🚀 Hack Weeks, Labor Markets & Annual Planning in 2026 | The AI CFO

As we head into the thick of annual planning season, this week's newsletter examines how AI is reshaping the fundamentals of business strategy. Playbooks that worked as recently as 3 years ago are being scrapped, from how companies get funded to how work actually gets done.

We're in a genuine platform shift. VCs have thrown out traditional scaling metrics. The automation vs. augmentation divide is restructuring labor markets in real-time. Yet the core finance discipline of reconciling ambition with reality remains critical.

The irony? AI makes strategic planning both harder and more important. Harder because we're operating in extreme uncertainty. More important because companies that treat this as a 10-year organizational experiment, while maintaining financial discipline, will pull ahead.

This week's reads offer practical frameworks for navigating that balance: where to place your bets, how to think about talent, and why your annual planning process matters more than ever.

I've spent my entire career in startup finance but there was always something calling me to be a software developer. Turns out, I already thought like one.

At airCFO, I built financial models and reporting tools that pushed spreadsheets to their limits. I knew they'd work better as software, but I didn't know how to code. Then AI-powered coding tools changed everything.

This year, I ran three "hack weeks" — clearing my calendar each time a new tool dropped to build software. Here's how they went:

April: Built a prototype that never shipped

July: Got real tools into production

October: Built tools I use daily, including one that gives our team CFO-level financial analysis superpowers

If I can do this after years of failing to learn code, what could you build? Read the full story on my Substack.

The Fund CFO: 2025 AI Landscape & Venture Returns

AI has fundamentally shifted venture capital expectations and deal-making norms. The explosive growth of AI companies has made traditional scaling metrics (like T2D3) obsolete, leading VCs to abandon conventional playbooks.

Why it matters: This shift directly impacts how we should think about fundraising, valuation expectations, and competitive positioning. If you're at an AI company (or any tech company competing for capital), the bar for "success" has been dramatically raised.

Benedict Evans: The AI Presentation

Benedict Evans is an analyst whose superpower is viewing current tech trends within the context of prior cycles. In this podcast, he recaps his annual AI presentation, arguing that AI represents a major platform shift on par with the Internet, mobile, and computing (each of which reshaped the world in unpredictable ways).

Why it matters: Finance leaders need to make multi-year bets amid maximum uncertainty. Build flexibility into your systems to avoid both utopian over-investment and dismissive under-investment. Benedict's advice: don't invest heavily in infrastructure that will be table stakes in 18 months. Focus on product differentiation and customer experience where sustainable advantages actually live.

The Leverage: AI Job Disruption is Here (and Very, Very Real)

A chasm is opening between roles that will be automated versus augmented. Early data suggests companies are using AI to raise aspirations rather than cut headcount, but leverage flows disproportionately to senior talent.

Why it matters: If junior roles get automated away, the traditional "hire junior, train up" pipeline breaks. Every company must evaluate which roles face automation versus augmentation. We're thinking a lot about this at airCFO recently — future-proofing our advisory team is a top priority for 2026.

Only CFO: Annual Planning Guide

Building a beautiful financial model is table stakes within the annual planning process. The real value comes from driving alignment between department leaders and reconciling top-down vision with bottom-up execution. Based on the other pieces in the roundup, 2026 may be the most important annual planning cycle to get right.

Why it matters: This is a good reminder of where finance leaders actually add value. It's not the model, it's facilitating the Tops Down/Bottoms Up negotiation, managing the politics, and maintaining buy-in through multiple rounds.

That's all for this edition of The AI CFO - we'll be back in your inbox every other week with more musings on the future of AI-powered finance & operations. Please reply to this email directly with any feedback/suggestions/just to say hi!

Cheers,

Alex Wittenberg, CEO @ airCFO