Jonathan – Kubernetes, AWS, CI/CD

A unified education technology platform created through the merger of multiple software companies. The ecosystem consisted of four independent products running on four different technology platforms across four separate data centers, supporting educational institutions with a broad range of academic and administrative services.

• Initiated Infrastructure as Code (IaC) using Terraform and GitHub Actions;
• Built an Azure Kubernetes Service (AKS) cluster on Microsoft Azure;
• Built a RabbitMQ cluster on top of AKS;
• Built a Redis cluster on top of AKS;
• Fully automated SQL Server migration from on-premises environments to Azure, including removal of all PII;
• Migrated numerous technologies from on-premises solutions to Azure;
• Implemented Aikido across 25 GitHub repositories spanning four GitHub organizations, blocking all critical security findings with GitHub Actions;
• Performed Azure, AWS, and on-premises system administration, as well as network administration.

A SaaS platform hosted on Microsoft Azure, featuring both web and mobile applications backed by a PostgreSQL database cluster. The infrastructure was managed with Pulumi (TypeScript) as Infrastructure as Code (IaC), while the platform transitioned from virtual machine-based web frontends to Azure Kubernetes Service (AKS) containerized frontends running on a Python runtime. The environment was also optimized by consolidating the PostgreSQL cluster from more than 12 instances to 9, improving operational efficiency.

• Mentored a small Site Reliability Engineering (SRE) team to improve operational processes and address technical gaps;
• Led SOC 2 audit readiness and compliance efforts, including implementation and management of Vanta controls;
• Managed Infrastructure as Code (IaC) using Pulumi;
• Optimized GitHub Actions workflows to reduce build times and minimize container image sizes;
• Facilitated the migration of web applications from virtual machines to container-based infrastructure;
• Coordinated incident response efforts and led post-incident reviews (postmortems).

A cloud-native SaaS platform for the digital forensics industry, designed to deliver scalable and secure forensic capabilities to customers worldwide. Initially developed as a proof of concept, the platform evolved into a production-ready SaaS offering deployed across AWS regions in North America, Europe, and Asia-Pacific. The infrastructure was defined with Terraform as Infrastructure as Code (IaC), while fully automated CI/CD pipelines replaced manual build and deployment processes, improving delivery speed, consistency, and reliability.

• Built reusable Infrastructure as Code (IaC) modules using Terraform to provision and manage a wide range of AWS services across three regions (US East, EU Central, and Asia Pacific);
• Built the complete CI/CD infrastructure using an ephemeral Jenkins architecture;
• Migrated software delivery from manual build and deployment processes to fully automated CI/CD pipelines;
• Transformed a proof-of-concept (PoC) solution into a production-ready SaaS product.

A cloud consulting engagement focused on helping organizations define and execute their AWS cloud migration strategies. The engagement provided ongoing technical guidance through recurring advisory sessions, enabling development teams to adopt AWS best practices and accelerate their cloud migration efforts.

• Consulted on customers' development and adoption of public and private cloud environments;
• Acted as a technical liaison to resolve customer challenges and remove implementation obstacles;
• Focused primarily on AWS architecture and CI/CD pipeline design and implementation;
• Designed and planned AWS Virtual Private Cloud (VPC) architectures.

A large fintech organization with hundreds of products supporting a diverse portfolio of financial services. The engagement focused on partnering with multiple product teams to improve CI/CD maturity, eliminate operational toil, and enhance the developer experience while ensuring compliance with regulatory and security requirements.

• Supported automation pipelines across numerous products as part of an 11-member DevOps team;
• Managed the entire CI/CD platform, including infrastructure and build systems, using Terraform and Ansible;
• Maintained libraries and patches, resolved issues, and continuously monitored platform health;
• Bridged technical concepts and processes for non-technical stakeholders;
• Led AWS adoption, including migration, greenfield, and brownfield Infrastructure as Code (IaC) deployments across multiple AWS regions and Availability Zones;
• Built and maintained automated CI/CD pipelines;
• Resolved audit and process bottlenecks that impacted software delivery;
• Addressed technology roadblocks, staffing constraints, timeline challenges, and evolving requirements;
• Improved planning processes and team readiness to meet delivery priorities and timelines;
• Collaborated with cross-functional teams, including Security, to align technical solutions with business needs;
• Protected sensitive data by implementing data scrubbing processes and defining appropriate data-sharing practices;
• Mentored team members and monitored performance;
• Fostered cross-functional knowledge sharing through rotating service ownership;
• Developed, deployed, and maintained Terraform code for products transitioning to Kubernetes;
• Maintained configuration management platforms using Ansible and Chef, providing 24×7 operational support;
• Provided 24×7 support for Bitbucket and JFrog Artifactory serving external applications across multiple business verticals;
• Measured and improved CI/CD maturity across multiple products and business verticals;
• Compiled product maturity matrices and created heatmaps to track continuous improvement.

A large fintech organization focused on modernizing its API platform on AWS. The initiative centered on building a scalable, cloud-native architecture to support secure, high-performance services while meeting strict regulatory and compliance requirements.

• Maintained multiple AWS accounts across performance, staging, and production environments;
• Organized and migrated enterprise data to the cloud;
• Built Infrastructure as Code (IaC) using CloudFormation, Chef, Ansible, Test Kitchen, Vagrant, Packer, and Ruby/Bash AWS CLI scripts;
• Built and maintained continuous integration and deployment pipelines using Test Kitchen, Jenkins, and SparkleFormation;
• Wrote infrastructure tests before implementing infrastructure changes;
• Built a cloud-native product and supported on-premises deployments in collaboration with the Sales team;
• Improved deployment reliability using Test Kitchen;
• Monitored cloud infrastructure using AWS CloudWatch and PagerDuty;
• Collected operational metrics, monitored error rates and escalation thresholds, and distinguished actionable alerts from operational noise;
• Implemented ELK/EFK for centralized log aggregation and built load-balancing solutions across multiple systems;
• Implemented proof-of-concept monitoring solutions using Graphite, Grafana, and Prometheus for metrics and alert management;
• Managed and maintained a Hortonworks HDP cluster on Amazon EC2, including Kafka, Storm, ZooKeeper, Phoenix, and HBase.

A SaaS startup focused on cloud network observability, providing organizations with visibility into network performance, reliability, and operational health across cloud environments. The platform was built on AWS from the ground up, establishing a scalable cloud foundation to support product growth and future expansion.

• Maintained multiple AWS accounts and built Infrastructure as Code (IaC) using CloudFormation, Chef, Test Kitchen, Vagrant, Packer, and Ruby/Bash AWS CLI scripts;
• Built the initial cloud platform using multiple AWS services across front-end and back-end components;
• Developed a chatbot to automate code deployments and improve team autonomy;
• Built an automated end-user agent as a pre-packaged OVA for simplified deployment;
• Developed the onboarding installation process and a custom Linux-based system;
• Created an end-user agent installation script using Bash;
• Automated an Akka cluster with a single Auto Scaling Group supporting multiple roles, including seed, frontend, and backend nodes;
• Managed the software delivery pipeline from source code commit through production deployment;
• Built and maintained continuous integration and deployment pipelines using Bamboo, Jenkins, and Capistrano;
• Monitored cloud infrastructure using AWS CloudWatch and PagerDuty.

A Canadian-owned data center, colocation, and web hosting provider that evolved from a personal hobby project into a commercial business. The company operated infrastructure across multiple data centers, delivering reliable hosting, colocation, and managed infrastructure services to businesses with a focus on scalability and operational resilience.

• Built, scaled, and maintained multiple data centers and network infrastructures;
• Procured and deployed enterprise hardware, including Juniper routers, HP ProCurve switches, Cisco Catalyst switches, and Pillar SAN storage systems;
• Hosted and maintained government websites and management portals;
• Delivered professional services, technical consulting, and infrastructure modernization engagements;
• Successfully grew and sold the company in 2014.

A large-scale search platform processing more than 7 billion queries per month. The platform operated on approximately 1,000 physical servers hosted in a remote colocation facility, requiring highly available infrastructure to support large-scale search indexing and query processing.

• Migrated configuration management from CFEngine to Puppet;
• Fully automated the hardware burn-in and provisioning process;
• Managed thousands of physical servers across more than 40 infrastructure roles, supporting a platform processing over 7 billion queries per month;
• Built and maintained development environments using the Proxmox hypervisor;
• Initiated the migration of infrastructure from physical servers to AWS;
• Built, administered, and maintained a Cloudera Hadoop environment.

An enterprise technology organization supporting a diverse portfolio of companies across multiple industries. The role spanned approximately 10 business units and included responsibilities across IT operations, software development, product support, and mergers and acquisitions (M&A), with extensive travel to support teams and business initiatives across North America.

• Built an embedded Linux I/O device for deployment in restaurant refrigeration systems;
• Led the migration of infrastructure from Rackspace to an internal data center;
• Integrated with multiple point-of-sale (POS) systems to collect operational data for analytics;
• Automated business reporting using Crystal Reports.

A telematics platform that collected and streamed real-time automotive data over GSM networks to centralized data centers. The solution operated across multiple continents, enabling continuous vehicle monitoring, data collection, and analytics for fleet and automotive applications.

• Implemented bidirectional communication between in-vehicle telematics devices and centralized data centers;
• Built and commissioned an on-premises data center as part of a new office construction project;
• Performed system and network administration across the production environment;
• Traveled to the United Kingdom to support Vodafone integration activities;
• Planned and executed data center migrations.

A large-scale infrastructure platform supporting a high-density, 4 MW data center with more than 25,000 physical servers. The environment provided enterprise-grade hosting and computing services, requiring highly available infrastructure, efficient operations, and reliable capacity to support mission-critical workloads at scale.

• Physically racked, stacked, cabled, maintained, repaired, and operated an infrastructure of more than 25,000 physical servers;
• Reduced the percentage of failed or unavailable servers from approximately 7% to less than 1% through proactive maintenance and operational improvements.

A multilingual CRM platform designed to support global customer operations. The application provided real-time translation across 12 languages, enabling organizations to manage customer interactions and collaborate seamlessly across international teams.

• Relocated to Tokyo, Japan, for a nine-month assignment to support the company's headquarters and collaborate with local engineering and business teams.