Yes. If your cleaning company pays a subcontractor $600 or more during the calendar year and that subcontractor is not a corporation, you are required to file a 1099-NEC with the IRS. This applies to payments made by check, ACH, direct deposit, Zelle, Venmo (personal accounts), or cash. Payments made by credit card or through business payment platforms like PayPal Goods & Services are reported by the payment processor instead, so you would not issue a 1099 for those.

The single most important step is collecting a W-9 from every subcontractor before you pay them for the first time. The W-9 gives you their legal name, address, taxpayer identification number, and entity type. Without it, you cannot file a 1099 accurately at year end. This is where most cleaning companies in the Bronx and across NYC fall behind. Crews get hired, work starts, payments go out, and nobody collects the paperwork. By January when 1099s are due, owners are chasing down contractors who may have changed phone numbers or stopped responding.

Make W-9 collection part of your onboarding process before any work begins. No W-9, no first payment. It sounds strict but it saves you from a painful scramble every January and keeps you on the right side of IRS requirements.

The filing deadline for 1099-NEC forms is January 31 of the following year. You send one copy to the subcontractor and file one with the IRS. If you miss the deadline, penalties range from $60 to $310 per form depending on how late you file, and they can go higher for intentional disregard.

Many cleaning operators in the Bronx and outer boroughs rely heavily on subcontractor crews, and it is common for documentation to lag behind the actual work. This is the most frequent bookkeeping gap we see in the industry. The payments go out regularly but nobody tracks cumulative totals per subcontractor throughout the year. Then at year end, the owner has to dig through bank statements to figure out who got paid what. That process is slow, error-prone, and avoidable.

A better approach is to track subcontractor payments as they happen. Your bookkeeping software should have a vendor record for each subcontractor with their W-9 information attached. Every payment gets recorded against that vendor. At year end, pulling the totals takes minutes instead of days.

If you have subcontractors from prior years where you did not file 1099s, it is worth getting caught up. The IRS can match payments you deducted as expenses against 1099s you should have filed. A mismatch raises flags. Working with Bronx bookkeepers who understand the cleaning industry can help you clean up past gaps and build a system that keeps you compliant going forward.

Whether you file 1099s yourself or use a 1099 preparation service, the real work happens throughout the year by collecting W-9s upfront and tracking every subcontractor payment as it goes out. Do that consistently and January filing becomes straightforward instead of stressful.