5 Ways Finance Can Be More Helpful to Sales

Most CFOs I know didn't get into finance to chase receipts.

But that's where the time goes. Reviewing expenses that should have been blocked before they happened. Closing books that take longer to close than the month took to live. Approving spend that should have been approved automatically three days ago.

That's not a people problem. That's a systems problem.

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Here's something they don't tell you when you become a finance leader at a startup… People start handing you problems that don’t really have anything to do with finance.

Congrats! You’ve been anointed the company’s patron saint of maths.

It’s what happens when you're the most analytically gifted organism on the executive team.

The question I get most often is how to apply your talents to assist sales.

Said another way:

It's not an obvious answer for many finance folks who were trained on the merits of gaap accounting. And many of the answers out there on the interweb are super woo woo and focus on “being a team player” and vague platitudes about trust.

Those are the B cuts. The stuff that Drake put on the second and third albums he just released.

So I called my friend Paul Stansik for something that slaps.

Paul's firm, ParkerGale, has been buying B2B software companies from founders for ten years. He spends his hours nestled uncomfortably between the sales and finance leaders at every portco.

Hilariously enough, not only has he seen this movie, he’s currently acting in the movie. When I interviewed him on the pod he was the “acting VP of Sales” for one of his companies and had to cut the recording short so he could go run a demo (LMAO).

Before he went to close that deal, here are the five things we landed on.

There are way too many companies out there that speed past the annual budgeting process. They treat it as a tax, or a toll booth you pass.

That's a miss, because the budget is the one moment in the year where you get to pull the leadership team into the same room and force agreement on:

Paul's #1 coaching tip here is to segment the top line.

In other words, don’t plan bookings as a single, monolith of a number.

Cleave it by product, by region, by motion (pick at least one). This way, when something's off three to six months later, you'll have at least the scaffolding in place to dissect. You won't be arguing in a non descript Boston WeWork conference room about whether it's a Europe problem or a new product problem or a sales cycle problem (sorry, that was a personal flashback).

Most sub-$50M companies treat the top line as one big lump. Then when it underperforms, they spend two weeks reverse-engineering what broke, which is kind of impossible if you weren’t tracking it in segments to begin with. Very difficult to put the toothpaste back into the tube.

Now, to be fair, the pushback I often get on this is some version of "but we don't actually know what Asia is going to do."

Right.

Neither did I when I was running FP&A at a $30M ARR business with one rep in Israel selling into the entire land mass of Asia (we used to joke it was Jimmy and a trick duck selling $4M of code scanning tools. Approve my man’s international phone bill, no questions asked.).

We put a number down with some dimensionality to it anyways. It was wrong. But it got better with time as we collected more data points in the coming quarters. And we had something to base the conversation around in that WeWork conference room.

Look at your sales leader's calendar this week. It's chaotic in a way that you, as a finance person, will find incredibly disorienting.

Paul filled me in on his current schedule as he subbed in as the sales leader:

The muscle to move a deal forward and the muscle to forecast accurately are completely different muscles. One is conversational and persuasive, while the other is analytical. Most sales leaders are great at the first and still building the second as they mature in their careers.

Your job is not to add pressure, but to serve as a pressure valve, helping to figure out what’s going on.

My friend Dave Kellogg has a line I think about often:

You don't get to decide what's helpful. They do.

Here's what's not helpful:

Maybe you get a sweaty, impromptu causal answer. But you def don’t lay the foundation for a more accurate forecast next quarter. I’d bet dollars to donuts it’s going to get sandbagged to shit because of the way you treated them.

What is helpful is whiteboarding out the forecast model with your sales leader before there's a number they’re asked to defend (and the CEO is in the room).

Once again, you’ve gotta do this before you ask them to defend an outcome. Imagine if I asked “how big is this desk”, but I got to make up my own ruler that’s used in the measurement? Not fair.

Pull up the org chart of a $20M revenue company.

Where is there excess capacity for analysis? It’s probably not on the sales side.

One of the highest-return uses of that excess capacity is pointing it across the aisle. Activities may include:

Your best FP&A analyst will say yes to this work if you frame it as development, rather than a loan (no one likes to be pawned out).

The other component to lending a hand with metrics is to make them mean something in the sales team’s OWN TERMS. That means tying the metrics back to what they see in the course of their daily lives.

I used to drone on about net dollar retention in QBRs. Every quarter, I gave my TED talk.

Until one day the SVP of Sales asked me in a weird way why it had moved, and I realized he had no idea what the four levers underneath the metric even were. So I stopped what we were doing and walked him through all four. It took like 60 minutes, but during the next meeting, he was citing one of the levers and tying it back to how we were hiring CS reps versus implementation engineers. He'd internalized it and was now playing it back to me. A beautiful thing if you’ve ever seen it.

TBH, the original gap was my fault. Nobody had ever taken the time to explain what was in each bucket of NDR.

Make the metrics mean something the same way you make the budget mean something.

Paul puts it this way:

There's a moment in a deal where momentum dies, and it’s often not the actual sales process.

Then everything slows down like the Quaalude scene in Wolf of Wall Street.

For two weeks, the quote bounces around in purgatory. The customer sits on their hands, wondering if you’re serious people.

This is where finance leaders should poke their nose in. The front end of most commercial processes is wildly over-engineered relative to the back end. You spend six months building a sales motion that gets people to fall in love with you, and then the proposal is a Word doc somebody copied from a deal in 2021.

(You ever save down a version of a document and realize in the meta data that the original author doesn’t even work at the company any more?)

There is nothing worse than sprinting toward a verbal yes and then realizing it's going to take two weeks to get the guy a quote. It’s a shitty dénouement for the sales rep.

Paul has a phrase for this whole bucket: selling with certainty. The further into the cycle you go, the scarier it gets for the buyer. Anything in your quote that adds doubt is poison.

Every one of those gives the buyer's brain a new reason to pause and potentially hit the eject button.

Here's a move you can steal - we were a hypergrowth pre-IPO company slugging it out with the public guys for enterprise logos. We weren't necessary a lock to be there in 5 years, at least from many outsider standpoints, given the way startups come and go and the sheer amount of cash we were burning. So every customer above a certain ACV got a one-page letter from the CFO bundled into the quote.

It was written in first person, and in plain English, and even included a head shot to show we had a real CFO. It went something like this:

It killed a major objection the sales team knew was there, but was often unsaid: is this company going to exist long enough so I don't look like an idiot for buying their product?

Because at seven-figure ACVs the buyer is risking their own career as much as their budget. Remember - no CFO ever got fired for buying IBM. And yet, the proposal almost never gives them anything to point to when their boss asks why they picked the smaller vendor.

OK, I said no woo woo shit. But give me one point out of the five to be in my feelings. None of the above happens unless the two of you trust each other.

If your sales leader thinks you're a jackass who’s asking about the forecast because you're building a case to fire them, you'll never have a real conversation about anything. The forecast you get will be coooooked.

Paul says it best:

Most of what holds a business back is small, ugly stuff nobody wants to verbalize.

The fastest way to break down that barrier is to be relentlessly curious about someone’s business. And remember, being curious means asking questions and listening; it’s not explaining what you THINK they should be working on.

I've interviewed a few hundred CFOs at this point on my podcast. And the best ones have higher EQ than IQ. They know math, but they really, really know people.

Because you can build a big, bad, beautiful budget and still be a real shit finance leader. The job, in the end, is about pulling things out of dark corners and into conversations so the management team can resolve them.

Remember: Your sales leader is allocating people (and dollars) in pursuit of a risk-adjusted return on capital. That is what’s really underneath the quota’s you’re deploying. And as a finance leader, you gotta be a human to get the most out of those humans.

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Tune into my discussion with Paul, PE renaissance man and author of newsletter Hello Operator

Wishing you an only moderately sandbagged sales forecast,

CJ