sean.midkiff ~/$
ENTERPRISE DEVSECOPS LEAD  ·  ATLASSIAN EXPERT

I build the systems
& teams that keep
engineering moving.

$ whoami
› sean midkiff — devsecops lead
$ sean --focus
› I make engineering effective
# to some, I'm known as Yoda.
$ ./connect.sh
📍 Charlotte, NC | 20+ yrs in tech | EN · DE
Sean Midkiff
// sean.jpg ● online
$330K+
RECURRING SAVINGS / YEAR
5.3M+
WORK ITEMS & PAGES MIGRATED
2,400+
SPACES MIGRATED
151K+
VULNERABILITIES REMEDIATED
// about

I'm an IT leader who turns busy engineering organizations into effective ones — optimizing the Atlassian tools they run on, automating the toil, and growing the people behind them.

For 20+ years I've worked across the stack, from embedded software to enterprise DevSecOps. Today I lead Atlassian platform strategy and CI/CD delivery for a major financial institution: part architect, part builder, part the person who makes the tools behave.

I've spent years solving team problems with the Atlassian platform: inefficiency, friction, lost knowledge. Somewhere along the way I became the person people come to first. Hence the nickname.

~/profile.json
location
Charlotte, North Carolina
current
Enterprise DevSecOps Lead @ Ally
building
Forge apps @ enterprise scale
languages
English · German
// currently

What I'm exploring

Lately I've gone deep on Atlassian Forge — building apps that solve enterprise-scale problems other teams would buy a Marketplace tool, or whole consulting engagements, to fix.

And the bigger question I keep pulling at: how do you keep code quality high and vulnerabilities remediated when agentic AI writes more and more of the code? That's where a lot of my tinkering lives right now.

sean@forge — zsh
~/explorations forge deploy --env=enterprise
✓ shipping Forge apps for enterprise-scale problems
~/explorations forge lint --scope=agentic-ai
→ keep code quality + vulns remediated as AI writes the code
~/explorations forge tunnel
▸ listening for the next hard problem
// expertise

The stack I work in

Atlassian Suite
Jira Confluence JSM Bitbucket OpsGenie Fisheye Crucible StatusPage Forge Atlassian Cloud
DevSecOps & CI/CD
Jenkins GitLab CI/CD Nexus Repo Nexus Lifecycle SonarQube
Observability
Splunk AppDynamics Datadog Prometheus
Cloud & Platforms
AWS Salesforce ServiceNow Slack
Scripting & Data
PowerShell Python Shell SQL HTML Java / Spring Boot
Ways of Working
Agile Scrum Kanban Product Mgmt Change Mgmt IT Strategy
AI & LLM Tooling
Claude ChatGPT Local LLMs Claude Skills Guardrails Model Pen-Testing
Custom App Development
Atlassian Forge Java 21 Spring Boot 3 HTMX REST APIs
// impact

Selected work

$ git log --oneline --author="sean" --grep="impact"

a1f9c2e   feat: cloud-migration  (HEAD)
Led an enterprise Data Center → Cloud migration as the lead and primary point of contact

Owned the migration end-to-end with a two-person technical team: 6,500+ Jira users and 5,500+ Confluence users across 2,400+ spaces (679 Jira, formerly "projects," and 1,726 Confluence), with 3.5M+ work items and ~1.8M pages.

679 Jira spaces 3.5M+ work items 1,726 Confluence spaces
b7d3a01   test: de-risk
De-risked the cutover with 163 trial migration runs

Evaluated 4 candidate strategies across 163 trial runs (111 Jira, 52 Confluence) — varied space sets and configuration permutations — to validate the lowest-risk path before go-live.

c4e8b15   feat: powershell
Engineered the PowerShell tooling under the migration

A project-aware issue-key reconciliation script handling Cloud's token-based JQL pagination and mid-migration key renames, plus a resumable bulk-archival utility with CSV checkpointing and auto-retry on 502/504 timeouts.

d9a02f7   feat: forge-apps
Shipped a portfolio of custom Atlassian Forge apps

Admin/governance and end-user apps replacing Marketplace equivalents — eliminating ~$120K/yr in licensing — plus a production status & incident-communication app. Built an async self-chaining pattern to beat Forge's FaaS time limits.

e1c7d44   feat: nexus-platform
Modernized a Nexus platform serving 250M+ requests/month

Drove resiliency and modernization of the artifact-management stack, and shipped automation for IQ quarantine re-evaluation and streaming component export with continuation-token pagination.

f3b6e90   feat: ai-platform
Built a model-agnostic AI assistant for Jira & Confluence

A custom app that connects to any AI model — from locally-hosted LLMs to Claude, ChatGPT and beyond — for in-context issue creation and Confluence summarization. Hardened it with built-in guardrails, then ran penetration testing across models to validate them.

b2e9f51   feat: claude-skills
Authored custom Claude skills for Jira & Confluence Cloud users

Guided skills that walk users through setup, conventions, and best practices — turning repetitive ramp-up and how-do-I questions into instant, self-serve answers.

a0c5d18   perf: savings
Cut $330K+/yr in recurring platform & license costs

$120K/yr from custom Forge apps, $110K from SonarQube consolidation, $100K+ from clustering duplicate instances.

d4b9e30   fix: security
Remediated 151,445 vulnerabilities to zero open issues

Drove secure, compliant environments with zero incidents — and kept the backlog at zero through automated scanning, policy gates, and quarantine enforcement rather than one-off cleanup sprints.

// work

Experience

Jun 2022 — Present
Ally Financial
Enterprise DevSecOps Lead

I lead Atlassian platform strategy and CI/CD delivery, working at the intersection of engineering, governance, and security. I co-founded an enterprise Jira Council to align teams on shared practices, led a four-person engineering team as Product Owner and Scrum Master, and built the automation that keeps the platform fast and auditable: reporting pipelines, AD provisioning that cut process time by 85%, and installation tooling that cut deploy time by 80%. Along the way I consolidated Jenkins from six instances to two, saved $110K a year by consolidating SonarQube and replacing vendor software with native solutions, and drove vulnerability remediation down to zero open issues with zero security incidents.

Nov 2019 — Jun 2022
Ally Financial
Senior Architect / Atlassian Administrator

I designed and built the high-availability foundation the platform still runs on: clustered Jira, Jira Service Management, Confluence, and Bitbucket environments on RHEL, instrumented with AppDynamics, Datadog, and Prometheus. Consolidating multiple instances into those clusters saved the company over $100K a year. I also created the postmortem process for high-impact outages, hosted training classes for internal teams, and did the deep diagnostic work (Splunk, memory analysis, GC tuning) that keeps clustered systems honest.

Oct 2018 — Nov 2019
Ally Financial
IT Business Operations / Jira Administrator

I served as sustain architect for Agile teams, guiding system implementation and durable processes. This is where my automation instincts took root: REST API integrations in Jira, StatusPage wired to Jira and Jira Service Desk, and monitoring with Datadog feeding automated alerting through OpsGenie. I also ran Salesforce development operations as project manager in a Scrum environment.

Oct 2017 — Oct 2018
Ally Financial
IT Analyst / Jira Administrator

My entry point into the Atlassian world: I built and managed the Jira and Confluence environment for the Mortgage organization, designing workflows, documentation, and procedures from scratch while administering Salesforce, Velocify, and DocuSign and running UAT across mortgage systems.

2003 — 2017
before Ally
A broad path into IT leadership

For eight years I ran my own consulting practice, doing whatever clients needed: web and graphic design, hardware and software support, mobile integration, training. It's where the "across the stack" habit comes from. Earlier still, my roots are in embedded software.

Experis AT&T Mobility Raindrop Web Design Motorola Mobility
// services

What I can provide

Experienced IT Leadership01
Atlassian Optimization02
DevSecOps & Process Automation03
Agile Transformation Leadership04
Security & Compliance05
Cross-Functional Team Leadership06
// certifications
Kanban Management ProfessionalKanban Univ.
Certified CI/CD SpecialistGitLab
Certified AssociateGitLab
Jira & Confluence FundamentalsAtlassian
Six Sigma Green BeltAT&T
Microsoft Office CertifiedMicrosoft
// education & honors
B.S., Computer/IT Administration & Management
University of Phoenix
Business Administration
Harvard Business School
Pre-Medicine
Humboldt University of Berlin
Paul Harris Fellow President's Volunteer Service Award International Scholar Laureate Service Excellence Award
$ ./connect.sh

Let's connect.

Have a thorny Atlassian problem, an Agile transformation to run, or an idea worth building? I'd love to hear about it.

// email
sean@seanmidkiff.com
send a message →
// linkedin
/in/seanmidkiff
connect →
// resume
Download PDF
cat resume.pdf ↗
© 2026 Sean Midkiff — Charlotte, NC built with care  ·  exit 0