Quick question: If you were building a finance team from scratch in 2026, would your first hire be a controller?
That's one of the topics I'll be debating live on stage at Abacum's What-If Summit on April 9 in NYC. I'm moderating a session called Buy, Sell, Hold: What Survives the AI Era? I'll be pressure-testing finance conventions live on stage - annual budgets, spreadsheet dependency, whether the best CFOs came up through FP&A or accounting - and the audience votes in real time with actual paddles. Buy, sell, or hold.
Beyond my session, OpenAI's Head of Finance is keynoting on how to operationalize AI responsibly, and there's a boardroom simulation that walks through real AI-driven decisions.
The event is a half-day built for CFOs and FP&A leaders who are past the "should we use AI?" conversation and into the "how do we actually do this?" one.
Spots are limited - See you there!
“I think the best Sales Leaders could have been CFOs”
Who’s the master resource allocator at your company?
It’s a trick question.
It’s the guy / girl holding a bag.
In this case, Will Smith’s character was holding the medical equipment
At tech companies, the majority of the costs are people, and the most concentrated (and expensive) group of people are sales folks.
I was speaking to Sam Jacobs, founder of the professional GTM network Pavilion, about what separates a ‘good’ sales VP from a ‘great’ one. He’s worked that role, hired for that role, and seen the good and bad as a CRO.
He didn’t hesitate:
“They can connect the company’s overall finances to revenue.”
In fact, he thinks they could credibly have had other jobs in the org besides running revenue. They just happened to like the game, the competition, the quick feedback loops, and the scoreboards that come with being on the front lines each day. But the best VPs of Sales, the best CROs, understand finance.
To go a level deeper, “understanding finance” manifests itself in how they think about the value of a dollar.
They’re not wasteful with company capital.
They don’t try to hire into a lack of demand.
They realize they’re managing a roster of players who subsidize the existence of everyone else in the org.
They’re not building fiefdoms for the sake of it.
For a sales leader, contrary to popular belief, your job is not to look like you played linebacker at Bucknell and recruit a bunch of lacrosse players. You are a capital allocator, and your job is to earn a return on behalf of that capital that’s deployed, one that will meet the parameters of the business that you work for. It’s not to hire people. It’s to produce results with the people you hire. There’s a subtle difference.
Sam teaches a class at Pavilion called “Developing a Theory of Enterprise Value.” The point of the class is you need to understand numbers, because numbers tell the story of the business in a different language. And the C Suite speaks many languages. They can talk deal specific anecdotes with BDRs in the bull pens, and switch to talking about long term risk adjusted bets on the product roadmap.
As a CFO, you know that hiring is a byproduct of your capital allocation strategy. This may be lost on VPs of sales who have worked at good companies with solid product market fit, and thought the company was successful because they showed up strong on the last day of the quarter and ran spiffs.
In fact, some may not even understand that spiffs have a cost to the organization that needs to be contemplated. That spiffs can make a fully blended commission rate balloon from 18% to 25%, without any incremental value. Further, they don’t understand that we can’t just pay 20% on every deal to every rep. That there’s There is a gross margin profile and lifetime value calculation that goes on, which determines how we reward the team for the quality of the annuity streams we lock in.
The best VPs of sales understand:
What we can pay on a deal is a function of the product’s gross margin and the customer’s expected lifetime
The sales supporting human resources are linked in a mathematical formula to our underlying deal sizes and deal velocities.
We can’t “make it up in volume” if the unit economics don’t work.
The best VPs of sales connect finance to revenue. They understand that it’s all connected, and we aren’t budgeting for sales in isolation to the rest of the org.
In fact, in any position, whether that be sales, engineering, product… you are going to be far, far more effective as a leader if you can speak the language of the P&L
Now, I’ve railed on a certain class of sales leaders for a few too many words. Let me make it clear: there are stupid CFOs too. So many.
For example, if I’m building a financial model where my primary input is how many salespeople I hire, and that just isn’t the reality of how the company generates demand, I’m part of the problem for sure.
In that situation, I took the easiest route to building a model, without thinking through the physics of how we sell and to whom. Because, you know, building a demand driven waterfall is really hard.
So it absolutely goes both ways.
The best sales people understand finance.
And the best finance people understand sales.
And you can never “make it up in volume” if you’re selling a product at a negative gross margin.
Mostly Talent - Finance Recruiting
Mostly Talent is actively placing a Director of Strategic Finance, Controller, FP&A Manager, and VP of IR across Series B through Pre-IPO companies. These searches move fast.
If you're hiring, work with us here.
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