The Hiring Guide for Founders Past $500K
TL;DR:Founders earning $500K–$10M often wonder if they need a bookkeeper, tax CPA,fractional CFO, financial planner, or financial advisor. This guide explains the 6 financial roles, when to hire each, and how not to confuse them—so you stop wasting money on the wrong fit.
Running a growing business is exhilarating. Also? Confusing as heck when it comes to hiring financial help.
You’ve probably experienced this:
You hired abookkeeperbut still feel totally blind on cash flow.
You assumed yourtax accountantwould help with pricing decisions.
You brought in aCFOtoo early and burned through cash without clarity.
AtSam's List, we hear this all the time: "I know I need help with the money side... but I don't knowwhoto hire."
This guide is here to fix that. It's built for founders in the $500K–$50M range, who are growing fast and ready to stop guessing.
Step 1: Understand the 6 Financial Roles
Let’s decode the types of finance experts you might find onSam’s List(and when to hire each).
1.Bookkeeper
What they do:
Categorize transactions
Reconcile accounts
Maintain yourgeneral ledger
Prepare monthly financials (usually cash-basis)
When to hire:
You're past a few hundred thousand in revenue
You want reliable books for tax prep and visibility
Common trap:Expecting analysis or strategy from a bookkeeper. Their job is to maintain, not advise.
Sam's List Tip:Find vetted bookkeepersforecommerce, service, and tech businesses.
2.Tax Accountant (CPA or EA)
What they do:
Prepare and file tax returns
Help with compliance andentity structure
May offer tax planning for high earners or business owners
When to hire:
You have business income, 1099s, or multi-entity complexity
You want to minimize tax liability without taking risky positions
Common trap:Assuming they’ll advise on operations, pricing, or monthly reporting. Many CPAs focus only on tax.
Sam's List Tip:Browse top-rated tax proswho understand founder tax challenges.
3.Fractional CFO
What they do:
Forecastcash flowand profitability
Buildfinancial models
Advise on pricing, margins,capital structure
Partner in strategic decisions (hiring, fundraising, expansion)
When to hire:
You're crossing $1M+ and need numbers to guide decisions
You’re preparing for a raise, acquisition, or big pivot
Common trap:Hiring too soon. A CFO is a strategic partner—not a glorified bookkeeper.
Sam's List Tip:Connect with fractional CFOswho specialize in your stage.
4.Financial Planner
What they do:
Help you align business income with personal wealth goals
Advise on saving,investing,retirement,insurance
Tax-efficient distributions from your business
When to hire:
You’re paying yourself consistently and want to grow personal net worth
You’re approaching a liquidity event or big income year
Common trap:Assuming planners give business finance advice. Most focus onyou, not your business.
Sam's List Tip:Explore financial plannerswho specialize in founder finances.
5.Financial Advisor / Investment Advisor
What they do:
Manage investments (brokerage, retirement, trusts)
Advise onasset allocation, risk tolerance, and wealth goals
Often overlap with financial planners, but with investment focus
When to hire:
You have investable assets (typically $250K+)
You want a proactive partner in wealth building
Common trap:Confusing "advisor" titles. Make sure they're fiduciary, fee-transparent, and licensed.
Sam's List Tip:Find trusted financial advisorsfor founders building long-term wealth.
6.Financial Coach
What they do:
Help with personal budgeting, money mindset, financial literacy
Build habits and accountability for managing income and debt
When to hire:
You're early in building healthy money systems or paying down debt
You want 1:1 support without needing investment or tax advice
Common trap:Confusing a coach with a CFP or investment advisor. Coaches don't manage assets or file taxes.
Step 2: Match Help to Your Stage
| Stage | Revenue Range | Core Needs | Who to Hire |
|---|---|---|---|
| Lean + Growing | $500K–$1M | Clean books, basic tax prep, personal finance setup | Bookkeeper, Tax CPA, Financial Planner |
| Scaling w/ Complexity | $1M–$3M | Accrual accounting, cash flow forecasting, tax strategy | Bookkeeper, Fractional CFO, Tax CPA |
| Strategic Growth | $3M–$10M | Financial modeling, capital planning, investment strategy | CFO, Financial Advisor, Tax CPA |
Step 3: Don’t Confuse the Roles
Even though they all touch your money, each of these professionals brings a different skill set.
Bookkeepers = maintenance
Tax CPAs = compliance
CFOs = strategy
Planners = personal finance
Advisors = investing
Coaches = mindset + habits
Expecting one to do the work of another? That’s where most founders get stuck.
UseSam's Listto find exactly who you need, when you need them.
FAQs
Q: Do I need a CFO or just a bookkeeper?
A: If you’re under $1M, a bookkeeper and tax CPA are usually enough. Once you need forward-looking strategy (forecasting, fundraising, modeling), that’s when a CFO makes sense.
Q: What’s the difference between a financial planner and advisor?
A: Planners help align business income with yourpersonal goals(saving, retirement, tax-efficient planning). Advisors focus oninvestments(asset allocation, managing portfolios).
Q: Can my tax CPA help with business decisions?
A: Most CPAs focus on compliance. They’ll keep you tax-compliant but won’t build models or advise on growth strategy.
Q: When should I hire a financial coach?
A: Coaches are great if you want to build better money habits or get control of personal budgeting. They don’t manage investments or file taxes.
Q: Who should manage my finances as a $3M+ founder?
A: At this stage, you likely need accrual accounting, a fractional CFO or full-time finance lead, and a tax CPA. Add a planner/advisor if you’re growing wealth personally.
You Might Also Like
- What is the difference between an accountant and a CPA
- What is the best way to find a personal accountant?
- The Difference Between An Accountant And Bookkeeper
Author: Kimi, Co-founder of Sam’s List
Kimi writes about what she's learning while building Sam’s List and shares honest takeaways from her conversations with accountants and financial advisors across the country. None of this is financial advice—just the stuff most people wish someone told them sooner.
