CI/CD DevOps learning roadmap

Build. Ship. Observe. Repeat.

A focused roadmap to learn CI/CD and DevOps foundations with a clear flow and practical milestones. Use this as a learning plan or share it as a portfolio project on LinkedIn.

Linux GitHub Actions Jenkins Docker Kubernetes Terraform Datadog PostgreSQL AWS RDS
Weekly focus
  • Weeks 1-2: Linux + Git + Networking
  • Weeks 3-4: Docker + Images + Registry
  • Weeks 5-6: CI pipelines + Jenkins
  • Weeks 7-8: Kubernetes + Deployments
  • Weeks 9-10: Terraform + Cloud basics
  • Weeks 11-12: Datadog monitoring + Incident drills
  • Weeks 13-14: PostgreSQL + DB Migrations to AWS RDS
Goal: Ship a real project.

Roadmap stages

Follow the sequence. Every stage ends with a deliverable.

1. Linux foundations

Shell, processes, filesystems, SSH, permissions, and systemd basics.

Deliverable: run a web server on a VM.

2. Git + GitHub

Branching, PRs, reviews, tags, and release notes.

Deliverable: release a versioned repo.

3. Docker + containers

Dockerfiles, multi-stage builds, Compose, registries.

Deliverable: containerize a full stack app.

4. CI pipelines

Testing, linting, caching, build artifacts, secrets, and Jenkins jobs.

Deliverable: CI pipeline on push + PR with Jenkinsfile.

5. CD deployments

Automate deployments to dev, staging, prod with approvals and Jenkins CD.

Deliverable: gated production deploy from Jenkins.

6. Kubernetes

Deployments, services, probes, ingress, config, secrets.

Deliverable: app running in K8s.

7. Terraform

VPC, IAM, clusters, modules, remote state, environments.

Deliverable: infra in code.

8. Observability

Metrics, logs, traces, Datadog dashboards, alerting, SLOs, incident response.

Deliverable: Datadog dashboard + alert monitor.

9. PostgreSQL in DevOps

Schema versioning with Flyway/Liquibase, connection pooling (PgBouncer), backups, PITR, and CI-driven migration pipelines.

Deliverable: CI pipeline that validates and applies schema migrations before every deploy.

10. DB Migration to AWS RDS

Migrate large-scale on-prem PostgreSQL/MySQL to AWS RDS using AWS SCT, DMS continuous replication, cutover planning, and post-migration validation.

Deliverable: on-prem database live-replicated to RDS with a tested cutover runbook.

Hands-on tool path

Use Jenkins for continuous delivery and Datadog for production visibility.

Jenkins for CD

Start with a declarative Jenkinsfile that installs dependencies, runs tests, builds the site, and publishes static files after a manual approval step.

Deliverable: Jenkins pipeline that deploys to a target environment.

Datadog for monitoring

Track uptime, frontend errors, synthetic checks, and response times with a dashboard that tells you whether a release improved or degraded the site.

Deliverable: dashboard, synthetic test, and alert policy.

Suggested flow

Git push triggers Jenkins, Jenkins builds and deploys, Datadog validates health, and alerts route back to your incident or rollback process.

Deliverable: end-to-end CI/CD plus monitoring loop.

CI/CD flowchart

Conceptual pipeline for modern DevOps delivery.

Plan Code Build Test Release Deploy Observe Learn

Portfolio checklist

Use this to structure your LinkedIn post and repo README.

Repo with CI pipeline + badges
Jenkinsfile with build, approval, and deploy stages
Dockerized services with versioned images
Automated deployment to dev/staging
Terraform infra with environments
Datadog dashboard with alerts and uptime checks
Short demo video or screenshots
CI-integrated schema migration pipeline (Flyway or Liquibase)
AWS RDS instance provisioned via Terraform with parameter groups
DMS replication task with CDC and cutover runbook documented