Leaving my career in Finance

The Weary Entrepreneur
3 min readApr 27, 2022

Career Reflection

I spent 20 years of my career, i.e. half my life, as a Finance leader in large multibillion dollar companies. Financial Strategy and Planning will always be my first love, and there are very few things I enjoy more than building out a fun financial valuation model that calculates and triangulates enterprise value using multiple valuation methodologies. Within the Finance space, I have done everything from leading multi-billion m&a transactions, to fundraising and leading recapitalization efforts, to managing the Decision Support functions such as FP&A, Corporate Strategy, or Controllership/Fin Ops teams.

My deep expertise notwithstanding, I however recently pivoted into a non-Finance role, as Head of Marketing and Operations for a data analytics startup. Why? Because I wanted to drive business strategy and results. As head of Marketing for a hyper-growth startup in the data analytics space, I have the opportunity to do just that.

As head of Marketing for a hyper-growth startup in the data analytics space, I have the opportunity to drive business results.

Finance as a function, on the other hand, is going through a significant coming of age moment. Most leaders cling to the idea that CFO is their “right-hand person” in the organization, i.e. the proxy to the COO or CEO. They look to innovation like RPA and AI to free up a CFO’s time to allow for a more strategic role. However what they don’t often appreciate is that for the CFO to be in that strategic influential role, the day-to-day operations of Finance have to run smoothly like a well-oiled machine. Only then can the CFO and key members of their team use their financial expertise on decision support modeling and scenario planning to drives business results.

A Finance organization that runs like a well-oiled machine is however often a pipe dream, especially with the new innovation coming on board. For RPA or AI or any technological innovation to be deployed effectively, data within Finance has to be structured and cleaned appropriately. Most large companies however still rely on legacy general ledger systems and a disjointed data warehouse solutions to close books and do most of their reporting. Data standardization is often done in a way that standardizes for 40–50% of the entities, and for the others requires multiple manual touch points in order to report management or GAAP results in an accurate manner. We haven’t even gotten into the complexities often required to then use this data for planning or forecasting purposes, which is often also an unnecessarily manual process.

For the CFO to be in that strategic influential role, the day-to-day operations of Finance have to run smoothly like a well-oiled machine.

Finance professionals are too valuable to be used in rote processing roles — we should have strategic roles, yet we often get stuck manually closing books every month and doing manual processes on WD15 in order to pass audits or report out to the BOD. In order for Finance to be strategic in a company, its own strategy has to be well defined and well funded. We also need Finance Transformation that is done correctly.

There needs to be a culture change as well. I have been in multiple organizations now where the long hours that finance team spends during book close is worn as a badge of honor. This is the wrong culture for strategic finance. If hours are to be spent, and effort made by the team as a whole, they should be spent on activities that drive the business, not do something administrative like closing books or reporting.

If hours are to be spent and effort made by the Finance team, they should be spent on activities that drive the business, not do something administrative like closing books or reporting.

I am always all ears for all ideas on how to move Finance out of Administrative roles and into more strategic ones — and give my $0.02 on how to build a strategic Finance organization. Anyone interested, share below or DM me to chat further.

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The Weary Entrepreneur

Finance and Strategy leader in large multibillion dollar companies. Recovering Startup founder. Current Head of Marketing at a Data Analytics Startup.