We value your privacy. Learn more.
2025 EOY compliance checklist for startups
Protect your startup from IRS penalties and legal risks by following a structured timeline of year-end filings and upcoming 2026 regulatory changes.
You’re probably missing a compliance deadline right now.
Between now and year-end, you’ve got W-2s, 1099s, payroll tax filings, benefits reconciliations and state-specific requirements coming at you fast. If you miss one? You’re looking at potential IRS penalties, surprise tax bills and potential lawsuits from employees.
To help founders avoid these thorny hurdles, our team of startup-certified HR experts compiled this simple checklist specifically tailored for early startup founders. It walks you through what’s actually due before December 31st and what changes are hitting in 2026 including:
New pay transparency laws
Expanded leave requirements
AI hiring rules
Don’t get caught off guard when these changes take effect. Download the guide now.
What’s inside:
✅ Every filing deadline you need to it before year-end (and what happens if you don’t)
✅ 2026 regulatory changes that’ll affect your hiring, payroll and benefits
✅ A ready-to-copy checklist so you can keep yourself organized and on track
Get the First Principles newsletter in your inbox
Weekly essays on how to build great companies in unconventional ways. Read by 17,000+ startup founders and operators.
More startup resources
Newsletter
Why Rippling’s board doesn’t watch decks — they debate strategy
The crawl‑walk‑run guide Rippling’s former CFO used to turn a 20-slide deck into the KPI backbone of a $16B company.
Newsletter
Stop building AI for perfect conditions
Rippling’s Ankur Bhatt shares how brittle workflows break AI agents — and the frameworks teams need to ship reliable, reasoning-driven agents into production.
Newsletter
996 vs. 4-day work week: What founders actually chose
Live debate: 996 vs. 4-day work week. Founders share what really drives performance — grind or balance — and how to avoid burnout while scaling.
Newsletter
He hired exactly right — and still lost 3 months of runway
Rillet co-founder Nicolas Kopp shares how a hiring mistake cost months of runway — and the frameworks he built to turn contrarian bets into standout startup talent.
See Rippling in action
Increase savings, automate busy work, and make better decisions by managing HR, IT, and Finance in one place.