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A Resume is Just a Data Problem

A reflection in building a better resume, and the frustrations of uncoupling data from presentation

Donald Coles

• 8 min read
A Resume is Just a Data Problem
But it doesn't have to be.

It all started from a simple premise:

A resume is just two things — data and formatting.

And in the tech world, it's a well-known sin to bind the two together. We separate data from presentation, because doing otherwise makes change brittle, slow, and expensive. That’s why we have HTML and CSS. JSON and React. Models and Views.

So like any responsible architect, I asked:

“Why don’t I store the resume data in one place… and render it however I want?”

What follows is a retrospective on that process — one part case study, one part therapy.

The Easy Part: Structure

Resume data is fairly predictable in its anatomy. Sure, there’s variation across roles and styles, but the bones are consistent:

  • A name and contact block
  • A summary or personal statement
  • A skills or tools section
  • Education
  • And of course, work experience

We call them different things — “Professional Overview,” “Core Competencies,” “The Journey So Far” — but the structure is universal. That means you can model it. You can build a schema.

So I did. I converted my resume into structured YAML. Every field. Every bullet point. Every punchy quote. It was clean, simple, and expressive.

Then I rendered it back out as Markdown — and it looked great.

Mission accomplished, right?

The Hard Part: Output

Then reality smacked me with a clipboard.

Try uploading a resume to any ATS, job board, or application portal. What do they accept?

  • PDF
  • DOCX
  • Maybe TXT
  • RTF, if you're cursed

Take a second and savor the absurdity:

I had to take my structured data, render it into an unstructured DOCX, so a recruiter or machine could parse it back into structured data.

That’s when it got messy.

Sure, Pandoc can generate DOCX. Python can build DOCX documents programmatically. But "can generate" ≠ "looks good." My first few outputs were technically correct and visually heinous. Page breaks landed mid-section. Bullets were misaligned. Paragraph spacing went rogue.

The machines could read it. But humans? Not so much.

Humans Are the Problem

Turns out, we don’t just want to be competent — we want to look good doing it.

Resumes aren’t purely utilitarian. They are presentation. Impression. Visual narrative. And that meant I was no longer just a builder — I was in layout design purgatory.

Each iteration solved one problem and revealed two more:

  • Fix a page break, ruin a margin.
  • Compress the bullets, bloat the spacing.
  • Adjust the font weight, break the alignment.

At this point, the phrase “resume tailoring” took on entirely new meaning.

Solving It Properly

Eventually, we landed on a clean architecture:

  • The resume lives as a modular YAML file. Structured. Immutable. Easy to swap, version, and diff.
  • Styling lives in a Word template with named styles like Role_Heading, Section_Body, Role_Bullets, and more.
  • A Python script acts as the renderer — reading the YAML, injecting content into the styled document, and producing a polished .docx ready for human and machine alike.

Want to change the order of sections? Update one line in the script.
Want to build a short-form version? Filter out the last two jobs.
Want to tailor for a PM vs TPM vs SWE role? Swap in a skills matrix block.

It’s modular, composable, repeatable.

What We Learned

This wasn’t a solo process. I collaborated with ChatGPT to build, test, and refine the system — and that collaboration was fluid. Not prompt/response. Not "generate 10 resume bullets." Real-time refactoring. Logic tweaks. Spacing debates. Style testing.

The system we built together:

  • Understands that resume structure is data, not decoration
  • Respects human-readable formatting while remaining machine-friendly
  • Treats design and layout as interchangeable components
  • Produces DOCX files that broadly mirror hand-crafted resumes

This wasn’t just about formatting a résumé.

This was about reclaiming control over a system that’s been treated as static for decades.

A Modest Proposal

We have the tools. We have the standards. There is no reason resumes should be manually rebuilt in Word for every application.

Imagine:

  • A resume.yaml as the single source of truth
  • A style system for rendering (Word, PDF, HTML, Markdown)
  • A universal spec for resume structure

If JPEGs and PDFs and MP3s can be standardized, why not resumes?

Standardize the data. Separate the presentation. Declare your truth once, and render it as needed.

We don't need another résumé template.

We need a résumé compiler.

If you want to see the Markdown version, open the toggle block. Some elements don't display correctly within a toggle (section breaks and headers), but you can get the gist of it.

Pseudo Markdown Version

Donald Coles, PMP

linkedin. http://linkedin.com/in/donaldcoles

blog. http://aeon.ghost.io


Start With Why

I believe clarity is the most powerful tool in a leader’s arsenal.

I’ve spent my career building systems that cut through noise—whether that means aligning teams, untangling legacy infrastructure, or designing processes that scale. I don’t just want to ship; I want to understand what we’re building, why it matters, and how to make it repeatable.

My north star? Better systems, better thinking, better outcomes—for teams and the people in them.


Who I Am

I’m a systems-first builder with a background that spans infrastructure, cloud, software, and strategy. For nearly two decades, I’ve worked across startups and Fortune 500s—leading programs that untangle legacy systems, introduce modern tools, and scale processes with intention.

I’m the person teams call when the mission is complex, the path is unclear, and the cost of getting it wrong is high. Whether I’m solving for architecture, operations, or human dynamics—I zoom out, ask better questions, and get the right work moving.


How I Work

I build systems that work—at scale, across teams, and under pressure. That means knowing the tools and the terrain.

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 | Jul 2024 – Nov 2024 (Contract)

Brought in mid-flight to rescue a failing PC refresh project spanning 3,500 machines across 100+ dealership sites. Rebuilt team trust, redesigned delivery workflows, and delivered the full program ahead of schedule after regaining executive confidence.

  • Reorganized project execution into fast, one-week Agile sprints with daily standups across multiple time zones and technician teams
  • Revamped all technician documentation for clarity and accuracy; eliminated process ambiguity and reduced escalations by >50%
  • Built direct communication lines using SMS and ad hoc email, overcoming lack of standard IT infrastructure for contract techs
  • Led coaching and coordination for 50+ technicians and 6 regional technology managers across 20+ geographic markets
  • Implemented structured decommissioning processes and solved logistical gaps in end-of-life device handling

“More than just a project rescue—it was a full system reboot. And I made sure it shipped with confidence.”

Sr. Project Manager -- United Airlines

Remote / Hybrid (Houston, TX) | Jul 2023 – Nov 2023 (Contract via Apex Resources)

Joined the Corporate Real Estate (CRE) group as a generalist IT project manager supporting a diverse portfolio of infrastructure and facilities upgrades. Tasked with bringing structure to loosely defined projects across multiple airport and warehouse sites.

  • Initiated early-stage project planning for a proposed 500,000 sq ft distribution warehouse in Houston—designed to centralize aircraft parts procurement and logistics across all U.S. hubs
  • Took over midstream delivery of a narrowbody hangar renovation at Portland International Airport (PDX), managing vendor coordination, equipment logistics, and implementation schedules
  • Led regular coordination calls with architects, builders, and airport authorities to ensure retrofit alignment and schedule adherence
  • Supported analytics improvement efforts for TSA foot traffic reporting systems at Newark Airport
  • Operated without a formal project toolset; built and maintained all plans using personal MS Project license and custom Teams sites to close operational gaps

“Not every role is a fit—but even in the wrong system, I still deliver.”


Sr. Project Manager -- Sysco

Houston, TX (Hybrid) | Sep 2022 – Apr 2023 (Contract via Emergent Professional Resources)

Initially hired to lead a regional customer realignment initiative, I pivoted into a collaborative planning role for the launch of a new regional operating company (OpCo) in Allentown, PA. While not the lead, I acted as a strategic partner—facilitating stakeholder discovery, surfacing hidden dependencies, and helping to craft one of the most comprehensive execution roadmaps I’ve ever contributed to.

  • Co-developed Sysco’s first OpCo “foldout” plan in a decade—a fully detailed, scalable playbook for launching future business units
  • Collaborated with 15+ cross-functional teams (Ops, Finance, HR, Engineering, Sales) to extract needs, define processes, and align sequencing across domains
  • Led working sessions, stakeholder discovery, and documentation curation efforts that dramatically accelerated trust-building and systems visibility
  • Translated iterative workshops into structured workflows using Smartsheet and SharePoint; plan was finalized at 98% readiness at contract end
  • Acted as a force multiplier to the Program Manager—enabling concurrent engagement with business units and reducing total discovery time by weeks

“There was no documentation. No map. We built the plan from scratch—and it was a good one.”


Technical Program Manager, CVS

Remote (Houston, TX) | Feb 2022 – Aug 2022 (Contract via Xsell Resources)

Hired to lead a nationwide enterprise PC refresh, I coordinated one of the largest infrastructure programs of my career—spanning three business units, six parallel tracks of work, and over 100 field technicians. Despite limited tooling and contractor constraints, we beat all initial targets months ahead of schedule, closing the program with stretch goals in reach and 18,000 devices deployed.

  • Oversaw planning and execution of a multi-division PC refresh for ~18,000 endpoints across CVS Retail, Aetna, and PBM business units
  • Delivered 95% of target migrations within 5 months—enabling early contract completion and organizational cost savings
  • Managed program-level tracking across six project streams; served as cost steward, logistics coordinator, and executive liaison for the PMO
  • Built scalable communication infrastructure using Teams + SharePoint to coordinate ~100 field technicians and multiple vendor teams
  • Operated within Agile sprints for prioritization while aligning final delivery to a Waterfall-style closeout cadence

“Sometimes, the best value is just doing exactly what’s needed—faster than anyone thought possible.”


Organizational Change Manager --> Sr. Project Manager -- BP

Houston, TX (Hybrid) | Aug 2018 – Mar 2020 (Full-time via Prosource.it)

Brought on as a Swiss Army knife of change, training, and IT strategy, I helped modernize BP’s internal culture through a global Office 365 transformation—then pivoted to lead infrastructure readiness for major US asset divestitures. From driving digital adoption for 60,000+ users to coordinating remote field transitions in the high desert, I thrived at the intersection of technology, people, and scale.

  • Delivered a global Office 365 adoption campaign for 60k+ users across BP, doubling daily Teams engagement from 30% to 66% in under 6 months
  • Designed and executed the “Champions Network” advocacy program, training internal evangelists to accelerate digital adoption at scale
  • Led communications strategy, training updates, stakeholder engagement, and product rollout planning across Yammer, Planner, Stream, SharePoint, and more
  • Shifted to BPX’s M&A division to co-lead infrastructure and data readiness for the sale of two major energy assets in CO and WY
  • Developed full discovery, remediation, and handoff strategies including IT transition plans, runbooks, and post-divestiture continuity documentation
  • Adapted seamlessly between Agile (Digital Workplace) and Waterfall (Divestiture Program) approaches, flexing to the needs of the mission

“This was my first taste of real-scale impact. One project lit my soul on fire. The next taught me how to deliver, no matter the weather.”


Project Manager --> Practice Manager -- Interdyn BMI (a Columbus AS Company)

Houston, TX | Feb 2017 – Dec 2017 (Full-time)

Hired to bring structure to chaos—and stayed to prevent collapse. I joined to formalize project delivery for a scrappy Managed Services group, only to step into full departmental leadership after the abrupt dismissal of our boss. What followed was nine months of keeping the lights on, teams together, and projects delivered—despite growing silence from a parent company that no longer saw value in our existence.

  • Oversaw 30–40 simultaneous projects across Azure, Office 365, infrastructure upgrades, and full IT services for Houston-area SMB clients
  • Delivered 100% of client projects on time and on spec, from network and server builds to VOIP overhauls and PC refreshes
  • Took over billing operations, project oversight, and people management after department head was terminated without transition plan
  • Balanced engineering workload, ran daily standups, and kept project momentum alive under resource and morale strain
  • Documented tribal knowledge and streamlined internal operations to preserve business continuity amid organizational upheaval
  • Helped define long-term IT strategy for managed clients, acting as vCIO and trusted advisor across dozens of industries

“After the leader fell, I didn’t just keep the wheels turning—I held the line. We made it through together, even if the company left us behind.”

Education & Certification

University of Houston – Interdisciplinary Studies
Focus areas in History, Communication, and Philosophy

Project Management Professional (PMP) – PMI, earned 2016
Active through 2025; currently maintained and in good standing

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