Published on
September 5, 2025
How to Hire Finance Talent: Dos and Don'ts
Learn the best practices for hiring finance professionals, including dos, don'ts, and when to consider fractional CFOs.
As your business grows and crosses major milestones - like $5 million in annual revenue - it often becomes clear that managing finances with outsourced professionals is no longer sufficient. At this stage, the need for a more centralized and strategic finance function becomes critical. However, hiring finance talent, whether it’s a bookkeeper, accountant, or CFO, is a daunting task. This article dives into the strategic considerations, common pitfalls, and actionable guidance based on insights from Shannon Weinstein, a CFO, CPA, and expert in helping businesses scale while maximizing profitability.
If you’re a mid-market business owner managing between $500K and $10M in revenue, this guide will help you evaluate whether to bring finance talent in-house, choose between hiring full-time or fractional support, and lead your financial team effectively.
Why Growing Businesses Struggle with Finance Roles
For many entrepreneurs, the early stages of business involve cobbling together a piecemeal approach to finance. You may rely on an outsourced bookkeeper, a CPA for tax filing, and perhaps some self-management of financial strategy. While this works for a time, there comes a point where this setup stops being efficient.
Here are the common pain points entrepreneurs face:
- Time Drain: Even if you outsource, you remain the glue holding the financial function together - answering questions, overseeing professionals, and ensuring tasks are completed. This doesn’t free up your time; it redirects your energy toward coordination.
- Disjointed Insights: Fragmented financial data from multiple sources (bookkeeper, CPA, etc.) often lacks clarity, speed, or depth. This makes it hard to make informed decisions quickly.
- Lack of Leadership: Many entrepreneurs find themselves overwhelmed by financial jargon and processes. Without a clear understanding of what a finance function should deliver, they struggle to hold professionals accountable.
Recognizing these issues is the first step toward building a scalable and effective financial infrastructure within your business.
Step 1: Assess Whether It’s Time to Hire In-House
One of the first key decisions is whether to transition from outsourcing to hiring an in-house finance team. According to Shannon, this decision often coincides with reaching $3M–$5M in annual revenue. While early-stage businesses prioritize revenue-generating roles like sales and marketing, businesses at this level must shift focus to keeping their earnings and minimizing risks.
Questions to ask yourself before hiring in-house:
- Are your current outsourced solutions consuming too much of your time due to inadequate communication or slow response times?
- Do you lack the timely, consolidated, and actionable financial data needed for strategic decision-making?
- Can your business afford to allocate resources to a full-time finance hire without jeopardizing other priorities?
If the answers point to inefficiencies or gaps in your current setup, it may be time to consider evolving your finance function.
Step 2: Understand the Kind of Finance Talent You Need
Hiring the right financial professional isn’t as simple as placing a job ad. It’s critical to understand the different roles and their responsibilities to ensure you get the right fit for your business stage.
The Bookkeeper:
Handles day-to-day transactional tasks like recording expenses, reconciling accounts, and managing payroll. A good option for businesses in early stages but often too junior for larger-scale operations.
The CPA:
Focuses on tax compliance and filing. While invaluable during tax season, CPAs rarely provide the real-time, strategic financial insights that growing businesses need.
The CFO:
A strategic leader who delivers high-level financial planning, risk management, cash flow forecasting, and decision-making support. However, full-time CFOs command salaries starting at $200,000 annually - an investment many businesses aren’t ready for.
The Fractional CFO:
A middle-ground solution that offers access to CFO-level expertise on a part-time or project basis. Fractional CFOs can help businesses transition from a reactive, patchwork finance model to proactive financial management without the full-time cost.
By understanding these roles, you can identify which position aligns with your current challenges and growth trajectory.
Step 3: Avoid These Common Hiring Pitfalls
Hiring finance talent is often challenging for entrepreneurs, particularly if they lack expertise in this area. Here are the three most common mistakes and how to avoid them:
1. Hiring Without Leadership Clarity
Many business owners don’t know how to lead or hold a finance professional accountable. Without understanding what the role should deliver, they risk overpaying for underperformance.
Solution: Before hiring, clarify the scope of responsibilities. Partner with a finance expert or fractional CFO to help you define the role, set expectations, and create measurable performance metrics.
2. Underestimating the Costs
Hiring full-time finance staff involves more than just a salary. There are recruitment costs, employee benefits, onboarding processes, and IT setup. For businesses not ready for this commitment, fractional solutions are often the better choice.
Solution: Consider the total cost of a full-time hire versus the flexible, scalable costs of fractional services. A fractional CFO can provide high-value expertise without the overhead of hiring full-time.
3. Failing to Evaluate Technical Skills
Many entrepreneurs hire finance talent based on resumes or interviews without assessing technical proficiency. This can lead to costly mistakes, especially if the individual lacks the expertise to handle messy books or complex financial scenarios.
Solution: Use case studies or technical evaluations during the hiring process. Fractional CFOs can assist in vetting candidates by conducting interviews or reviewing technical skills.
Step 4: Leverage Fractional CFOs for Strategic Insights
Fractional CFOs aren’t just temporary placeholders; they’re strategic partners who can save you time, money, and stress. Beyond managing day-to-day finances, they can:
- Conduct financial audits and clean up messy books.
- Help you evaluate and hire permanent finance staff.
- Provide clarity on financial metrics to guide business decisions.
- Offer tailored guidance for scaling operations, managing cash flow, or securing funding.
Additionally, engaging a fractional CFO on a project basis - even temporarily - can help you diagnose your business’s specific financial needs and create a roadmap for future hires.
Key Takeaways
- Recognize the Limits of Outsourcing: If your business has outgrown the capabilities of a bookkeeper or CPA, it’s time to rethink your finance strategy.
- Define the Right Role: Understand the responsibilities of bookkeepers, CPAs, CFOs, and fractional CFOs to determine what aligns with your needs and budget.
- Fractional CFOs Fill the Gap: For businesses not ready to pay for a $200K CFO, fractional CFOs provide high-level expertise at a fraction of the cost.
- Avoid Hiring Mistakes: Clarify leadership expectations, evaluate technical skills, and account for hidden costs to prevent costly missteps.
- Get Expert Help: Partnering with a fractional CFO, even on a project basis, can streamline the hiring process, improve accountability, and set up your financial function for success.
Conclusion
Bringing finance talent in-house is a critical step for businesses transitioning from startup to a scalable enterprise. However, it’s essential to approach this decision with strategic clarity and a plan for leadership. Whether you hire full-time or choose the flexibility of a fractional CFO, investing in the right talent ensures that your financial systems aren’t just supporting growth - they’re driving it.
By understanding the nuances of these roles and leveraging expert insights, you can build a finance team capable of supporting your business’s goals and mitigating risks. Remember: it’s not just about generating revenue. It’s about keeping what you earn and using it to fuel long-term success.
Source: "Your Finance Hire - Dos and Don'ts" - Keep What You Earn, YouTube, Aug 25, 2025 - https://www.youtube.com/watch?v=T8LVvAH_wX4
Use: Embedded for reference. Brief quotes used for commentary/review.
