Tax Season 2025
We'll handle your 1099 filings
We'll handle your 1099 filings
We'll handle your 1099 filings
Stop stressing about tax season. Let us collect W-9s, track payments, and file all your 1099s with the IRS—automatically and accurately.
Stop stressing about tax season. Let us collect W-9s, track payments, and file all your 1099s with the IRS—automatically and accurately.
Stop stressing about tax season. Let us collect W-9s, track payments, and file all your 1099s with the IRS—automatically and accurately.
ABOUT CLEO PAY
More than just 1099 filing—complete vendor payment automation
More than just 1099 filing—complete vendor payment automation
Cleo Pay is a complete accounts payable automation platform built for modern finance teams. We help you manage vendor relationships, automate payments, and stay compliant year-round
Cleo Pay is a complete accounts payable automation platform built for modern finance teams. We help you manage vendor relationships, automate payments, and stay compliant year-round
Our platform tracks every vendor payment automatically, collects W-9s as you onboard new vendors, and ensures you're always ready for tax season—no last-minute scrambling required.
Our platform tracks every vendor payment automatically, collects W-9s as you onboard new vendors, and ensures you're always ready for tax season—no last-minute scrambling required.
Beyond 1099 filing, Cleo Pay Pro handles:
• Invoice processing and approval workflows
• Invoice processing and approval workflows
• Bill payments via ACH, check, or virtual card
• Bill payments via ACH, check, or virtual card
• Real-time spend tracking and reporting
• Real-time spend tracking and reporting
• Purchase order management
• Purchase order management
• Vendor portal for self-service
• Vendor portal for self-service
• Integration with your accounting software
• Integration with your accounting software
THE CHALLENGE
Here's what tax season typically looks like for busy finance teams
Here's what tax season typically looks like for busy finance teams
The Old Way
Digging through emails and invoices to find every vendor you paid over $600. Chasing people down for W-9 forms. Manually entering data into spreadsheets. Double-checking TIN numbers. Hoping you didn't miss anyone. Then discovering errors after you've already filed.
The Cost
The IRS requires accurate 1099s for every vendor paid over $600. Miss a form or file incorrectly, and penalties start at $60 per form—up to $630 for intentional disregard. With 100 vendors, that's potentially $60,000+ in avoidable fines, not counting the stress and time spent fixing mistakes.
THE SOLUTION
Cleo Pay handles everything automatically, so you can focus on running your business
Cleo Pay handles everything automatically, so you can focus on running your business
Cleo Pay handles everything automatically, so you can focus on running your business
01
Automatic W-9 Collection
When you add a new vendor, Cleo Pay automatically sends them a request to complete their W-9 online. No paper forms, no follow-up emails, no data entry. Their information flows directly into your system, encrypted and secure.
01
Automatic W-9 Collection
When you add a new vendor, Cleo Pay automatically sends them a request to complete their W-9 online. No paper forms, no follow-up emails, no data entry. Their information flows directly into your system, encrypted and secure.
01
Automatic W-9 Collection
When you add a new vendor, Cleo Pay automatically sends them a request to complete their W-9 online. No paper forms, no follow-up emails, no data entry. Their information flows directly into your system, encrypted and secure.
02
Smart Payment Tracking
Every payment you make is automatically tracked against the $600 threshold. You'll always know exactly who needs a 1099, with no manual calculations or spreadsheet reconciliation required.
02
Smart Payment Tracking
Every payment you make is automatically tracked against the $600 threshold. You'll always know exactly who needs a 1099, with no manual calculations or spreadsheet reconciliation required.
03
One-Click Filing
When tax season arrives, simply review your vendor list and click submit. Cleo Pay generates compliant 1099-NEC forms, files them electronically with the IRS, and sends copies to your vendors—all in minutes.
03
One-Click Filing
When tax season arrives, simply review your vendor list and click submit. Cleo Pay generates compliant 1099-NEC forms, files them electronically with the IRS, and sends copies to your vendors—all in minutes.
03
One-Click Filing
When tax season arrives, simply review your vendor list and click submit. Cleo Pay generates compliant 1099-NEC forms, files them electronically with the IRS, and sends copies to your vendors—all in minutes.
04
Built-In Compliance
Our system validates TIN numbers, flags missing information, and ensures you meet all IRS requirements before filing. No surprises, no penalties, no stress.
04
Built-In Compliance
Our system validates TIN numbers, flags missing information, and ensures you meet all IRS requirements before filing. No surprises, no penalties, no stress.
04
Built-In Compliance
Our system validates TIN numbers, flags missing information, and ensures you meet all IRS requirements before filing. No surprises, no penalties, no stress.
02
Smart Payment Tracking
Every payment you make is automatically tracked against the $600 threshold. You'll always know exactly who needs a 1099, with no manual calculations or spreadsheet reconciliation required.
02
Smart Payment Tracking
Every payment you make is automatically tracked against the $600 threshold. You'll always know exactly who needs a 1099, with no manual calculations or spreadsheet reconciliation required.
SIMPLE PRICING
1099 filing doesn't have to be expensive
1099 filing doesn't have to be expensive
Transparent pricing that scales with your business
How many vendors do you need to file for?
Everything included:
Unlimited W-9 collection • TIN validation • IRS e-filing • E-delivery to vendors • Compliance checks • Support
How many vendors do you need to file for?
Everything included:
Unlimited W-9 collection • TIN validation • IRS e-filing • E-delivery to vendors • Compliance checks • Support
How many vendors do you need to file for?
Everything included:
Unlimited W-9 collection • TIN validation • IRS e-filing • E-delivery to vendors • Compliance checks • Support
Get unlimited 1099 filing with Cleo Pay Pro
Get unlimited 1099 filing with Cleo Pay Pro
$299
/ month
Get Started Today
Complete Solution
Unlimited 1099 filing (no per-vendor fees)
Unlimited 1099 filing (no per-vendor fees)
Complete accounts payable automation
Complete accounts payable automation
Automated vendor payments (ACH, check, card)
Automated vendor payments (ACH, check, card)
Invoice processing & approval workflows
Invoice processing & approval workflows
Virtual cards with spend controls
Virtual cards with spend controls
Real-time spend tracking & reporting
Real-time spend tracking & reporting
Purchase order management
Purchase order management
Vendor self-service portal
Vendor self-service portal
Accounting software integration
Accounting software integration
Priority support
Priority support
Cancel anytime
Cancel anytime
Still more affordable than: Tax1099 ($2.99/form) • TaxBandits ($3.49/form) • Avalara ($3.99/form) • 1099Online ($3.99/form) • 1099Pro ($4.99/form)
IMPACT
What happens when you automate 1099 compliance.
What happens when you automate 1099 compliance.
Hours saved per tax season
Fewer filing errors
IRS compliance rate