Rise of the AI-first Employee

Welcome to the latest edition of The Sunday Prompt, where we explore the AI-driven shifts redefining work.

Startups have always been lean, fast, and resourceful. Now, a new hiring trend is taking shape: AI-first employees. These people are not just using ChatGPT to draft the occasional email. They are integrating AI into every part of their workflow, automating routine tasks, and amplifying their output in ways that were unthinkable just a year ago.

This shift raises big questions: Are AI-first employees the future of startups? Will AI fluency matter more than deep domain expertise? And how can those willing to adapt use this moment to their advantage?

Spoiler: this is not just a startup story. The trend is already gaining traction across the broader market.

Let’s dig in. 👇

A well-known investor recently posted a job listing for an “AI-first” Director of Finance.

Not just someone who knows their way around ChatGPT and QuickBooks. Someone who can automate bookkeeping, build sophisticated financial models, fine-tune LLMs on company data, and prompt their way through legal risk without racking up five-figure bills. One hire expected to operate at the scale of ten, without the burn rate.

That stopped me cold. You can easily imagine the same listing for marketing, engineering, operations, even HR.

And you should. This is where work is going. And startups are leading the way.

Startups have always been the bellwether for workplace trends. Leaner, faster, and first to adapt. The rest of the market follows. Early-stage companies are built on thin teams and brutal prioritization. Before AI, that meant outsourcing: fractional CFO, contract bookkeeper, outside accounting firm, external counsel, etc. Every function came with its own vendor, invoice, and lag time. It was fragmented. It was inefficient. And it got expensive fast.

I have spent most of my career building startups. This shift is not theoretical. It is already happening. I am not talking about hiring prompt engineers or replacing people with bots. I am talking about real professionals who know how to build with AI.

Engineers now use AI for intelligent code completion, static analysis, test case generation, and documentation. Marketers tap AI to boost content production, build campaigns, optimize SEO, and surface insights.

And finance? Have you ever met a startup finance director who is not in a perpetual state of frazzle? They’re always herding cats. Reporting, planning, compliance, investor updates, receivables, vendor oversight. Buried from day one. Overwhelmed and under-resourced, they rely on a patchwork team of contractors, consultants, and fractionals, none of whom have any real skin in the game. Coordination is a job unto itself. The work is a stressful slog. The bills add up.

AI blows up the equation.

That same finance lead, equipped with the right tools, can now manage more with greater agility and efficiency. Bookkeeping, modeling, board prep, compliance, even receivables. Assisted, not outsourced. The workload stays closer to the company. The cost stays down. The signal gets sharper. And the company maintains more control.

This is the edge. Not automation for its own sake. Not headcount reduction. Just better leverage.

Not every role requires AI fluency. A standout designer, a closer in sales, a world-class recruiter can still thrive on instinct and craft. But for most roles, AI fluency will separate those who can do more with less from those who get left behind. Startups are built by people who make a big impact with minimal resources. AI-first employees take that model even further.

Hiring patterns will shift. An up-and-coming, AI-savvy marketer who can cover a lot of bases will be far more attractive to an early-stage company than a seasoned VP accustomed to a team of specialists and a steady diet of contractors and high-priced agencies.

For mid-career professionals—especially those recently displaced by layoffs—this is a rare chance to reframe your value. To reinvent yourself. Mastering AI now is not yet a matter of staying relevant. It is a way to gain an edge in a tumultuous job market. The most enticing hires will be those who mesh domain expertise with AI fluency and use it as a force multiplier.

This advantage will not last forever. It may not last two years. Soon, it will be the baseline. But today, AI fluency is still a differentiator. The edge will belong to those who move early. Those who integrate AI into their workflows, reshape their roles around it, and build momentum while others are still in denial.

What begins in startups rarely stays there. And in typical AI fashion, what started as a post on X is already showing up in boardroom discussions, earnings calls, and hiring strategies. It is moving at the speed of light. AI-first talent is changing how companies of every size think about hiring, structure, and scale.

As has been said many times to the point of cliché, the future of work is being built in real time. Don't miss the moment.

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