One of the most expensive mistakes founders make is hiring the wrong finance help at the wrong time. Hire a CFO too early, and you burn cash on strategy when you just needed bookkeeping. Rely on automation too long, and you might face a tax audit.

Here is the roadmap for scaling your finance stack.

Stage 1: The "Robot" CFO ($0 - $500k ARR)

At this stage, you do not need a human accountant on payroll. You need clean data.

• The Stack: Xero/Quickbooks + A receipt capture tool (Dext) + A spend management card (Ramp/Brex).

• The Human: You (the founder) spend 1 hour a week categorizing transactions.

• Why: You need to understand your own unit economics before you hand them off.

Stage 2: The Fractional Controller ($500k - $2M ARR)

You are too busy to categorize receipts, and the complexity is increasing (payroll across states, sales tax).

• The Hire: A fractional bookkeeper or controller agency.

• The Role: They close the books monthly, reconcile accounts, and handle tax compliance. They do not provide strategy. They provide accuracy.

• The Trap: Don't ask them for financial modeling. That is not their job.

Stage 3: The Strategic CFO ($5M+ ARR)

This is when you are preparing for Series B, an acquisition, or complex M&A.

• The Hire: A VP of Finance or CFO.

• The Role: They look forward, not backward. They negotiate debt, manage investor relations, and plan capital allocation.

• The Cost: Expensive. Do not make this hire until the ROI of their strategy outweighs their salary.