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Principal Delivery Architect Engineering Systems & Process SME

25+ years engineering systems + business processes — scaled with precision, accelerated by AI.

Engineering delivery without the administrative drag.Two decades across systems engineering and enterprise delivery taught me one thing: most teams don't have a talent problem; they have an overhead problem. I help technical organizations make frameworks like SAFe and Scrum actually work for engineering teams instead of slowing them down—automating project pipelines, eliminating Jira babysitting, and deploying pragmatic AI tools that get software out the door faster.

Let's Talk Delivery See Case Studies & Hands-On Builds
SYSTEMS ENGINEER. DELIVERY LEADER. BUILDER.
Todd Bailey
Todd BaileyEngineering Systems & Delivery Lead

Active Secret Clearance CISM PMP SAFe RTE CSM Security+ M.S. Computer Science & InfoSec (4.0 Summa Cum Laude)

Career Snapshot

Where I Come From & How I Work

I started in the server room, moved into enterprise delivery leadership, and now spend my time cutting process overhead with automation and practical AI.

The Foundation · 12+ Years

Systems Engineering & Infrastructure (12+ Years)

I started out doing the actual engineering work: FedRAMP security compliance, high-availability IaaS builds, zero-downtime database migrations, and DevSecOps pipelines across federal and defense environments.

Enterprise Delivery · 10+ Years

Agile Delivery & Workflow Automation (10+ Years)

Leading large Agile Release Trains (ARTs) and multi-agency programs taught me where teams get bogged down. I focus on turning Jira and Confluence from manual ticketing chores into automated workflows that keep work moving without the busywork.

What I Do Now · 3+ Years

Pragmatic AI & Pipeline Modernization (3+ Years)

Leading delivery for enterprise AI/LLM platforms and rolling out role-specific AI tools that actually help engineers, QA, and ops teams ship 30%+ faster—instead of just handing out generic chatbot licenses.

The takeaway after 25+ years: Good process shouldn't feel like bureaucracy—it should feel like good systems engineering applied to how teams work.

01 / Core Strengths

What I actually do
for engineering organizations.

Six areas where I help teams cut through the noise, automate the routine, and get reliable systems out the door.

01

Making SAFe & Scrum Work for Engineers

Leading cross-functional teams, running PI Planning, and steering Agile Release Trains (ARTs) that deliver on schedule—without drowning developers in pointless meetings or process theater.

02

Pragmatic AI & AIOps Rollouts

Leading delivery for enterprise AI/LLM platforms, compute pipelines, and AIOps initiatives. Instead of blanket tool rollouts, I match the right AI tools to specific engineering, QA, and ops roles—and measure whether they actually speed up delivery.

03

Eliminating Jira Babysitting

Turning Jira Data Center, Jira Cloud, and Confluence into automated pipelines instead of manual status trackers. I build custom triggers, automated SLA tracking, and live dashboards so engineers can stay in their code while leadership still gets clear visibility.

04

Speaking Both Engineering & Leadership

Because I came up through systems engineering and hold dual degrees in Computer Science and InfoSec, I can talk shop with developers, DevSecOps, and cloud architects—and translate technical reality into clear plans for executives without anything getting lost in the middle.

05

Cleared Cloud, IaaS & FedRAMP Delivery

Hands-on delivery leadership for secure L3 facilities, zero-downtime MongoDB migrations, multi-cloud platforms (MCMP), and FedRAMP environments where security and federal compliance aren't optional.

06

Building Real Tools, Not Just Slide Decks

I don't just write slide decks about workflow and AI—I still write code and build working tools. I build custom apps, automated data pipelines, and lightweight workflow tools in Python and JavaScript to test what actually works in practice.

02 / Case Studies

Real delivery results across
federal agencies, defense, and enterprise tech.

A track record of untangling workflows, automating tracking, and shipping complex infrastructure and AI systems on time.

Federal Oversight · Jira Data Center · AI/LLM DeliveryDec 2023 — Present

Featured Case Study 1 · Federal Oversight Agency Contract

Scaling Delivery & Jira Automation for an Enterprise AI/LLM Analytics Foundry.

Role: Senior Delivery Lead & AI Architecture PM

Context: Data science, engineering, and cloud teams needed a unified way to track work, automate handoffs, and measure progress while scaling a new Analytics Foundry and AI/LLM initiatives.

Challenge: Disconnected tools and manual coordination were creating friction between teams and slowing down cloud deployments.

What I Did
Led the enterprise rollout of Jira Data Center for the Analytics Foundry. Built custom workflow automations, set up practical delivery metrics for data science teams, and streamlined agile ceremonies so teams spent less time reporting status and more time shipping.
Result
Sped up AI/LLM model delivery and cloud infrastructure work while giving leadership real-time visibility and cutting cross-team bottlenecks.
Talk About AI & Delivery Workflows
AIOps · 30%+ Efficiency Lift · Role-Specific AIJan 2023 — Dec 2023

Featured Case Study 2 · Commercial Technology & AIOps

Role-Specific AI Rollout: Cutting Overhead for a 30%+ Delivery Lift.

Role: AIOps Technical Delivery Lead

Context: Teams were handed generic generative AI tools with no clear workflow integration, leading to tool sprawl and zero real impact on delivery speed.

Challenge: Without matching specific tools to actual engineering, QA, and ops bottlenecks, developers were just switching tabs more often without shipping any faster.

What I Did
Built a practical role-by-role AI evaluation matrix across engineering, QA, and operations. Tested tools against real day-to-day bottlenecks in the delivery pipeline and rolled out workflows tied to clear team metrics.
Result
Delivered a 30%+ overall efficiency gain across the organization and an extra 20% throughput boost in role-specific pipelines.
Talk About Practical AI Rollouts
Oct 2023 — Dec 2023 · Enterprise AI Compute

AI Compute Workflows & Jira Cloud Pipeline Integration

Technical Delivery PM

Jira Cloud Automation & AI Tool Integration

Connected Jira Cloud event hooks directly to internal AI compute pipelines and developer tools. Cut out manual status updates, cleaned up compute queue bottlenecks, and helped developers get work through the pipeline faster.

Oct 2021 — Dec 2022 · Enterprise Cloud Services

AI-Enabled Multi-Cloud Management Platform (MCMP)

Transition & Transformation Tools PM

AI-Enabled MCMP · SAFe Agile Release Train

Led the delivery team rolling out an AI-enabled Multi-Cloud Management Platform (MCMP) across enterprise client environments. Ran the Agile Release Train (ART) to keep cloud resource optimization on track, cutting operational costs and hitting schedule targets.

Nov 2020 — Oct 2021 · Federal & Association Portals

Public-Sector & Association SaaS Modernization

SaaS Delivery Project Manager

SAFe Delivery · PI Planning · Jira & Confluence

Led cross-functional teams delivering major public-sector and association web platforms (including the US Forest Service and USGA). Ran PI Planning, kept SAFe ceremonies lean, and organized Confluence documentation so technical teams and stakeholders stayed on the same page.

Oct 2019 — Sep 2020 · Space Force Contract

Secure L3 Facility Construction & Space Awareness MongoDB Migration

DevSecOps & Infrastructure Delivery Lead

L3 Facility Build · MongoDB Migration · Active Secret Clearance

Managed the ground-up build of a secure L3 IaaS facility at Vandenberg and led the zero-downtime migration of the Space Awareness database to MongoDB. Built DevSecOps checks right into Jira to stay 100% compliant with strict federal security and launch schedule requirements.

Apr 2007 — Aug 2019 · Homeland Security Contract (12-Year Tenure)

FedRAMP Infrastructure Modernization & Automated SLAs

Senior Systems Engineering & Technical Delivery Lead

FedRAMP Infrastructure · Automated SLAs · Enterprise Agile Rollouts

Spent 12 years bridging hands-on systems engineering and program delivery. Led Agile rollouts across multiple subcontractors that improved delivery efficiency by 20%, and built automated Jira SLA tracking across FedRAMP infrastructure to speed up incident resolution without cutting security corners.

25+ years shipping SaaS, IaaS, and AI-enabled systems across cloud and cleared environments.

03 / Staying Technical — Personal Builds & Workflow Tools

A delivery leader who still builds.
Personal tools, workflow experiments, and web plumbing.

Too many delivery leaders and process consultants lose touch with the tech their teams actually use. Outside of enterprise work, I build my own tools, automate my daily reading workflows, write a self-hosted microblog, and run my own web infrastructure—bringing the same practical systems mindset to everyday problems.

Lable — Minimalist Workflow Engine

Born from 25 years of watching teams drown in over-complicated issue trackers. I built Lable around a dead-simple 5-step flow — List → Assign → Build → Learn → End — as a working experiment in how stripping out clutter keeps work moving.

Personal Workflow Build · 5-Stage FlowExplore Live App ↗

Scrolz — Automated AI Signal Digest

The AI space moves too fast to track by hand. I built Scrolz to automatically pull, filter, and summarize daily shifts in LLMs and developer tooling—using the same API automation and noise-reduction habits I bring to engineering teams.

Automated Daily Digest · Personal AI PipelineExplore Live Digest ↗

Microblog — blog.baileypc.com

A lightweight, self-hosted microblog on my own domain where I share short notes on fixing broken Jira workflows, cutting unnecessary meetings, and testing AI tools in real engineering work—no algorithms or fluff.

Self-Hosted Microblog · Process & AI NotesRead Microblog ↗

Personal Projects, Infrastructure & Hobbies

Staying hands-on with domain plumbing, publishing workflows, and personal data tracking.

Cloud Virtue

A domain and web-hosting storefront built on a simple belief: professionals and businesses should own their own domain name and control their DNS identity. Running it keeps me hands-on with registrar plumbing, DNS routing, and hosting setup.

Digital Ownership & Web Plumbing

Editorial Publishing Tool

A custom newsletter builder created to replace clunky, manual formatting steps with a clean editorial toolbar—turning a tedious recurring publishing chore into a repeatable 5-minute workflow.

Removing Everyday Friction

KarlGolf

In engineering delivery, you watch leading indicators instead of waiting for a missed deadline. I built KarlGolf to bring that same habit to my golf game—tracking Greens-in-Regulation and round-over-round trends on the course.

Metrics Mindset Applied to a Hobby

04 / Credentials & Education

Certifications & Education.
Grounded in Computer Science & InfoSec.

Industry delivery and security certifications backed by dual 4.0 GPA degrees in Computer Science and Information Technology.

CSMSAFe RTEPMPCISMSecurity+CompTIA A+Python & JavaScriptData Science & Cloud Computing

Master of Science (M.S.) — Computer Science & Information Security · Capella University · 4.0 GPA · Summa Cum Laude
Bachelor of Science (B.S.) — Information Technology Administration · Capella University · 4.0 GPA · Summa Cum Laude · Active Secret Clearance

05 / Connect

Let's fix your
delivery bottlenecks.

Whether you need someone to untangle a messy Jira setup, make SAFe or Scrum actually work for your developers, or lead a complex cloud or AI program, I'd love to talk.

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