Kansas City · Engineering leadership × AI

I build systems that outlast me — and teams that outgrow me.

Engineering leader, AI builder, and entrepreneur. I lead a 33-person organization spanning business analysis, quality engineering, and test automation inside an enterprise insurer. I build practical AI workflows used by business teams and create companies around automation and technology education. I don't just automate tests. I automate businesses.

Work with me See what I've built

At scale

Enterprise automation spanning UI, API, and database testing

33

Analysts, quality professionals, and automation engineers in my organization

6+ yrs

Leading teams, developing people, and building engineering capabilities

Early adopter

Enterprise AI workflows in active use by business teams

About

Curiosity, compounded daily.

I didn't start in a corner office or a computer science lecture hall. I started in operations — close to the work, close to the friction, watching smart people lose hours to processes that software should have handled years ago. That bothered me enough to do something about it. It still does.

That instinct pulled me from operations into IT, from analysis into automation, and from automation into leadership. Along the way I learned the thing that shapes everything I build: technology problems are almost always people problems wearing a disguise. The best automation in the world fails inside a team that doesn't trust it. The best AI strategy dies in an organization that wasn't led through the change.

So I work both sides of that line. I build the systems — agentic AI pipelines, automation frameworks, the unglamorous infrastructure that makes delivery fast and boring in the best way. And I build the people — mentoring engineers into leads, analysts into engineers, and teams into organizations that don't need me in the room to do great work.

Away from a keyboard, I'm a husband and a father of four. I train mixed martial arts before sunrise, coach youth football on weekends, and read like it's a competitive sport. Discipline beats motivation — I just try to prove it daily.

The journey

From the ops floor to the AI frontier.

Every step earned, none of them accidental.

Where it started

Operations

Learned the business from the inside — and started noticing everything technology could fix.

The pivot

Enterprise IT

Crossed over. Traded observing problems for owning them.

The translator years

Business Analysis

Became fluent in both languages — what the business needs and what engineering can deliver.

The builder years

Automation Engineer

Built the automation practice from zero. First framework, first pipeline, first proof that quality could scale.

The multiplier years

Engineering Manager

Grew a function into a 33-person organization spanning business analysis, quality engineering, and test automation.

Now

AI Transformation Leader

Early adopter of enterprise AI, building practical workflows across quality engineering, claims, documentation, knowledge management, and software delivery. Several of these solutions are now used by business teams in their day-to-day work.

Next

Founder & Executive

Building companies, teaching in public, and leading engineering organizations through the AI era.

Leadership philosophy

Principles I run on.

Not wall art. These are the defaults I return to when the decision is hard.

Leadership is service

My job is to remove obstacles, grow people, and take the blame. The team gets the credit. That's the whole deal.

AI augments humans

I build AI that makes engineers, analysts, and claims professionals better at their jobs — not systems designed to make people irrelevant.

Discipline beats motivation

Motivation shows up sometimes. Systems show up every day. I bet on systems — in engineering, in fitness, in life.

Automation creates freedom

Every hour a machine handles is an hour a human gets back for judgment, creativity, and higher-order work.

Learning compounds

A little better every day is unbeatable over a decade. I read, build, and study like the interest rate depends on it.

Leave it better

Every team, codebase, and process I touch should be stronger after I'm gone. Systems that outlast me are the point.

Selected work

Case studies, not project cards.

Real problems, real systems, real impact. Tap a case to expand it.

Enterprise Automation Practice

Built a quality engineering function from zero into an enterprise-scale automation practice.

Quality Engineering

Problem

Regression testing was manual, slow, and entirely dependent on tribal knowledge. Every release was a bottleneck, and quality was a person, not a system.

Solution

Designed and built the automation practice from scratch: framework architecture, coding standards, CI/CD integration, and a hiring-and-mentoring pipeline that turned analysts into automation engineers.

Impact

An enterprise-scale automation portfolio spanning UI, API, and database layers. Regression cycles that once took weeks now run continuously. Quality became infrastructure.

Lessons learned

Standards before scale. A framework without conventions becomes a second legacy system — invest in the boring parts first.

Technology

C#SeleniumPlaywrightPostmanSQLAzure DevOpsGit

AI Medical Record Summarization

AI-assisted workflow that significantly accelerates medical-record review while keeping final decisions human-owned.

Enterprise AI

Problem

Claims professionals may need to review medical records containing hundreds or thousands of pages. Important facts can be difficult to locate consistently, and manual review limits the time available for judgment.

Solution

Built an AI-assisted workflow that reviews lengthy medical records, surfaces potentially decision-relevant facts, and provides a structured summary for claims professionals.

Impact

Substantially reduced review effort, created a more standardized way to surface important information, and gave claims professionals more time to focus on judgment and decision-making.

Lessons learned

The strongest enterprise AI systems do not remove human accountability. They reduce cognitive load, improve consistency, and help experienced professionals focus on the decisions that require judgment.

Technology

ClaudeAI workflow designPythonPrompt engineering

Agentic Documentation Pipelines

Turning tribal knowledge into living, generated documentation.

Knowledge Systems

Problem

Critical system knowledge lived in a few senior heads and a graveyard of stale wiki pages. Onboarding was slow; every departure was a small crisis.

Solution

Built agentic pipelines that generate and maintain documentation and knowledge bases from source systems and artifacts — so the docs stay as current as the code.

Impact

Knowledge stopped being a single point of failure. New engineers ramp faster, and "ask the one person who knows" is no longer the architecture.

Lessons learned

Documentation nobody maintains is documentation nobody trusts. Generation beats good intentions.

Technology

ClaudeAgentic AIPythonAzure DevOps

Visio-to-Test Generation

Process diagrams in, executable test cases out.

AI × Testing

Problem

Analysts drew detailed process flows in Visio; test designers then re-derived the same logic by hand into test cases. Duplicate effort, drifting artifacts.

Solution

Built an AI workflow that reads process diagrams and generates test cases directly from them — making the diagram the single source of truth.

Impact

Test design time dropped dramatically, coverage tracks the process by construction, and analysts and QA stopped maintaining two versions of reality.

Lessons learned

The highest-leverage AI wins are often at the seams between roles — where the same knowledge is manually translated twice.

Technology

AI visionClaudeC#Test design

Executive Analytics & Engineering Tooling

Power BI dashboards and productivity utilities used across engineering.

Data & DevEx

Problem

Leadership decisions ran on anecdotes and quarter-old spreadsheets. Engineers lost time to repetitive tasks nobody owned fixing.

Solution

Built executive Power BI dashboards for delivery and quality visibility, plus a suite of automation utilities adopted across engineering teams.

Impact

Leaders see quality and delivery health in real time. Small tools, multiplied across dozens of engineers, quietly return significant engineering time.

Lessons learned

Developer productivity is an engineering product with internal customers. Treat it like one and adoption follows.

Technology

Power BISQLC#JavaScript

Ventures

Building beyond the day job.

Assets over hours. Leverage over titles.

01 · Founder · AI Automation

Grindstein Digital

An AI automation consultancy helping businesses eliminate repetitive work and build smarter operating systems. Four projects delivered across practical business automation, with each engagement focused on creating measurable value rather than adding technology for technology's sake.

02 · Builder · STEM Education

NFormal Comics

A STEM education venture using original characters and comic-book storytelling to make AI, cybersecurity, software engineering, blockchain, robotics, and emerging technology more accessible to the next generation of builders.

03 · In the lab

What's next

Exploring SaaS products for engineering teams, practical AI agents, and educational platforms for the AI era. The through-line remains the same: build systems that create leverage, then make what was learned useful to others.

Writing

Ideas worth stealing.

What I'm thinking about at the intersection of AI, engineering, and leadership.

AI × Engineering

Software Engineering After the Autocomplete Era

Agentic AI won't replace engineers. It will replace engineering organizations that refuse to redesign how they work.

Coming soon.

Quality Engineering

The Test Case Is Dead. Long Live the Quality Signal.

Why the future of QA isn't more tests — it's better, faster, cheaper answers to "can we ship?"

Coming soon.

Leadership

Managing People Who Are Smarter Than You

The uncomfortable skill that separates engineering managers from engineering leaders.

Coming soon.

Agentic AI

Your First Agent Should Be Boring

The unsexy workflow automations that build organizational trust in AI — and fund the ambitious ones.

Coming soon.

Data

Dashboards Executives Actually Open

Lessons from building Power BI reporting that changed decisions instead of decorating meetings.

Coming soon.

Career

From Ops Floor to AI Leader: The Compounding Career

A nontraditional career path from operations to enterprise technology, automation, leadership, and AI — and the compounding lessons learned along the way.

Coming soon.

The library

Currently reading & learning.

Learning compounds. This is the deposit schedule.

Leadership

Extreme Ownership

Jocko Willink & Leif Babin

AI

Co-Intelligence

Ethan Mollick

Business

$100M Offers

Alex Hormozi

Investing

The Psychology of Money

Morgan Housel

Psychology

Atomic Habits

James Clear

Engineering

Accelerate

Forsgren, Humble & Kim

On the bench right now

Agentic AI & LLM workflowsClaude CodePlaywrightNext.js + TypeScriptSystems for algorithmic trading research

Toolbox

The stack.

Tools change. The instinct for picking the right one doesn't.

AI

Claude & Claude Code
ChatGPT / OpenAI
GitHub Copilot
Microsoft Copilot
Agentic AI workflows

Languages

C#
Python
JavaScript / TypeScript
SQL

Automation

Playwright
Selenium
Postman

DevOps

Azure DevOps
Git & CI/CD
Terraform
ARM Templates

Analytics

Power BI
SQL

Leadership

Agile / Scrum at scale
Org design & hiring
Mentoring & coaching
AI change management

What people say

In their words.

What it's like to work with me—from someone who did.

Darion has truly been an exceptional leader and one of the best managers I have ever had the pleasure of working for. His approachability, ability to make insightful decisions, and staunch advocacy for his team are unmatched. His thoughtful leadership has fueled my professional development and nurtured a positive, inclusive environment that spurs everyone to give their best. His unique blend of technical acumen, respectful demeanor, and personable nature are truly commendable.

Christian Dye

Senior SDET · Former direct report

LinkedIn recommendation · July 2023

Read the full recommendation

As the Manager of Quality Analysis and Business Analysis, Darion has truly been an exceptional leader and one of the best managers I have ever had the pleasure of working for. His approachability, ability to make insightful decisions, and staunch advocacy for his team are unmatched. His unique talent in combining diverse perspectives into harmonious solutions and fostering an open dialogue makes everyone feel valued under his leadership. On a professional level, Darion's contributions, including the introduction of our automation framework, his own Selenium-based case creation tool that has significantly boosted productivity throughout the department, and his selection of tools like Mailosaur and Browserstack, have massively amplified our efficiency. His thoughtful leadership has fueled my professional development and nurtured a positive, inclusive environment that spurs everyone to give their best. In short, Darion's deft management skills and infectious positivity make him an outstanding leader. His unique blend of technical acumen, respectful demeanor, and personable nature are truly commendable.

Contact

Let's build something that outlasts us.

Whether you're rethinking an engineering organization, exploring practical applications of AI, or building systems that create leverage, my inbox is open.

dariongatson@gmail.com LinkedIn