Your 2026 Compliance & Tax Survival Guide

The compliance and tax burden on businesses is growing with new laws going into effect across the national, state, and even local level. Find out how you can stay ahead of the changes and make sure your business and your people are protected. Plus, you’ll learn about the key tax deadlines coming up and what you can do now to get ahead to ensure a smooth January.

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Find out what’s new in 2026

Get a clear breakdown of the 2026 changes and what they mean for hourly teams and multi-location businesses.

Get clear guidance for year-end prep

Avoid the January scramble by cleaning up your W-2 and 1099 data. Find out the key payroll and tax tasks you need to complete.

Let automation handle the hard stuff

See how When I Work and Rippling work together to simplify payroll and compliance and give you peace of mind going into the new year.

Hosts

Jenny Roselyn

Jenny Roselyn

Product Marketing Manager

Jenny Roselyn is a Product Marketing Manager at When I Work with over 7.5 years of experience helping customers succeed. She began her career in Customer Care, where she developed a deep, hands-on understanding of the product and the real-world challenges hourly teams face. Today, Jenny serves as the voice of the customer across the organization—specializing in uncovering user pain points, shaping product value, and leading go-to-market strategies that help businesses get the most from When I Work.

Grace Carpenter

Grace Carpenter

Finance Technical Account Consultant

Grace Carpenter is a Finance Technical Account Consultant at Rippling with 8.5 years of experience in the HR, payroll, and benefits industry. Specializing in payroll and compliance, Grace works closely with clients to configure Rippling’s Finance suite—including Payroll, Accounting, Time Tracking, and Spend Management—to align with their unique business needs and ensure the most seamless experience possible. Over the past eight years, she’s supported hundreds of small businesses through successful year-end cycles, offering guidance on checks, reporting, and evolving compliance requirements. Outside of Rippling, Grace is a small business owner running a boutique event floral company and loves spending her free time exploring the mountains of southwest Colorado.