Owolade is available for hire
Hire OwoladeOwolade Sobowale
Verified Expert in Engineering
DevOps Engineer and Developer
Washington, DC, United States
Toptal member since December 8, 2021
Bio
Lade is an enthusiast and advocate of everything DevOps, with over nine years of experience in the DevOps space. He's worked with startups and big corporations. As a subject matter expert in Terraform and AWS services, he holds all AWS associate certifications. Lade has a solid background in networking and automating everything.
Portfolio
JumpCloud
Amazon EKS, Amazon Elastic Container Registry (ECR), Kubernetes, SaltStack...
Nike
Google Cloud Platform (GCP), AWS IoT, IBM Cloud, Azure...
Notarize
CI/CD Pipelines, DevOps, Amazon Web Services (AWS), Docker, Jenkins, Containers...
Experience
- Networking - 10 years
- Linux - 9 years
- Bash - 9 years
- Amazon Web Services (AWS) - 7 years
- Jenkins - 7 years
- Ansible - 6 years
- Python - 5 years
- Terraform - 5 years
Work Experience
Senior Cloud Operations Engineer
2023 - 2026
JumpCloud
- Deployed multi-cloud infrastructure on AWS and GCP using Terraform and Spacelift, leveraging modular code, remote state backends, and cross-account role assumptions to provision secure, isolated environments with consistent IAM and network topology.
- Led the migration of 900+ Terraform Cloud workspaces to Spacelift, scaling to over 1,000 Git-integrated stacks and implementing policy-as-code (OPA), drift detection, automated plan enforcement, and integration with GitHub Actions pipelines.
- Enforced infrastructure governance by implementing Spacelift OPA policies to validate tagging standards, IAM least-privilege, encryption-at-rest, and VPC isolation across all environments.
- Engineered CI/CD pipelines with GitHub Actions, supporting matrix builds, environment-specific workflows, gated deployments, and Terraform integration for complete application and infrastructure lifecycle automation.
- Provisioned production-grade Amazon EKS clusters using GitOps workflows with ArgoCD, managing application and infrastructure deployments with Helm, Kustomize, and custom overlays and patches across dev, staging, and production environments.
- Configured and deployed Kubernetes add-ons, including VPC-CNI, Istio, cert-manager, CoreDNS, ExternalDNS, and metrics-server, enhancing traffic management, DNS automation, TLS certificate provisioning, and service-to-service encryption via mTLS.
- Integrated dynamic secrets management using HashiCorp Vault and Consul, with Kubernetes Service Account authentication and Vault Secrets Operator (VSO) to securely inject short-lived credentials into Kubernetes workloads.
- Developed container image pipelines using Docker, with CVE scanning, layer caching, and promotion to Amazon ECR; deployed applications to EKS using Helm and Kustomize for flexible release management.
- Built automated EC2 configuration using SaltStack, Jinja2, and Consul Template for dynamic runtime values and service discovery; validated Salt states with Test Kitchen and used Packer to build hardened AMIs preloaded with secure configurations.
- Built observability solutions using Datadog, developing SLO-based monitors, burn rate alerts, and performance dashboards. Integrated PagerDuty and Slack for incident response.
Technologies: Amazon EKS, Amazon Elastic Container Registry (ECR), Kubernetes, SaltStack, PagerDuty, Nomad, Terraform, Python, Bash, GitHub, Docker, Crossplane, CircleCI, Travis CI, AWS Lambda, Architecture, Snowflake, Serverless, Helm, Go, Virtualization, Google Cloud Platform (GCP), AWS DevOps, Cloud Architecture, Enterprise Architecture, Infrastructure, Large-scale Production Deployments, GitOps, Argo CD, Infrastructure Security, TypeScript, Claude Code
Senior DevOps Engineer
2022 - 2023
Nike
- Managed and optimized Azure infrastructure (VMs, AKS, storage, and load balancers) supporting Nike's global ERP systems, tuning for scalability, performance, and high availability under heavy global load.
- Led a zero-downtime migration from AWS to Azure using dependency mapping, staged cutovers, traffic shifting, and rollback validation, with no disruption to business-critical ERP operations.
- Refactored Terraform into reusable modules, cutting deployment times and keeping configuration consistent across five environments.
- Designed and maintained Jenkins CI/CD pipelines across all five environments, standardizing build, test, and deploy stages to speed up delivery.
- Built and deployed the AKS infrastructure behind Nike Forge, Nike's internal deployment tool, shortening release cycles and smoothing developer workflows.
- Automated Azure VM provisioning, configuration, and maintenance with SaltStack, replacing manual, error-prone setup.
- Set up monitoring and alerting integrated with PagerDuty and Slack to catch issues early and reduce disruption to dependent teams.
- Automated deployment workflows and environment setup with Python and Bash for repeatable provisioning across the fleet.
- Mentored new engineers and drove the adoption of engineering standards and better workflows across the team.
Technologies: Google Cloud Platform (GCP), AWS IoT, IBM Cloud, Azure, High-performance Computing (HPC), Terraform, Python, Bash, GitLab CI/CD, Linux, Bicep, Azure Kubernetes Service (AKS), GitOps, Infrastructure Security, TypeScript
Cloud Infrastructure Engineer
2022 - 2022
Notarize
- Architected and built a multi-environment AWS ECS cluster using Terraform.
- Migrated all microservice containers from Heroku to AWS ECS.
- Configured Telegraf to run inside containers in AWS ECS, collect application logs, and ship to AWS CloudWatch. Designed Datadog dashboards to inject the application logs from CloudWatch.
- Wrote bash scripts to enable SSM running on AWS ECS containers.
- Configured Sumo Logic to collect the AWS ECS container logs.
- Wrote Terraform configurations and modules to manage the organization's GitHub repositories. Imported all existing repositories into Terraform to be managed through Terraform.
Technologies: CI/CD Pipelines, DevOps, Amazon Web Services (AWS), Docker, Jenkins, Containers, Terraform, Amazon EKS, CircleCI, New Relic, Kubernetes, Azure, Heroku, Datadog, Redis, PostgreSQL, Elasticsearch, NoSQL, Sumo Logic, Telegraf, Amazon Elastic Container Service (ECS), Microservices, Infrastructure as Code (IaC), Serverless Architecture, Amazon CloudWatch, Resource Management, Cloud Services, Architecture, Snowflake, Serverless, Helm, Scalable Architecture, Virtualization, AWS DevOps, Cloud Architecture, Enterprise Architecture, Infrastructure, Large-scale Production Deployments, Cloud Migration, Infrastructure Security
Site Reliability Engineer
2017 - 2022
SparkPost
- Configured and managed a diverse suite of AWS services expertly, such as EC2, RDS, VPC, S3, CloudWatch, CloudFront, and Route 53, ensuring high availability and performance.
- Orchestrated continuous integration and continuous deployment (CI/CD) pipelines using Jenkins, CirceCI, Git, AWS ECS, EKS, and Docker, enabling rapid and reliable software delivery.
- Implemented robust automation strategies using Python and Bash scripting to orchestrate deployments, environment provisioning, and service configurations, enhancing operational efficiency.
- Applied site reliability engineering (SRE) principles to improve system reliability, scalability, and performance, including error budgeting, service level indicators (SLIs), and service level objectives (SLOs).
- Established a comprehensive monitoring and alerting ecosystem, integrating Datadog alongside PagerDuty, Opsgenie, and Slack to proactively identify and address operational issues, ensuring seamless service delivery while adhering to SLAs and SLOs.
- Managed incident response and resolution processes effectively through PagerDuty, coordinating cross-functional teams and escalating critical issues promptly to minimize downtime and mitigate risks.
- Conducted blameless post-incident reviews (PIRs) to identify root causes of outages and implemented preventive measures to enhance system resilience and stability.
- Developed internal tooling in Python and Go templating to enable developers to automate repetitive tasks and enhance development productivity.
- Collaborated closely with development teams to design and implement developer-friendly tooling, facilitating smooth software development lifecycle and deployment processes.
- Provided mentorship and guidance to junior team members, fostering their professional growth and development in site reliability engineering practices.
Technologies: Amazon Web Services (AWS), Python, Terraform, Jenkins, GitHub, Continuous Delivery (CD), Continuous Deployment, Amazon EKS, Nomad, CI/CD Pipelines, Bash, Kubernetes, Vault, Vagrant, Ansible, SaltStack, Datadog, PagerDuty, Amazon RDS, DevOps, Infrastructure as Code (IaC), REST APIs, Serverless Architecture, REST, Amazon CloudWatch, Linux Server Administration, Resource Management, Unix, Cloud Services, Site Reliability Engineering (SRE), Node.js, VPN, Proxies, Architecture, Serverless, Helm, Scalable Architecture, Virtualization, AWS DevOps, Cloud Architecture, Enterprise Architecture, Infrastructure
DevOps Engineer
2015 - 2017
Center for Advanced Transportation Technology (CATT Lab)
- Worked on infrastructure development on AWS using various services like EC2, S3, RDS, Route 53, CloudFormation, CloudWatch, IAM, and VPC.
- Utilized CloudWatch to monitor resources such as EC2, CPU memory, Amazon RDS DB Services, and EBS volumes.
- Configured Jenkins to automate the build deployments based on the changes captured in Version Control.
- Gained knowledge in Ansible playbook, YAML for maintaining roles, inventory files, and groups variables.
- Configured various performance metrics using AWS CloudWatch and CloudTrail.
- Used Git for branching, tagging, and maintenance of version control and source code management.
Technologies: Amazon Web Services (AWS), Jenkins, Ansible, Bash, Python, Continuous Delivery (CD), Continuous Deployment, DevOps, Infrastructure as Code (IaC), AWS CloudFormation, Amazon CloudWatch, Linux Server Administration, Resource Management, Unix, Cloud Services, VPN, Architecture, Serverless, Scalable Architecture, Virtualization, AWS DevOps, Cloud Architecture, Infrastructure
Solutions Architect
2011 - 2014
Intertel
- Automated and managed AWS infrastructure and deployment processes, including production, testing, and development environments.
- Worked on automation continuous integration and continuous delivery pipeline processes for multiple projects using GitHub, Jenkins, Maven, Artifactory, and Docker.
- Configured and managed Elastic Load Balancing (ELB) for fault tolerance and to avoid single point of failure of applications, providing high availability.
- Implemented identity and access management solutions for infrastructure and applications, to ensure that appropriate access controls are in place and applied effectively and continuously.
- Managed and automated all aspects of our AWS infrastructure, including compute, storage, network, permissions, and cost using shell scripts and configuration management tools like Ansible.
Technologies: Amazon Web Services (AWS), Jenkins, Bash, Ansible, Docker, Continuous Delivery (CD), Continuous Deployment, DevOps, Infrastructure as Code (IaC), AWS CloudFormation, Amazon CloudWatch, Linux Server Administration, Resource Management, Unix, Cloud Services, Cloud Architecture, Infrastructure
Project History
Terraform Architecture for Enterprise Client
The project involved the Terraform infrastructure for the core ERP systems across all business units worldwide. I took ownership and re-architected the Terraform infrastructure automation, which resulted in reducing the deployment of parallel systems from 2-3 days to less than an hour. This Terraform architecture deploys and manages thousands of virtual machines in AWS and Azure.
Container Migration from Heroku to AWS ECS
http://www.notarize.comI architected and built a multi-environment AWS ECS cluster using Terraform and migrated all microservice containers from Heroku to AWS ECS. Furthermore, I configured the application logging using Telegraf, AWS CloudWatch, and Datadog and the container logging in sumo logic.
Cloud Infrastructure and Pipeline for an Email Analytics Company
A web-based application for an email analytics company. I designed and built the cloud network infrastructure, the global database cluster, replication across multiple regions, and the CI/CD pipeline using GitHub Actions and ECS clusters.
Migration from Nomad to EKS
• Led the migration from HashiCorp Nomad to Amazon EKS, enabling a scalable and Kubernetes-native orchestration platform.
• Utilized Kustomize and Helm charts to manage Kubernetes manifests efficiently, ensuring modular, reusable, and environment-specific configurations.
• Implemented ArgoCD for GitOps-based continuous delivery and Argo Rollouts for progressive deployments such as canary and blue-green strategies.
• Automated infrastructure provisioning with Terraform, optimizing cluster setup and application deployments.
• Enhanced observability by integrating Datadog for monitoring, providing real-time insights into application performance and cluster health.
• Addressed networking and security challenges with AWS VPC CNI and IAM roles for service accounts, ensuring a secure and resilient migration.
The transition minimized downtime, improved DevOps efficiency, and modernized deployment workflows.
• Utilized Kustomize and Helm charts to manage Kubernetes manifests efficiently, ensuring modular, reusable, and environment-specific configurations.
• Implemented ArgoCD for GitOps-based continuous delivery and Argo Rollouts for progressive deployments such as canary and blue-green strategies.
• Automated infrastructure provisioning with Terraform, optimizing cluster setup and application deployments.
• Enhanced observability by integrating Datadog for monitoring, providing real-time insights into application performance and cluster health.
• Addressed networking and security challenges with AWS VPC CNI and IAM roles for service accounts, ensuring a secure and resilient migration.
The transition minimized downtime, improved DevOps efficiency, and modernized deployment workflows.
Education
2014 - 2016
Master's Degree in Telecommunications and Networking
Stratford University - Falls Church, VA, USA
2007 - 2011
Bachelor's Degree in Computer Engineering
Babcock University - Nigeria
Certifications
FEBRUARY 2023 - PRESENT
Certified Kubernetes Application Developer
Cloud Native Computing Foundation
MAY 2021 - PRESENT
Certified Jenkins Engineer
Jenkins Project
APRIL 2021 - APRIL 2023
HashiCorp Certified: Terraform Associate
Hashicorp
MARCH 2021 - MARCH 2024
AWS Certified SysOps Administrator
Amazon Web Services (AWS)
JANUARY 2021 - JANUARY 2024
AWS Certified Developer
Amazon Web Services (AWS)
JUNE 2020 - JUNE 2023
AWS Certified Solutions Architect - Associate
Amazon Web Services (AWS)
NOVEMBER 2015 - MAY 2022
Cisco Certified Network Associate (Security)
Cisco
DECEMBER 2012 - MAY 2022
Cisco Certified Network Associate
Cisco
Skills
Libraries/APIs
Node.js, REST APIs
Tools
Git, Terraform, GitHub, Amazon EKS, CircleCI, Amazon CloudWatch, VPN, Helm, Claude Code, Ansible, Jenkins, Amazon Elastic Container Service (ECS), Azure Kubernetes Service (AKS), Sumo Logic, Telegraf, Puppet, Vault, Vagrant, SaltStack, AWS CloudFormation, Travis CI, AWS IAM, Amazon Elastic Container Registry (ECR), GitLab CI/CD, Kustomize
Frameworks
Crossplane
Paradigms
Continuous Delivery (CD), Continuous Deployment, DevOps, Serverless Architecture, Microservices, REST, High-performance Computing (HPC)
Platforms
Amazon Web Services (AWS), Docker, Kubernetes, Azure, Google Cloud Platform (GCP), AWS Lambda, Linux, Unix, New Relic, Heroku, PagerDuty, AWS IoT
Languages
A+, HTML, Snowflake, TypeScript, Python, Bash, Java, Go, Bicep
Storage
Datadog, Redis, PostgreSQL, Elasticsearch, NoSQL, Amazon Aurora
Other
Networking, Cloud, CI/CD Pipelines, Nomad, Infrastructure as Code (IaC), Resource Management, Cloud Services, Architecture, Serverless, Scalable Architecture, Virtualization, AWS DevOps, Cloud Architecture, Enterprise Architecture, Infrastructure, Large-scale Production Deployments, Cloud Migration, GitOps, Argo CD, Infrastructure Security, Network Security, Cisco, Linux Server Administration, Site Reliability Engineering (SRE), Proxies, Containers, Amazon RDS, IBM Cloud, GitHub Actions, Consul
Collaboration That Works
How to Work with Toptal
Toptal matches you directly with global industry experts from our network in hours—not weeks or months.
1
Share your needs
Discuss your requirements and refine your scope in a call with a Toptal domain expert.
2
Choose your talent
Get a short list of expertly matched talent within 24 hours to review, interview, and choose from.
3
Start your risk-free talent trial
Work with your chosen talent on a trial basis for up to two weeks. Pay only if you decide to hire them.
Top talent is in high demand.
Start hiring