The Startup CFO Challenge—Wearing Too Many Hats?
Mar 20, 2025
The Reality of Being a Startup CFO
When people hear “CFO,” they assume you’re sitting at a desk, crafting high-level financial strategies, overseeing a strong finance team, and working on investor relations.
Sounds great, right?
Now, let’s talk about reality—the startup version.
As a Startup CFO, you are:
✅ The Head of Finance (obviously).
✅ The Financial Controller (because who else is closing the books?).
✅ The Tax Specialist (since there’s no in-house expert for that).
✅ The Legal Consultant (founders often assume finance understands contracts).
✅ The HR Advisor (payroll and benefits land on your desk).
✅ The Office Manager (who else is sorting out budgets for office space?).
✅ The Data Guru (because finance is supposed to “know the numbers”).
Basically, you’re expected to do it all.
Why This Happens
Startups don’t have large teams or endless resources, so functions tend to blend. The finance function—which should be focused on financial strategy—ends up absorbing HR, legal, compliance, and operations by default.
Why?
Because we deal with numbers, and that makes us “the logical ones” in the leadership team.
The founder is usually focused on fundraising, growth, and product, while finance gets thrown everything else.
If you don’t set boundaries and structure your role, you’ll end up stuck in firefighting mode, unable to add real strategic value.
5 Key Challenges for a Startup CFO (And How to Handle Them)
1. You’re Managing Finance, But You’re Also Doing HR
- You run payroll, set up benefits, and review employment contracts—but HR isn’t really in your job description.
- Solution: Push for proper HR software (or an outsourced HR firm) to offload the admin and keep finance focused on finance. Sometimes you may need to hire a part-time HR manager.
2. You’re the Legal Point of Contact
- Contract reviews? That lands on your desk. Investor agreements? Also you. Founder needs a term sheet reviewed at 10 PM? Guess who’s getting the Slack message?
- Solution: Push back when needed and get a good external legal team that founders trust. The best CFOs know when to delegate. Take a look at an interview I did with a Fractional GC here.
3. You’re Expected to Fix Operational & Office Problems
- Office budgets, IT infrastructure, procurement—all mysteriously end up as “finance problems.”
- Solution: Set clear ownership boundaries with the CEO and leadership team. You’re a strategic partner, not an admin officer.
4. Data & Metrics? That’s Apparently Finance, Too
- You might have zero background in data analytics, yet somehow you’re expected to manage the dashboards, set up KPI tracking, and explain business intelligence.
- Solution: Find a strong data analyst early. If the business is growing fast, insist on a proper data function rather than finance & the accounting team absorbing the workload. This could still under you, but you need data analysts, not the accounting team resources.
5. You’re Overloaded & Stretched Too Thin
- You’re managing finance, legal, HR, data, and office admin—so when exactly do you get to be a strategic CFO?
- Solution: Set expectations early. If you take on too much, you’ll never have time for investor relations, strategic finance, or actual business growth.
Being a Startup CFO is one of the toughest finance jobs out there. You’re expected to wear multiple hats, balance execution with strategy, and deal with a ridiculous amount of moving parts.
But here’s the thing—you don’t have to do it all forever. A great CFO knows when to push back, delegate, and restructure the role into something sustainable.
If you’re struggling with this, you’re not alone. Every finance leader in a startup feels the same way at some point. That’s why structured training, mentorship, and leadership development matter so much—because figuring it out on your own is painfully slow.
Want to be a confident and skilled Finance leader in 12 months? Then follow these steps:
- Sign up to our next free workshop.
- Book a FLF Career Planning session.
- Download the Advanced Management accounts course to showcase your skills as a finance leader to the Founder, leadership team and the Board.
- Work with me in the Financial Leadership Foundations course that includes monthly Q&A sessions where we can discuss all of your questions and how to apply your learnings to your current role.