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Why AI Can Write Code But Can’t Keep It Running (Yet)

AI can write production code in minutes. But can it debug and operate that code when something goes wrong? Grepr CEO Jad Naous argues that running real-world systems is a fundamentally harder challenge, with unpredictable workloads, failures, and countless possible states. Jad joins a16z General Partner Martin Casado to discuss how coding agents have transformed engineering inside his 10-person team, including projects that once took six months and now take roughly 10 days. They also explore whether AI can troubleshoot production systems by detecting changes, forming hypotheses, and running experiments, and why the best engineers may be gaining the most leverage from AI. Timestamps: 00:00 Intro 00:54 From Stanford to founding Grepr 07:23 Why observability got so expensive 10:15 How AI is changing engineering 18:25 Jad's AI stack and workflow 22:55 A six-month project in ten days 24:55 Can AI reason about operations? 30:10 How Grepr catches incidents early 42:16 Why security is the harder problem 53:33 What comes after code Resources: Follow Jad Naous on X: https://x.com/jadtnaous Follow Martin Casado on X: https://x.com/martin_casado Learn more about Grepr: https://www.grepr.ai/ Stay Updated: If you enjoyed this episode, be sure to like, subscribe, and share with your friends! Find a16z on X: https://twitter.com/a16z Find a16z on LinkedIn: https://www.linkedin.com/company/a16z Listen to the a16z Show on Spotify: https://open.spotify.com/show/5bC65RDvs3oxnLyqqvkUYX Listen to the a16z Show on Apple Podcasts: https://podcasts.apple.com/us/podcast/a16z-podcast/id842818711 Follow our host: https://x.com/eriktorenberg Please note that the content here is for informational purposes only; should NOT be taken as legal, business, tax, or investment advice or be used to evaluate any investment or security; and is not directed at any investors or potential investors in any a16z fund. a16z and its affiliates may maintain investments in the companies discussed. For more details please see http://a16z.com/disclosures.

Martin CasadohostJad Naousguest
Oct 16, 202658mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

AI writes code fast, but ops needs change-detection workflows

  1. Jad Naous traces Grepr’s founding to a widespread push to cut infrastructure spend, where engineering leaders repeatedly singled out observability costs as the most painful line item.
  2. He argues observability spend ballooned as microservice architectures increased telemetry volume, while reliability improvements per additional observability dollar plateaued.
  3. Naous describes how AI has moved from autocomplete to a structured, multi-agent development workflow that can produce production-grade infrastructure features dramatically faster—especially for engineers who can precisely specify constraints and validate results.
  4. On operations, he contends AI struggles to “predict” runtime behavior directly but can succeed when paired with deterministic change detection, then guided through human-like debugging workflows and experiments.
  5. He contrasts operations with security, arguing security is harder because an adversary intentionally searches for rare states, making purely data-driven coverage more fragile.

IDEAS WORTH REMEMBERING

5 ideas

AI’s big gap is moving from writing code to managing running systems.

Naous argues that code generation is easier because the “syntax manifold” is well-covered by training data, while operations requires reasoning over runtime behavior, changing workloads, hidden human context, and heavy-tailed failure modes.

Observability became expensive because telemetry exploded and marginal reliability returns collapsed.

Grepr’s origin story is cost-driven: microservices massively increased telemetry volume, making observability spend rise faster than delivered functionality, while reliability gains per extra dollar flattened.

AI amplifies engineer skill gradients rather than equalizing them.

Naous reports that strong engineers get disproportionately stronger with AI because they can decompose problems, specify constraints, and validate outcomes; AI doesn’t remove the need for systems-level understanding.

High-leverage AI coding is a managed, multi-agent pipeline—PRD first, code second.

He describes a workflow using Claude Code (Opus 5.5) with multiple persistent command-line “sub-agents,” starting with a PRD/design doc, then parallel implementation, followed by human re-integration and review.

For well-specified infrastructure work, AI can compress months of effort into days.

A concrete example: implementing “auto-promotion/shredding” in a data lake (schema evolution, metadata commits, writer coordination) took ~10 days solo, which he estimates would have taken ~6 months previously.

WORDS WORTH SAVING

5 quotes

The dirty secret for the longest time of running, like, a distributed cluster was just human beings managing it.

— Martin Casado

There, there, there's, the last PR that I worked on, or, like, the last set of PRs, was what we call auto, auto promotion in a data lake... that took maybe about 10 days. In previous days, that would've taken maybe about six months... for a single person.

— Jad Naous

The goal isn't to like have the model just be like, "This is what happened." It's, "Hey, run through this workflow to determine what happened."

— Jad Naous

The world that the AI lives in is all digital, and there's the actual world. And, like, those things are not necessarily the same.

— Martin Casado

Self-driving cars is around the corner... And it took 20 years and $170 billion of investment to get to worse unit economics than Uber, right?

— Martin Casado

Grepr founding journey and backgroundObservability cost inflation in microservicesReliability vs. telemetry spend trade-offsAI coding productivity and skill amplificationClaude Code/Opus multi-agent workflowBenchmarks, experiments, and groundingOps troubleshooting via change detection and log novelty clustering/triage

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