Diamond, Director of Engineering for AI at Datadog, joined the company through the acquisition of his AI startup, Augmend. With over a decade in AI, he now leads the Bits AI group, a series of high-energy teams building agent-based automation to transform how teams operate and secure software.
“I think 2025 is the year of the AI Agent,” Diamond said. “We’ve made strides in developer, security, and SRE automation, and we’re just getting started.”
Why Datadog is Built for AI
Diamond sees Datadog as uniquely positioned in the AI landscape. The reason? Data.
“Most AI companies struggle with the cold-start problem. We don’t,” he said. “We already have massive volumes of telemetry data, and the infrastructure to learn from it.”
This makes Datadog an ideal place to build. From incident response to self-improving software, the Bits AI team is exploring how agents can save time, reduce toil, and surface better insights faster.
Building the Bits AI Team
Diamond’s approach to hiring focuses on curiosity. “We’ve hired people without an AI background who dove in, experimented, and became leaders in how we implement AI day-to-day.”
He looks for engineers who are hands-on with AI tools, whether it’s building prompts in Claude or prototyping with APIs. “You’d be surprised how many engineers want to work on AI but don’t use it day-to-day,” he noted. “We look for the ones who do, and who are genuinely curious about new technology.”
The Bits AI group functions like a series of startups inside Datadog. “We build small agentic teams who focus on a specific task and customer problem, ship fast, learn from users, and iterate quickly. Experimentation is part of our daily rhythm,” he said.
What Leadership Looks Like on the AI Team
In a field evolving as quickly as AI, Diamond believes leadership must prioritize urgency, experimentation, and calculated risk. “It’s easy to fall into the trap of waiting for perfection,” he said. “We aim to be operationally sound, but we also have to make bold bets.”
His philosophy? Hire high agency people who are energized by ambiguity, build small high-powered teams, and give them room to run. “Leadership means creating the conditions where smart people can try bold things. That’s how we’ll discover what works, what doesn’t, and what’s next.”
A Vision for 2025 and Beyond
From on-call incident agents to observability copilots and security AI assistants, Datadog’s AI teams span from cutting-edge research to real-world deployment.
Beyond its data advantage, Datadog’s willingness to experiment and to spend on research and development also stands out for engineers, according to Diamond. “Datadog backs its AI ambitions with real investment: In Q1 2025 alone, 30% of total revenue went into research and development, a signal of how seriously we take innovation.”
As Diamond puts it, “For Bits AI, our ultimate aim is to build AI systems that serve as your DevSecOps teammates, systems that not only understand your infrastructure, but actively support it and take on work your human engineers used to do. We want to help engineers like ourselves spend less time firefighting and more time building what’s next.”
If you’re excited to shape the future of AI and build systems that empower engineers, Datadog’s AI teams are hiring – and looking for builders like you.
