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  • Dennis Bingham

Is an S Corporation the Right Structure for Your Business

Updated: Jun 6

S Corporation on green baclground with abstract drawings

Deciding on your company's ideal legal and tax structure is complex.

Entrepreneurs are often drawn to the potentially alluring benefits of S corporations. The reduced self-employment taxes and liability protections seem like a slam dunk compared to operating as a sole proprietorship or general partnership.

However, there are still plenty of complexities involved in electing this specialized corporate status that gives some business owners pause, especially the strict eligibility criteria and extensive filing demands from the IRS.

So, how do you know if transitioning to an S Corp truly makes sense for your enterprise? What exactly even constitutes an S corporation in the eyes of the tax code, and how does it compare to structures like LLCs?

This comprehensive guide aims to explore all facets of S corps so that you can make an informed assessment of whether an S corporation is right for your organization.

While every company faces unique needs and constraints, understanding the complete picture of the upsides and drawbacks associated with this entity will lead to the optimal outcome.

A little systematic evaluation can provide the roadmap to operate under the ideal framework today and for years ahead as your enterprise evolves. 

The keys to establishing your empire on a solid foundation lie within grasp!

What is an S Corporation?

An S corporation refers to a specific legal business structure organizations can use for taxation and liability purposes.

Rather than operating as a traditional C corporation, sole proprietorship, partnership, or LLC by default, business owners can elect S Corp status by filing IRS form 2553. This election enables pass-through taxation while still providing limited liability protections.

Specifically, an S corporation is an incorporated entity that meets special IRS qualifications related to the maximum number of shareholders, shareholder eligibility criteria, issuing only one class of stock, and other factors. By conforming to these rules, the business gains unique tax treatment and takes on formal operations and profit allocation obligations.

The "S" refers to Subchapter S of the tax code. While electing S status causes increased administrative responsibilities like payroll, accounting, and record-keeping, this choice unlocks significant tax incentives that can benefit eligible organizations. Income earned by the S corp gets passed straight through to the shareholders rather than being taxed at the corporate level first.

In essence, S corps aims to blend elements of partnerships, which pass income directly to partners to avoid double taxation, with attributes of corporations that shield owners from personal liability. This hybrid approach squares the benefits of each structure into one.

Now that we've covered the basic definition let's explore the pros and cons of operating as an S corporation.

S Corporation Pros and Cons

Electing S corporation status offers some alluring benefits but also has downsides. Let's explore the pros and cons of operating as an S corporation versus remaining structured as a partnership, LLC, or sole proprietorship.


  • Reduced Self-Employment Taxes - Shareholders only pay Medicare and Social Security payroll taxes on wages earned, not the entire company's profits. This can unlock huge federal tax savings annually.

  • Pass-Through Taxation - Income passes straight through to shareholders without being taxed at the corporate level first, avoiding double taxation. Overall, this approach often significantly reduces the income tax burden.

  • Limited Liability Protection - Shareholders' assets are shielded from corporate debts and legal claims, limiting financial exposure risks in ways that sole proprietors and general partnerships do not.


  • Administrative Overhead - Extensive annual tax compliance and financial reporting requirements to maintain S corp status qualification create added operational burdens.

  • Payroll Tax Administration - Shareholders still owe full Medicare and Social Security payroll taxes on reasonable wages paid to themselves as company employees. This tax obligation does not apply to LLC member distributions or limited partnership payments to partners.

  • Ownership Restrictions - An S corporation is limited to 100 U.S. resident shareholders. Rules about who can own shares also apply, as only specific individuals, estates, exempt organizations, or certain trusts qualify as eligible shareholders in an S corporation.

Evaluating the unique tax planning advantages and operational responsibilities can clarify whether transitioning to an S corporation better aligns with your entrepreneurial visions or clouds your aspirations.

Armed with eyes wide open, moving forward offers the best path to achieving small business success.


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Tax Benefits In-Depth 

Potential tax incentives are a primary reason business owners consider pursuing an S corporation election with the IRS. But how do these benefits translate when it comes time to file taxes? Let's explore the two primary tax perks in more tangible detail.

Reduced Self-Employment Taxes

Self-employment taxes refer to the 15.3% tax rate all small business owners pay, which funds Social Security and Medicare. This tax applies to your total business earnings when your business is structured as a sole proprietorship or partnership.

However, by becoming an S Corp, you only pay self-employment taxes on the reasonable salary you draw from the company, not the total profits. This shields distribution and your salary from that 15.3% tax, significantly reducing your overall tax obligation.

For example, if your S corp has $200,000 in net income this year, and you pay yourself a $100,000 salary, you would only owe self-employment taxes on the $100,000 salary portion. This could save well over $15,000 compared to if you remained structured as an LLC or sole proprietorship.


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Pass-Through Taxation

S corps allow business income, losses, deductions, and credits to "pass-through" to shareholders' tax returns. This means earnings are taxed once at the individual level rather than twice (known as "double taxation") under the traditional C corporation structure.

LLCs provide pass-through status automatically, but the added self-employment tax reduction capability squares S corps away as an even more favorable structure from an income tax perspective. This framework allows shareholders to save enormously between federal and state-level rates.

Consult Experts

With strategic tax planning guidance from accounting professionals, your business could see sizable tax savings by transitioning to an S-Corp structure. Contact experts who understand your operations intimately to run comparisons and assess the financial upside.

Operational Considerations In-Depth

While the tax incentives of S corps appeal to many entrepreneurs, evaluating if this structure aligns with your goals requires assessing how the election could impact your business operations.

Let's explore some critical considerations around administrative overhead and payroll taxes.

Increased Filing and Accounting Demands

To elect and maintain S Corp status, businesses must adhere to strict IRS compliance rules around record-keeping, shareholder agreements, corporate bylaws, holding shareholder meetings, and directors' meetings. Detailed records must trace things like officer salaries and profit allocations.

Since accounting complexity rises considerably, transitioning to an S corporation can result in a 20-40% increase in tax preparation fees.

Many small businesses must implement payroll systems to account for officer salary payments. Legal fees also often increase when making the S election.

Payroll Tax Considerations 

While only reasonable salaries owed by shareholder-employees trigger self-employment taxes, the company must pay payroll taxes on all employee wages, like an LLC or corporation. This category includes salaries, retirement contributions, health insurance, and other benefits.

So, while self-employment tax exposure decreases, your business sees no payroll tax savings by being an S Corp versus alternative structures. With employees beyond just owner-shareholders, these taxes add up substantially. Be sure to scrutinize the complete financial impact.

Informing Operational Changes 

Pursuing an S Corp election causes fundamental changes across accounting, payroll, HR, and your legal obligations as a company. Ensure you proactively address these complexities with input from financial and legal advisors. You are navigating operational impacts with eyes wide open, which sets the stage for success.

Evaluating Is an S Corporation the Right Structure for Your Business 

Not all small businesses make ideal candidates for transitioning to S Corp status after weighing operational changes against tax incentives. Take an objective assessment guided by advisors to determine whether this structure aligns with your goals. Key questions to ask:

  • Do you expect your profit trajectory revenue and pro to continue growing significantly? The tax advantages compound as your income scales up.

  • Do you plan to reinvest most profits into the business for expansion or retain most earnings? If so, the pass-through taxation may offer fewer current benefits.

  • Do you foresee needing outside investor funding within the next five years? The 100-shareholder cap could constrain financing options down the road.

  • Does your team have the capacity and skills to handle the increased administrative workload? Lacking capacity could overwhelm your focus.

When choosing an entity structure, every business faces unique needs and constraints. Your advisors can quantify scenarios to estimate impacts specific to your circumstances.

Call To Action - Next Steps 

If exploring the S Corp election, have candid conversations with your CPA and business attorney to assess suitability across financial modeling and legal perspectives before filing for the transition. Key next steps include:

  1. Review your last two years' financial records and the current year's P&L to model tax impact

  2. Analyze your current operating agreement or bylaws for needed changes

  3. Compare income tax and self-employment tax liability under your current business structure to the projected S Corp scenario.

  4. Estimate costs of added accounting support, tax prep fees, payroll system, etc.

  5. Formalize future operating processes and agreements to conform to S Corp governance requirements.  

You are arming yourself with 360-degree clarity on how the transition could unfold, which positions you to make the most informed decision—privacy before profits.


Electing S corporation status opens the door to compelling tax incentives, such as reduced self-employment taxes and pass-through income tax rates.

However, the increased operating complexities around payroll, accounting, and reporting requirements also demand careful evaluation. 

Assess your motivations and risk appetite to determine if an S corp aligns with your financial and functional business objectives.

The soundest structures enable your brightest visions.

Additional Resources

Thank you for reading this article. Is an S corporation the right structure for your business? We recommend these additional articles related to choosing a legal structure.


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