AIZ ASSURANT, INC. Insider Trading

SVP/CAO Dimitry Dirienzo sold 2,000 shares of AIZ at $255.68 for $511.4K; holdings drop from 4.7K to 2.7K.

Dimitry Dirienzo, SVP and Chief Administrative Officer, sold 2,000 shares at $255.68 on 2026-05-26, reducing his holdings from 4,741 to 2,741 shares. The current price of $252.06 is -3.4% from the 52-week high of $260.96, and the stock has advanced +8.3% over 30 days and +9.9% over 90 days. At a market cap of $12,488,977,382.22 and net income of $274,100,000.00, Assurant remains solidly profitable with annual revenue growth of +7.9%. The sale represents a substantial reduction in Dirienzo's proportional stake and occurs within the context of recent upward price momentum.

CFO Keith Meier sold 25,000 shares of AIZ at $254.31; scheduled 10b5-1 plan execution

Keith Meier, EVP and CFO of Assurant, sold 25,000 shares (representing 57.4% reduction in his holdings from 43,552 to 18,552 shares) on 2026-05-15 at $254.31 per share under a 10b5-1 trading plan adopted on 2026-02-13. This was a pre-arranged, scheduled transaction rather than a discretionary trade, and therefore reflects no timing signal or conviction-based positioning decision. The stock has appreciated 13.4% over the preceding 30 days and 16.8% over 90 days, trading near the 52-week high of $257.17, suggesting a period of strong momentum in the security. While the sale represents a material reduction in the CFO's direct holdings, the planned-trade framework limits the evidentiary value for inferring management confidence or concern about valuation.

AIZ EVP Rosenblum sells 2,000 shares at $251.77; holds 12.8K post-trade as stock approaches 52-week peak of $254.43

Jay Rosenblum, Chief Legal Officer, sold 2,000 shares at $251.77, reducing his holdings from 14.8K to 12.8K shares. The sale occurred near the stock's 52-week high of $254.43 (current price $254.61 is +0.1% from that peak), and AIZ has appreciated 17.1% over the prior 90 days. Rosenblum's single prior sale at AIZ (August 2025) posted a 90-day return of +8.4%, meaning the stock rose after that sale—not a pattern of well-timed exits. With a P/E of 12.61 and solid fundamentals (revenue $3.4B, net income $274.1M, annual growth +7.9%), the company's valuation remains reasonable even at current price levels. The sale itself does not carry strong directional signal given the modest reduction in holdings and the insider's limited history of market-timing success on this ticker.