Handbook
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Finance & Operations
When to Hire an Accountant vs Bookkeeper vs CFO
Different financial roles serve different purposes. Here's when you need each and what to look for.
Founders often conflate bookkeeper, accountant, and CFO. They’re different roles that become necessary at different stages. Understanding the differences helps you hire the right help at the right time.
The Three Roles
Bookkeeper
What they do:
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Record daily transactions
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Categorize expenses
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Reconcile accounts
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Maintain clean books
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Handle accounts payable/receivable
Skills needed:
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QuickBooks/Xero proficiency
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Attention to detail
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Understanding of accounting basics
Not responsible for:
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Tax strategy
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Financial planning
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Board reporting
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Strategic advice
When you need one:
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First hire (or service) when bookkeeping takes more than 2-3 hours/week
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Usually when you have employees or 50+ transactions/month
Cost:
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Service (Pilot, Bench): $400-1,000/month
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Part-time: $25-50/hour, 5-15 hours/month
Accountant (CPA)
What they do:
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Prepare and file tax returns
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Tax planning and strategy
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Financial statement preparation
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Audit support
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Compliance advice
Skills needed:
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CPA certification
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Knowledge of tax code
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Experience with your company type (startup, C-corp, etc.)
Not responsible for:
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Day-to-day bookkeeping
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Strategic financial planning
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Fundraising support
When you need one:
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Immediately for tax preparation (your first tax year)
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Ongoing for tax planning and compliance
Cost:
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Tax prep: $2,000-10,000/year depending on complexity
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Advisory: $200-500/hour
CFO / Controller
What they do:
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Financial strategy and planning
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Budgeting and forecasting
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Investor relations and reporting
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Cash management
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Financial modeling
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Board presentations
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Fundraising support
Skills needed:
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Deep financial expertise
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Strategic thinking
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Experience with startups and fundraising
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Leadership ability
When you need one:
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Controller: Series A+ or when financial complexity demands it
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CFO: Series B+ or when strategic finance becomes critical
Cost:
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Fractional CFO: $3,000-10,000/month
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Full-time controller: $120,000-180,000/year
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Full-time CFO: $200,000-400,000+/year
The Evolution
Pre-Revenue / Solo Founder
DIY bookkeeping: QuickBooks, minimal transactions
Accountant: Needed for first tax filing. Find one before tax season.
Seed Stage / Small Team
Bookkeeper or service: When bookkeeping takes more than a few hours weekly
Accountant: Ongoing for taxes and compliance
No CFO needed: Founder handles financial strategy
Series A
Bookkeeper or outsourced finance: Clean books are essential
Accountant: More complex taxes, potentially audit prep
Consider fractional CFO or controller: Financial complexity increasing, board reporting needed, possible future fundraising
Series B+
In-house finance team: Controller at minimum, possibly finance associate
CFO: Strategic finance, investor relations, board level
Accountant: Ongoing for taxes, audit support
Finding the Right Help
Finding a Bookkeeper
What to look for:
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QuickBooks proficiency
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Experience with startups
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Responsiveness
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References from similar companies
Sources:
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Bookkeeping services (Pilot, Bench)
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Upwork, Toptal for individuals
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Referrals from your accountant
Finding an Accountant
What to look for:
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CPA credential
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Startup experience (not just small business)
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Familiarity with your entity type (C-corp, etc.)
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Proactive about tax planning
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Responsive communication
Sources:
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Referrals from other founders (best source)
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Startup-focused firms
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YC accountant directory (if applicable)
Questions to ask:
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How many startup clients do you have?
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What types of entities do you work with?
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How do you handle tax planning vs. just prep?
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What’s your communication style and response time?
Finding a CFO/Controller
What to look for:
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Startup experience (not just big company)
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Fundraising experience (if you’ll be raising)
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Board reporting experience
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Cultural fit
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Strategic thinking, not just execution
Sources:
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Referrals from investors
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Fractional CFO firms (Burkland, Finvisor)
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Executive recruiters
Questions to ask:
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What’s your experience with companies at our stage?
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How do you approach financial planning?
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How do you work with the CEO and board?
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What would you prioritize in the first 90 days?
Fractional vs. Full-Time
For CFO/controller roles, fractional (part-time) can work well:
Fractional works when:
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You need strategic input but not full-time work
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Budget constraints
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Specific projects (fundraising, systems setup)
Full-time needed when:
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Finance work exceeds 15-20 hours/week
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Continuous strategic input required
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Building a finance team
Many companies start fractional and transition to full-time as they scale.
Working with Finance Help
Set Clear Expectations
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What deliverables do you expect?
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What’s the communication frequency?
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What decisions need their input?
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What systems should they use?
Provide Access
Finance people need:
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Bank and card access (view at minimum)
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Accounting software access
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Revenue data (Stripe, billing system)
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Key contracts and agreements
Regular Check-ins
Bookkeeper: Weekly or as needed
Accountant: Quarterly for planning, monthly during tax season
CFO: Weekly, with formal monthly reviews
Trust But Verify
Review their work:
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Do financial statements make sense?
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Are categorizations correct?
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Do projections seem reasonable?
You don’t need to be an expert, but you should understand the basics.
Signs You Need to Level Up
Bookkeeper → More help:
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Books are always behind
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Errors are increasing
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Complexity exceeds their skills
Accountant → Better/bigger accountant:
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Not proactive about tax planning
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Doesn’t understand startup specifics
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Poor communication
No CFO → Need CFO:
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Board requests sophisticated reporting
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Fundraising requires financial support
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Strategic financial decisions are frequent
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You’re spending too much time on finance
Common Mistakes
Hiring too late: By the time you’re drowning, you’ve already made mistakes.
Hiring the wrong type: Getting an accountant when you need a bookkeeper, or vice versa.
Not vetting for startup experience: Corporate finance is different from startup finance.
Penny-wise, pound-foolish: Cheap bookkeeping that requires expensive cleanup.
Abdication without oversight: Handing over finance and never looking at it.
Key Takeaways
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Bookkeepers record transactions; accountants handle taxes; CFOs do strategy
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Get an accountant before your first tax year
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Get bookkeeping help when it takes more than 2-3 hours/week
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Consider a controller or fractional CFO at Series A
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Look for startup experience in every hire
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Start fractional, then go full-time as needs grow
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Set clear expectations and maintain oversight
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