Hamilton, Ontario, Canada
With 17 years of experience in software development and DevOps, I specialize in building scalable, reliable systems and optimizing developer workflows. My expertise spans cloud providers, infrastructure as code, and CI/CD pipelines, with a strong focus on automation, security, and efficiency. I actively integrate AI copilots (Claude, ChatGPT, and Microsoft Copilot) into my daily work, and extend this further by applying large language models (LLMs) to DevOps workflows. This includes generating infrastructure‑as‑code templates, automating CI/CD pipeline reviews, summarizing logs and alerts for faster incident response, and embedding AI‑driven security and compliance checks. These practices accelerate delivery, reduce operational overhead, and give teams actionable insights in real time. By leveraging LLMs in DevOps, I free up time to focus on architecture, mentorship, and long‑term strategy while ensuring projects move faster without sacrificing quality. Key strengths include: • DevOps LLM Integration – applying large language models to automate IaC, CI/CD, observability, and security workflows • AI‑Augmented Development – embedding copilots into daily engineering for speed and quality • Cloud & Infrastructure as Code – designing scalable, reproducible systems • CI/CD Automation – secure, efficient pipelines for continuous delivery • Technical Leadership – guiding teams and designing fair, structured hiring processes I’m currently working full‑time, but I’m always open to remote DevOps contracts where I can apply my skills to help teams scale, modernize, and deliver with confidence.
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 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.
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.
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.
Clients I've worked with: - Blue Ocean Gear (IoT & Satellites) - Dark Web IQ (Cybersecurity)
I am available as freelance DevOps Engineer via the Gun.io platform.