Why I Joined Holly (And Why You Should Too)
Keiv Holding, Founding Engineer, shares about his journey to building AI that makes public service better
From Medicine to Engineering
I never planned to become a software engineer. Five years ago, I was hunched over textbooks, studying medicine while building an e-commerce store on nights and weekends. What started as a side project to bring my business ideas to life quickly pulled me in a direction I never expected. As I worked to scale my business with code, my fascination with engineering grew - to the point that I decided to pursue it seriously, trading anatomy books for programming languages and a stethoscope for a keyboard.
The Search for Something Different
Late 2022 was a turning point in my engineering journey. When GPT-3.5 was released, I jumped in headfirst, building everything from AI customer support chatbots that resolved issues autonomously to agentic systems that discovered influencers, handled outreach emails, and managed ongoing relationships. I realized this was exactly the kind of innovative technology I wanted to work with, and I wanted to be at a company where I could help shape how these technologies would transform industries.
I wasn’t looking for companies merely using AI as a buzzword on their pitch decks. I wanted to join a team building meaningful solutions around these new capabilities, tackling problems that couldn’t be solved before. That’s what led me to Holly.
Finding Holly
My first conversation with Brendan and Cherie felt different from the start. They didn’t just talk about improving government operations - they walked me through the very real problems they were solving for local governments. When I saw how government HR teams were managing complex job classifications with outdated tools and spreadsheets, I immediately saw the opportunity for AI to transform this space.
I've rarely seen such prominent founder-market fit tackling what's clearly a hair-on-fire problem, yet in a space where few others are competing. A burning need in a blue ocean - that's what every founder dreams of finding, and that genuinely excited me.
What really caught my attention? How they operate as leaders. They listen. Really listen. In a world where everyone's trying to be the loudest voice in the room, they create space for ideas to breathe. I've found that the best leaders spend more time listening than talking - they build teams through communication, not dictation. Brendan and Cherie embody this principle in how they run Holly, and it makes all the difference.
Life at Holly
Now that I’m here, the technical challenges are exactly what I’d hoped for. It's the kind of work that keeps you constantly learning new things.
Just last month, I built our "Position Insights" tool – an AI assistant that lets HR officials query workforce data in natural language to analyze license requirements, evaluate roles through a skills-based lens, or get clarity on FLSA classifications. Seeing a city HR director generate a comprehensive analysis in minutes instead of days was validating, as was hearing from a new pilot partner: "We've envisioned this system for quite some time but could never find a product that gives us exactly what you're giving us here." This impact drives my motivation with every line of code.
What's Next?
Looking ahead, I'm excited about:
Building our AI salary benchmarking tool that delivers market comparisons in seconds not months
Scaling our architecture to support more jurisdictions while maintaining performance
Developing natural language interfaces for HR teams to easily access workforce insights
But equally exciting is growing our engineering team. As founding engineer, I've shaped our foundation – now I want to bring on teammates who share our vision for transforming government with AI.
Why You Should Join Us
We're looking for our second engineer - job description here. And, honestly, this is a unique opportunity. You'll work directly with the founders, own major parts of our tech stack, and help build something that makes a real difference in how the government operates.
If you're interested in joining us, let's talk! I'm happy to answer any questions about what it's really like working here.
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