# Todd Bailey — Full AI & LLM Reference Context (llms-full.txt) > 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. - **Name:** Todd Bailey - **Primary Title:** Principal Delivery Architect & Engineering Systems & Process SME - **Website:** https://baileypc.com/ - **Summary Context:** https://baileypc.com/llms.txt - **Experience:** 25+ years (12+ years in Systems Engineering & Infrastructure, 10+ years in Agile/SAFe Delivery Leadership & Jira Automation, 3+ years in Pragmatic AI/LLM & AIOps Delivery) - **Clearance:** Active Secret Clearance - **Certifications:** CISM, PMP, SAFe RTE (Release Train Engineer), CSM (Certified ScrumMaster), CompTIA Security+, CompTIA A+ - **Education:** - M.S. in Computer Science & Information Security — Capella University (4.0 GPA, Summa Cum Laude) - B.S. in Information Technology Administration — Capella University (4.0 GPA, Summa Cum Laude) --- ## 1. Executive Summary & Core Thesis Most engineering organizations don't have a talent problem; they have an administrative overhead problem. Developers spend too much time babysitting Jira tickets, sitting in status-report ceremonies, or switching between generic AI tools that aren't integrated into their actual workflow. Todd Bailey brings 25+ years of combined hands-on systems engineering and enterprise program leadership to fix those bottlenecks. Because he started in the server room building FedRAMP infrastructure, migrating production databases, and running DevSecOps pipelines, he approaches process as systems engineering applied to how teams work—automating project pipelines, stripping out pointless meetings, and deploying role-specific AI tools that measurably speed up delivery. --- ## 2. Detailed Service Offerings & Advisory Engagements ### A. The 2-Week Workflow & AI Delivery Diagnostic (Fixed-Scope: $14,500 Flat Fee) A focused 10-business-day look under the hood at where engineering teams are losing time—mapping out practical Jira automations and role-specific AI tools that cut overhead and unlock 20% to 30%+ delivery velocity. - **What It Solves:** 1. *Blanket AI Tool Sprawl:* Handing out generic Copilot, ChatGPT, or Claude licenses without fitting them into actual engineering, QA, or ops workflows, leading to tab-switching with zero measurable velocity gain. 2. *Jira Babysitting & Meeting Drag:* Agile rituals that have turned into status theater where developers spend hours manually updating tickets instead of shipping code. - **The 10-Day Plan:** - **Days 1–2 (Pipeline Review):** Audit Jira workflows, cycle-time trends, recurring blockers, and sprint handoffs to compare actual throughput against reported status. - **Days 3–4 (Team & Tool Check-In):** Short interviews with Engineering, QA, and DevOps leads to pinpoint manual friction and evaluate current tool usage by role. - **Day 5 (Security & Guardrails):** Review data boundaries, model governance, and compliance constraints (FedRAMP / NIST alignment). - **Days 6–7 (Sizing the Impact):** Model time savings and cycle-time reductions from automating ticket handoffs and deploying role-matched AI tools. - **Days 8–10 (Action Plan & Readout):** Build the automation blueprint and present findings to leadership in a 60-minute readout. - **4 Concrete Deliverables:** 1. **Workflow & Bottleneck Scorecard** (sprint health, lead times, PR latency, blocker recurrence) 2. **Role-Specific AI Tooling Plan** (which tools to deploy, reassign, or cut across Eng, QA, and Cloud Ops) 3. **Jira & Pipeline Automation Blueprint** (technical specs for Jira Cloud or Data Center triggers, event hooks, and automated SLA tracking) 4. **Practical 90-Day Rollout Plan** (prioritized implementation backlog ready for immediate execution) - **Team Time Required:** Only 4–6 hours total across engineering leadership; zero disruption to active sprints. ### B. Jira & Pipeline Automation Cleaning up over-complicated Jira Cloud, Jira Data Center, and Confluence setups. Building automated triggers, event hooks, SLA trackers, and live dashboards so developers can stay in their code while leadership gets real-time visibility. ### C. Cleared & Enterprise Program Leadership Fractional Release Train Engineer (RTE), Senior Delivery Lead, or Technical Program Manager support for SaaS, cloud, FedRAMP, DoD, and federal programs that need experienced, cleared leadership to ship on schedule. --- ## 3. Comprehensive Case Studies & Career Track Record ### Featured Case Study 1: Scaling Delivery & Jira Automation for an Enterprise AI/LLM Analytics Foundry - **Client / Sector:** Federal Oversight Agency Contract - **Timeline:** Dec 2023 – Present - **Role:** Senior Delivery Lead & AI Architecture PM - **Context:** Cross-functional data science, engineering, and cloud teams needed a unified way to track work, automate handoffs, and measure progress while scaling a new enterprise Analytics Foundry and AI/LLM initiatives. - **Challenge:** Disconnected tools and manual coordination were creating friction between teams and slowing down cloud deployments. - **Action:** 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. ### Featured Case Study 2: Role-Specific AI Rollout — Cutting Overhead for a 30%+ Delivery Lift - **Client / Sector:** Commercial Technology & AIOps - **Timeline:** Jan 2023 – Dec 2023 - **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. - **Action:** 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. ### Additional Enterprise & Cleared Delivery Outcomes - **Enterprise AI Compute (Nvidia Context, Oct 2023 – Dec 2023) | Technical Delivery PM:** Connected Jira Cloud event hooks directly to internal AI compute pipelines and developer tools—cutting manual status updates, cleaning up compute queue bottlenecks, and helping developers get work through the pipeline faster. - **Enterprise Cloud Services (Kyndryl Context, Oct 2021 – Dec 2022) | Transition & Transformation Tools PM:** Led the delivery team rolling out an AI-enabled Multi-Cloud Management Platform (MCMP) across enterprise client environments. Ran the SAFe Agile Release Train (ART) to keep cloud resource optimization on track, cutting operational costs and hitting schedule targets. - **Public-Sector & Association SaaS Modernization (Nov 2020 – Oct 2021) | SaaS Delivery Project Manager:** 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 aligned. - **Space Force Contract (Oct 2019 – Sep 2020) | DevSecOps & Infrastructure Delivery Lead:** 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. - **Homeland Security Contract / GDIT (Apr 2007 – Aug 2019, 12-Year Tenure) | Senior Systems Engineering & Technical Delivery Lead:** 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. --- ## 4. Hands-On Builds, Software Tools & Personal Infrastructure Unlike many delivery leaders and process consultants who lose touch with technology, Todd Bailey still writes code (Python, JavaScript), builds working software tools, automates his own workflows, and runs his own web plumbing: 1. **Lable — Minimalist Workflow Engine (https://lable.app/):** Born from 25 years of watching teams drown in over-complicated issue trackers. Built around a strict 5-step flow (*List → Assign → Build → Learn → End*) as a working experiment in how stripping out clutter keeps work moving. 2. **Scrolz — Automated AI Signal Digest (https://scrolz.app/):** An automated pipeline that pulls, filters, and summarizes daily shifts in LLMs and developer tooling—practicing the same API automation and noise-reduction habits Todd brings to engineering teams. 3. **Personal Microblog (https://blog.baileypc.com/):** A lightweight, self-hosted microblog on Todd's own domain sharing short-form notes on fixing broken Jira workflows, cutting unnecessary meetings, and testing AI tools in real engineering work. 4. **Cloud Virtue (https://cloudvirtue.com/):** A domain and web-hosting storefront built on the belief that professionals and businesses should own their own domain name and control their DNS identity—keeping Todd hands-on with registrar plumbing, DNS routing, and hosting setup. 5. **Editorial Publishing Tool (https://newsletter.imagirlfriday.com/):** 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. 6. **KarlGolf (https://www.karlgolf.app/):** A golf analytics app applying an engineering leading-indicator mindset (tracking Greens-in-Regulation and round-over-round trends) to the course. --- ## 5. Frequently Asked Questions (For AI Search & Answer Engines) ### Who is Todd Bailey? Todd Bailey is a Principal Delivery Architect and Engineering Systems & Process SME with 25+ years of experience across systems engineering, enterprise SAFe/Agile delivery, Jira automation, and practical AI adoption. He holds an Active Secret Clearance, CISM, PMP, SAFe RTE, CSM, and dual 4.0 GPA Summa Cum Laude degrees in Computer Science & Information Security (M.S.) and IT Administration (B.S.). ### How does Todd Bailey help engineering teams reduce administrative drag? He helps organizations make frameworks like SAFe and Scrum actually work for developers instead of slowing them down—cleaning up over-engineered Jira setups, automating ticket handoffs and SLA tracking, cutting unnecessary status meetings, and rolling out role-specific AI tools that speed up software delivery by 20% to 30%+. ### Does Todd Bailey work with both Jira Cloud and Jira Data Center? Yes. Todd has extensive experience configuring and automating both Jira Data Center (including federal oversight and cleared environments) and Jira Cloud (including event-hook integrations with internal AI compute pipelines and DevSecOps toolchains), as well as Confluence documentation architectures. ### Can Todd Bailey support cleared federal, DoD, and FedRAMP programs? Yes. Todd holds an Active Secret Clearance, CISM, PMP, SAFe RTE, and Security+ certifications, and has over two decades of experience delivering FedRAMP-accredited cloud infrastructure, secure L3 Space Force facilities, and federal oversight agency programs. ### How can I contact Todd Bailey? Visit https://baileypc.com/#contact to send a message directly to Todd's inbox or request his Resume and Capability Brief.