CrowdStrike Holdings (CRWD) is a leading cybersecurity company known for its cloud-based Falcon platform, which protects endpoints and cloud workloads for businesses worldwide.
Co-founded by CEO George Kurtz in 2011, the company has grown into one of the largest players in cybersecurity.
Its leadership team features high-profile executives, including President Michael Sentonas, Chief Financial Officer Burt Podbere, and Chief Security Officer Shawn Henry.
Recently, however, some of these executives’ stock transactions have come under scrutiny.
In this article, we’ll break down CrowdStrike insider trading allegations involving their top brass, examine the timing of their stock sales, and explain how insider trading laws and 10b5-1 plans factor into the story.
Understanding Insider Trading Laws and 10b5-1 Plans
Insider trading refers to corporate insiders (like executives or directors) buying or selling stock based on material nonpublic information, which is illegal.
U.S. regulators like the SEC vigilantly monitor unusual trades and will investigate suspicious activity. Violations can result in hefty fines or even prison time.
To stay on the right side of the law, executives of public companies must either trade only during approved windows when they aren’t aware of undisclosed major news, or better yet, use SEC Rule 10b5-1 trading plans.
SEC Rule 10b5-1 plans are prearranged trading schedules that insiders can set up when they have no inside information. These plans predetermine when and how many shares will be bought or sold in the future.
The idea is to remove discretion so that even if an insider later learns confidential news, the trades go ahead as scheduled. Such plans shield insiders from accusations that a trade was timed based on confidential knowledge.
In other words, if an executive’s shares sell automatically on set dates or price triggers, it’s harder to allege they “knew something” at the time.
Many of the CrowdStrike executive stock sales we discuss were conducted under these 10b5-1 plans or as part of routine financial management, according to the company’s disclosures.
However, even with a 10b5-1 plan, perception matters. If a trade happens right before bad news, people will ask questions.
Let’s look at the key instances where CrowdStrike’s leadership’s timing drew attention.
Crowdstrike Insider Trading Sales That Raised Eyebrows
Case 1: July 2024 – Sale Before a Major Outage
One of the most talked-about incidents involves Shawn Henry, CrowdStrike’s Chief Security Officer. According to SEC filings, on July 15, 2024, Henry sold 4,000 shares of CrowdStrike stock at an average around $371, totaling roughly $1.48 million.
Just four days later, on July 19, a major global IT outage hit many of CrowdStrike’s customers, which was traced back to a flawed software update from CrowdStrike itself.
The outage disrupted airlines, hospitals, banks – a nightmare scenario – and when it became public, CrowdStrike’s stock plunged about 11% in a single day.
Henry’s trade was pre-scheduled under a 10b5-1 plan that he had set up back in December 2023. In fact, the sale represented only a small portion of his holdings (he still had over 183,000 shares afterward.
On paper, this looks legitimate: it was an automated sale designed to avoid any insider trading violations. Nonetheless, the timing was so uncanny that it raised a lot of eyebrows.
It’s important to stress that as of now, no evidence has emerged that Henry knew the outage was coming or that his sale was improper. CrowdStrike stated the sale was part of an approved plan, and such plans exist precisely to prevent allegations of insider trading.
Case 2: September 2024 – Multiple Executives Cash Out After a Stock Surge
The next notable cluster of insider sales came in September 2024. By this time, CrowdStrike’s stock had recovered from the July outage shock and was riding high on other positive news.
In late September, just after the company’s quarterly earnings report, several top executives sold significant shares. CEO George Kurtz himself unloaded 55,325 CRW shares on September 23, 2024, netting about $16.4 million at prices around $293–$302 per share.
Filings show this was related to Kurtz’s restricted stock units (RSUs) vesting – essentially, part of his stock-based compensation becoming actual shares that he then sold for liquidity. Even after selling, Kurtz still held over 1.1 million shares (worth around $320 million at the time), so this was a slice of his stake.
He wasn’t the only one. President Michael Sentonas sold about $3.2 million worth of stock, CFO Burt Podbere sold about $3.3 million, and the Chief Accounting Officer sold roughly $965,000 in shares, all around that same late-September period.
In total, TipRanks data showed roughly $29.8 million in “informative sell” transactions by insiders over the prior three months, which actually gave CrowdStrike a “Negative Insider Confidence” signal on TipRanks’ tracking system.
Generally, large insider selling can signal insiders are not extremely bullish on the stock’s near-term future – or simply that they’re taking some profit.
In CrowdStrike’s case, these sales followed a big rally (the stock had surged in the second half of 2024), so it’s possible executives were just cashing in on strength.
Nonetheless, seeing multiple leaders sell at once can make investors uneasy.
To be clear, these September sales were disclosed in regulatory filings and came after (not before) the company’s earnings announcement, meaning the information about that quarter was already public. There’s no indication of wrongdoing in these trades.
In fact, they may well have been done under pre-set plans or for ordinary reasons like portfolio diversification. But combined with the earlier July episode, they contributed to a narrative that CrowdStrike’s insiders might be heading for the exits whenever they get a chance.
Case 3: May 2025 – CEO’s Big Stock Sale Amid Layoffs News
Fast forward to May 2025, and CrowdStrike hit another bump: the company announced a plan to lay off about 5% of its workforce (roughly 500 employees) as part of cost-cutting and “aligning with market conditions” in a tougher tech economy.
The layoff news on May 7, 2025 sent CrowdStrike shares down over 4% that day, adding to investor jitters.
But what really shook investor confidence was what happened just two days before that announcement. On May 5, 2025, CEO George Kurtz executed another large stock sale – 55,556 shares at an average price of about $447.54, a windfall of roughly $24.9 million. This was Kurtz’s second big sale of the year (he had sold 22,449 shares in March 2025 as well).
According to trading records, this May 5 sale by Kurtz was again linked to RSU vesting and tax obligations – essentially an automatic sale to cover the income taxes on recently vested stock awards.
A TradingView report confirms that both Kurtz’s May sale and a coinciding $6.99 million sale by CFO Podbere on May 5 were mainly to cover tax withholdings on vested RSU.
In other words, this wasn’t necessarily Kurtz deciding to reduce his holdings; it was likely a planned move to handle a tax bill. After the sale, Kurtz still directly owned over 2.19 million shares (worth hundreds of millions of dollars) and additional shares via a family trust.
It’s worth noting that CrowdStrike’s business fundamentals at that point were strong – the company had just reported 23% revenue growth and over $1 billion in annual free cash flow.
Kurtz’s remaining stake showed he was still heavily invested in CrowdStrike’s future success. Yet, perception is reality on Wall Street in the short term.
This episode reinforced why insider trades, however legal, are scrutinized so closely.
Is Crowdstrike Guilty of Insider Trading?
When it comes to CrowdStrike insider trading allegations, the story so far is less about outright wrongdoing and more about perception and timing.
CrowdStrike’s executives – from the CEO and CFO to security and board personnel – have indeed sold a lot of stock, but mostly through legally structured plans and often for benign reasons.
However, a few of those sales coincided a little too closely with negative news events, providing ample fodder for skeptics. The facts on record however show no smoking gun of illegal insider trading.