Compliance

How to Build, Manage, and Maintain Them

How to eliminate weeks of manual reconciliation and ensure seamless January filing

Stop scrambling every January: automate the manual work now and walk into tax season completely prepared

Hint: the solution involves automation.

Build a W-9 collection and TIN matching workflow with clear owners, secure updates, mismatch resolution, and records ready for 1099 review.

The next payment is due sooner than you might think.

Streamline Tax Compliance for Claims Adjusters: Simplify Your 1099 Process This Season

How Telehealth Providers Can Simplify Tax Season—Simplify 1099 Filing with Automation to Save Hours and Eliminate Errors

A fast-growing telehealth enterprise needed a better way to manage the processes behind creating and delivering thousands of 1099 forms to its growing network of mental health providers around the country. They partnered with Wingspan to make it happen.

Webinar Recap: 3 Key Challenges with 1099 Filing (and How to Solve Them)

Compare 1099 software, outsourced filing, and hybrid workflows with an ownership map, cost worksheet, and practical tests for data and corrections.

Understand 1099 filing penalties by return due year, separate IRS and recipient obligations, and follow a practical process for missed or incorrect forms.

Choose between 1099-NEC, 1099-MISC, and 1099-K using payment type, 2026 thresholds, reporting responsibility, and the correct filing deadlines.

Streamline Your 1099 Filing: How to Tackle Tax Season Stress-Free for Your Contractors and Business

Use a practical COI review checklist to define contractor insurance requirements, route exceptions, track renewals, and retain clear decisions.