When a CEO reaches into his own pocket and buys $3 million of his company’s stock while four other executives simultaneously cancel their plans to sell, that’s not a press release — it’s a signal. ServiceNow CEO Bill McDermott just filed paperwork to purchase $3 million in NOW shares on February 27, and his CFO Gina Mastantuono plus three other C-suite officers have terminated their 10b5-1 automatic stock-selling plans. In a software sector that’s been getting absolutely demolished, this is the loudest insider conviction signal we’ve seen in months.
The context matters. Software stocks have been in freefall since late January, with the iShares Expanded Tech-Software ETF (IGV) diverging from the Nasdaq 100 (QQQ) by the widest margin in history. This isn’t a normal rotation — it’s an existential repricing. Investors are terrified that AI agents from Anthropic, OpenAI, and others are about to replace the per-seat software model that generated trillions in market cap. Salesforce is down 25% year-to-date. Adobe is getting gutted. The entire SaaS complex is trading like the business model itself has an expiration date.
ServiceNow has been swept up in this carnage despite posting better-than-expected Q4 results and solid guidance. McDermott, never one for understatement, told investors on the January earnings call: “The worry is gone, you can give us back the market cap.” Wall Street didn’t listen. The stock kept falling. So now he’s putting his money where his mouth is — literally.
Here’s why this matters beyond ServiceNow. Insider buying during sector-wide panic is one of the most reliable contrarian signals in the market. When the people who know the business best are buying while everyone else is selling, it historically marks an inflection point. The software selloff may have further to go — fear is a powerful force — but the executives running these companies are telling you with their wallets that the AI-kills-SaaS narrative is overdone.
McDermott isn’t buying because he thinks software is dead. He’s buying because he thinks the market has confused disruption with destruction. That distinction tends to be worth a lot of money for investors paying attention.