Why every scaling finance team is understaffed

Every scaling finance team is understaffed, and it’s almost always for the same reason. We do it to ourselves.

Finance leaders are all too familiar with the more-than-double-what-we-could-ever-afford headcount wish list returned from other departments. We’re also exhausted by the countless battles trying to get folks to understand why they can’t hire everyone they want.

Our trap is to lead by example. We’re often the only ones at the company worried about efficiency and how to achieve leverage through scale. We’re trying to save the company money! If only others could see how lean we run our team, maybe they’d do the same! Headcount is a vanity metric! Besides, our ask for that extra accountant will never prevail against that additional product marketer or engineer.

And so we suffer. We grit our teeth and take on the mounting requests. We try to automate as much as possible. At some point someone will notice how much we do with so little and will surely congratulate us for being excellent stewards of company money. Worst of all though, our teams suffer. Those we’ve convinced to come work for us are stretched across a growing list of half-complete projects and reactionary work.

To all the scaling finance leaders out there, this mindset is inherent to the role we play as finance leaders. It’s our bias and it’s natural. I totally get it, and I challenge you then to do a few things in response.

First, be overly intentional about how you plan your headcount needs. Put your mask on before helping others - make sure you have a clear headcount wish list and org design prior to starting your company planning process. Once in the throes of planning, the details of managing that process will overwhelm your ability to have the conversations and do the deep thinking necessary.

Single points of failure in finance can be disastrous - identify them. Have only one payroll person, billing specialist, accounts receivable specialist? Make a plan to shore those up and make them a priority.

Don’t plan alone. Involve your stakeholders. Run a deliberate process in which you ask your stakeholders for feedback on what they want to see and need from finance. What does an ideal partnership with finance look like? Where could they use more support? Get them aligned to the ways in which you can support them, and pin your headcount requests against that. As tradeoffs arise, be upfront about what of your shared vision you'll support and forego.

Then involve your team. Share with them the feedback from stakeholders. Know that your team likely has the same bias as you - they want to save the company money! Treat “I’m not sure that’s a full time job” as an orange flag - something to deliberately investigate. It’s usually a sign of an issue that will quickly propagate as the rest of the organization scales around it.

Finally, self awareness is key. Be hyper aware that your bias will be to over index on frugality and running lean. Perhaps then you should feel uncomfortable with the amount of headcount you're requesting. You will not make it through hyper growth if you don’t at least somewhat invest ahead of the growth.

Bobby Pinero

Bobby Pinero

CEO and Co-Founder of Equals. Previously built and led Finance and Analytics at Intercom, from <$1M ARR to $150M+ (20 employees to 600+).
San Francisco