Career Roadmap: Cloud Engineering Excellence

Executive Summary

This roadmap outlines a strategic path from ministry leader to cloud engineering executive, with a hybrid strategy focusing on general cloud engineering skills initially, then specializing in cost optimization and security.

Master Strategy

Execute a 90-day sprint (August 5 - November 4, 2025) to land a $110-130K remote cloud engineering role with AWS SAA certification and a focused project portfolio. Position as a “Cloud Engineer Who Can Actually Code” leveraging MSP founder + programming + leadership combination.

Success Formula

MSP Founder Experience + Programming Skills + Cloud Expertise + Cost/Security Focus = Premium Cloud Engineer

Current Position & Target

What You Are

  • Strong programmer with rigorous backend training (9 courses: Ruby, Python, SQL, databases, OOP)
  • Proven leader with 20 years driving transformation
  • Quick learner who masters new technologies rapidly
  • Builder who can create tools and automate solutions
  • Remote-ready with proven self-management skills

Target Position (Phase 1)

“Cloud Engineer Who Can Actually Code”

  • Cloud engineering role ($110-130K)
  • 100% remote (non-negotiable)
  • Strong automation and IaC capabilities
  • Business acumen as key differentiator

Evolution Position (Phase 2)

“Cloud Cost & Security Specialist”

  • Senior cloud engineer with specialization ($180-220K)
  • Cost optimization and security focus
  • Consulting opportunities ($300-500/hour)
  • Thought leadership in FinOps/Security

90-Day Sprint Strategy

Timeline: August 5 - November 4, 2025

Phase 1: Foundation (August 5 - September 3)

  • Weeks 1-2: AWS Fundamentals + Environment Setup
  • Weeks 3-4: AWS Advanced + Exam Prep
  • Complete 40% of Adrian Cantrill course
  • Begin portfolio projects

Phase 2: Build & Brand (September 4 - October 3)

  • Week 5: Pass AWS SAA certification
  • Weeks 6-8: Complete portfolio projects
  • Build GitHub presence
  • Publish technical content

Phase 3: Land the Role (October 4 - November 4)

  • Weeks 9-10: Strategic application blitz (5+ daily)
  • Weeks 11-12: Interview preparation and negotiation
  • Target December 2025 start date

Daily Schedule During Sprint (45 hours/week)

6:00 AM - 9:00 AM: Deep learning (AWS course)
9:00 AM - 9:30 AM: Break
9:30 AM - 12:30 PM: Hands-on labs
12:30 PM - 1:30 PM: Lunch
1:30 PM - 3:30 PM: Project development
3:30 PM - 4:00 PM: Break
4:00 PM - 5:00 PM: Networking/applications
5:00 PM+: Family time (protected)

Weekend: 4 hours Saturday only

Career Progression Path

Years 1-2: Foundation + Specialization Prep

  • Role: Cloud Engineer → Cloud Engineer (Cost/Security Focus)
  • Salary: $110-130K → $140-160K
  • Focus: Master AWS, add Security+, begin specialization

Years 3-4: Specialized Senior Engineering

  • Role: Senior Cloud Engineer (Cost & Security)
  • Salary: $160-200K base + $50K consulting
  • Focus: Lead optimization initiatives, launch consulting

Years 5-6: Architecture & Consulting Growth

  • Role: Principal Cloud Architect / Consultant
  • Salary: $220-250K base + $100-150K consulting
  • Focus: Enterprise strategies, scale practice

Years 7-8: Senior Leadership

  • Role: Director of Cloud Operations / FinOps
  • Salary: $280-350K base + $200K consulting
  • Focus: Lead cloud cost centers, advisory positions

Years 9-10: Executive & Empire

  • Role: VP Cloud Strategy / Consulting Firm Owner
  • Salary: $400K+ base + $400K+ consulting
  • Focus: C-suite advisor, firm with 10+ employees

Certification Roadmap

Sprint Phase (August-November 2025)

  • CompTIA Security+ (August 3)
  • AWS Solutions Architect Associate (September 5-7)

Year 1 (Post-Employment)

  1. AWS Developer Associate (Q3 2026)
  2. AWS Security Specialty (Q4 2026)
  3. FinOps Certified Practitioner (Q4 2026)
  4. Cloud Security Alliance CCSK

Year 2+

  • AWS Cost Optimization Specialty (when available)
  • PCI Professional (PCIP)
  • Kubernetes CKS
  • AWS Solutions Architect Professional

Portfolio Projects

Project 1: Multi-Cloud Cost Dashboard

  • Real-time cost tracking across AWS/Azure/GCP
  • Automated anomaly detection and alerts
  • Savings recommendations engine
  • Tech: Python, Boto3, Terraform, React

Project 2: Security Automation Platform

  • Automated compliance checking
  • Auto-remediation for misconfigurations
  • Integration with Security Hub/GuardDuty
  • Tech: Lambda, EventBridge, Python

Project 3: Serverless CI/CD Pipeline

  • Complete GitOps implementation
  • Multi-environment deployments
  • Automated testing and rollback
  • Tech: GitHub Actions, CodePipeline, Docker

Project 4: Infrastructure Monitoring Solution

  • Custom CloudWatch dashboards
  • Predictive scaling algorithms
  • Cost optimization recommendations
  • Tech: Python, Terraform, Grafana

Target Companies

Tier 1: Remote-First Tech Leaders

  • GitLab, HashiCorp, Datadog, MongoDB
  • Elastic, Confluent, Cloudflare

Tier 2: Cloud Consultancies

  • 2nd Watch, CloudReach, Slalom
  • Onica/Rackspace, DoiT International

Tier 3: High-Growth SaaS

  • Stripe, Twilio, Okta, Snowflake
  • Databricks, Grafana Labs

Interview Positioning

Phase 1 Core Pitch

“I bring a unique combination: I founded and scaled an MSP to $250K revenue, giving me deep understanding of infrastructure at scale and business impact. Combined with strong programming fundamentals from 9 backend courses (Ruby, Python, SQL, databases, OOP) and AWS expertise, I can build automation solutions, not just configure services.”

Key Differentiators

  • Business Acumen: Understand ROI, not just technology
  • Leadership Experience: Can communicate up and down
  • Real Builder: Create production systems, not tutorials
  • Mature Perspective: Bring wisdom to technical decisions
  • Self-Directed: Proven ability to manage yourself

Success Metrics

Sprint Phase (90 Days)

  • AWS SAA certification passed
  • 4 portfolio projects deployed
  • 100+ cloud engineering connections
  • 50+ applications submitted
  • Multiple offers in negotiation

Year 1

  • Employed as cloud engineer ($130K+)
  • 3-4 additional certifications
  • Known for specific expertise
  • First consulting clients
  • $180K+ total compensation

Year 5

  • Senior/Principal level role
  • Consulting practice established
  • Thought leadership position
  • $400K+ combined income

Year 10

  • Executive or firm owner
  • Multiple revenue streams
  • Financial independence
  • $1M+ annual income

Family-First Principles

Non-Negotiables

  1. 100% Remote Work - No compromise
  2. Maximum 25% Travel - Family presence priority
  3. Protected Family Time - 5-7 PM daily
  4. Sabbath Observance - Friday evening to Saturday evening
  5. Arkansas Base - Community and cost advantages

Next Actions

This Week

  • Complete AWS environment setup
  • Begin Adrian Cantrill AWS SAA course
  • Start first portfolio project
  • Update LinkedIn profile
  • Connect with 10 cloud professionals

Sprint Week 1

  • Complete AWS fundamentals modules
  • Deploy first project iteration
  • Publish first technical blog post
  • Apply to 5 cloud positions

Remember: You’re building a unique position as “The Cloud Engineer Who Saves Companies Millions While Keeping Them Secure.” Your path is clear. Your timeline is set. Your success is inevitable.

Sprint starts Monday, August 4. Execute with confidence!