Technical Senior Scrum Master AI Delivery Leader

15+ years leading Agile delivery —
grounded in engineering, powered by AI.

I'm a Technical Senior Scrum Master and AI Delivery Leader who brings a systems engineering background and a sharp eye for operational efficiency to every team I lead. By day, I guide Scrum teams delivering SaaS, IaaS, and AI/LLM initiatives. Outside of work, I'm still the engineer at heart — an AI enthusiast who loves to tinker and build.

Start a conversation See what I'm tinkering with

SCRUM LEADER. ENGINEER. AI BUILDER.

Todd BaileyScrum Master. Engineer. AI Enthusiast.

Active Clearance CSM SAFe RTE PMP CISM Security+ M.S. Computer Science & InfoSec

Career Snapshot

The Foundation

Systems Engineering

Started hands-on in systems engineering and IT administration — FedRAMP compliance, IaaS builds, database migrations, and DevSecOps.

Past 15+ Years

Technical Senior Scrum Master

Leading Scrum teams and SAFe Agile Release Trains across multiple organizations — pairing Jira/Confluence automation with real technical context.

AI Delivery & Tinkering

AI Leader & Builder

Delivering enterprise AI/LLM, AIOps, and AI-enabled cloud projects on the job while tinkering with frontier models and building live apps in my lab.

One thread across it all: bringing an engineer's understanding and an AI builder's curiosity to Agile team delivery.

01 / Core Capabilities

Scrum leadership
backed by an engineering background.

Six practical strengths forged over 15+ years as a Technical Senior Scrum Master, SAFe practitioner, and hands-on AI enthusiast.

Technical Scrum & SAFe leadership

15+ years leading Scrum teams, facilitating SAFe ceremonies and PI Planning, and running Agile Release Trains (ART) that keep cross-functional teams aligned and delivering.

AI, LLM & AIOps delivery

Guiding Agile delivery for AI/LLM analytics platforms, AI compute workflows, and AIOps rollouts — matching AI tools to team roles and tracking real KPI gains.

Jira & workflow automation

Deploying and customizing Jira Data Center, Jira Cloud, Confluence, and Monday.com with custom automation, SLA tracking, and KPI dashboards that cut busywork.

Engineering-grounded facilitation

Bringing a systems engineering foundation and dual Summa Cum Laude CS/IT degrees to Scrum — speaking the same language as developers, DevSecOps, and cloud engineers.

SaaS, IaaS & DevSecOps projects

Delivering cloud portals, multi-cloud platforms (MCMP), secure L3 facilities, MongoDB migrations, and FedRAMP infrastructure across federal and commercial environments.

Hands-on AI tinkering & prototyping

An AI enthusiast who learns by building — experimenting with Python, JavaScript, LLM workflows, and agentic tools to turn ideas into working software.

02 / Selected outcomes

15+ years helping teams
ship across AI, cloud, and federal.

From enterprise AI/LLM infrastructure and AIOps rollouts to Space Force and Homeland Security contracts — real Agile delivery backed by technical execution.

AI / LLM Delivery · Jira Data CenterDec 2023 — Present

Federal Oversight Agency Contract

[Role: Senior Scrum PM · Analytics Foundry & AI/LLM Scalability]

Scaling Agile delivery for an AI/LLM Analytics Foundry.

Senior Scrum PM · Agile Transformation & Jira Automation

Context: Cross-functional data science and cloud teams needed scalable Agile tracking, automation, and clear KPIs to support an Analytics Foundry and AI/LLM initiatives.

Challenge: Manual workflows and fragmented coordination slowed delivery timelines and cloud infrastructure efficiency.

What I Did: Led deployment of Jira Data Center for the Analytics Foundry, implemented custom Jira automation, defined KPIs, and spearheaded Agile transformation initiatives.
Result: Enhanced AI/LLM scalability and cloud infrastructure efficiency while significantly improving team collaboration, productivity, and project delivery timelines.

Discuss AI & Scrum delivery

AIOps · 30%+ efficiency gainJan 2023 — Dec 2023

Commercial Technology & AIOps

[Role: AIOps Technical Scrum Manager · SaaS & AI Rollout]

Role-matched AI tools.
30%+ efficiency gains.

AIOps Technical Scrum Manager

Context: Organizations adopting AI needed practical integration into their SaaS workflows and cross-functional teams rather than generic rollouts.

Challenge: Without role-by-role evaluation and KPI tracking, teams struggled to align AI tools with business goals.

What I Did: Deployed AI tools across organizations, ranked AI solutions by job role, led cross-functional teams to streamline SaaS processes, and used KPIs to guide strategic adjustments.
Result: Achieved 30%+ overall efficiency improvements and an additional 20% efficiency increase by matching and ranking AI solutions by specific role.

Discuss AI adoption & Agile

Oct 2023 — Dec 2023

AI compute workflows & Jira Cloud integration

Scrum PM · Enterprise AI Compute

[Scope: Jira Cloud Automation & AI Tool Integration]

What I did: Assisted in deploying Jira Cloud with custom automation to enhance AI compute infrastructure efficiency and team collaboration. Integrated Jira directly with internal AI tools to boost workflow productivity, streamline project management processes, and troubleshoot deployment issues for seamless operations.

Oct 2021 — Dec 2022

AI-enabled multi-cloud transformation

Transition & Transformation Tools Scrum PM · Enterprise Cloud Services

[Scope: AI-Enabled MCMP · SAFe Agile Release Train]

What I did: Led a team in deploying an AI-enabled Multi-Cloud Management Platform (MCMP) that enhanced efficiency by streamlining processes. Optimized resources using an Agile Release Train (ART) for significant cost reductions, and led Agile projects using Scaled Agile Framework (SAFe) and Jira to ensure on-time delivery.

Nov 2020 — Oct 2021

Public-sector & enterprise SaaS portals

SaaS Scrum Project Manager · Federal & Association Portals

[Scope: SAFe Ceremonies · PI Planning · Jira & Confluence]

What I did: Facilitated Scrum team efforts to achieve stakeholder sign-off and launch major public-sector and association web portals. Led Scrum sessions, SAFe ceremonies, and Program Increment (PI) Planning using Jira and Confluence to maintain stakeholder alignment and drive continuous improvement.

Oct 2019 — Sep 2020

DevSecOps & Space Awareness infrastructure

DevSecOps IaaS Scrum PM · Space Force Contract

[Scope: L3 Facility Build · MongoDB Migration · IaaS]

What I did: Led the L3 facility build and migrated the Space Awareness database to MongoDB, contributing to launch success by ensuring data integrity and accessibility. Constructed a high-efficiency IaaS facility, implemented Agile DevOps principles in Jira to reduce downtime, and reviewed contractual deliverables for scope, cost, and schedule compliance.

Apr 2007 — Aug 2019

Systems engineering & Agile transformation

Senior Systems Engineering TPM · Homeland Security Contract

[Scope: FedRAMP Infrastructure · Automated SLAs · Agile Transformation]

What I did: Spent 12 years bridging systems engineering and technical project leadership. Led Agile transformation initiatives and subcontractor coordination — boosting project efficiency by 20% — while automating SLAs using Jira to reduce response times and managing FedRAMP infrastructure projects for security compliance.

15+ years delivering SaaS, IaaS, and AIaaS solutions across cloud and on-prem environments.

03 / The Lab — Working Proof

An AI enthusiast who
tinkers, builds, and ships.

I don't just talk about AI and Agile in standups — I'm a hands-on AI enthusiast who loves tinkering with frontier models, workflow automation, and code. These live projects are my working proof.

Lable (Kanban App)

A lightweight Kanban and delivery app born from 15+ years of running Scrum boards. Turns a simple flow — List → Assign → Build → Learn → End — into clean software that keeps ownership and next actions visible.

Agile workflow toolExplore live app

Scrolz & Newsletter

Built out of my own obsession with keeping up with AI. An automated content pipeline that pulls together agentic engineering, frontier models, and AI tooling shifts into one high-signal daily feed.

AI content pipeline · TinkeringExplore live app

More side builds & web platforms

Experiments in cloud hosting, publishing workflows, and data tracking.

Cloud Virtue

Domain registration and cloud infrastructure platform — built to explore clean hosting and DNS tooling.

Cloud & web infra

Commercial Publishing Engine

Custom client publishing system engineered with a purpose-built editing toolbar for newsletter workflows.

Content systems

KarlGolf

Golf performance tracker for greens-in-regulation, trend analytics, and round-over-round metrics.

Data & metrics

04 / Credentials & Education

Certified Agile practitioner.
Computer Science & Security degrees.

Industry certifications in Scrum, SAFe, project management, and cybersecurity — backed by dual 4.0 GPA Summa Cum Laude degrees.

CSMSAFe RTEPMPCISMSecurity+CompTIA A+Python & JSData Science & Cloud

M.S. Computer Science & Information Security (4.0 GPA, Summa Cum Laude) · Capella University
B.S. Information Technology Administration (4.0 GPA, Summa Cum Laude) · Capella University · Active Clearance

05 / Connect

Start a
conversation.

Open to Technical Senior Scrum Master, SAFe Release Train Engineer (RTE), and AI Delivery Leader opportunities — as well as Agile and AI workflow consulting.

Technical Senior Scrum Master & SAFe RTE roles
AI / LLM, AIOps & Cloud Agile delivery leadership
Jira automation, Agile transformation & AI workflow consulting

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15+ years leading Agile delivery —grounded in engineering, powered by AI.