We recently sat down with a potential new client for a tax consultation. Within 15 minutes of reviewing their previous year’s tax return, we found a $20,000 mistake, a mistake that could’ve been avoided with one simple move.
They didn’t do anything wrong. They worked with a competent tax preparer. But that’s the problem, they had a tax preparer, not a tax planner.
If you’re only looking at taxes in March or April, you’re reacting to the past. Tax planning is about being ProActive about making smart decisions throughout the year that legally lower your tax liability. And if you’re not doing that, you’re probably paying more than you should.
If your business is generating over $10 million in annual revenue, the stakes are higher. You’re not just filing taxes, you’re managing complex compensation structures, multiple entities, and aggressive growth targets. In that environment, tax planning isn’t optional, it’s a strategic imperative.
The Limitation of Compliance Only Thinking
Most mid-market companies work with experienced tax preparers. But preparation is backward-looking, it’s about recording what already happened. Once the year ends, your flexibility ends with it.
Tax planning, by contrast, gives you control over timing, structure, and optimization, and that translates directly into higher cash flow and lower risk.
If your advisors only engage at tax time, you’re playing defense. Strategic planning lets you play offense, minimizing liabilities, aligning with growth plans, and protecting your capital.
What You Could Be Missing
When your company is growing and reaching the next level, your tax landscape is far more nuanced. Without a ProActive plan, here’s what may be slipping through the cracks:
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Inefficient entity structure costing hundreds of thousands in excess taxes
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Compensation strategies that fail to optimize payroll tax exposure and benefits
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Asset purchase timing that misses out on accelerated depreciation opportunities
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Underutilized tax credits, such as R&D, 45L, or energy efficiency incentives
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Unnecessary exposure to audit risk due to poor documentation or timing decisions
We’ve helped mid-size clients uncover six-figure tax savings by aligning their financial decisions with a well-structured tax strategy.
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What a Mid-Market Tax Plan Should Include
A tax plan for a business of your scale goes far beyond checklists and spreadsheets. It should be a living, dynamic strategy aligned with your executive roadmap. Key components include:
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Entity Optimization: Strategic review of structure across business lines, ownership tiers, and long-term exit strategy
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Executive Compensation Planning: Integrated W-2, distributions, fringe benefits, and deferred comp arrangements
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Capital Expenditures & Depreciation: Timing, cost segregation, and utilization of bonus depreciation and Section 179
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Tax Credit Strategy: Comprehensive evaluation of federal, state, and industry-specific credits
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Multi-State Tax Compliance: Nexus risk management, apportionment analysis, and filing optimization
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Forecasting & Scenario Planning: Real-time modeling based on cash flow projections, investments, and tax law updates
Practical Moves You Can Make Now
Even without a formal plan in place, there are immediate steps you can take to improve your tax posture:
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Assess your structure — Is your current entity still aligned with your business model and goals?
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Review owner and executive compensation — Are you balancing tax efficiency with retirement planning and risk exposure?
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Ensure asset purchases are timed strategically — Especially in years with significant capex
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Audit your current use of tax credits — Many credits go unclaimed due to lack of proactive review
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Schedule a Q3 or Q4 tax strategy meeting — Waiting until March is too late
The Cost of Inaction
Missed tax strategies don’t just cost a few thousand dollars, they can compound into six or seven figures in lost cash flow, increased audit exposure, and misaligned financial decisions. Worse, they often remain hidden unless someone knows what to look for.
At Whittaker CPAs, we specialize in ProActive tax strategy for growth-stage and mature private companies. Our clients rely on us not just to file returns, but to design strategies that strengthen their margins, reduce volatility, and support scalable growth.
