Tyler Bailey

About

DevOps and CloudOps leader with 17 years of software development and DevOps experience, specializing in scalable infrastructure, CI/CD automation, and developer workflow optimization. Builds secure, reproducible cloud environments using infrastructure-as-code and leads cloud modernization efforts across AWS and GCP. Actively integrates AI copilots (Claude, ChatGPT, Microsoft Copilot) and LLMs into DevOps workflows for IaC generation, CI/CD review automation, log/alert summarization for faster incident response, and AI-driven security/compliance checks—freeing teams to focus on architecture, mentorship, and long-term strategy.

Experience

• Principal CloudOps Engineering Lead · Revvity05-01-2023

  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‑hands engineering with strategic leadership to ensure scalable, secure, and efficient cloud environments. Key Contributions & Achievements: Cloud Migrations: Led successful GCP to AWS infrastructure migrations, ensuring minimal downtime and improved scalability. Identity & Access Management: Migrated the organization to AWS SSO, simplifying user management and strengthening security posture. Security Enablement: Deployed CrowdStrike and Snyk across products, embedding security into the development lifecycle. AI & GPT Solutions: Designed and delivered AI‑driven product solutions, including GPT‑powered workflows that enhanced automation, knowledge management, and customer‑facing features. Developer Productivity: Integrated Claude, OpenAI/ChatGPT, and Microsoft Copilot into daily development workflows — accelerating code delivery, automating documentation, and improving decision‑making across projects. Technical Leadership: Provided guidance on CloudOps best practices, infrastructure as code, and CI/CD pipelines, while mentoring engineers on adopting AI‑augmented development responsibly.

• DevOps Engineer · Tyler Bailey DevOps Services03-01-2020

  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 real estate firms - GiftCash – gift card platforms - Educational platforms – e‑learning and content delivery - Pro Fitness Program – fitness and coaching platforms Key Contributions: - Designed and deployed cloud infrastructure with a focus on scalability and cost optimization. - Implemented infrastructure as code and CI/CD pipelines to streamline delivery. - Integrated security tooling and monitoring solutions across client environments. - Leveraged AI copilots daily for faster code generation, automated documentation, troubleshooting, and clear stakeholder reporting.

• DevOps Engineer · Toptal04-01-2020

  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 -FNBTech / Craftable – Hospitality technology -Random Games Company – Crypto / Gaming -Tzuchi – Non‑profit initiatives -Clear Law Institute – Legal compliance training -Traliant – Legal and workplace compliance - Wheelhouse DMG - Performance-driven digital marketing agency - Chloris Geospatial – Climate tech / Forest carbon monitoring Key Contributions: - Cross‑cloud strategy: Supported clients in adopting hybrid and multi‑cloud approaches, ensuring portability and resilience. - Performance optimization: Tuned infrastructure and pipelines to reduce latency and improve cost efficiency. - Compliance & governance: Helped organizations in regulated industries (law, defense, non‑profit) align infrastructure with compliance standards. - Developer enablement: Built self‑service tooling and documentation, often accelerated with AI copilots, to empower engineering teams. - AI‑driven support: Used Claude, ChatGPT, and Copilot to generate infrastructure templates, automate repetitive tasks, and provide rapid technical insights during client engagements.

• DevOps Engineer · Gun.io06-01-2022

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

• DevOps Engineer · Braintrust07-01-2021

  I am available as freelance DevOps Engineer via the Braintrust platform. https://app.usebraintrust.com/talent/6137/

• DevOps Engineer · 10x Management03-01-2022

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

• DevOps Engineer · Contra04-01-2024

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

• DevOps Engineer · A.Team04-01-2024

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

• Cloud Architect · PlayOn Media09-01-2013

  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

• Principal CloudOps Engineering Lead · PerkinElmer, Inc.08-01-2022 – 05-01-2023

  - 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.

• DevOps Manager · PerkinElmer, Inc.04-01-2021 – 10-01-2022

  - 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 management and external stakeholders or customers.

• Senior DevOps Engineer · PerkinElmer, Inc.05-01-2020 – 09-01-2021

  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 Cannabis & Hemp. Migrated and re-built the infrastructure from one cloud platform to another for the PKeye Mobile Operations Monitor which provides researchers with around the clock access to their automated liquid handling workstation through integration of on-deck cameras with the PKeye™ cloud based platform. A few things I've worked on: - Built out highly available ECS Fargate clusters for various microservices. - Provisioned Kubernetes clusters with Terraform, Rancher, and RKE in a cloud-native manner. - Created proof of concepts for AWS IoT for on-prem data collection. - Implement Datadog across our cloud infrastructure. - Worked with security teams to patch zero day vulnerabilities.

• DevOps Engineer · Parallel Digital Studio06-01-2019 – 05-01-2020

  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%. Infrastructure was created with a GitOps approach using Terraform and containers based applications being built, tested, and deployed through Gitlab CI/CD pipelines. Things I've specifically worked on: - Migrate existing and new infrastructure to Infrastructure as Code (IaC) through Terraform & AWS Cloudformation - Develop CI/CD (Continuous Integration / Continuous Delivery) pipelines with Gitlab CI & AWS Code Pipeline - Created custom Git hosted Terraform modules to encapsulate application-specific cloud resources to setup and tear down of various environments - Automated processes using scripting languages such as Python, PowerShell, and Bash - Stood up ELK (Elasticsearch, Kibana and Logstash) monitoring and log aggregation stacks - Created a plethora of dashboards within Grafana for monitoring - Built out serverless applications using AWS Lambda, Cloudfront, S3 - Performed failure testing to understand how components fail and monitor and alert accordingly - Instrumented load tests for apps, which helped to eliminate performance bottlenecks - Explore emerging technologies and evaluate the feasibility and benefits of implementing them

• Search Engine Optimization Specialist · Tyler Bailey SEO01-01-2014 – 04-01-2020

  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 - StormFree Cloud Corporation

• DevOps Engineer · StormFree Cloud Corporation03-01-2019 – 05-01-2019

  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

• Operations · Postmedia Network Inc.07-01-2014 – 03-01-2019

  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 with Ansible and deployed via Jenkins. Worked with multiple stake holders including developers, QA, product, and project managers. Things I've personally worked on: - Assisted in the building and testing of infrastructure of applications that power some of the largest media websites in Canada including nationalpost.com - Create internal and external tools to significantly reduce cost, save time and streamline processes - Monitor and diagnose server issues using products such as AppDynamics, Grafana, Nagios, Amazon CloudWatch, and New Relic - Managed Windows, CentOS, RHEL, and Ubuntu Linux systems in AWS - Contributed to internal applications, scripts, and utilities written in Python, JavaScript, and Bash - Create and maintain micro sites on WP Engine & Carbon60 - Implemented cluster-wide, application-agnostic monitoring - Automated MySQL upgrades, optimizations to server/database instances and scripted Windows/Linux server migrations - Multiple iterations of Site Speed projects to improve website performance focusing on ATF (Above The Fold). - Built a web crawler with Scrapy to collect SEO metrics on our websites to better inform the newsroom on how our content performs and how to improve on key metrics - Mine SEO data and provide big data solutions for the organization based on its current strategic directives

• Design Verification Engineer · Evertz03-01-2012 – 05-01-2012

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

• Network Analyst · Juch-Tech Inc Teleport05-01-2011 – 09-01-2011

  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

• Technical Support · Telecom Computer04-01-2011 – 05-01-2011

  Spring Co-op placement through Mohawk College. - Assist with computer hardware repair

• Application Technologist Assistant · City Of Hamilton08-01-2009 – 01-01-2010

  Summer Co-op placement through Mohawk College. - Assist with GIS placements of Public Works jobs

Education

• McMaster UniversityBachelor of Technology (B.Tech.), Computing & Information Technology
• Mohawk CollegeOntario College Advanced Diploma, Network Engineering & Security Analyst

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