I'm Darren Chow — employee #10 and Head of Operations & People at Extend, the AI-native document-processing company in New York. Before this, I was Chief of Staff to MrBeast, and before that, a strategy consultant at Monitor Deloitte. My job is building the parts of a company that don't have a team yet — recruiting, compliance, go-to-market, culture — and then hiring myself out of each one so I can find the next fire.
I joined Extend as its first generalist hire, back when the company was around ten people. Within about a year we were roughly thirty, revenue had grown 6× year over year into the millions in ARR, and net revenue retention ran well above 100%. Along the way, I built each operational function that growth demanded. Eventually the title caught up with the work: Head of Operations & People.
I had a hand in nearly every hire we made — sourcing, closing, onboarding — on a simple conviction: the only true competitive lever an early-stage startup controls is who it lets in the door. The best candidates are only on the market for a few days, so we mobilized in hours, did the unscalable things, and treated every candidate like someone worth winning over.
On my first day at Extend, I was handed the company's SOC 2 program — I call it professional hazing, affectionately. I learned a compliance regime from scratch and worked to keep it boring. Early trust infrastructure is part of what lets a small startup sell to customers like Brex, Mercury, and Flatiron Health without flinching.
I built Extend's internal data-labeling team from nothing — the hiring, the workflow, the quality bar — to feed the model pipeline that the product's accuracy depends on. Then I did the most important part: I made myself unnecessary to it. Every function I build has the same exit criteria.
I helped drive major product launches at Extend and wrote the technical blogs behind them — the positioning, the copy, the coordination, the ship. Together they built real reach and compounding developer awareness. Distribution instinct from the creator world, pointed at a technical audience.
As Chief of Staff, I was Jimmy's second brain — in every meeting, negotiating priorities, preemptively solving bottlenecks before they reached him. I helped orchestrate content calendars measured in billions of views: 13 long-form videos and more than 50 verticals, each one a logistics operation dressed up as entertainment.
A shoot changed with thirty minutes' notice, and a double-decker tour bus was suddenly headed straight through our frame. The reasonable answer was to give up the shot. Instead, we worked with the local police and rerouted the tour in real time. It wasn't scalable, it looked ridiculous, and it worked. That day gave me a rule I operate by: elegance is the enemy, and most of the constraints stopping people are imaginary.
At Monitor Deloitte, I was Deputy Chief of Staff on the firm's Cloud Hyperscaler Alliance, reporting to the US Chief Commercial Officer. I helped drive the go-to-market redesign for a $6B+ cybersecurity company moving to a platform model, and led RFP pursuits across retail, CPG, and tech — my classical training, before the unscalable education.
Elegance is the enemy. Most people are stopped by imaginary rules — strip a problem to first principles and most of them turn out to be suggestions, not laws.
On first principles · in my wordsThe only true competitive lever an early-stage startup controls is who it lets in the door. Treat every candidate like someone worth winning over.
On hiring · how we built the Extend teamOptimize for adventure. Pick whatever scares you most — the opportunity that scared me is the one I learned the most from.
On careers · why I cold-DM foundersI messaged Extend's founders five times before they took a call. I joined as employee #10 and the first generalist hire, spent my first stretch as Chief of Staff, and later stepped into Head of Operations & People. The role spans hiring, org design, compliance, and the operating cadence of a company that has grown 6× YoY.
I was Jimmy Donaldson's second brain — in every meeting, negotiating priorities, clearing bottlenecks before they reached his desk. I helped run content calendars measured in billions of views, and once rerouted a double-decker bus tour with the police on thirty minutes' notice.
My classical education: go-to-market strategy for Fortune 500 clients in financial services, retail, and tech. As Deputy Chief of Staff on the Cloud Hyperscaler Alliance, I reported to the US Chief Commercial Officer — with a $6B+ platform GTM redesign to show for it.
As a peer financial educator and resident assistant, I was the first call at 3 a.m. when something actually went wrong. Berkeley is where I learned to be the adult in the room — and that composure is a skill you can practice.
Recurring ideas from what I post — summaries, not standalone essays. The writing itself lives on LinkedIn.
Why the best candidates are gone in days, why we mobilized in hours, and why hiring is the one competitive lever an early-stage startup fully controls.
Going from around ten people to roughly thirty inside a year, and building each function the growth demanded — a little at a time.
Reaching for the tool first, automating the repeatable, and rebuilding the workflow as the tools keep changing under you.
Cold-messaging founders, choosing the thing that scared me most, and betting on the rooms where I'd learn the fastest.