Making Infrastructure Changes Safer, Faster, and More Human with AI: A Conversation with Brit Myers

Host Damien Filiatrault welcomes Brit Myers, VP of Engineering at System Initiative, to unpack a new model for infrastructure automation built for the realities Terraform and traditional GitOps often struggle with: drift, legacy systems, manual console “stop the bleed” fixes, and the rising need to collaborate safely with AI. Brit explains why System Initiative is betting on a “digital twin” of your infrastructure—a one-to-one model that holds intent, current reality, and the transitions between them—so teams get faster feedback, tighter control over change, and a lot less “merge and pray.”

What you’ll learn

What System Initiative is building: an AI-native infrastructure automation platform that can handle the same categories of work as Terraform and GitOps pipelines, but with different core assumptions.

The first assumption they challenge: infrastructure automation doesn’t have to be only static, declarative files that get versioned and processed later.

The second assumption: state and reconciliation shouldn’t live as a separate, fragile artifact (like a state file) that engineers sometimes have to manually repair.

Why “all changes must go through Terraform” breaks down in the real world—especially during incidents, cost overruns, or when someone has to make an emergency console change without creating future landmines.

Where the pain is worst: organizations with long-lived, legacy, or stateful systems (common in insurance and financial services) that can’t cleanly modernize everything at once.

How System Initiative uses programmable TypeScript functions to define behavior: propagation of shared values (like regions), organizational policy checks, compliance guardrails, and security logic.

How “change sets” work: safe simulations of proposed infrastructure updates that show not just what you want to change, but how it would ripple through the system and what actions (create/update/delete) would be required in reality.

Why this is especially useful with AI agents: you can bring an external agent (Claude, etc.) to propose changes through an API, iterate inside a change set, and only apply when a human—or your checks—approves.

A concrete AI workflow: using an architecture diagram as input, an agent can iteratively build a high-fidelity model and propose infrastructure in minutes while you watch changes happen live in the collaborative UI.

What’s live today: a multi-tenant SaaS at Systeminit.com with AWS coverage now, and plans to expand to GCP, Azure, DigitalOcean, and more—plus the ability for users to author and extend schemas/functions inside the product.

Chapters
0:00 Intro + Brit Myers joins (VP Engineering, System Initiative)
1:22 Brit’s background: software engineering → DevOps (why it’s compelling)
2:06 What System Initiative is + why it exists (Adam Jacob/Chef context)
4:34 What’s broken in IaC today (assumptions: declarative-only, state, reconciliation, out-of-band changes)
7:30 Digital twin in practice: legacy/stateful systems, modernization, who needs this
11:17 Programmable functions + security via simulations (TypeScript, policy, “more than plan”)
16:19 Change sets + AI agents (safe collaboration, examples, discovery, API/MCP interaction)
26:23 Launch, pricing, and roadmap (providers like GCP/Azure/Hetzner; usage-based pricing)
33:12 Wrap-up + how to connect (Discord/LinkedIn)

Memorable sound bites

“We want a little less ‘merge and pray’ and a little more ‘yeah, I got this.’”

“Terraform assumes all changes are made through Terraform—and that’s not how the world works.”

“You should be able to stop the bleed in the console without creating baggage later.”

“Everything is a function—behavior, policy, even what an asset is—and it’s all TypeScript.”

“Change sets let you collaborate with AI in safety, before anything touches production.”

“We haven’t found an AI use case that flops yet—bring us the one you think will.”

Tune in for a practical look at infrastructure automation after drift: digital twins, simulation-first changes, and how to let AI help with ops work without handing it the keys to production.

System Initiative Discord:   / discord  

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