In 2019 I set my sights on becoming a Director of Finance.

To me, that was the perfect blend of being ‘in the room’ and enjoying the fruits of the senior leader life (more on that later), but still close enough to the work to not get lost in corporate politics.

Boy, was I wrong!

When I became a Director of Finance in 2021 I quickly learned that it actually was the worst of both worlds - just enough accountability to feel the weight of the position without enough compensation to feel adequately compensated for the work.

To be clear, I’m not saying that becoming a Director is a bad goal…

But I am saying that every role in my career through Head of Finance has had pros and cons. It’s not always better or worse.

And I’m here to talk about what I believe is the 2 primary paths any finance professional should take if they want to maximize their career.

Because, in hindsight, it’s very clear to me that I got lucky by taking 1 of the 2.

Let’s talk about career paths, compensation, and how to win where you are…

This is where I got lucky.

By nature, I’m ambitious in my day-to-day but not in the grand scheme.

I like to be excellent in everything I do and I believe that good things come to those who put in the hard work.

Is that always true? Nope.
In fact, I coach a lot of mentees who I regularly have to tell to get a new job if they aren’t getting promoted fast enough.

But when you play the big company game as a finance professional, you should have a healthy balance of patience (in the long term) and persistence (in the short term).

Yet, it’s all worked out for me.

It’s because I’m playing a different game than most. I’m playing the long-game at big companies. I’ve been at big companies (11-figures in revenue) for nearly my whole career. Yet, the currency these companies trade in is trust.

If you are excellent, a team player, and patient you’ll go far.

In hindsight, I played everything correctly. But I didn’t do it on purpose. I’m just the kind of person that fits well in the system I’m in. I got lucky.

Like most good things in life, compound growth starts to take hold here if you’re patient (and good) enough.

We’re talking about promotions every 1-2 years, plus merit, and maintaining ~10% annual comp increases before finally getting into meaningful bonus and equity pools.

If you’re not hitting those benchmarks, you need to know that the above graph won’t happen for you.

For a while there in the beginning, it can feel frustratingly slow.
And in the middle, your volume of work and stress skyrockets (not your comp).
But if you stick it out, you can reap the rewards of your hard work.

Looking for a faster, but more risky path to the top?

Look no further than the next big tech/AI/xyz startup.

$NVDA ( ▲ 1.53% ) is an excellent example of this.

Many of their employees have found themselves millionaires by simply showing up and doing their jobs.

The only problem with this strategy is that for every 1 Nvidia, there are 1,000+ other tech companies who expired worthless.

In fact, I have a few software engineering friends who have been burned by companies who promise sky-high valuations, pay under market, ask for late nights, then sell the company for less than the stock option valuation - leaving the employees with little to show.

It’s a tough game to play, but if you play your cards right you can win big personally. The key here is finding the right company at the right time with the potential for a meaningful exit (easier said than done!)

To me, this is less about risk versus reward and more about your ability to pick a winner. In the big company game, you don’t really need to pick great.

If the company is big, the market is tested and corporate politics will ensure top performers will get paid well

But in a high-growth company, you really need to find the right balance of excellent company leadership, product, market, culture, and runway.

And the best part of starting in a growing company early is that you will find yourself rising with the business. Most rapidly scaling businesses will promote internally and hire externally for lower-level positions - meaning if you are good and stick around, you can grow with the company.

Maybe one day you are 1 of 5 people in finance, but in a few years you are the Director of Finance over a team of 15.

Maybe.

Sure, there is a strategy were you find middle-market companies that have recently been bought by PE and looking to institutionalize finance.

Then if you perform well you can get bounced around by the PE firm from opportunity to opportunity.

That’s another good path, but I’d say it’s far less common or predictable.

And I’ve just had enough friends who haven’t been able to break into the PE-cycle after years of high-performance.
(if you have an example of this working, please share!)

But for the most part, it’s best to aim for both ends of the spectrum - either startup or enterprise.

That’s where the money flows most predictably.

This newsletter would be incomplete if I didn’t mention this last option.

Mostly because I have a few friends who have taken this approach and found massive success.

It’s the business ownership path.
And it’s not for everyone.

In fact, it’s probably not for you.

Starting a business is hard work and often requires both time and money investment before you ever see a single $ in return. We’re talking about pure financial and personal risk.

But the upside is asymmetric (when you win, you win BIG).

And technically this path is far more lucrative than the others we mentioned, it’s just much harder to go down the business owner/founder path than finding a job.

Here’s a few options for a finance professional to start their own thing:

I’m sure there are other ideas but these are the main ones I see out there.

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