Every founder eventually runs into the same wall.
Revenue’s growing.
Payroll is getting heavier.
Investor conversations are beginning.
You’re making decisions with bigger consequences, faster than ever before.
And one day, you realize that you don’t actually know what your numbers are telling you.
You’ve got an outsourced accountant. Maybe a bookkeeper. You’ve got a Stripe dashboard, a payroll tool, and a few spreadsheets that haven’t been touched since the last raise.
But there’s no single source of truth. No one is asking the second-order questions. No one is flagging risk before it becomes a mistake. The numbers look fine until someone needs to actually rely on them.
That’s when the founder says, “We need to hire someone in finance.”
The right hire will build visibility, control, and confidence.
The wrong one will add noise, bureaucracy, or worse - lull you into a false sense of security.
As a Fractional CFO, I’ve worked with over 250 founders through this exact moment. And I’ve seen what happens when finance becomes a box to check instead of a function to invest in.
The truth is, your first finance hire doesn’t just process data. They shape the way you understand your business.
The Most Common Mistake: Hiring for Familiarity, Not Fit
Early-stage founders don’t have time. So when the finance function becomes too big to ignore, they look for quick solutions:
- A recommendation from their accountant
- A friend’s cousin who “worked in a finance department”
- Someone who helped during the incorporation
- A junior analyst who seems organized and eager
These are rarely strategic hires. They’re safe hires.
The founder thinks: “We don’t need someone fancy. Just someone who can take care of this.”
But finance isn’t admin. It’s interpretation. And your first finance hire becomes the lens through which the company reads its own reality.
If that lens is foggy, the decisions will be too.
What You’re Really Hiring For: Knowledge, Skills, and Attitude
Every finance hire brings a mix of three things:
Knowledge
Do they understand accounting principles? Can they interpret a P&L, balance sheet, and cash flow statement? Do they know the difference between gross margin and contribution margin?
Knowledge can be acquired. A good hire will level up quickly with context and feedback.
Skills
Can they build a working model? Handle reconciliations? Prepare investor reports? Automate financial workflows?
Skills are learned. And most smart generalists can grow into the skill set.
Attitude
This is the one you can’t train for. Do they ask second-order questions? Do they chase clarity? Do they have the discipline to sweat the details, and the confidence to admit what they don’t know?
Attitude is the difference between someone who reconciles books and someone who interprets reality.
You can teach finance.
You can’t teach ownership.
How Your Finance Team Should Evolve by Stage
There’s no one-size-fits-all finance hire. The right profile changes as the business scales. Here’s what it should look like at each stage:
Less than $1M ARR: Don’t Overbuild, But Don’t Ignore
At this stage, your finance “team” can be lean. You don’t need a full-time CFO. But you do need structure:
- Clean books
- Monthly reporting
- Tax compliance
- Basic cash flow visibility
Most of this can be handled by an external accounting firm. But someone in the leadership team must be accountable for interpreting the numbers. If no one is reviewing the data for insight, not just compliance, you’re running blind.
This is a good stage to bring in a fractional finance lead - someone who spends a few hours a month guiding structure and building toward what’s next.
$1M–$5M ARR: Time for a Strategic Finance Lead
You’re now raising capital, growing headcount, managing burn, negotiating contracts, and reporting to investors.
At this point, you need your first in-house finance hire. Not a controller. Not a compliance officer. A generalist with enough range to:
- Own the monthly close
- Track financial metrics
- Build the first internal dashboards
- Work directly with leadership on budget vs. actuals
- Prepare the data room when fundraising
This person may have a background in FP&A, audit, or operations - but they need one thing above all: the judgment to connect numbers to reality.
$5M–$10M ARR: Start Building the Function
By now, finance is no longer just numbers - it’s navigation.
You’re forecasting cash, evaluating spend, hiring across departments, and answering to a board that expects timely, accurate reporting.
The finance function here should include:
- A finance manager who handles planning and modeling
- A staff accountant or controller who owns reporting, compliance, and systems
- Potentially, a fractional CFO or head of finance overseeing the function strategically
This is the stage where founders often realize that finance is not just “back office.” It’s where company-building discipline actually starts.
$10M-$50M ARR: From Finance to Strategy
Once you’re in this bracket, you’re likely raising institutional rounds, exploring international expansion, or preparing for secondaries.
Your finance team now needs to handle:
- Complex modeling and scenario planning
- Multi-entity structuring
- Revenue operations
- Cost center accountability
- Board reporting and investor relations
- Audit readiness
This is where the role of a full-time Head of Finance or CFO becomes essential - someone who doesn’t just report numbers but sits in strategic conversations and contributes to capital planning, pricing strategy, and resource allocation.
If you underbuild here, you’ll pay for it in your next raise. Or in your next missed signal.
Greater than $50M ARR: Finance as Infrastructure
At scale, finance becomes the nervous system of the company.
The function includes:
- FP&A
- Treasury
- Accounting
- Tax and legal
- Internal audit
- Investor relations
- M&A support
The CFO is now a peer to the CEO - not a service provider. Their job is to think in capital, risk, and long-term shareholder value.
What Happens When You Get This Wrong
Finance is one of the few hires where mediocrity is dangerous.
A weak marketing hire might cost you some growth. A weak product hire might slow the roadmap. But a weak finance hire will give you false confidence. You’ll make decisions based on incomplete or misleading data. You’ll defer cleanups that compound into crises. You’ll walk into investor conversations unprepared - and not even know it.
The worst part? You’ll think everything is fine. Until it isn’t.
Your Numbers Aren’t Just a Reflection of the Business. They’re a Reflection of You.
Hiring your first finance lead is not about outsourcing math. It’s about institutionalizing visibility. You want someone who’s brave enough to bring you bad news early, and skilled enough to turn it into insight.
Don’t hire because someone is convenient.
Don’t hire because your accountant “recommends” them.
Don’t hire because they’re available.
Hire because they bring clarity.
Because they ask better questions than you do.
Because they’ll help you understand your business more deeply than you currently can.
Your first finance hire will shape how you see the company.
Make sure they don’t just report numbers.
Make sure they understand the business behind them.
💼 About the Author
Kishore Dasaka is a Chartered Accountant and Fractional CFO who has worked with over 250 founders across the US, Europe, Southeast Asia, and beyond. He helps growth-stage companies hire strategically, model confidently, and build capital structures that actually work.
Explore more at https://kishoredasaka.com