The Startup's 30-Day DevOps Transformation Guide

Building production-ready infrastructure doesn’t have to take months. This guide gives you a realistic 30-day roadmap to go from “it works on my machine” to “we’re ready for scale.”

Each section includes what you need to accomplish, common pitfalls to avoid, and how Webera can accelerate the process if you need help.

Week 1: Foundation (Days 1-7)

The first week is about establishing the fundamentals that everything else builds on.

Days 1-2: Infrastructure as Code Setup

Goal: Stop clicking around in cloud consoles. Everything should be code.

What to do:

• Choose an IaC tool (we recommend Terraform for most teams)
• Set up remote state management (S3 + DynamoDB for AWS, or Terraform Cloud)
• Create base modules: VPC, networking, IAM foundations
• Establish naming conventions and tagging strategy

Common mistakes:

• Starting with local state (you’ll regret this when your laptop dies)
• Over-engineering modules before you need them
• Not enforcing tagging from day one

Webera angle: This is 2-3 points of work for us, delivered in 48 hours. We’ve done this setup dozens of times and know exactly which patterns work for startups.

Days 3-4: CI/CD Pipeline Foundation

Goal: Automated builds, tests, and deployments on every commit.

What to do:

• Set up GitHub Actions or GitLab CI
• Configure build, test, and lint automation
• Set up artifact storage (container registry, S3 for builds)
• Establish branch protection rules

Common mistakes:

• Skipping tests “because we’ll add them later”
• No caching strategy (slow builds kill productivity)
• Deploying from local machines “just this once”

Webera angle: Our Conductor agent monitors pipeline health 24/7, catching failures before they cascade.

Days 5-7: Environment Strategy

Goal: Separate dev, staging, and production with clear promotion paths.

What to do:

• Create environment separation (separate AWS accounts if possible)
• Establish environment parity principles
• Set up secrets management (AWS Secrets Manager, HashiCorp Vault)
• Document the promotion process

Common mistakes:

• Staging that doesn’t match production
• Hardcoded secrets (we’ve all done it, stop now)
• No rollback strategy

Webera angle: 3-point task that typically includes a runbook for your team.

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Week 2: Observability (Days 8-14)

You can’t fix what you can’t see. Week 2 is about knowing what’s happening in your systems.

Days 8-10: Monitoring Setup

Goal: Know when things are broken before your users tell you.

What to do:

• Deploy metrics collection (Prometheus, CloudWatch, or Datadog)
• Identify key metrics: latency, error rate, saturation (the RED method)
• Create dashboards for each service
• Set up baseline thresholds

Common mistakes:

• Monitoring everything (signal vs. noise problem)
• No baseline for normal behavior
• Dashboards nobody looks at

Webera angle: Our Sentinel agent watches your infrastructure while you sleep, establishing baselines and detecting anomalies.

Days 11-12: Logging Infrastructure

Goal: When something goes wrong, find out why in minutes, not hours.

What to do:

• Set up centralized logging (ELK, CloudWatch Logs, Datadog)
• Establish log retention policies
• Implement structured logging standards
• Create correlation IDs for request tracing

Common mistakes:

• Logging everything forever (costs add up fast)
• No structured format (good luck grepping that)
• Sensitive data in logs

Webera angle: Proper logging setup is 2 points and saves hours of debugging later.

Days 13-14: Alerting Strategy

Goal: Get notified about real problems, not noise.

What to do:

• Define alert thresholds and severity levels
• Set up escalation paths (PagerDuty, OpsGenie, or Slack)
• Create on-call rotation basics
• Document runbooks for common alerts

Common mistakes:

• Alerting on symptoms, not causes
• Alert fatigue from too many warnings
• No runbooks (alert fires, then what?)

Webera angle: Our Dispatcher agent routes alerts to the right person based on context and runbooks.

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Week 3: Security & Compliance (Days 15-21)

Security isn’t optional, and it’s easier to build in than bolt on later.

Days 15-17: Security Baseline

Goal: Lock down the basics before you become a target.

What to do:

• Implement network security (security groups, NACLs, private subnets)
• Apply IAM least privilege principles
• Enable secrets rotation
• Set up security scanning in CI/CD

Common mistakes:

• “We’ll secure it later” (you won’t)
• Overly permissive IAM roles
• No audit trail for access

Webera angle: Our Guardian agent continuously scans for vulnerabilities and misconfigurations.

Days 18-19: Compliance Foundations

Goal: Be ready when customers ask about SOC 2 or HIPAA.

What to do:

• Review SOC 2 readiness checklist
• Consider HIPAA requirements if applicable
• Enable audit logging across all services
• Document your security controls

Common mistakes:

• Thinking compliance doesn’t apply to you yet
• No evidence collection (auditors want proof)
• Mixing compliance requirements

Webera angle: Our Elite tier includes compliance concierge services.

Days 20-21: Incident Response Plan

Goal: Know what to do when (not if) something goes wrong.

What to do:

• Create runbook templates for common scenarios
• Establish communication protocols
• Define severity levels and response times
• Set up post-mortem process

Common mistakes:

• No plan means panic during incidents
• Skipping post-mortems (“it’s fixed, move on”)
• Blame culture that hides problems

Webera angle: We’ve handled 100+ incident responses. We know what works.

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Week 4: Optimization & Scale (Days 22-30)

The final week is about making sure your infrastructure can grow with your business.

Days 22-24: Cost Optimization

Goal: Stop paying for resources you don’t need.

What to do:

• Right-size your resources based on actual usage
• Evaluate reserved instances or savings plans
• Implement cost allocation tags
• Set up budget alerts

Common mistakes:

• Assuming bigger is always better
• Not tracking costs by service/team
• Ignoring data transfer costs

Webera angle: Our Optimizer agent finds savings you miss, typically 20-40% reduction.

Days 25-27: Scaling Strategy

Goal: Handle 10x traffic without 10x the stress.

What to do:

• Configure auto-scaling for compute resources
• Set up load balancing with health checks
• Plan database scaling patterns (read replicas, connection pooling)
• Load test your critical paths

Common mistakes:

• Scaling up instead of out
• No connection pooling (database connection exhaustion)
• Untested scaling policies

Webera angle: Architecture work like this is 5 points, with full documentation.

Days 28-30: Documentation & Handoff

Goal: Anyone on your team can understand and operate the infrastructure.

What to do:

• Create architecture decision records (ADRs)
• Write runbooks for common operations
• Document onboarding process for new engineers
• Create system diagrams

Common mistakes:

• “The code is the documentation”
• Tribal knowledge that walks out the door
• Outdated docs that mislead

Webera angle: Everything we build is documented. It’s yours, forever.

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Key Takeaways

Your 30-Day Checklist

By the end of 30 days, you should have:

• Infrastructure as Code with remote state
• Automated CI/CD pipelines
• Separate dev, staging, and production environments
• Centralized monitoring and logging
• Alerting with runbooks
• Security baseline and audit logging
• Incident response process
• Cost monitoring and optimization
• Auto-scaling configuration
• Complete documentation

Self-Assessment

If you completed all of this: Congratulations, you probably don’t need us (yet). But when you need to scale further or move faster, we’re here.

If you’re 3 months in and still on Day 5: That’s exactly why we exist. Let’s talk.

The Reality Check

Most startups don’t have time to do all of this themselves. You’re building a product, not an infrastructure company.

We only make money if we automate your problems away. Our AI agents and senior engineers can compress this 30-day journey into a matter of days, with the documentation and runbooks you need to maintain it.

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Next Steps

Ready to accelerate your infrastructure journey?

Option 1: Use this guide and do it yourself. We’ve given you everything you need.

Option 2: Book a discovery call and let us show you where you are in this journey and how we can help.

Either way, your infrastructure is about to get a lot better.