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C-Note from the United Kingdom asked:

Your "long and winding road to CFO" email, particularly the part about the value being in 2-3 cycles, made me think about my own career. I'm currently in a good role that is growing, but have an offer as "chief of Staff to the CFO" at a much larger, but still fast-growing company. I think both are good options - keen to get your thoughts.

Current role as most senior finance person in a fast-growing VC-backed company of 100 FTEs, vs. Exec Assistant to a brilliant and experienced CFO at a hyper-growth company with 2,500 FTEs about to IPO.

Hey C-Note.

First up, congratulations. You have two great options on the table… you clearly are very talented, and crushing it.

Onto your question… this will be a short answer.

Unless there is a serious equity tie-in at your current place, I think this is a no-brainer.

You can go get a front-row seat to an IPO working at the shoulder of a CFO who has been there and done it. Chief of Staff gives you a wide brief to do whatever the hell you want and get involved with all the interesting stuff.

And there is only one reason a CFO hires a chief of staff. They are overloaded. They are looking for a span breaker to take some load from them. So you aren’t going to get any opposition to however you want to help.

Sounds like you’ll have a free pass to ‘play CFO’ at a much larger business on the IPO Ramp.

Do this well enough and next up you will have your pick of the senior finance vacancies, which then puts you one step away from being CFO of a huge and growing business.

I have hired chief of staff/senior exec assistants in this way in the past. They have always ended up being great platforms for talented finance leaders on the growth curve.

Unless I’m missing something, I don’t think this is a tough choice. Just make sure you validate that the CoS role is what you think it is.

But… you are in a great position either way here. Nice job playing your cards so well.

Albert from New York asked:

I'm an investment banker with 10+ years of execution experience at a bulge bracket. I've been considering transitioning to a corporate career with a CFO track. Your newsletters have been very inspiring in that regard, as you always present interesting problems a CFO solves.

I've had limited luck in getting interviews thus far with startups and large corporates, and beginning to wonder if my FIG background is working against me or if bankers rarely make good CFOs.

What is the best way to network my way into the aforementioned career track?

Investment bankers can make good CFOs.

Let me rephrase that… investment bankers can make outstanding CFOs.

Many of the CFOs of the top companies in the world have some investment banking experience. I interviewed Jeff Hoffmeister (Shopify CFO) over the summer, who did 20 years in investment banking before switching straight into the CFO chair at the tech giant.

So it’s definitely possible.

Here is the issue… as an investment banker, you deal with big companies with big company problems. And you are advising outside in. You are one part removed from the hands-on action in the business. And when you see CFOs on the other side of the table, what you see of them is less than 10% of the job.

A common misconception of IB pros when talking about the CFO role is that they think CFOs spend most of their time doing market/investor-facing things. That is not the case at all.

CFOs earn their money leading their team to deliver in the business. Improving controls, reporting, building teams, tightening FP&A cycles, and strategic support for the CEO.

None of these things are rocket science, but they are skills that CFOs need. And they are not skills you build in IB.

So I would say there are two optimal ways to move out of banking directly onto the CFO path:

1. Move after 3 years or so of IB experience. Move into a middle management role in FP&A or Corp Dev. Build some broader business skills, and use them to climb the ladder.

2. Climb the IB ladder to MD. Build deep sector expertise and an even deeper network. And get some experience managing a team of a decent size. Then leverage those assets to move across at the CFO level and bypass the ladder climb (like Jeff did).

It sounds like you might be stuck a little between these two. So my advice would be either take path 2 or accept that you are going to have to take a step backward to go forwards.

One other option to consider… I have seen a few people move from IB into a PE fund, then move later into a portco CFO role. That could be worth considering. You’ll keep your options open too.

You should get yourself to a place where you can leverage your sector experience and network. You are working with CEOs, PE funds, lawyers, other banks, etc. every day. All of them are a good source for roles in business finance teams. If your network isn’t yet strong enough to make that ask, then focus on building those relationships first.

Thank you for the question. Best of luck, Albert.

Fezarelli from London, UK asked:

Once one has fixed “the biggest, hairiest finance problem” and therefore put the cherry on the CFO skill-building cake, do you have any advice for getting recognized adequately by investors? Think: turning a pat on the back at the next board meeting into a pay raise or a promotion from FD to CFO?

Thanks for the question, Fezarelli.

This is a common problem. You are leveling up, and your market value is increasing… but how do you get tangible recognition for that?

My rule on asking for increased comp or title has always been to ask infrequently but push hard when you do. And do so at the time that you have the most leverage possible.

So the answer depends on a number of variables. When did you last get a pay bump outside the regular annual inflationary increase? If it’s measured in months, then shhh, and get back to your job.

If it’s measured in years, then definitely time to ask.

Think about what your justification is. Has your role expanded? Or is your argument that you are now better at your job? The first is easier to justify than the second: “Um, we’ve always paid you under the assumption that you are good at your job.”

And think about how this plays into your bonus. If you are over-performing, to what extent is that being recognized in a bonus or long-term award?

If you think you have a valid request, then I’d suggest testing the request 1-on-1 with someone who is close to the decision-making (the CEO or one of the board members). Whoever you have the most credit with.

Don’t be too forceful, just test the water and see what response you get. The feedback will tell you a lot.

Ultimately, if you feel like you are being paid less than your true market value, and your company won’t fix it, then you should test the job market.

The tone you should take into an internal negotiation like this is that leaving the company would be your last resort. But you are prepared to do it if you need to. It gives you the most amount of optionality. You have leverage, but you can also quickly ‘rewind’ if you need to.

Go get ‘em Fez.

Every week I’ll share a book I loved or found useful.

A few of the biggest stories that every CFO is paying close attention to. This is the section you probably don’t want to see your name in.

Synapse Executive Alerted Accountants Before $100 Million Missing Funds Scandal

What a sh*tshow. Synapse was an intermediary between fintechs offering too-good-to-be-true savings yields and banks. Now nearly $100M of customer money is missing. Synapse is blaming its bank partner. And its bank partner is pointing at Synapse. Meanwhile, the customers are the real losers because Synapse aren’t FDIC-insured. Now the feds are questioning the Synapse accountant who blew the whistle on the whole house of cards. Stay tuned…

OpenAI CFO talks possibility of going public, says Musk bid isn’t a distraction

This job just screams “mental breakdown.” Not only does Sara Friar have to figure out how to convert OpenAI into a for-profit, but she’s also got the company on the IPO glide path. And that’s before you get to the affiliate transaction hell that comes with the Sam Altman/Elon Musk bid soap opera.

IRS cuts over 6,000 jobs in the middle of tax season

Oh great … looks like the IRS won’t be getting any more responsive this tax season.

ICYMI, some of my favorite finance/business social media posts from this week. In the words of Kendall Roy, “all bangers, all the time”:

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We wrapped up the playbook series on the future of finance last weekend. A special one-off ‘spotlight’ newsletter coming on Thursday, keep an eye out for it!

Disclaimer: I am not your accountant, tax advisor, lawyer, CFO, director, or friend. Well, maybe I’m your friend, but I am not any of those other things. Everything I publish represents my opinions only, not advice. Running the finances for a company is serious business, and you should take the proper advice you need.