Professional Portfolio

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

Start With Why

I build software that matters — by aligning people, systems, and purpose.

My background spans enterprise IT, cloud transformation, and infrastructure, but at the core, I’ve always been a builder. Over time, I moved beyond execution into product strategy — rediscovering how much I care about why we build, who we’re building for, and how the systems we create shape human outcomes.

Today, I bring a product mindset grounded in systems thinking, delivery experience, and a relentless drive for clarity. I work best at the intersection of business, engineering, and user needs — where ambiguity is high, and alignment is make-or-break.

I thrive where strategy meets delivery, where culture is as vital as code, and where better questions lead to better outcomes — for the work and the people doing it.

Who I Am

I’m a product-driven problem solver with deep roots in systems thinking. My path has taken me through infrastructure, cloud, and software — but what’s defined my career isn’t the tech stack. It’s the ability to see the whole system, connect the dots, and move the work that matters.

Whether I’m aligning stakeholders around a product vision, building delivery engines that scale, or turning user insight into roadmap clarity — I bring calm to chaos, structure to ambiguity, and energy to execution.

How I Work

Approaches & Methods:
Agile, Scrum, SAFe, Kanban, Waterfall, Hybrid, DevOps, Roadmapping, Delivery Strategy, Change Enablement, Team Formation, Risk & Stakeholder Management

Tools of the Trade:
Jira, Notion, Smartsheet, Microsoft Project, Confluence, Teams, Excel

Technical Fluency:
Microsoft 365, Exchange, Azure, AWS, SharePoint, Git, Python, SQL, HTML/CSS

I’m not a hands-on engineer, but I speak the language—and I make sure the people who are building always have what they need to succeed.

What I’ve Done

Sr. Project Manager — Sonic Automotive

Remote | July 2024 – Nov 2024

Jumped into a failing enterprise refresh mid-flight and rebuilt it from the inside out — not just delivering the work, but redesigning the systems and workflows that made success repeatable. Led rollout across 100+ dealership sites with a focus on clarity, trust, and user-centered execution.

• Rebuilt delivery process into fast, weekly Agile sprints across time zones
• Rewrote technician docs to eliminate ambiguity and cut escalations by 50%+
• Designed SMS-first workflows to support frontline techs with limited tools
• Rebuilt trust across 50+ techs and 6 regional leads by aligning expectations

This wasn’t just a project rescue — it was systems thinking under pressure, with users, logistics, and outcomes all in the loop.

Sr. Project Manager — United Airlines

Houston/Remote | July 2023 – Nov 2023

Brought on to support a broad portfolio of infrastructure and facilities upgrades — and quickly became the connective tissue across stakeholders, strategy, and execution. Thrived in undefined systems, helping turn vague initiatives into actionable plans with long-term impact.

• Led discovery and early planning for a proposed 500k sq ft distribution hub centralizing aircraft parts across U.S. operations
• Took over delivery of a complex hangar retrofit at PDX — aligning vendors, airport authorities, and internal teams
• Supported analytics improvements for TSA reporting at Newark Airport
• Operated without a formal toolset — built custom systems in Teams and MS Project to create visibility where none existed

I didn’t just move work forward — I gave it shape, structure, and strategic clarity.

Sr. Project Manager — Sysco

Houston/Remote | Sept 2022 – Apr 2023

Initially brought in for a customer realignment initiative, I quickly shifted into a strategic planning role for launching a new regional operating company — Sysco’s first in over a decade. While not the official lead, I served as a systems thinker and force multiplier, helping teams see the whole map and move faster together.

• Co-developed a comprehensive, scalable execution roadmap for the launch of a new regional business unit
• Facilitated stakeholder discovery across Ops, Finance, HR, Sales, and Engineering — surfacing blockers and sequencing needs
• Turned ambiguous inputs into structured workflows using Smartsheet and SharePoint
• Accelerated trust-building and alignment by turning workshops into actionable clarity

We didn’t just build a plan — we built the system to make future launches faster, smarter, and better.

Technical Program Manager — CVS

Remote | Feb 2022 – Aug 2022

Led one of the largest infrastructure refreshes of my career — coordinating 18,000+ device upgrades across three business units and six concurrent tracks. I focused on more than execution: I built the systems, communication flows, and tracking models that enabled teams to deliver early and with confidence.

• Delivered 95% of device migrations within five months — ahead of schedule, under budget
• Managed coordination across CVS Retail, Aetna, and PBM units — aligning scope, schedules, and dependencies
• Created scalable tracking and communication systems using SharePoint and Teams
• Balanced Agile sprints for prioritization with a Waterfall-aligned program closure cadence

This was product thinking at infrastructure scale — designing for clarity, velocity, and trust across an enterprise landscape.

Organizational Change Manager & Sr. Project Manager — BP

Houston | Aug 2018 – Mar 2020

Wore two hats across two missions — first as a digital transformation leader, then as an infrastructure strategist for divestiture. In both, I applied systems thinking to human and technical complexity, building clarity and momentum in high-stakes environments.

• Led a global Office 365 rollout for 60,000+ users — driving Teams adoption from 30% to 66% in under 6 months
• Created and scaled the “Champions Network” — an internal advocacy engine that drove behavior change from the inside out
• Designed training, communication, and rollout strategies for tools across the M365 suite (Yammer, Planner, Stream, SharePoint)
• Shifted into BPX’s M&A division to co-lead infrastructure and data readiness for major asset divestitures in Colorado and Wyoming
• Delivered full discovery, remediation, and transition plans including runbooks, continuity docs, and post-sale support

One project lit my soul on fire. The other taught me how to build handoffs that actually hold.

Project Manager & Practice Manager — Interdyn BMI

Houston | Feb 2017 – Dec 2017

Hired to bring structure to chaos — and stayed to prevent collapse. When the head of the Managed Services group was abruptly let go, I stepped in to keep the lights on, lead the team, and stabilize delivery across dozens of projects and clients.

• Oversaw 30–40 simultaneous infrastructure and cloud projects across Houston-area SMBs
• Took over team leadership, billing, and operational management with no transition plan
• Balanced engineering workloads, ran daily standups, and maintained client momentum under severe resource strain
• Documented tribal knowledge and streamlined internal systems to preserve continuity
• Acted as vCIO for managed clients — guiding long-term IT strategy across industries

I wasn’t just keeping things running — I was making the system hold, one decision at a time.

Education & Certification

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