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Should I ditch my Fortune 500 job for a faster path to CFO?
Plus: What’s keeping execs up at night in 2025, according to Forbes
Wassia Kamon
April 30, 2025
My take on business news stories through a CFO lens to sharpen your strategic thinking and executive brand. Plus, off-the-record career lessons and Q&A, every other week.
Welcome to the first edition of The Diary of a CFO Newsletter!
I wanted to start with a question many finance leaders often ask themselves:
Should I stay in this stable role, or take a leap that could get me to CFO faster?
It came up recently in a conversation I had with a Fortune 500 FP&A director and this is what he told me:
“Wassia, if I leave my Fortune 500 FP&A job for a smaller company now, I know I could become a CFO faster. But if I stay 5 more years at this company, I’ll unlock a huge retirement package. What should I do?”
Before we get into that, here’s what’s inside this edition:
Let’s dive in ⤵️
What This Tells Us:
The days of building the "perfect" plan and executing it flawlessly are over.
In 2025, leadership means building flexible plans because rigidity is a liability.
What I’d Be Asking as a CFO:
Where are we most exposed?
If tensions escalate, which line items in our budget are most at risk?
What assumptions are baked into our financial model that no longer hold?
Have we quantified the financial impact of potential tariffs on our cost structure?
What I’d Be Doing as a CFO:
Challenge Supply Chain to review our supplier network through a geopolitical risk lens, not just who offers the best price.
Work with the COO/Operations Team to map out our top 3 operational risks and pressure-test our response to each
Revisit cash buffers, covenant headroom, and borrowing capacity
Over-communicate with the board and the leadership team to discuss what needs to shift in our current plans
Pro Tip:
Set up Google Alerts for your company and a few key competitors and customers. Have them delivered every Monday morning. This simple habit helps you start the week thinking bigger, with the industry and your market positioning in mind.
 | A deep dive on how to do more strategic work when you feel like like you are stuck in the weeds. |
Off The Record
Question:
“If I leave my Fortune 500 FP&A job for a smaller company now, I know I could become a CFO faster. But if I stay 5 more years at this company, I’ll unlock a huge retirement package. What should I do?” - Married man with kids
My Answer:
👉 Don't quit!
Instead, build your CFO resume outside of your day job.
Speak at conferences.
Join the board of a nonprofit or association.
Advise a small business, a local startup or a PE firm (even if it is for free at first).
That way, you're positioning yourself for the CFO seat without walking away from the financial upside you've already earned.
Moving between company sizes is a growth hack I have used myself and also teach in my leadership bootcamp.
You would go between Big → Small → Medium companies…
The advantage is that anytime you move from large organizations to smaller ones, you get broader responsibilities. And a smaller organization would welcome you because you can help them implement better systems and workflows to scale. So, it's win-win.
Within 2-4 years, when you return to a mid-sized or larger org, you will be seen as a high-impact leader because you would probably have achieved a lot with fewer resources. Plus, you will have a better "change" story for the "jumps" on your resume.
I know it is tempting, but stay put! 5 years will go by fast and with the right career coach you can achieve a lot right where you are.
Got another question? Just hit reply to this email or complete this form.
Before you go,
How was the ROI on this edition? |
If you enjoyed, share it with others!
If you working on becoming a VP of Finance, CAO or CFO within the next 5 years, check out The Finance Executive Accelerator (Formerly known as The Office of The CFO Bootcamp).
That’s it for today. See you next time👋 Wassia |
DISCLAIMER: The advice and insights shared in this newsletter are based on personal experience and general industry knowledge. They are not intended to replace professional financial, legal, or career counsel. Your situation is unique, and what works for one person may not work for another. Before making significant career or financial decisions, consult with qualified professionals familiar with your specific circumstances. I am not liable for any actions taken based on the content of this newsletter.
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