Discover when your business needs a bookkeeper, controller, or CFO. Compare roles, costs, revenue milestones, and learn about fractional alternatives.
Your business is growing, and your spreadsheets are becoming overwhelming. You know you need financial help, but should you hire a bookkeeper, controller, or CFO? The short answer: Bookkeepers handle transaction recording ($0-$500K revenue), Controllers provide analysis and reporting ($500K-$5M), and CFOs drive strategic planning ($2M-$10M+). Most growing businesses benefit from fractional services before committing to full-time hires.
If you've ever found yourself drowning in receipts at 11 PM, frantically trying to reconcile bank statements before a tax deadline, you're not alone. As your business grows, managing finances becomes exponentially more complex. The challenge? Knowing exactly when to hire financial expertise and which role you actually need.
The confusion is understandable. The titles "bookkeeper," "controller," and "CFO" are often used interchangeably, but they represent vastly different roles with different responsibilities, costs, and business impacts. Hiring too early can strain your budget. Hiring too late means missed opportunities, poor decisions, and potential compliance issues.
This guide will help you understand exactly when to hire each role, what they'll do for your business, and how fractional alternatives can give you strategic financial leadership without the full-time commitment.
Before diving into when to hire each role, let's clarify what they actually do. Understanding these distinctions is critical to making the right hiring decision at the right time.
The key difference? Bookkeepers record what happened. Controllers explain what it means. CFOs help you decide what to do next.
Revenue Milestone: $0-$500,000
You need a bookkeeper when manual financial tracking starts consuming significant time or when accuracy becomes critical for tax compliance and business decisions.
Bookkeepers handle the foundational financial tasks that keep your business compliant and organized:
For most businesses under $500K in revenue, outsourced bookkeeping delivers better value than hiring full-time. You get experienced professionals without the overhead of benefits, training, or backup coverage when your bookkeeper is sick or on vacation.
Most businesses should engage a bookkeeper by the time they reach $100K-$150K in annual revenue, or sooner if they have employees, inventory, or complex transactions.
Revenue Milestone: $500K-$5M
You need a controller when you're making decisions based on financial data and need someone who can explain what the numbers actually mean, not just produce them.
The telltale sign you need a controller: You're looking at your financial statements and thinking "These numbers are probably right, but I have no idea what they're telling me about my business."
Controllers oversee your entire financial operation and turn data into actionable insights:
Here's what changes when you bring on a controller: Instead of just knowing you made $50,000 last month, you'll understand that your gross margin dropped 5% due to increased shipping costs, that Product A drives 70% of your profit despite being 40% of revenue, and that you'll need an additional $75,000 in working capital to support your Q4 growth plans.
Controllers bridge the gap between basic bookkeeping and strategic finance. They're essential for businesses that have moved beyond simple transactions into more complex financial operations.
Most businesses in the $500K-$2M range benefit more from fractional controller services, which provide senior-level expertise at a fraction of the full-time cost.
Revenue Milestone: $2M-$10M+
You need a CFO when financial strategy becomes critical to your growth trajectory. This typically happens during major transitions: fundraising, M&A, scaling rapidly, or preparing for exit.
CFOs operate at the strategic level, focusing on future growth and value creation:
A strong CFO changes the conversation in your executive team. Instead of reacting to financial results, you're proactively planning three scenarios for expansion, modeling the financial impact of different pricing strategies, and negotiating favorable terms with investors because you have compelling financial projections backed by data.
Most businesses between $2M-$10M in revenue don't need a full-time CFO. A fractional CFO can provide strategic leadership at 20-40% of the full-time cost, scaling up as your needs increase.
The fractional model is ideal for businesses that need strategic CFO expertise but don't yet have the complexity or budget to justify a full-time executive hire.
Fractional financial services have transformed how growing businesses access financial expertise. Rather than choosing between no help or a costly full-time hire, you can engage experienced professionals on a part-time basis.
Cost efficiency: Pay only for the hours you need, typically 40-60% less than full-time equivalent
Immediate expertise: Access professionals with 15-20 years of experience on day one, no training required
Scalability: Increase or decrease hours as your needs change, from 10 hours/month to 80 hours/month
Specialized knowledge: Fractional professionals often work across multiple companies and bring best practices from your industry
Flexibility: No long-term employment commitments, making it easier to adjust as your business evolves
Fractional services work best when:
Make the switch when you consistently need 30+ hours per week of that role's expertise, when the position requires daily presence and deep institutional knowledge, or when the cost differential narrows due to your complexity. For most businesses, this happens around $5M+ revenue for controllers and $10M+ for CFOs.
Fractional Bookkeeper: 5-20 hours/month for transaction processing and basic compliance
Fractional Controller: 10-30 hours/month for reporting, analysis, and financial operations oversight
Fractional CFO: 20-60 hours/month for strategy, fundraising, modeling, and executive partnership
Use these quick scenarios to determine which role matches your current needs:
Start with a fractional bookkeeper (5-10 hours/month). They'll handle transaction recording, reconciliations, and ensure you're ready for tax season. You can likely manage the strategic decisions yourself at this stage.
Add a fractional controller (15-20 hours/month). They'll provide the analysis and insights you need to make better decisions while supervising your bookkeeper to ensure quality and consistency.
You need a fractional CFO (30-40 hours/month minimum) to lead the raise, build investor materials, create financial models, and manage investor relations. Keep your controller for day-to-day operations.
Most successful businesses follow this progression:
This path optimizes cost while ensuring you have the financial expertise needed at each growth stage.
At Jumpstart Partners, we specialize in providing fractional financial services that grow with your business. We understand that most businesses don't need a full-time CFO on day one, but they do need strategic financial leadership to make better decisions and accelerate growth.
Essentials Tier: Fractional controller services including monthly close, financial statement preparation, analysis, and decision support. Perfect for businesses in the $500K-$2M range that need more than bookkeeping but aren't yet ready for strategic CFO services.
Growth Tier: Fractional CFO services including strategic planning, financial modeling, fundraising support, and executive partnership. Designed for businesses scaling from $2M-$10M that need strategic financial leadership.
Scale Tier: Comprehensive CFO services with additional team support for businesses over $10M preparing for exit, managing complex growth, or building institutional-grade financial operations.
All our engagements are flexible, scalable, and designed to deliver immediate value while building the financial foundation your business needs for long-term success.
Learn more about our services or schedule a free consultation to discuss which solution is right for your business.
Knowing when to hire a bookkeeper, controller, or CFO comes down to understanding your business's current complexity and strategic needs. Bookkeepers handle the foundation, controllers provide the insights, and CFOs drive the strategy.
The good news? You don't have to commit to full-time hires right away. Fractional services allow you to access the expertise you need, when you need it, at a fraction of the cost. This approach gives you strategic financial leadership without the overhead, helping you make better decisions and grow faster.
The key is to hire proactively, not reactively. By the time you're desperately searching for financial help, you've likely already missed opportunities or made costly mistakes. Start with fractional services, scale as you grow, and transition to full-time roles when the economics make sense.
Your finances are too important to manage on instinct alone. Whether you need basic bookkeeping or strategic CFO services, having the right financial expertise at the right time is one of the best investments you can make in your business's future.
Need help determining which financial role is right for your business? Contact Jumpstart Partners for a free consultation. We'll assess your current situation and recommend the right level of financial expertise to support your growth goals.