Navigating the CFO’s Mindset: What Every Seller Should Know

Jeff Epstein

Here are some of the key principles sellers should note when engaging financial decision-makers in large enterprises.

In the high-stakes realm of B2B enterprise sales, understanding the decision-making nuances of a CFO can significantly influence a deal's trajectory.

My recent roundtable event on this topic in the Strategic Sales Network helped demystify some of the key principles and considerations that often guide financial decision-making processes in large enterprises. Here are some of the main takeaways from that discussion.

The primacy of ROI

In my years as CFO, ROI was consistently the most compelling factor. When someone proposed a significant investment, like a software purchase worth a million dollars, the potential return on this investment was always my first concern. If you are positioning a product or solution to a CFO, or if you know the CFO will need to weigh in on the purchase (and usually, this is the case) anticipate this scrutiny.

So what kind of ROI would tip the scales for me? Personally, I wouldn't consider investing in a project unless it claimed to offer 10:1 returns. Here’s why:

  • Money talks. Most CFOs aren’t going to invest a million just to make a million back—or at least, we won’t prioritize a project with those numbers. I’d much prefer salespeople come to me with the potential of $10 million in annual savings for my $1 million invested. That sounds like something that delivers results.
  • Optimism often skews projections. I expect sellers to be wholly confident in their solutions. And I expect them to give me best-case outcome scenarios. That’s why, if a seller gives me 10:1 ROI projections, I'll realistically halve that estimate to around 5:1. My experience has taught me that’s usually the more reliable number, and knowing I could still count on that level of return felt comfortable.
  • Jeff Epstein is an Operating Partner at Bessemer Venture Partners and a Lecturer at Stanford University. He specializes in B2B Software, Marketplaces and Vertical AI. He serves on the Boards of Directors of Twilio, Okta, Kaiser Permanente and other companies. He served on the Board of Priceline/Booking Holdings for 16 years, as it grew from $1 billion to $80 billion in market value. He is the former Executive Vice President and Chief Financial Officer of Oracle, one of the world’s largest and most profitable technology companies, with a market value of over $150 billion. Prior to joining Oracle, Jeff served as Chief Financial Officer of several public and private companies, including DoubleClick (sold to Google), King World Productions (sold to CBS) and Nielsen’s Media Measurement and Information Group. Earlier in his career, he was an investment banker at The First Boston Corporation. He holds an MBA from the Stanford University Graduate School of Business, where he was an Arjay Miller Scholar, and a BA from Yale College, where he graduated summa cum laude, Phi Beta Kappa.

Connect with Jeff

How prioritization pans out

I know sellers are taught these days that ROI metrics won’t get enough traction to get your foot in the door—and maybe that’s true for initial outreach. But make no mistake: ROI is still vital to getting CFO buy-in. It’s not just about the promise of value; it’s about where your project falls on our to-do list. When we have hundreds of solutions to evaluate, we have to rank them somehow.

At Oracle, we regularly juggled 350 IT projects at once, each evaluated by weighing its estimated value against its cost. As I mentioned, projects with compelling returns, especially those promising tenfold ROI, naturally took precedence. Many initiatives, even with a seemingly respectable two-to-one ROI, would be deprioritized. Thus, the competition for top spots was fierce, emphasizing the significance of a standout ROI.

Of course, while ROI was the north star on approximately 80% of our go-forward decisions, there were still situations where other factors took the forefront. If Larry (Ellison) wanted a project to move ahead, for example, we moved it ahead regardless of the numbers. Bear in mind, then, that things like legal mandates, strategic imperatives, or top-down directives can always supersede regular evaluations.

Beyond the numbers: Testimonials and references

Once a project passed the ROI scrutiny, the next step was due diligence. References and case studies came into play here. We'd probe into not only the software costs but the entire gamut of associated expenses — from implementation and maintenance to IT support and training.

As a seller, you can help prepare for this step by lining up those case studies to the best of your ability. But keep in mind, we’re looking to get an unbiased view. Even when sellers give us names to contact, we'll seek out unsolicited user feedback, both positive and negative. That’s how we know it’s real.

Implementation strategy: Phasing & time-to-value

How a solution is rolled out can be just as critical as the solution itself. Why? Because time-to-value is another critical metric we evaluate. CFOs always want to know: How long until the solution starts yielding tangible benefits post-implementation?

At Oracle, we'd typically test a solution with a subset of users before a full-scale implementation. This isn't about a short trial but a strategic phased deployment to mitigate potential issues. This phased approach would help us determine the feasibility of the project and a realistic timeline to achieving our expected results.

The budget reallocation strategy

One invaluable lesson I learned from Larry was the emphasis on reprioritization rather than always seeking additional budget. When additional funds were sought for a new initiative, he would challenge those making the requests to find room within their existing budgets. That’s my approach now, too.

In other words, if you’re selling to someone who already has a $50M budget, don’t expect their CFO to simply hand over more money to invest in your solution. If they ask me for $2M, I’ll tell them to find the $2M to cut somewhere else. This approach enforces discipline and strategic thinking about real priorities. As a seller, then, you need to help your champion prepare to make these tough decisions.

Sales efficiency & the rule of 40

For SaaS businesses, understanding the balance between growth and profitability is crucial. This is where the 'Rule of 40' comes in. If you're targeting the enterprise market, particularly CFOs, understanding this rule can be a unique differentiator. In simple terms, the sum of a company's growth rate and profit margin should aim to exceed 40%. A firm grip on this metric is not only indicative of a company's health but also its strategic maturity.



To succeed in B2B enterprise sales, especially when engaging CFOs, a deep dive into their priorities and mindset is essential. It's less about spotlighting product features and more about unmistakably demonstrating tangible value. With this insider view, you're better equipped to navigate the intricacies of the CFO's decision-making landscape, giving you an undeniable competitive edge.

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