Datadog

Why Your Agent Disagrees With Itself (And What To Do About It) - Diane Lin, Datadog

Jul 20, 2026 · 25:38

Diane Lin, Tech Lead at Datadog, argues that AI agent inconsistency is not a model failure but a signal of ambiguous data near the decision boundary, known as the gray zone. She presents a workflow combining active learning with semantic memory (domain policies) and episodic memory (past similar cases) to automatically identify flip-flopping outputs, focus human review, and continuously adapt agents without expensive fine-tuning. In a real experiment with 93 cybersecurity alerts, 25% initially flip-flopped; episodic memory reduced that to 10%, with the remainder resolved via human review and policy clarification. Lin emphasizes treating each disagreement as an opportunity to clarify labels and policies, building trustworthy, customer-adaptive agents.

How agent o11y differs from traditional o11y — Phil Hetzel, Braintrust

May 28, 2026 · 20:43

Phil Hetzel of Braintrust argues that agent observability differs fundamentally from traditional observability, which only answers 'is the system up?' Agents are non-deterministic, with individual traces exceeding a gigabyte and spans reaching 20 megabytes, packed with unstructured text that traditional tools like Datadog or Grafana cannot handle. Braintrust built a custom database from scratch—featuring a write-ahead log for instant visibility, analytical indexes for filtering, and a forked Rust-based Tantivy index for full-text search—to ingest and query this data in real time. Unlike traditional observability, agent observability involves non-technical experts (e.g., clinicians, lawyers) who grade traces and write justifications that become training signals for automated scoring functions. Braintrust also runs lightweight LLMs on traces to perform clustering and topic modeling, surfacing user intent, sentiment, and failure modes to accelerate the iteration loop between production issues and fixes. The episode also covers Braintrust's shift from ClickHouse to a custom database due to ClickHouse's limitations in text indexing.

Building durable Agents with Workflow DevKit & AI SDK - Peter Wielander, Vercel

Jan 6, 2026 · 1:09:49

Peter Wielander from Vercel introduces the Workflow DevKit, an open-source library that adds durability, observability, and resumability to AI agents by wrapping them in a workflow pattern. He demonstrates converting a coding agent into a workflow-supported agent, showing how steps like LLM calls and tool executions become isolated, retryable units. The toolkit enables long-running agents that can sleep for days, resume streams after disconnection, and integrate human-in-the-loop via webhooks. Deployable on Vercel or any cloud, it provides built-in observability through a local UI. The Workflow DevKit is currently in beta with general availability targeted for January.

Shipping AI That Works: An Evaluation Framework for PMs – Aman Khan, Arize

Dec 26, 2025 · 1:26:16

Aman Khan, AI PM at Arize, presents a framework for product managers to evaluate LLM-powered products beyond gut-feel 'vibe checks.' He demonstrates building an AI trip planner with multi-agent LangGraph, then using Arize's tracing and prompt playground to iterate on prompts. Khan shows how to create datasets from production traces, run A/B experiments on prompts, and use LLM-as-a-judge evals for friendliness and discount offers, comparing against human labels to refine evaluators. He argues evals are the new requirements docs, enabling PMs to own the product experience by writing acceptance criteria as eval datasets. The talk covers building eval teams, handling variance with temperature settings, and continuously improving golden datasets with hard examples, citing real-world analogies from self-driving cars at Cruise.

AI Copilots for Tech Architecture: The Highest-ROI Use Case You’re Not Building — Boris B., Catio

Nov 24, 2025 · 27:29

Boris Bogatin and Tofiq Boubaz, CEO and CTO of Catio, argue that AI architecture copilots represent the highest-ROI use case most organizations overlook, surpassing coding copilots in strategic impact. They identify three critical challenges—visibility across tech estates, ROI-backed prioritization, and autonomous developer guidance—and propose three pillars: a live digital twin for holistic system visibility, AI-driven multi-agent recommendations tied to business objectives, and a conversational agent embedding governance into developer workflows. The episode details a four-step approach: ingest messy system data, align recommendations with goals, generate compliant designs, and track outcomes. Concluding that companies adopting architecture copilots early will stay modern while laggards drown in technical debt, they invite listeners to catio.tech to pilot the approach.

2025 is the Year of Evals! Just like 2024, and 2023, and … — John Dickerson, CEO Mozilla AI

Aug 6, 2025 · 19:14

John Dickerson, CEO of Mozilla AI and former co-founder of Arthur AI, argues that 2025 is finally the year for AI evaluation (evals) due to three converging forces: ChatGPT making AI tangible to the C-suite, enterprise budget freezes that funnelled funding into GenAI pet projects, and the rise of agentic systems acting autonomously. He traces how ML monitoring existed pre-2022 but lacked C-suite attention, with Jamie Dimon’s JPMC spending only $100 million on AI from 2017 to 2021. The ChatGPT launch on November 30, 2022, unlocked CEO discretionary budgets for GenAI, leading to 2023 science projects, 2024 production deployments, and 2025 scaling. Now, as agents reason and act, connecting evals to downstream business KPIs—risk mitigation, revenue gains—is a first-class discussion for CEOs, CFOs, CISOs, and CTOs. Dickerson notes that evaluation companies have shifted to multi-agent system monitoring, and while LLM-as-judge is popular, biases require human validation, with companies like Mercor hiring experts at $50–200/hour to lockstep multi-agent outputs.

The Rise of Open Models in the Enterprise — Amir Haghighat, Baseten

Jul 24, 2025 · 16:50

Amir Haghighat, CTO of Baseten, argues that enterprises are increasingly moving from closed frontier models like OpenAI and Anthropic toward open source models, driven by four specific cracks in the assumption that closed models will work indefinitely: quality for specialized tasks (e.g., medical document extraction), latency requirements (especially for voice), unit economics ballooning from agentic use cases where a single user action triggers 50 inference calls, and the desire for competitive differentiation. Drawing on conversations with over 100 enterprises, he explains that while most started with dedicated deployments on Azure/AWS for toying around in 2023, by 2024 about 40-50 had production use cases, and in 2025 the shift accelerated. However, adopting open models forces enterprises to build inference infrastructure, facing challenges like speculative decoding, prefix caching, guaranteeing four-nines reliability with hardware failures and VLM crashes, and scaling replicas—with one Fortune 50 soft drink company reporting an eight-minute spin-up time. Haghighat concludes by contrasting the simple API-call world with the complexities of mission-critical inference, where…

The State of MCP observability: Observable.tools — Alex Volkov and Benjamin Eckel, W&B and Dylibso

Jun 20, 2025 · 16:56

Alex Volkov (Weights & Biases) and Benjamin Eckel (Dylibso) argue that MCP-based AI agents create observability blind spots, and that OpenTelemetry-based distributed tracing, combined with community initiatives like observable.tools, can provide end-to-end visibility. They show how Weave's MCP support and mcp.run's upcoming OTel export enable tracing across client and server, using context propagation via MCP's metadata to stitch traces together. Volkov shares a meta story where Claude Opus 4 used MCP to automatically fix its own observability code, discovering and querying a support bot without human intervention. The episode calls for tool builders to adopt OTel and join semantic conventions efforts for agent observability.

The Devops Engineer Who Never Sleeps — Diamond Bishop, Datadog

Apr 22, 2025 · 16:18

Diamond Bishop, Director of AI Engineering at Datadog, explains how his team builds AI agents—the On-Call Engineer and Software Engineer—that automate DevOps tasks like incident investigation, remediation, and postmortem writing. He details how the On-Call Engineer wakes up for alerts, reads runbooks, queries logs and metrics, and suggests fixes to let human engineers sleep. The Software Engineer proactively fixes errors by generating code diffs and pull requests. Bishop shares four key lessons: scope tasks and evaluate rigorously, assemble teams of optimistic generalists and UX experts, adapt UX for human-agent collaboration, and treat observability as critical for debugging multi-step agent workflows. He predicts that within five years, AI agents will surpass humans as primary users of SaaS platforms like Datadog, urging builders to design for agent consumers.

OpenLLMetry is all you need

Feb 22, 2025 · 9:12

Nir, CEO of Trace Loop, introduces OpenLLMetry, an open-source project extending OpenTelemetry for tracing and monitoring GenAI applications. OpenTelemetry, maintained by CNCF, standardizes logging, metrics, and traces across cloud environments, supported by platforms like Datadog, New Relic, and Grafana. OpenLLMetry provides over 40 automatic instrumentations for foundation models (OpenAI, Anthropic, Cohere), vector databases (Pinecone, Chroma), and frameworks (LangChain, LlamaIndex, CrewAI). These instrumentations emit logs, metrics, and traces in OpenTelemetry format, allowing users to send data to any supported observability backend with a configuration change, avoiding vendor lock-in.