The Impossible Job: Why Finance Leaders Are Set Up to Fail - Wiss

The Impossible Job: Why Finance Leaders Are Set Up to Fail

January 30, 2026


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There’s a quiet crisis happening in finance departments across the country, and it has nothing to do with the market.

It’s this: We keep asking CFOs and controllers to be strategic visionaries while burying them in operational quicksand.

The mandate is clear—spot trends, deliver insights, build dashboards that tell the story behind the numbers, anticipate what the board is going to ask before they ask it. Be the trusted advisor. Think like a strategist. Move fast.

And then we hand them a system held together with duct tape and a team that’s underwater just trying to close the books on time.

The Insight Gap

Here’s what I’ve seen working with controllers and CFOs over the years: They want to be strategic. They didn’t get into finance to reconcile GL accounts for the rest of their lives. But the reality is, most of their bandwidth gets eaten up doing the blocking and tackling—chasing down invoices, reconciling systems that don’t talk to each other, manually pulling reports that should auto-generate but don’t.

By the time they get to the “insights” part of the job, they’re exhausted. And the data’s already two weeks old.

The frustration is real. They know what good looks like. They can see the questions the business needs answered. But the infrastructure won’t let them get there. So they do what they’ve always done: throw more people at it.

Except now, that doesn’t work either.

The Talent Cliff

The accounting talent shortage isn’t coming. It’s here. And it’s not a temporary blip—it’s structural.

Baby Boomers are retiring in waves, and there aren’t nearly enough new accountants coming up to replace them. Enrollment in accounting programs has been dropping for years. The pipeline is broken, and it’s not fixing itself anytime soon.

So the old playbook—hire more staff, spread the load, grind it out—doesn’t apply anymore. Even if you could hire your way out of this, the economics don’t work. The cost of talent is rising, margins are tightening, and clients expect more, not less.

And here’s the uncomfortable truth: even if we magically solved the talent shortage tomorrow, it wouldn’t fix the underlying problem. Adding more people to a broken process just scales the dysfunction. You’d still be buried in manual work. You’d still be late to insights. You’d just have more people who are frustrated about it.

What Actually Works

The way forward isn’t about hiring faster. It’s about rethinking the model entirely.

First, trying to do everything in-house is changing. The idea that every company needs a fully staffed, end-to-end finance function is a relic of a different era. There are ways to be adaptable through Co-sourcing models.  External talent can be plugged into your Internal team.  It’s an easy solution to create capacity and add expertise without the overhead and recruiting headaches.

Second, invest in systems that actually reduce the grind, not just digitize it. Cloud-based platforms, AI-powered reconciliation, automated reporting are finally providing solutions!  If your finance team is still living in Excel hell, you’re asking them to compete with one hand tied behind their back.

And third—this one’s harder—let go of the idea that finance is a back-office cost center. Treat it like the strategic function it’s supposed to be. That means investing in tools to create the time to think, not just execute. 

A Different Kind of Pressure

The pressure on finance leaders isn’t going away. If anything, it’s intensifying. The demands to provide more insights, better forecasts with more real-time visibility are increasing. Everyone is looking for answers faster than ever.

The system is being forced to change as the AI tools continue to become more evolved. The pressure isn’t going to be solved by hiring.  It’s so much more complicated.  Existing processes that have been harnessed for years must change and adapt.  This brings an entire new way of thinking about operations and customer experience.  

What I find most exciting with what’s to come is that the CFO and the accounting department will finally have a front row seat!


Questions?

Reach out to a Wiss team member for more information or assistance.

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