Your annual business tax checklist

Tax season hits right when you're busiest. While you're managing holiday sales and wrapping up the year, the IRS still wants their paperwork on time.

Skip the tax headaches. We've filed for hundreds of businesses and know exactly what you need to do. Here's your roadmap.

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Key deadlines that matter

Most small businesses and startups need to hit these four dates:

January 31: W-2s and 1099s to employees and contractors

March 1: Delaware franchise tax (if incorporated there)

March 15: S-corp and partnership returns (or file extension until September 15)

April 15: C-corp returns and estimated payments (or file extension until October 15)

Need the full timeline? We track every deadline, such as state and local taxes, paper vs. electronic filing deadlines, and estimated taxes, so you don't have to.

Close your books first

Clean financials mean faster tax prep and fewer questions later.

Before anything else, wrap up your year-end accounting:

• Confirm all balance sheet items
• Clear outstanding liabilities
• Make final adjustments

At Pilot, we close books with customers through January, then hand off to our tax team. No back-and-forth, no delays.

Handle your 1099s

Paid contractors or lawyers more than $600 this year? You owe them a 1099 by January 31.

The smart move: collect W-9 forms from every contractor when you hire them. It makes the 1099 generation automatic.

Didn't do this? Don't panic. Our tax team has an automated process to collect missing info and generate 1099s on time.

Foreign contractors: Different rules apply. You need W-8 forms regardless of payment amount. We handle these too.

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Delaware franchise tax

Incorporated in Delaware? You owe $225 minimum—$175 tax plus $50 filing fee.

The actual amount depends on your assets and shares. We calculate this using your closed financials and cap table. Most of our customers owe the minimum.

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City taxes you might forget

Cities love their own taxes on top of federal and state. Easy to miss, especially with multiple locations.

San Francisco has a gross receipts tax. New York has a business corporation tax. Both due at different times with different rules.

Our team identifies what you owe based on where you operate, then files everything. You handle initial registration; we take it from there.

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K-1 forms

Single-member LLC? Skip this section.

Multi-member LLCs taxed as partnerships need K-1s for every investor. These show each person's share of income, losses, and deductions.

We've handled simple K-1s and complicated ones. Both get filed correctly and on time.

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Federal and state returns

The final stretch. S-corps and partnerships file by March 15. C-corps file by April 15.

Here's what we recommend: file for a six-month extension every time. This moves your deadline to September or October and gives everyone room to get things right.

By then, your books are closed and your return prep is smooth.

Some businesses make quarterly estimated payments. Others don't know which states they need to file in. We catch both issues during onboarding—no surprises at tax time.

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Beyond the basics

Made it this far? There's more to consider:

• Sales tax registration and filing
• R&D tax credits for development work
• Accounting method changes for tax purposes

Our tax team handles all of these. Experience matters when regulations change and deadlines multiply.

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Let us handle your taxes

Taxes don't have to be complicated. We've done this hundreds of times.

You get seamless handoff from bookkeeping to tax prep, white-glove service for everything tax-related, and peace of mind from a dedicated team that knows your business.

Ready to skip the tax stress? Reach out to our team.

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