CheckMark 1099 Software vs Stripe Connect
CheckMark 1099 Software
checkmark.com
Stripe Connect
stripe.comSide by side
| Figure | CheckMark 1099 Software | Stripe Connect |
|---|---|---|
| Price from | $19.92/mo | $20.25/mo |
| Free plan | — | Yes |
| Free trial | Yes | — |
| Open source | — | — |
| Web | — | Yes |
| Windows | Yes | — |
| macOS | Yes | — |
| iOS | — | Yes |
| Android | — | Yes |
| API | — | Yes |
| Plans published | 4 | 3 |
| Spec score · 1099 Filing Software | 8.1 (#8) | 8.8 (#3) |
| Headquarters | Fort Collins, Colorado, United States | San Francisco and Dublin |
| Purpose | The software prepares, prints, and e-files 1099 forms for businesses and accounting professionals. | Connect embeds payments in software platforms and marketplaces and helps orchestrate money movement across multiple parties. |
| Security | CheckMark says 1099 data is stored locally, not uploaded or accessed by CheckMark, and files are encrypted and opened with its software. | The Connect features page lists PCI DSS Level 1 certification and PSD2 Strong Customer Authentication compliance. |
| Support | The plans include US-based customer support, with up to 60 minutes for Pro and 120 minutes for Pro+ within the tax year. | Connect’s features page advertises 24x7 support by phone, chat, and email. |
| Who it serves | CheckMark describes the product as suitable for business owners, CPAs, accountants, tax preparers, bookkeepers, and 1099 filing service providers. | Stripe describes Connect as suitable for software platforms, marketplaces, and businesses that need to coordinate payments among multiple parties. |
Plans
CheckMark 1099 Software
- CheckMark 1099 Print Pro$239 a year
- CheckMark 1099 Print Pro+$259 a year
- CheckMark 1099 E-File Pro$319 a year
- CheckMark 1099 E-File Pro+$339 a year
Stripe Connect
- Stripe handles pricing for your usersFree
- You handle pricing for your users$20.25 a month
- Stripe handles pricing for your usersPriced on request
In their own words
CheckMark 1099 Software
CheckMark 1099 Software prepares, prints, and e-files forms for businesses and accounting professionals. It supports 1099-NEC, 1099-MISC, 1099-INT, 1099-DIV, 1099-R, and 1099-S, and is intended for the 2026 tax filing year; it cannot file forms for earlier years. The desktop application runs on Windows and macOS, including Intel-based and Apple Silicon Macs. Data can be imported from CheckMark Payroll, CheckMark MultiLedger, or a tab-delimited text file. For IRS IRIS filing, the software creates CSV files that users upload and submit through the IRIS Taxpayer Portal, which requires an IRIS account and TCC. CheckMark says data remains on the user's computer and is not uploaded or accessed by the company; files are encrypted and opened with its software. Password-protected users can have permissions restricting access to sensitive screens or information. Plans start at $239 a year for the 2026 tax year version. A free demo uses sample company data for printing or creating electronic files.
Stripe Connect
Stripe Connect embeds payments in software platforms and marketplaces and coordinates money movement among multiple parties. Platforms can choose Stripe-hosted, embedded, or custom onboarding, including identity verification and networked onboarding for existing Stripe users. Connect supports payments in 135+ currencies and 40+ payment methods across online, mobile, subscription, invoicing, and point-of-sale flows. Platforms can split payments, route funds across borders, control payout timing, and offer instant payouts. Prebuilt connected-account dashboards include controls for payments, payouts, settings, notifications, and payment methods. Risk and compliance features include KYC and AML checks, sanctions screening, MATCH list checks, and fraud management. Connect can automatically generate US 1099 forms; e-filing and delivery fees vary by pricing model. Its listed security features include PCI DSS Level 1 certification and PSD2 Strong Customer Authentication compliance. Pricing may involve no platform fees when Stripe handles user pricing, or $2 per monthly active account plus 0.25% + 25¢ per payout sent; other usage fees may apply.