Tyler Bailey

I am available as freelance DevOps Engineer via the Contra platform.

I am available as freelance DevOps Engineer via the A.Team platform.

As Principal CloudOps Engineering Lead, I serve as the technical lead for CloudOps operations, driving infrastructure modernization, security, and developer productivity across the organization. My role combines hands‑on engineering with strategic leadership to ensure scalable, secure, and efficient cloud environments.

Key Contributions & Achievements:

Cloud Migrations: Led successful GCP to AWS

I am available as freelance DevOps Engineer via the Gun.io platform.

Clients I've worked with:
- Blue Ocean Gear (IoT & Satellites)
- Dark Web IQ (Cybersecurity)

I am available as freelance DevOps Engineer via the Braintrust platform.

https://app.usebraintrust.com/talent/6137/

Worked as DevOps Engineer at Pangea.

Worked as DevOps Engineer at Upwork.

Worked as DevOps Engineer at Arc.dev.

Worked as DevOps Engineer at Turing.

I deliver DevOps engineering solutions enhanced by AI workflows, combining 15 years of experience with tools like Claude, ChatGPT, and Microsoft Copilot to help clients modernize infrastructure, improve security, and accelerate delivery. I am available for freelance DevOps projects via my Toptal profile.

Clients include:
-Bazze – Defense / AI solutions
-Sumersports – Entertainment / AI platforms

I provide AI‑augmented DevOps engineering services, combining 15 years of experience with tools like Claude, ChatGPT, and Microsoft Copilot to deliver scalable, secure, and efficient solutions. In addition to my full‑time role, I am available for freelance DevOps projects through my website: tylerbailey.com.

Clients include:

- Shiptis – shipping logistics platforms
- Remax Escarpment – large rea

A small Hamilton based IT consultant company focusing on helping clients migrate to the cloud.

- Create and consult cloud architecture for clients
- Deployment of infrastructure through GitOps & Github Actions to all environments
- Infrastructure monitored through IaC (Infrastructure as Code)
- Migrate legacy applications and environments to the cloud

- Technical Lead for CloudOps operations

Things I've been working/worked on:
- Migrated organization over to AWS SSO for easier management of users.
- Setup Crowdstrike across products.
- Setup Snyk across products.

- Lead DevOps team across Software Platforms department.
- Empower DevOps team to increase velocity of deploying our releases, while decreasing technical debt and increasing the quality of our software.
- Hiring, coaching, mentoring, feedback and hands-on career development with the DevOps team.
- Set and manage expectations with other engineering and operational teams.
- Coordinate with managemen

Day to day activities include: Infrastructure as Code, Building and maintaining CI/CD pipelines, Proof of concepts, Security patching, monitoring.

Through a combination of Terraform, Cloudformation and Github Actions built the infrastructure for SimplicityLab420 which is a dedicated Cloud-based laboratory execution system and is apart of the larger workflow of Laboratory Automation Solutions in C

Building a technical stack including AWS, Cloudformation, Terraform, Docker, Gitlab CI, Python, ELK Stack.

My day to day activities include: Building CI/CD pipelines, Infrastructure as Code, designing and delivering new container based platforms, and troubleshooting production issues.

Migrated a NASDAQ/S&P 600 companies web infrastructure from Rackspace to AWS reducing their bill by over 75%. In

Toronto based SEO agency focusing on building platforms for small-to-medium sized businesses, specifically local search.

- Improve local client rankings thorugh both on-page and off-page methods.
- Consult and white-label for other digital agencies.
- Create lead generation funnels.

Clients I've worked with:
- Welcome PEI

Worked with a remote DevOps team to help build turnkey solutions on AWS using Kubernetes, Ansible, and Packer.

- Build and maintain high-performance, high-availability Kubernetes clusters
- Deploy micro services to Kubernetes through custom Helm charts
- Containers built with Docker and configured with Ansible
- Harden and secure base infrastructure docker containers
- Provisioning with Packer

Specialties: AWS, Ansible, Python, Jenkins

Daily activities include: Building AWS infrastructure through Ansible, automating developer code deployments through Jenkins, supporting & monitoring web resources using Grafana, ELK Stacks, Nagios & Icinga.

Helped migrate +100 small-medium sized community websites across Canada from on-prem to AWS in a month. Infrastructure was built out and configured

- System level testing and firmware/software validation for various product lines
- Collaborating with development teams to plan tests through product design cycle

Summer Co-op placement through Mohawk College.

- Monitor a 24-7 NOC at the Hamilton Teleport
- Setup & troubleshoot satellite broadcast systems
- Implement video compression over IP
- Maintain rack hardware

Jul 2020

Jun 2019 · Expired Jun 2022

Oct 2015 · Expired Oct 2016

Oct 2015

Oct 2015 · Expired Oct 2016

Oct 2015 · Expired Mar 2021

Oct 2015 · Expired Feb 2020

Oct 2015 · Expired Feb 2020

Oct 2015 · Expired Oct 2016