The AI Native Dev - from Copilot today to AI Native Software Development tomorrow

Datadog's Language Foundations team deleted an entire folder of AI context files that had been carefully written and maintained for over a year, expecting a performance hit. Instead, their evals got better. Simon Boudrias, who runs Language Foundations at Datadog, walks Guy through what that taught his team about context rot, and the full journey of scaling AI coding agents to 4,000 engineers.

What we cover:
– How Datadog scaled Cursor and Claude Code to 4,000 engineers in under a year
– Why Datadog deleted all of its AI context files, and what happened to eval scores
– Building an eval-driven code review system that replays old PRs to catch real incidents
– Where open-weight models like GLM 5.2 stand against the frontier
– Rethinking hiring and career ladders now that AI can run a real codebase interview

Chapters:
00:00:00 - Introduction
00:03:19 - Simon's role and Datadog's 4,000-engineer org
00:04:31 - The Cursor rollout that took off overnight
00:07:53 - How Claude Code entered the picture
00:10:51 - Building dedicated Signals and Flows teams
00:11:58 - Why Datadog bet early on evals
00:33:44 - Deleting all their AI context and getting better evals
00:47:51 - Where open-weight models stand today
00:51:45 - Rethinking hiring and career ladders for AI
00:59:24 - The real prize: better decisions, not just productivity

🌐 Tessl: https://tessl.io
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What's the oldest file in your AGENTS.md or CLAUDE.md that you're afraid to delete? Tell us in the comments.

At Tessl, 95% of the code shipped by their internal "Dark Factory" has never been looked at by a human, and the team still ships hundreds of pull requests a week, including through entire weekends. Rob Willoughby, who leads AI engineering at Tessl, joins Simon to open up the hood on how it actually works: the orchestrator, the verification layers, and the failures that forced the team to rebuild trust from scratch.

What we cover:
– How Tessl routes 65-70% of its own pull requests through an autonomous "Dark Factory"
– Why context in the repo matters more to output quality than which model you use
– How natural language "verifiers" turn code review taste into fast, cheap checks agents can pass or fail
– The queue bug that took dozens of pull requests to fix, and the from-scratch Elixir rewrite that stress-tested the whole system
– How to start building your own software factory, one verification layer at a time

Chapters:
00:00:00 - Introduction
00:01:44 - Rob Willoughby joins: Tessl's PR numbers
00:04:01 - Live demo: kicking off two pull requests
00:14:03 - Building the Dark Factory: orchestrator vs. context
00:19:01 - Code review layers: Code Rabbit, Tessl Change Verify, and verifiers
00:29:58 - Earning trust: accountability in an autonomous system
00:33:20 - What broke: the queue bug and the Elixir rewrite experiment
00:39:56 - Onboarding new engineers into the factory
00:42:58 - Advice for teams starting their own software factory
00:52:03 - Back to the demo, and the road to 100% adoption

🌐 Tessl: https://tessl.io
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What would your own verification layer catch, and where would it break? Let us know in the comments.

One Snyk developer's AI skill quietly handed their coding agent production credentials, and the security team found out the hard way. Krzysztof Huszcza, who leads AI security incubation at Snyk, joins this special Tessl and Snyk live stream to unpack the ToxicSkills research that uncovered 76 malicious agent skills in the wild, and what it actually takes to run coding agents safely at scale.

What we cover:
– How Snyk's security team found 76 malicious skills hiding inside a popular open agent skill repository
– Why skills have become the go-to way developers hand context to their coding agents
– The internal incident at Snyk where a developer's skill exposed production credentials to an agent
– How the Tessl and Snyk integration scans every skill and MCP server for risk before you install it
– What's coming next with Snyk's new Evo product for governing coding agents at scale

Chapters:
00:00:00 - Introduction
00:01:33 - Chris's role: AI security incubation at Snyk
00:02:16 - Snyk's roots as a developer-first security company
00:03:58 - New security challenges from AI coding agents
00:06:26 - Skills: the new way to give agents context
00:07:35 - Inside Snyk's ToxicSkills research: malware and prompt injection
00:11:35 - How developers can vet skills before installing them
00:14:38 - A real incident: exposed production credentials at Snyk
00:17:45 - Building a secure-by-default agent stack
00:23:35 - What's next: Snyk's new coding agent security product

🌐 Tessl: https://tessl.io
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What's the riskiest skill you've installed without checking it first? Let us know in the comments.

An engineer builds an AI agent to manage his own life, decides an unrestricted "does everything" agent is too dangerous to trust, and ends up creating the internal agent platform that now runs 30 agents across his entire company. 

Ori Shoshan, tech lead at Cyera, walks through the guardrails, citation system, and knowledge graph that turned "let the agent do anything" into "let the agent do exactly what it's supposed to, and nothing else."

What we cover:
– Why one engineer built his own AI agent in his living room, and how it grew into Cyera's internal agent platform
– Whitelisting tools instead of blacklisting them, plus the "escape hatch" that keeps agents honest
– Backing every claim with a citation and using a second model to catch hallucinations before they reach a human
– Trading RAG for a knowledge graph the agent can walk like a wiki
– Turning "use this platform" into "build your own agent" to drive adoption across an entire engineering org
– Running agents on confidential data that can investigate everything but can only ever say what's been cleared

Chapters:
00:00:00 - Introduction
00:02:04 - Meet Ori Shoshan and what Cyera does
00:06:50 - The living-room spark: why Ori built his own agent
00:11:09 - Whitelisting tools instead of blacklisting them
00:12:55 - Why every claim needs a citation
00:15:35 - Reducing hallucinations with clean-context verification
00:21:04 - Taking Borg to Slack: the first agents at work
00:25:33 - Why naming your agent drives adoption
00:39:53 - Knowledge graphs over RAG
00:52:00 - The AI Captains: scaling adoption with carrots, not sticks

🌐 Tessl: https://tessl.io
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Have you built guardrails like this into your own agents? Let us know what's worked (or blown up) for you in the comments.

After DevOps, Patrick Debois has a new map. The godfather of DevOps returns to walk through his AI patterns research: how he tracks where AI-native development is heading by mining social signals instead of surveys, why the stack is settling into patterns worth learning, and why your AI budget problem is really an optimization problem.

What we cover:
– Inside the AI patterns site at Tessl.io/patterns and how it's auto-generated
– The four layers of AI enablement: agent, team, platform, and organization
– Solo, shared, and multiplayer modes: the compounding effect of shared context
– Managing agent costs: budgets as a forcing function for optimization
– Scaling adoption: find the success story, don't fight the skeptics
– Hiring system thinkers instead of elegant coders

Chapters:
00:00:00 - Introduction
00:02:28 - Why AI grips Patrick Debois
00:04:33 - Agent, team, platform and org enablement
00:06:36 - Is AI-native development maturing?
00:11:19 - Inside the AI patterns site
00:18:14 - Quality, security and the IDE as review interface
00:22:45 - Changing roles and harness engineering
00:26:32 - Hiring in the AI era
00:30:31 - Scaling adoption across the org
00:42:03 - Cost management and ROI

🌐 Tessl: https://tessl.io
🔔 Subscribe for weekly episodes on AI-native development

Where is your organization on the maturity curve? Drop your take in the comments.