Will any Datadog executive officer make an open market stock purchase within 90 days after the Q4 2025 earnings release?

The Q4 earnings update resolves the committee's key debate in favor of the benign interpretation of insider selling — results were uniformly strong (29% YoY growth, 4th consecutive acceleration). Critically, this means insiders were NOT selling because they anticipated weakness. But paradoxically, benign selling reduces the motivation to buy: if selling was routine diversification, there is no informational signal to 'correct' with a purchase. The 12+ month zero-purchase base rate, 64:1 lifetime ratio, and $545M SBC (massive existing equity exposure) all remain unchanged. The stock has rallied to ~$114 from ~$107, further reducing any 'catching a bargain' motivation. The blackout window has lifted, but prior open windows also produced zero buying.

Taking a slightly more generous view: the blackout has now lifted for real, and insiders now have confirmed strong Q4 data plus forward visibility into Q1 2026. If any insider ever felt conviction about the stock being undervalued at ~$114 (still 43% below the $199 high), this is their first clean window with confirmed results. The 90-day window is long enough for someone to act. However, the entire C-suite has been systematically selling, not buying. The behavioral pattern across all four named officers (CEO, CTO, CFO, COO) is unanimous selling. Converting from universal selling to any buying requires a qualitative behavioral shift that has not occurred in 12+ months despite a much steeper decline.

The update provides confirming evidence for the existing strong NO thesis. The key logical chain: (1) strong Q4 results confirm operational health, (2) operational health was never in doubt from operational lenses, (3) insiders were selling throughout the period of operational strength, (4) therefore strong results do not predict buying behavior. The relevant question is behavioral, not fundamental. Insiders with $545M in SBC and IPO-era equity have no financial incentive to buy more stock. The CTO's continued selling and share class conversion through January 2026 is the freshest behavioral signal and points firmly toward continued selling, not buying. I estimate a small bump from the pre-update 6.2% average because the window is now genuinely open, but the stock price rally partially offsets this.

The Q4 update changes nothing material about the insider buying probability. Strong earnings confirm operational health but do NOT change insider behavioral patterns. The 64:1 sell-to-buy ratio since 2019 is the dominant fact. The stock has actually risen to ~$114 from ~$107, making a 'buy the dip' trade even less compelling. All four named executives sold in September 2025, and the CTO continued selling through January 2026 — this is unanimous, persistent selling behavior. The $545M SBC means insiders are already heavily exposed to DDOG equity without needing to buy more. An open market purchase would be an extraordinary departure from established behavior, and nothing in the Q4 results provides a catalyst for such a departure.

Applying a structured base rate analysis: How often do SaaS company executives who have been exclusively selling for 12+ months suddenly make an open market purchase? The answer is almost never. The relevant comparison class is not 'will insiders buy after good earnings' but rather 'will executives who have been systematically selling for years and receiving massive SBC reverse course.' The Q4 results resolve the debate about whether selling was informed (it was not — results were strong), but this cuts against buying rather than for it. If insiders were selling routinely during a period of strong execution, they will likely continue selling routinely during continued strong execution. The blackout lifting is necessary but not sufficient — prior open windows also produced zero buying.

Considering this from a behavioral economics perspective: insider buying is a strong signal precisely because it is rare. For Datadog insiders, who hold massive equity positions through SBC, the marginal utility of buying more stock is very low. They are already heavily concentrated. The rational financial decision is diversification (selling), not concentration (buying). This is true regardless of Q4 results or stock price level. The only scenarios where buying becomes likely are: (1) activist pressure demanding insiders 'put skin in the game' — no evidence of this; (2) company announcing a buyback program where executives participate — this is not the same as open market purchase; (3) a new executive joining who buys as a statement — no indication of this. Without one of these unusual catalysts, the probability remains very low.

The core signal is unchanged post-earnings: zero open market purchases in 12+ months with a 64:1 lifetime sell-to-buy ratio. Q4 was strong (29% growth, every metric improved), but strong results have historically coincided with continued selling, not buying. The blackout has lifted, creating a trading window, but previous open windows also produced no purchases. Stock at ~$114 is still well below the $199 high, but this level of decline has been sustained for months without triggering any buying. The most recent insider action (CTO selling $4.6M in January 2026) confirms the prevailing pattern is firmly intact.

Playing devil's advocate slightly: this is the first post-earnings window where insiders have confirmed Q4 acceleration data AND the stock is still materially below highs. There is a small but non-trivial scenario where an executive (possibly the CEO or a board member) makes a symbolic purchase to signal confidence, especially given the disconnect between strong fundamentals and depressed stock price noted by the Myth Meter lens. Symbolic insider purchases do happen occasionally, especially when a company is perceived as undervalued. However, even in this scenario, the 12-month drought and systematic selling pattern make it improbable. I assign 8% to account for the full 90-day window and the possibility of symbolic action.

Calibration feedback from sibling markets is instructive: the ensemble was too uncertain on DDOG markets where the evidence clearly pointed one direction. For this market, the evidence overwhelmingly points to NO: zero purchases in 12+ months, 64:1 lifetime ratio, all C-suite selling, $545M SBC providing massive existing exposure. The Q4 update strengthens operational fundamentals but does not change insider behavioral patterns. The stock rally to ~$114 actually slightly reduces the probability by removing the 'catching a falling knife' motivation. Being more decisive based on sibling calibration, I maintain a low probability but ensure it reflects genuine confidence in the evidence.