-a-service (SaaS) stocks that once defined the cloud boom.

Jackson says his bearish position is rooted in what he calls the "AI Paradox." 

After reading 716 corporate earnings transcripts, Jackson claims to have found a statistically significant pattern: the more a company talks about artificial intelligence, the worse its forward stock returns — by an average 5.4% relative to peers.

"The companies that talk about AI the most have the worst forward stock returns," Jackson wrote. "It's statistically significant. I call it the AI Paradox."

I'm short Asana, Salesforce, Five9, DocuSign, and Atlassian.

I read 716 earnings calls and found a pattern: the companies that talk about AI the most have the worst forward stock returns. 5.4 percentage points. Statistically significant.

I call it the AI Paradox.

— Eric Jackson (@ericjackson) March 31, 2026

His thesis challenges the popular narrative that AI hype automatically translates to business growth. Many software executives, Jackson argues, have leaned heavily on AI buzzwords to excite investors rather than showcase operational results. 

In essence, frequent AI mentions are a red flag — not a bullish signal.

Cybersecurity Longs

Still, Jackson isn't writing off the entire software universe. He singled out cybersecurity leaders like CrowdStrike Holdings (NASDAQ:CRWD), Zscaler Inc. (NASDAQ:ZS), and Palo Alto Networks (NASDAQ:PANW) as exceptions.

Not all software is dying. CrowdStrike, Zscaler, Palo Alto — AI makes their products more necessary, not less.

The market is punishing both groups equally. That's the mistake.

I built a typology: Roadkill. Survivors. Quietly Recovering. Knowing which group matters more than…

— Eric Jackson (@ericjackson) March 31, 2026

Unlike overhyped SaaS platforms, he believes AI genuinely strengthens these companies' core business value, enhancing detection, prevention, and automation capabilities.

Jackson's data-driven strategy lands as software multiples compress and investors rotate into hardware and infrastructure AI plays — such as Nvidia Corp. (NASDAQ:NVDA), Nebius Group (NASDAQ:NBIS) and Palantir Technologies, Inc. (NASDAQ:PLTR) — that visibly benefit from AI adoption. 

His "AI Paradox" may ultimately capture a shift from storytelling to measurable execution as Wall Street reevaluates how much AI optimism is already priced in and what effect AI will have on the software industry.

Photo: Who is Danny / Shutterstock