The AI Stocks Being Overlooked: Datadog and Workiva Quietly Build Enterprise AI Dominance

While most investors fixate on pure-play AI companies, two lesser-known firms are reshaping how enterprises deploy artificial intelligence in their core operations. Datadog and Workiva represent a different breed of under the radar AI stocks—companies that aren’t household names but are capturing genuine AI momentum through strategic integration rather than speculative hype. Their recent quarterly results reveal something important: AI adoption among enterprise customers is accelerating faster than the broader market realizes.

When AI Integration Unlocks Untapped Potential

What makes these two companies particularly interesting is their approach to artificial intelligence. Neither builds AI models from scratch, and neither is racing to launch a ChatGPT competitor. Instead, they’ve embedded AI directly into platforms that enterprise customers already rely on for critical business functions. This distinction matters tremendously.

Datadog took its cloud observability platform—technology that helps organizations monitor their digital infrastructure—and wove in AI capabilities that make existing workflows dramatically more efficient. The company didn’t stop there; it created entirely new AI-native products designed specifically for the generative AI era. This hybrid strategy has proven remarkably effective at attracting both new customers and expanding spending from existing ones.

Workiva followed a similar playbook by launching an AI assistant that transforms how large organizations handle reporting and compliance. The platform now allows managers to draft regulatory filings and complex reports using simple prompts, fundamentally changing the economics of enterprise reporting. Both companies recognized early that AI’s real value lies not in replacing entire business functions, but in amplifying what their existing customers were already trying to accomplish.

Datadog’s Explosive AI Customer Adoption—By the Numbers

The Q3 2025 results paint a striking picture of momentum. Datadog had over 5,000 customers actively using at least one of its AI products, representing a 67% year-over-year increase. That growth rate alone would attract attention, but the revenue impact is even more compelling.

AI-related revenue from these customers accounted for 12% of Datadog’s total quarterly revenue in Q3, up from just 6% a year earlier—essentially doubling in 12 months. To put this in perspective, total company revenue hit $881 million that quarter, meaning AI revenue alone generated roughly $106 million in annualized revenue run-rate impact.

CFO David Obstler explicitly highlighted that revenue growth accelerated among AI customers, signaling this isn’t a one-quarter phenomenon but rather a sustained shift in customer spending patterns. The company’s ability to convert observability customers into AI customers represents genuine product-market fit, not marketing theater.

Workiva’s Strategic AI Advantage Attracts Enterprise Spending

Workiva’s performance tells a parallel story with different nuances. The company achieved 21% revenue growth in Q3 2025, reaching $224 million—the fastest growth rate of the year. That solid performance masks something more important happening among its highest-value customers.

The number of customers spending at least $300,000 annually with Workiva surged 41%, while those spending $500,000 or more jumped 42%. Both growth rates accelerated sequentially, meaning the company isn’t just adding AI features; it’s driving deeper wallet penetration among its most sophisticated customers. These aren’t price-sensitive buyers—they’re enterprise organizations making substantial commitments to modernizing their reporting and compliance infrastructure.

The company’s confidence in this trajectory was evident when management raised full-year 2025 revenue guidance to $881 million, precisely matching Datadog’s quarterly revenue. For investors tracking enterprise AI adoption, this commitment from management serves as a credibility signal that growth momentum is both real and sustainable.

Why the Market May Be Sleeping on These AI Plays

Here’s the curious disconnect: despite delivering concrete proof of AI revenue acceleration and customer growth, both Datadog and Workiva remain decidedly under the radar AI stocks in mainstream investment discussions. The media obsesses over whether OpenAI will succeed, whether new foundation model companies will survive, whether AI infrastructure providers will consolidate. Meanwhile, these two firms are quietly proving that AI’s economic value increasingly flows to companies that solve specific business problems rather than chase generalized technological breakthroughs.

Datadog’s 31% pullback from its 52-week high shouldn’t be interpreted as a failure of its AI strategy; rather, it reflects the broader market’s preference for pure-play AI narratives. Workiva’s attractive valuation creates a similar opportunity for investors willing to look beyond flashy headlines.

The consistent pattern across both companies—surging AI adoption, accelerating revenue concentration in AI customers, record spending from enterprise accounts—suggests these under the radar AI stocks have barely begun penetrating their addressable markets. As more enterprises move from AI pilot projects to production deployments, the demand for platforms that reduce complexity and risk will likely intensify. Both companies appear positioned to capture disproportionate share of that opportunity precisely because they’re solving problems that enterprise customers need solved today, not theoretical problems that might matter tomorrow.