AWS Specialist · Senior / Staff
I build AWS infrastructure ahead of your scale and keep it boring.
I started on EC2 with Chef and Packer AMIs, and these days I ship CDK, EKS, and Control Tower landing zones. The tooling turned over completely and the job didn’t. Put everything in code, keep the accounts separated, and find problems before customers do.
A decade of production AWS
Scale, compliance, and platforms other teams build on.
At Protectwise, acquired by Verizon, I administered the AWS environment behind a petabyte-scale ingestion platform. Thousands of Cassandra nodes, petabytes in S3, and every piece of it managed as infrastructure as code.
HIPAA-compliant patient-care infrastructure at Inception Health, a PCI-compliant payments installation at Cardfree, and a multi-account model at Cloaked that met SOC 2, ISO 27001, and ISO 27701 requirements. Auditors have signed off on my architecture in three different industries.
At Inception Health I designed the CDK patterns that application teams consumed to ship HIPAA-compliant microservices themselves, collaborated directly with AWS partner teams, and trained the product and mobile teams until they ran their own deploys.
At Cloaked I led the move from a legacy PaaS onto AWS EKS. The new platform was cheaper, more scalable, and paired with a GitOps pipeline that accelerated deployments 30x in my first 6 months.
For the keyword scanners: CDK, Terraform, Chef, EKS, S3, Cassandra, Kafka, Control Tower, multi-account AWS, GitHub Actions, Tailscale, Cloudflare. Every one of them attached to a company above or on the resume.
The day-2 receipts
Cut Cloaked’s AWS bill while raising its headroom, cheaper and more scalable in the same quarter, by migrating from a legacy PaaS onto EKS with cost weighed at build time rather than after the invoice.
Gave Cardfree’s PCI incidents a playbook the engineers actually followed, structured enough for the auditors and light enough that nobody drowned in paperwork, by replacing ad-hoc Slack firefighting with a written incident-response program.
Passed HIPAA, PCI, SOC 2, and ISO audits year after year, each one evidence collection rather than a fire drill, by building account boundaries and controls into the platform instead of bolting them on for the auditor.
“Jake and I ran the AWS behind a petabyte-scale security platform. Thousands of Cassandra nodes, Kafka pipelines, a $10M-a-year bill, all of it managed with Chef and deliberately boring tech. I’d sign up to do it with him again tomorrow.”
Alex Artigues, DevOps Engineer, Protectwise
“Jake is a force for good unlike any other. He migrated our infra to a cheaper and more scalable system, crafted a CI pipeline that accelerated deploys by 30x, and taught the whole company how to make data-driven decisions by building an entire product analytics stack. And that was just his first 6 months.”
Aaron Biller, Director of Platform Engineering, Cloaked
Sound like the role you’re hiring for?
Email me and let’s find out. My resume digs into the details if you need more convincing.
Or browse my projects & ventures. Screening with an AI assistant? Point it at ai.jakegaylor.com.