CEO Doubles Down on Match Group—$4M in 90 Days

Today's Top Insider Moves That Matter

Today was a broad-market sprint—tech, consumer cyclicals, and semis all surged as if recession risk never existed. From cloud software to electric cars, green dominated the screen. But while investors cheered, insiders moved differently. They didn’t chase the rally—they repositioned beneath it.

Application software execs took profits quietly. Entertainment insiders continued their steady retreat. But in the shadows, financial and industrial names saw some of the most aggressive insider buying we’ve tracked in weeks. Directors and C-suites aren’t buying the hype—they’re buying cash flow.

And that’s the story: while the crowd piled into momentum, the smart money got surgical. Strategic clusters formed in groceries, staples, and overlooked small caps. Meanwhile, a bold few doubled down—one CEO even averaged down twice in three months.

Markets run on emotion. Insiders move on information. Let’s dive into the trades that matter most.

Biggest Insider Sales

🏢 Insight Enterprises $NSIT ( ▲ 1.2% ) – ValueAct Unloads $78.6M

• Who’s Selling? ValueAct Holdings, L.P. (10% owner)

• What They Sold: 600,000 shares at $130.94

• Total Value: $78.6M

• Why It Matters: Activist firm ValueAct just trimmed its stake by 15%. They still hold over 3.4M shares, but this move suggests they’re locking in profits after a strong run.

💳 Sezzle Inc. $SEZL ( ▲ 6.76% ) – CFO Offloads 77% of Stake

• Who’s Selling? Karen Hartje (Chief Financial Officer)

• What They Sold: 432,552 shares at $75.36

• Total Value: $32.6M

• Why It Matters: When a CFO sells more than three-quarters of their holdings in one go, it raises a red flag. Whether it’s personal or performance-based, investors should take notice.

🏠 Lemonade, Inc. $LMND ( ▲ 11.52% ) – SoftBank Trims Again

• Who’s Selling? Softbank Group Capital Ltd. (10% owner)

• What They Sold: 971,960 shares at $31.19

• Total Value: $30.3M

• Why It Matters: SoftBank continues its quiet retreat from the insurtech darling. With sentiment still shaky around the stock, this sizable reduction doesn’t inspire confidence.

🚗 Carvana $CVNA ( ▼ 0.54% ) – Exec Pair Dumps $29.4M

• Who’s Selling? Daniel Gill (Chief Product Officer) & Thomas Taira (President, Special Projects)

• What They Sold: 105,166 shares combined at ~$279.65

• Total Value: $29.4M

• Why It Matters: When two senior execs sell big within days of each other, it’s rarely coincidence. Nearly half of Gill’s and 18% of Taira’s holdings are gone.

🔧 Johnson Controls $JCI ( ▲ 1.44% ) – Director Drops $9.2M

• Who’s Selling? George Oliver (Director)

• What They Sold: 100,000 shares at $91.70

• Total Value: $9.2M

• Why It Matters: The industrial stalwart has been quietly climbing, but this director-level move might suggest a plateau—or just prudent risk management.

While the selling was concentrated in tech-adjacent and fintech names, the scale of trimming signals a broader theme: insiders are cashing in where valuations have run hot.

Now let’s flip the script. Here are today’s biggest insider buys—and what they could be signaling about future upside.

*Money Mediary is for informational purposes only and should not be considered financial, investment, or legal advice. We analyze publicly available insider trading data to provide insights, but we do not recommend or endorse any specific securities, strategies, or investments. All trading decisions are made at your own risk.

Insider transactions reported in SEC Form 4 filings do not guarantee future stock performance. Past insider activity does not predict future market movements. Always conduct your own research or consult with a licensed financial professional before making investment decisions.

Money Mediary is not affiliated with the SEC, any financial institution, or any insider whose trades are reported. We make no guarantees about the accuracy, completeness, or timeliness of the data presented.

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