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Insiders are selling one of the top beneficiaries of the AI boom, a software behemoth facing a wave of negative sentiment, and an up-and-coming fintech name. Not only does the recent performance among these names differ significantly, but so do the details of their recent insider sales. Amid this, closely examining the insider moves at each name is necessary to understand how strong a bearish signal their recent sales actually send.

Seagate Sales Spike in Q3 With Shares Up Over 200% in 2026

Despite many AI-related stocks soaring in 2026, few have achieved gains as impressive as Seagate Technology's (NASDAQ: STX), with shares up well over 200%. The company’s main product is hard-disk drives (HDDs), which have seen a resurgence in demand amid the AI boom. This comes as hyperscalers look for high-capacity and economic storage products to house the immense amount of data generated and used by AI. This helped its sales increase by 48.5% year-over-year (YOY) last quarter, near Seagate’s fastest growth in over a decade.

However, the company has also seen a very significant amount of insider selling recently. In Q3, insider sales totaled $379 million, more than triple the $107 million seen in Q2, raising questions around whether Seagate insiders see the stock’s impressive run coming to an end. However, insiders made at least $125 million worth of these Q3 sales to satisfy tax withholding requirements upon vesting of employee stock units. Given that these sales are not optional, they do not constitute negative signals.

Still, many sales, including Teh Ban Seng’s large $41.2 million sale, were not attributable to tax withholdings. Additionally, most sales came at prices considerably below Seagate’s recent levels. Overall, Seagate’s recent sales provide a mildly bearish signal, but investors should recognize that non-discretionary sales contributed greatly to the spike.

Adobe CEO Initiates Large Sales With Shares Deeply in the Red

Software giant Adobe (NASDAQ: ADBE) has lost approximately $50 billion in market capitalization in 2026, with shares down around 30% on the year. Still, the company has generally maintained strong financial performance. It currently expects to generate adjusted earnings per share (EPS) of $24.45 to $24.50 in fiscal 2026, which would be a nearly 17% YOY increase at the midpoint. That would be a notable acceleration compared to 13.7% YOY EPS growth in fiscal 2025. Still, sentiment around this name remains weak, primarily because investors fear that AI tools will damage long-term demand for Adobe products.

Amid the stock’s poor performance, it is a bit concerning to see that CEO Shantanu Narayen recently sold over $31 million worth of the company’s shares. This equates to Narayen selling more than one-third of his holdings, a very significant percentage. This is not exactly a confidence-inspiring signal from Adobe’s top executive. However, the FORM 4 filing does note that the sales were “primarily made for the reporting person's tax and estate planning purposes.” Nonetheless, the size of his sales is difficult to ignore.

Narayen will step down as the CEO in December, which somewhat limits the negative signal as he moves away from day-to-day management. However, he will continue to hold a very prominent role as Adobe’s Executive Chair. Overall, it’s difficult not to take the sale as a bearish indicator, especially with Adobe shares down so significantly.

Chime’s Insider Sales Balloon After Blowout Earnings

Chime Financial (NASDAQ: CHYM) is an approximately $10 billion fintech company that provides consumer banking and payment solutions. The stock has soared recently, up approximately 50% in the last six months. This is largely a result of Chime’s latest earnings report, which caused shares to rise more than 20% in one day. The company posted strong growth and profitability improvements, with revenue rising 27% YOY and seeing its second consecutive quarter of positive GAAP EPS. Its adjusted earnings before interest, taxes, depreciation, and amortization margin also expanded by 12 points YOY to 15%.

However, since Chime’s report, the company has seen around $618 million worth of insider selling. For a company with a market capitalization of only $10 million, that is a huge percentage. With this, it appears that insiders are taking significant profits after the stock’s strong performance.

Still, it is important to note that many insiders continue to hold massive positions in the company. This includes DST Global Advisors, which still holds more than 35 million shares through several funds. Many sales also came at well above $30 per share, substantially higher than Chime’s recent levels. Overall, the sales are mildly bearish and may indicate that insiders see limited near-term upside above the mid-$30 range.

Not All Insider Sales Send the Same Signal

While none of these sales are positive signals for the companies involved, their circumstances differ enough that the raw dollar totals should not be viewed equally. Narayen's Adobe sale stands out because of its size relative to his prior holdings, but the filing explicitly ties it primarily to tax and estate planning. Looking ahead, it will be worth monitoring whether Narayen continues to greatly reduce his position over time. If the sales end up being an isolated incident, it would align with the tax and estate-planning rationale rather than signaling a real lack of confidence.

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