Why CFOs Kill Your Deals (& What to Do About It) | Sales Hacker


Why CFOs Kill Your Deals (& What to Do About It)

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Does this question sound familiar…

“Actually, can you make this out to our CFO?”

You’re closing a deal and after sending the order form to your so-called champion, you learn that they aren’t the one signing. The fate of your deal now depends on someone you’ve never met. To make matters worse, today is the close date of this forecasted opportunity and your manager asks you when it’s coming in.

What choice do you have? “I’m waiting for the CFO to sign,” you say, opening a can of worms you weren’t prepared to address.

Once upon a time, we might have been able to move the deal forward without involving a Chief Financial Officer until later stages, if at all. But in today’s current economic climate, CFOs are highly skeptical of where their company’s money is being spent.

This is why multi-threading, asking genuinely curious questions, and selling value directly to the person signing the check are critical skills. It’s also why, when you don’t leverage those skills — CFOs kill your deals.

So, how do we keep the deal alive and ensure that CFOs are bought in from Day 1?

First, we need to understand why CFO’s kill your deals and then follow up with solutions on how to sell directly to them in the first place.

Let’s dig in.

Problem: They Don’t Even Know You Exist

CFOs, especially if they’re at a company large enough to have a CFO, focus on much larger problems than the products each of their departments are evaluating at any given time.

Just to name a few “casual concerns they are fairly preoccupied with:

  • How the possible economic implosion happening around them impacts profitability and cash flow
  • How to allocate funds so their company has enough runway to remain viable
  • Ensure all business operations and systems are strategically aligned
  • Reporting to investors (if applicable)

Unless you sell a product directly to a finance team or similar customer profiles, the team you’re selling to likely knows how busy their CFO is and dreads involving them in any product evaluation just as much as you do.

For this reason, and the preoccupation with aforementioned concerns, you aren’t on the CFO’s radar — and won’t be unless you ask to be. This is why, when they get that random DocuSign in their inbox, they archive it, move on, and indirectly kill your deal.

RELATED: Land Bigger Deals Faster by Selling Straight to the C-Suite

SOLUTION: Ask your prospect to set the table before it’s time to sit down.

What does that mean?

It means that beyond involving the CFO, all executives who would be responsible for the trickle-down effect of purchasing your product should have a seat at the table for any discussion.

As C-Suites become increasingly involved in purchasing decisions — as evidenced by the latest call insights from Chorus — it’s your responsibility to include them from the get-go.

The sooner they are involved, the sooner they can recognize the (positive) business impact to initiatives that they own as they continue to reinforce internal strategic alignment.

The CFO is only one of the key players involved in making sure that business strategies are aligned, which means they are one of the first places you should set at the table.

How do you invite them to the table?

Begin by genuinely asking your main point of contact questions about their company. You need to understand their business as well as you know your own.

RELATED: 10 Tips to Build Rapport Internally to Navigate Complex Deals

Listen for hints about internal structure, overall company goals, and any power lines (shout out to John Barrows) that indicate where your prospect sits in regards to the ability to spend company funds.

Once you have a legitimate understanding of these issues, ask your prospect when (not if) they should bring in their CFO and suggest that you at least meet them during your second or third call in this process.

**Cringe** That’s so early!

I know what you’re thinking.

“CFOs don’t care that much about being involved that early, and this will 100% slow my deal down and waste their time.”

False. CFO’s definitely care about how you’re spending their money. Also, no one suggested you waste their time. Did you plan on wasting it?

Now, let’s address that last criticism you’re holding…

“My champion will be insulted.”

Prospects love to think they’re in charge (and sometimes they are), but for the most part, your goal is to communicate that you’re going to help them navigate their organization and that you’ll personally make them look good in this process.

Try something like this:

“In my experience, our most successful customers are able to articulate the value their decisions bring to their company — which starts with building a healthy relationship with other stakeholders (beyond themselves) internally.”

With that, you (a) acknowledge this is their decision and that they are a key stakeholder, and (b) impress upon them how critical the part they play on the decision-making team is to their initiative’s success.

Problem: They Don’t Know What You’re Selling or Why It Matters

OK, so miraculously, either….

  1. That DocuSign you sent to the CFO didn’t get deleted, but now they want to know what the heck it’s for, or
  2. You have a true champion who was able to successfully involve their CFO in the evaluation

But you’re not out of the woods.

Chances are high the CFO will still kill your deal because they have no clue what you’re selling or why it matters.

Before you think you’re going to demo them into submission or pitch them six ways from Sunday until “it” finally clicks and they sign, please stop.

Imagine for a moment that you’re a Chief Financial Officer of a somewhat successful mid-sized company, and the world’s on the brink of a major recession. Not only do your responsibilities include some of the aforementioned concerns, but you may also bear the weight of layoffs if the company can no longer afford to keep employees.

Yes, the burden of individual employees being able to pay their bills and support their families during an economic downturn is now a big concern of CFOs. Whether or not they are able to offset this by avoiding layoffs is an entirely different topic, but hopefully, you see where this is going.

You know that amazing feature you were about to wrap a bunch of buzzwords around? If you can’t tie it directly to how your product will make a company real money, real fast (in preferably 2–3 sentences), you need to rethink your strategy.

If there is any inkling of “too good to be true” without clear, objective, measurable data, the CFO will kill your deal.

RELATED: When You Should NOT Sell To The C-Suite

SOLUTION: Do your research. Don’t pitch. Keep it short. Provide an action plan.

Time is a limited resource for C-Suite executives. Don’t waste the time you have with them by asking questions you could have found the answers to on Google or in their 10k.

If possible, use other employees involved in the deal to get more information on specific metrics and company initiatives that are the main focus for the CFO (bonus points if you ask how they like data represented).

Use this information to create one or two slides max. One slide should be a high-level explanation of the monetary value your product will provide and the risk it will mitigate, and then a second slide should detail an action plan — not only for implementation of the product, but also reinforcement of use.

The action plan (best practice would be a mutual action plan) is critical here, because CFOs assume a lot of risk when a product becomes difficult to implement or, if left unattended, unwieldy. Solutions can quickly become problems when they suck up time and resources, or require extra capital to keep them working.

CFOs are rarely the end users of your product, so a demo in that scenario won’t be useful. Stick to your slides and sell value.

By putting these two slides together you should be able to concisely answer “What are you selling and why does this matter?” through the lens of the CFO you’re speaking with.

One more thing…

When you present this, avoid asking “does this make sense?” Instead, leverage a less pedestrian line of questioning:

“How are you thinking about this product in terms of [insert specific business strategies that you uncovered in earlier conversations]?”

Ask clarifying questions to crystalize how they are conceptualizing the value of what you’re selling and recognize if they can articulate why that matters to them.

Problem: They Are Dissuaded By Risk Or Anyone Who Presents Risk

If you’re currently working at a mid-sized or larger company (300+ employees), take a look at your CFO’s calendar. You aren’t the only one vying for their time and attention. Amongst the calendar blocks that you see, there are many you don’t see — all of them competing priorities.

When you talk to the CFO, you need to be fully transparent about the risks and downsides of implementing your solution. You also need to have a well-thought-out plan for mitigating these risks.

If you don’t, someone else will. An internal blocker is someone with the CFO’s ear who may have business goals the CFO deems more important. This person has their own agenda, and they’ll protect it at all costs. They will often highlight the risks of moving forward on your deal, so their initiatives don’t get derailed.

If you haven’t completely flushed it out the risks, or if an internal blocker gets in the way, the CFO will kill your deal.

SOLUTION: Know the business like you work there.

It’s critical that you understand the prospect’s business (and their people) as if you work there. More often than not, when you pitch a CFO on your product, you inspire them to check in on whether there are more cost-effective solutions — or whether a different team you haven’t consulted is solving a similar problem.

Yikes! Did you just create a hiccup in your deal that you may have otherwise avoided if you didn’t involve the CFO?

No. That scenario was going to play out regardless.

We’re solving for how it plays out, and whether or not you were in control of it. The risk and all other options associated with mitigating that risk were going to be on their radar once they got that DocuSign. But now, you’re sitting at the same table and have some control over that conversation instead of going straight to archive.

Remember, when we talked about inviting everyone to sit down? Well, hopefully you’ve done that and gotten to know them well. You can recall their motives, opinions, and understand whether or not everyone is on the same page.

Identify stakeholders that might volunteer to present risk to the CFO, be tasked with finding alternatives, or who highlight reasons not to move forward. Partner with these stakeholders early on and be transparent.

CFO’s are data-driven and analytical. They expect a similar problem-solving approach from their employees, whom they trust.

Whenever possible, build a business case for the CFO and their team. Give them actionable insights that show you are the least risky option with the highest return on investment.

If that’s not true, don’t bend the data. Be upfront and play to your strengths. After all, a good salesperson sells a product, but a great salesperson sells a solution.

If you provide more problems than solutions for a particular company and CFO, it’s better to get to a good no than a bad yes.


At the end of the day, Chief Financial Officers are not the Darth Vader of your prospect’s galaxy company.

In fact, it’s quite the opposite.

CFOs have a duty to ensure the viability of the companies they work for — including the job security of the employees working with them.

Align yourself with their business goals. Demonstrate your ability to be a true partner. Convey actionable insights concisely. And don’t leave anyone out of the process.

If you can execute on those 4 things, you will create a champion in the CFO as well as their teams, ensuring that your deal stays alive.

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