Professional Portfolio

Linkedin: http://linkedin.com/in/donaldcoles
Project Case Studies: @Portfolio
Github: /pythaeon

Start With Why

I believe clarity is the most powerful force in a technical organization.

Most delivery problems aren’t caused by a lack of talent. They’re caused by misaligned systems – unclear ownership, fragile processes, invisible risk, or architecture that wasn’t designed to scale.

I build systems that remove that friction.

Whether I’m stabilizing a failing program, launching a new operating model, or designing a self-hosted AI platform from scratch, my goal is the same: align people, process, and technology into something coherent, durable, and trustworthy.

I don’t chase tools. I design foundations.
I don’t optimize for short-term velocity at the expense of long-term resilience.
I treat platforms as products and infrastructure as a strategic asset.

Because when systems are intentional, teams move faster.
When ownership is clear, risk drops.
And when the foundation is strong, innovation stops feeling fragile.

That’s why I build.

Who I Am (Professional Summary)

I’m a systems-oriented program and product leader who thrives in high-ambiguity environments. I align people, process, and technology to stabilize delivery, strengthen execution discipline, and establish repeatable systems that support predictable outcomes and cross-functional trust.

In parallel, I built and operate a self-hosted AI and services platform spanning virtualization, secure access, automated backups, and AI workloads. I apply enterprise architecture principles at an appropriate scale, deepening hands-on fluency with modern tooling while maintaining a reliable and scalable platform.

My approach is consistent across contexts: treat systems as products, prioritize usability and trust alongside technical soundness, and iteratively build stable foundations before scaling capabilities.

How I Work (Core Competencies)

Approaches & Methods:
Agile, DevOps, Scrum, Kanban, Hybrid Delivery, SDLC, Continuous Improvement, Roadmapping, Delivery Strategy, Platform Thinking, Systems Design, Change Enablement, Risk & Stakeholder Management

Tools of the Trade:
Jira, Confluence, Smartsheet, Microsoft Project, Visio, Teams, Notion, Excel, Obsidian, Joplin, Vikunja, Airtable, Trello

Technical Fluency:
Virtualized Infrastructure, Self-Hosted Platforms, AI Tooling & AI Platforms, Ollama, Azure, Microsoft 365, Exchange, SharePoint, Linux, Docker, Kubernetes, Proxmox, Git, Python, SQL, JavaScript, XML, HTML/CSS

Quality Focus:
Process design, Release readiness, Metrics-driven visibility, Cross-team validation, and iterative improvement grounded in QA and delivery best practices

What I’ve Done (Experience)

Sonic Automotive – Stabilizing a Failing National Refresh

Context:
A multi-site IT refresh spanning 100+ dealerships was losing clarity, trust, and delivery momentum.

What I Did:
I rebuilt the delivery engine. Instituted weekly Agile sprint cycles across distributed technician teams, rewrote operational documentation to eliminate ambiguity, and implemented structured validation checkpoints to restore confidence.

I also designed an SMS-first support workflow for frontline technicians operating without standard enterprise tooling.

Impact:
Escalations dropped by 50%+. Stakeholder trust was restored. The program regained forward momentum and completed with renewed executive confidence.

United Airlines – Structuring Complex Infrastructure Initiatives

Context:
Infrastructure and facilities modernization efforts lacked cohesive program structure across operational and executive stakeholders.

What I Did:
Led early discovery and planning for a 500,000 sq. ft. aircraft parts distribution hub. Stabilized a major hangar retrofit at PDX by aligning vendors, airport authorities, and engineering teams. Built custom PMO tooling in Teams and Microsoft Project to create visibility where none existed.

Impact:
Transformed loosely defined initiatives into structured, trackable programs with executive-level clarity.

Sysco – Designing the Launch Framework for a New Regional OpCo

Context:
Sysco was launching its first new regional operating company in over a decade. Cross-functional alignment and execution structure were critical.

What I Did:
Co-authored the cross-functional roadmap aligning operations, finance, sales, HR, and engineering. Facilitated discovery workshops to surface dependencies and sequence milestones. Built Smartsheet-driven visibility systems to connect regional leadership with corporate governance.

Impact:
Created a repeatable execution framework designed to support future expansion initiatives.

CVS – Delivering Infrastructure at Enterprise Scale

Context:
A nationwide modernization initiative required upgrading 18,000+ endpoint devices across three business units.

What I Did:
Synchronized delivery across Retail, Aetna, and PBM organizations. Balanced Agile sprint prioritization with Waterfall-aligned executive reporting. Built SharePoint dashboards and Teams communication frameworks for cross-unit visibility.

Impact:
Delivered 100% of migrations ahead of schedule and under budget.

BP – Leading Digital Transformation and Divestiture Readiness

Context:
Simultaneously supported global digital transformation and high-stakes infrastructure divestiture programs.

What I Did:
Directed global Office 365 rollout for 60,000+ users, increasing Teams adoption from 30% to 66% in six months. Designed and scaled a Champions Network to drive sustained behavior change. Transitioned into infrastructure readiness and data remediation leadership for major M&A divestitures.

Impact:
Drove measurable adoption gains and ensured technical continuity during multi-billion-dollar asset transitions.

Interdyn BMI – Preventing Operational Collapse During Transition

Context:
The Managed Services practice lost its leader mid-flight, threatening delivery continuity across dozens of active client engagements.

What I Did:
Stepped into operational leadership. Managed 30–40 concurrent infrastructure projects, instituted daily standups and documentation standards, and delivered 60+ Azure-based deployments within nine months.

Impact:
Stabilized the practice, preserved client trust, and prevented service degradation during leadership transition.

Education & Certification

University of Houston-Downtown — Bachelor of Science in Interdisciplinary Studies (2013)
Project Management Professional (PMP) — PMI (2016-current)