Contractor 1099 Tax Compliance & E-Filing3 min readUpdated September 2026

Tax1099 vs Track1099 for a SaaS Company's Contractor Payouts

For a SaaS company's contractor payouts, Track1099's CSV import suits payments made through Stripe or another payments tool, while Tax1099 fits when your accounting system holds the data. The list mixes a retainer backend engineer, a per-article technical writer, part-time community help, and a one-sprint QA tester, none of them on payroll.

Filing their 1099s correctly starts with knowing who actually needs one. A contractor based outside the US generally gets a W-8BEN instead, not a 1099, and mixing that up is the single most common mistake engineering-heavy companies make in January.

Vendors Covered in this Article

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Separating US contractors from international ones before you file

Both platforms can generate a 1099-NEC for whatever payee data you upload, but neither decides whether a payee is a US or foreign person, so confirm before filing: a foreign individual typically provides a Form W-8BEN rather than a W-9, and payments to foreign contractors may be reported on Form 1042-S instead, so check with your CPA. Track1099 gives you a clean space to keep W-8BEN records alongside your 1099 recipients, but the separation is still manual. Whichever platform you use, do a manual pass on your contractor list before filing season to catch payees who are corporations, foreign persons or missing a W-9, since a filing tool can't decide the right form for you.

Pulling contractor payments out of Stripe, Gusto Contractor or your own ledger

Most SaaS finance teams don't pay contractors out of accounts payable software; they pay through Stripe, Mercury or a contractor-payments tool, then reconcile in the general ledger. Tax1099 can connect directly to some accounting systems, but if your contractor payments live somewhere else first, ask which systems it currently supports before assuming yours is covered, since you're exporting a CSV either way if it isn't. Track1099's import is built for exactly that: drop in a CSV from wherever the payment actually happened, map the columns, and you're done. For an engineering-heavy company where contractor payments rarely touch a traditional AP system, that flexibility usually matters more than a direct ledger connection.

TIN matching for a list that turns over every quarter

Contract engineers rotate faster than full-time hires at most software companies: a six-month contract ends, a new one starts, and last year's vendor list barely resembles this year's. Both platforms run TIN matching before you file, which catches a contractor who mistyped their SSN or gave you an old address, but the value compounds if you can check continuously as contractors are added rather than once in January. Ask each vendor whether that check runs the moment a new payee is entered or only once you submit a batch, since that timing matters more here than the brand name attached to it.

What a messy contractor list actually costs

An engineering team spending even a few hours a quarter untangling contractor payment records is time not spent shipping. Payroll and contractor costs in the information sector run over 31% of revenue at small firms1, so getting the underlying data clean once, rather than reconstructing it every January, is worth the setup time. Say your company pays fifteen contractors a year: the difference between a validated vendor list and a scramble through Slack threads and old invoices is the difference between an afternoon and a week.

Handling a contractor who becomes a full-time hire mid-year

It happens constantly at growing software companies: a contract engineer converts to a W-2 employee in September. If you paid them at or above the 1099-NEC reporting threshold as a contractor from January through the conversion date, you still owe them a 1099-NEC for that amount, separate from the W-2 covering the rest of the year. Neither platform automates that split for you; you need to know the conversion date and split the payment history yourself before uploading. Pricing and billing structure differ between the two and change over time, so get current numbers from each vendor and model your actual filing volume, contractors plus any 1099-MISC filings, against them before deciding which is cheaper for a list that shrinks as contractors convert to employees.

Filing 1099-NEC alongside 1099-MISC for the same contractor list

Most contractor payments at a software company land on a 1099-NEC, but occasionally you'll owe a 1099-MISC too, for example if you paid a contractor royalties for licensing a tool they built, separate from the service fee you paid them for the work itself. Both Tax1099 and Track1099 support filing both forms, but they're separate line items in your batch, not one combined record. If your engineering team ever licenses software from an individual contractor rather than just paying for their time, flag those payments separately before you build your filing batch, and check with your CPA on how to split the reporting between the two forms.

Work through this list before you file:

  1. Sort payees into US persons and foreign contractors, since a foreign individual typically provides a W-8BEN rather than a W-9.
  2. Export contractor payments from Stripe, your payments tool, or your ledger, because neither platform connects to Stripe directly.
  3. Run TIN matching on the current list, which turns over as contracts start and end during the year.
  4. Split out any contractor who converted to a W-2 employee, filing a 1099-NEC for the pre-conversion pay if it meets the threshold.
  5. Check for 1099-MISC payments, such as royalties for a licensed tool, that sit apart from service fees.
Executive Capability Standard

What Good Looks Like

A well-run engineering org keeps W-9s and W-8BENs collected before a contractor's first invoice, reconciles contractor payments against the ledger monthly instead of in January, and can produce a clean 1099 batch without reconstructing anyone's payment history from Slack.

Building The Capability (5-Stage Skill Ladder)

1. Learn:Pull your current contractor roster and sort it into US contractors, foreign contractors and anyone who converted to a W-2 mid-year, so you know what you're actually filing for.
2. Do Manually:Export payment history from Stripe or your payments tool, hand-build a CSV, and key it into an IRS-approved e-file portal one contractor at a time.
3. Delegate:Have finance ops own W-9 and W-8BEN collection at contractor onboarding, so the data is already correct when filing season starts.
4. Automate:Run contractor payments through a platform like Track1099 or Tax1099 with CSV import and built-in TIN matching, instead of a manual FIRE upload.
5. Buy:Add a vendor onboarding tool that captures the right tax form automatically based on contractor location and status, so nobody has to sort US from international by hand.

How to Get Started

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Frequently Asked Questions

Do we need to file a 1099 for a contractor based outside the US?

Generally no. A foreign contractor who performs work outside the US and isn't a US person typically provides a W-8BEN instead of a W-9, and you don't issue them a 1099-NEC. This depends on where the work is performed and the contractor's tax status, so confirm unusual cases with your CPA.

Can we import contractor payments straight from Stripe?

Neither platform connects to Stripe directly, so you'll export a CSV of contractor payments from Stripe or your payments tool and import it. Track1099's import is built around exactly this kind of CSV mapping, which makes it a fast path if your contractor payments don't live in a traditional accounting system.

What if a contractor converts to a full-time employee partway through the year?

You file a 1099-NEC for what you paid them as a contractor before the conversion date (if it meets the reporting threshold) and report their post-conversion pay on a W-2, as two separate records. Neither platform splits this automatically, so pull the conversion date from HR and separate the payment history yourself before uploading.

How far back should we keep contractor payment records?

Keep 1099 filings, W-9s and supporting payment records for at least the period the IRS can assess additional tax, and longer if your company's document retention policy calls for it. Ask your CPA what window applies to your specific situation, since it can vary.

Sources

Where we quote a benchmark, we show its source. Other figures in this guide are estimates or general guidance, so check them against your own numbers.

  1. Payroll as % of revenue by sector, US firms with <500 employees. US Census Bureau, Statistics of U.S. Businesses (SUSB) 2022, US NAICS sector by enterprise employment size, 2022.

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