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About

Matt Woolly

I'm a platform and infrastructure engineer in Castle Rock, Colorado. For fourteen years I've built and run cloud platforms: ecommerce agencies first, then healthcare at Aetna and MyRounding, defense at Raytheon, video at GoPro, and SMS marketing at Postscript, where I'm a Senior Staff engineer today.

The through-line is ownership. I take platforms from design to production and then stay on the pager. That end of the job, the scaling work, the upgrades, the cost reviews, the 3am incident, is where most of what I know comes from.

Lately a lot of my work involves agentic AI. I use Claude Code daily to orchestrate infrastructure work across 50+ microservices, and I built the guardrails that make that safe: an adversarial production-safety review and a create-only gate that runs before any terraform apply. In my experience that's where AI adoption succeeds or fails, and it's an infrastructure problem, which suits me.

I take contract and consulting engagements alongside full-time work. If you want the details of what that looks like, see services, or just get in touch.

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Skills

Cloud & infrastructure
AWS (EKS, ECS, RDS Aurora, MSK, VPC, S3, Lambda, IAM, KMS, SNS), Terraform, Terraform Cloud, CloudFormation, multi-region IaC
Kubernetes & GitOps
EKS, ArgoCD, Helm, Karpenter, KEDA, Bottlerocket OS, GitOps workflows
AI-augmented engineering
Claude Code, parallel sub-agent orchestration, AI safety guardrails, human-in-the-loop review
CI/CD & automation
GitHub Actions, Jenkins, CodeDeploy, Chef, Jira
Observability & operations
Datadog, CloudWatch, cost optimization, 24/7 on-call and SRE, incident response
Databases & languages
PostgreSQL / RDS Aurora, Python, Bash, Ruby, PowerShell, SQL

Experience

  1. 2023 – present

    Senior Staff DevOps Engineer · Postscript

    High-scale SMS marketing platform · Remote

    • Hybrid tech lead, people manager, and senior IC across platform engineering, reporting to the Senior Director of Platform Engineering and the VP of Engineering.
    • Operate infrastructure serving tens of millions of requests a day, with peaks above 200M. On call 24/7.
    • Re-architected the full AWS environment across VPC, ECS, EKS, MSK, Lambda, Elasticache, and RDS Aurora, on multi-region Terraform with Terraform Cloud.
    • Hold ~$4M/yr of cloud spend flat year over year while traffic grows; negotiated and implemented the company’s Datadog stack.
    • Built a safe, repeatable agentic-AI workflow (Claude Code): parallel sub-agents inventory 50+ microservices across Terraform, ArgoCD, and AWS, behind an adversarial production-safety review and a create-only gate enforced before any terraform apply.

  2. 2021 – 2023

    Staff DevOps Engineer · GoPro

    Cloud Infrastructure / Operations · Remote

    • Moved large video-transcode clusters to AWS Spot Instances, saving $350K+ a year, and migrated transcode from CPU to GPU.
    • Deployed S3 lifecycle policies across petabytes of stored video, worth hundreds of thousands of dollars annually.
    • Ran EKS via ArgoCD and Helm; rolled out Bottlerocket OS across ECS and EKS.

  3. 2018 – 2021

    Lead Cloud Infrastructure Engineer · Aetna Digital / CVS Digital

    AWS tech lead for a 5-engineer team · Denver, CO

    • Led a migration from CloudFormation to Terraform across hundreds of cloud resources.
    • Drove the move of business-critical microservices from ECS to EKS.
    • Led a cross-account cost-optimization effort; built Terraform patterns for IAM, Lambda, S3, KMS, and SNS.

  4. 2018

    Senior Automation Engineer (contract) · Raytheon IIS / GPS OCX

    Build & deploy automation · Aurora, CO

    • Automated AWS deployments with Chef, Ruby, and PowerShell inside large Jenkins pipelines, with Test Kitchen and InSpec suites.

  5. 2016 – 2018

    Senior DevOps Engineer · MyRounding Solutions / Huron

    Healthcare rounding platform · Chicago, IL

    • Designed the next-generation AWS environment (CloudFormation, EC2 Auto Scaling, ALBs, RDS) with automated disaster recovery.
    • Cut AWS cost from ~$500K to ~$200K a year while raising uptime from ~95% to over 99.9%. Owned 24/7 SRE duties.

  6. 2011 – 2016

    Director of DevOps → Lead Developer · Indaba Group

    Ecommerce agency · Denver, CO

    • Led development on the agency’s largest ecommerce accounts, then ran all technical production as Director of DevOps.