📬 Treading water: How tech CFOs can survive the AI squeeze

We take responsibility for getting your books right

Quanta's SF-based SaaS accounting team closes in 5 days or fewer, working directly in a platform where every transaction and judgment call stays connected, drillable, and traceable.

When the business asks what changed, you have the answer in seconds.

See how Quanta works

Thanks to everyone that joined the secret screening of the premiere of The Use Case. It was a lot of fun! Onto this week’s Mailbag:

Is there a knot you need untangled? Hit me up (anonymously if you wish), and you might see me answer your question below

👉 Send me your questions by filling out this form.

Now, on to today’s Mailbag.

We’ve got some great topics. Here’s what’s on tap:

Now, let’s get into it.

SaassyCFO from the US asked:

With AI advancing daily and SaaS models under threat - where do Tech CFOs turn?

SaassyCFO, I’ve had this question in a dozen different forms over the last few weeks. And almost never before that.

So this is clearly on people’s minds.

Full disclosure: I’m not a tech CFO and never have been. So whether I’m the right person to answer this is up to you. But I can give you an outsider’s perspective and think it through from first principles.

First up, I don’t quite buy the “Saaspocalypse.”

The loudest version of the argument says AI lets everyone vibecode their own software, so we won’t need software companies anymore.

Maybe in some niches.

But look at our own vertical; software for CFOs. Sure, in theory we could build our own tools. In the same way we could do our own plumbing or cut our own hair.

That doesn’t mean it’s a good idea.

My belief - for CFOs at least - is that when the dust settles, AI will look like a new generation of better software. Domain-trained, with guardrails, embedded in workflows, layered with company context. Cleaner data. Faster reporting. Smarter analysis at your fingertips.

And the margins of many lazy incumbents are so fat there’s still plenty to attack.

While that will mean a lot of winners and losers, to the layman CFO like me, that just looks like ‘different software.’

So at a market level? There’s still a ton of software to be built and sold. Isn’t it just a new era of the same game? Your job is to pick the winners and place your career bets accordingly.

Second, we are witnessing the greatest capital allocation event in history with the data center buildout.

That cost has to land somewhere. It will first flow into foundation models, then into applications, then into customers.

It’s not even obvious yet whether AI will be cheaper than humans at scale in every context. I suspect yes, eventually. But maybe not as quickly as LinkedIn thinks.

So before you panic about SaaS margins collapsing overnight, remember there are massive infrastructure economics underpinning all of this.

Third, lean into your advantage.

Tech CFOs tend to be more tech-native. You’ve worked in younger companies. Less legacy ERP baggage. You’ve seen modern tooling, modern engineering, and modern GTM execution.

That’s a strength.

It should mean you climb the curve faster on what the future CFO stack looks like. You’ve seen what great product and implementation discipline looks like, so lead that inside finance. Use that as your differentiator.

Finally, there is the choice to shift into a different vertical. This won’t be a popular opinion, but being a software CFO has, broadly speaking, been CFO-life on easy mode.

High gross margins. No inventory. Negative working capital in many cases. Clean revenue models. Capital-light.

Everything that made SaaS phenomenal for 15 years is what’s making you feel vulnerable now:

If the software is good enough. It gets funded. Then it scales. If not, it dies. Product and GTM are what make software businesses, not finance.

Finance pros who jump from SaaS into physical product businesses often underestimate the leap.

Inventory isn’t an accounting quirk; it reshapes the entire economic cycle. And if the SKU count of complexity is high, it can be really difficult to actually know why your performance is the way it is. Product mix buries performance issues, working capital is a strategic weapon, and forecasting complexity explodes.

There are more levers. More surfaces for things to go wrong.

And everything rolls downstream. If it’s harder to understand, it’s harder to explain. If it’s harder to explain, it’s harder to fund.

So moving out of tech would be an option. There are plenty of incredibly smart software CFOs who can and have made that leap. But don’t kid yourself, it’s a leap.

So where do tech CFOs turn?

Simple, you adapt.

AI will be like an earthquake through the software market, unquestionably. Use your insider understanding of the sector to make sure you jump on the back of a winning horse.

TLDR: The SaaS world is changing, not dying. AI will create new software economics, not eliminate them. Lean into your tech-native strengths, be thoughtful about where you place your bets, and don’t underestimate how different life is outside software.

Jack from the US asked:

I was CEO of a group of affiliated businesses and was granted sweat equity in one of the operating LLCs. We are currently under LOI to sell the operating entities as a group.

Over the years, when certain entities were tight on cash, the parent company advanced funds and booked those as intercompany debt. Some entities that I did not have equity in were later shut down.

Now, during the sale process, the majority owner has consolidated the intercompany debt from the defunct entities and allocated it to one of the active operating entities. Yup, the one in which I hold equity.

If that debt is repaid at closing, it could materially reduce or eliminate my proceeds.

Additional context, I filed an 83(b) election when I received my equity, so I have already incurred tax liability. If the reallocated debt wipes out my sale proceeds, I would effectively receive nothing while still carrying the tax burden.

I still work for this individual in another business, so I need to approach this carefully. Should I just shut up and be grateful I even got any equity in the first place, or do I have a right to be concerned?

If so, any tips on how to approach the conversation?

Jack,

This is pretty complicated, so you need to take any 10,000-foot advice like this with a pinch of salt. If ever there is an example of the devil in the detail, then this is it.

That said, at face value… it does sound like you got f*cked.

This wasn’t a lottery-ticket, it was sweat equity in exchange for real work. You’ve already taken tax risk. So no, you shouldn’t just shut up and be grateful you were “given a shot.”

But, and this is important, that doesn’t automatically mean malice. It could be a clumsy or overly neat attempt to clean up the group before the sale. These things often get “simplified” at the top level without fully appreciating second-order consequences.

If I’ve understood correctly, there’s a majority owner at the top of the structure who effectively called this consolidation shot. So you need to surface a conversation with that owner.

I would structure the conversation like this:

That framing does a few things:

If they’re reasonable, this is fixable. There are multiple ways to true it up (side letter, closing adjustment, separate settlement, etc.).

If they’re not reasonable… then you’ve learned something very important about who you’re working for.

TLDR: No, you shouldn’t just shut up. Frame it as an unintended consequence of a transaction clean-up, explain the economic and tax impact clearly, and ask to be made whole in a fair way. Don’t go in guns blazing.

Rodney Trotter from the UK asked:

I'm a fractional CFO based in London. Thanks to the brilliance of the UK education system, I was allowed to drop all writing subjects — including English language and literature — by the time I was 16.

As my role has become more writing-based (board updates, investor relations, outreach, and fundraising), I've started to feel my skills are below where they need to be, and it takes more effort than it should.

I'm a creative thinker — for an accountant — but I struggle to get my thoughts onto paper. Using LLMs makes it easier, but it isn't improving my underlying ability. How would you recommend I develop my writing skills?

I love this question, Rodney.

As you’ve probably read before, I’m a big advocate of CFOs leaning into writing as a skill. The truth is, most CFOs are bad writers, so you aren’t alone. Where you are unusual, though, is in recognizing it.

CFOs who can’t write probably don’t communicate well more broadly. Good business writing is about organizing your thinking so it can be shared with others. If you want to be impactful, what could be more important than that?

Being able to persuade people and think clearly through the written word has probably been the single most valuable skill I’ve developed in the latter part of my career. It unlocked outperformance in crucial 50:50 moments; in the boardroom, with investors, in high-stakes discussions.

It also happens to be the skill that unlocked this whole content adventure for me.

The good news is that some long-forgotten academic foundation in English isn’t important. In fact, it’s mostly counterproductive.

The skill you want to study is copywriting; the art and science of persuading people with writing. The other good news is that the books on this are (by design) very easy to read.

And the final piece of good news is that pretty much everything you need is in this post.

(Along with a few book recommendations.)

Happy writing.

TLDR: Writing for impact is very different from the kind of writing you studied at school. You probably even need to unlearn a thing or two. Study copywriting; it will help you get up the curve quickly. Clear writing = clear thinking.

A few of the biggest stories that every CFO is paying close attention to. This is the section you might not want to see your name in.

You probably cut your teeth on the ground floor of finance; reviewing bank recs, pulling data, chasing debt. It’s not fun, but it does give you a foundational understanding of how things work. I know I’d have been a worse CFO without my start in audit. So, assuming most of that entry work is abstracted away to AI in the future … how do the next generation of finance pros build the same foundation?

Here’s a CFO who’s spent 2.5 years clearing his name in a fraud case. Good quality audit trails, files and notetaking has never been more important.

Spence Neumann is laughing all the way to the bank with a $2.8 billion breakup fee in his pocket, proving that sometimes the best deals are the ones that never happen.

ICYMI, here are some of my favorite finance/business social media posts from this week.

Let me know what you thought of today’s Mailbag. Just hit reply… I read every message.

Last weekend’s Playbook kicked off a new series on dealing with CFO tech debt (and a rant about the ERP industrial complex).

And we tackled the sticky question of whether the CFO’s role has gotten too big in this week’s Boardroom Brief.

Disclaimer: I am not your accountant, tax advisor, lawyer, CFO, director, or friend. Well, maybe I’m your friend, but I am not any of those other things. Everything I publish represents my opinions only, not advice. Running the finances for a company is serious business, and you should take the proper advice you need.