Startup compliance is not a single event — it is a series of thresholds and milestones, each activating new obligations. The company that only had Delaware formation obligations at seed has employment law, sales tax, benefits, and multi-state entity maintenance obligations by the time it reaches Series B. This checklist maps the compliance landscape at each stage.
At Formation (Seed / Pre-Seed)
- Delaware C-Corp formation: Articles of Incorporation filed with DSOC, registered agent designated, organizational documents executed (bylaws, board resolutions, initial stock issuance).
- BOI initial report: Filed with FinCEN within 90 days of formation (entities formed 2024+) or 30 days (entities formed 2025+). Beneficial owners identified and reported. Civil penalty: $591/day for non-filing.
- EIN obtained: IRS Form SS-4, required for opening a bank account and filing taxes.
- State foreign qualification: If operating in a state other than Delaware (almost always — typically California), file Application for Authority within the first 30–90 days of operation there.
- 83(b) elections: Founders with restricted stock must file an 83(b) election with the IRS within 30 days of the stock grant. Missing this deadline has permanent tax consequences.
- Delaware annual report calendar: March 1 deadline immediately becomes a recurring obligation. Set the reminder before you forget to set it.
At First Hire (1–5 Employees)
- EIN for payroll: Same EIN as above, but register with IRS as an employer.
- State payroll tax registration: Register with state income tax withholding and SUI agencies in every state where employees work.
- I-9 verification: Complete Form I-9 for every employee within 3 business days of start date.
- New hire reporting: Report new hires to the state new hire directory within 20 days of hire.
- Workers' compensation: Most states require workers' comp insurance from the first employee. Ohio and Washington require enrollment in the state fund.
- Workplace posters: Federal and state labor law posters must be displayed (or provided electronically) to all employees.
At 15 Employees
- Title VII, ADA, ADEA: Federal anti-discrimination laws apply to employers with 15+ employees under 42 U.S.C. § 2000e. EEO-1 reporting for employers with 100+ employees becomes relevant later.
- FMLA (50 employees): Actually triggers at 50 — but start building FMLA policy infrastructure now.
- State anti-discrimination laws: California (FEHA applies at 5 employees), New York (NYSHRL applies at 4), and other states have lower thresholds than federal law.
At 50 Employees: The Major Threshold
- FMLA: Applies to employers with 50+ employees within 75 miles of a worksite. Requires written policy and designation process under 29 C.F.R. Part 825.
- ACA Employer Mandate: If 50+ full-time equivalents in the prior year, ACA large employer obligations apply. Must offer minimum essential coverage. File Forms 1094-C and 1095-C. Penalties up to $4,460/employee/year.
- COBRA: Applies to employers with 20+ employees — confirm you crossed this threshold and have COBRA notification procedures in place.
- OSHA Recordkeeping: If 10+ employees in a non-exempt industry, OSHA Form 300 recordkeeping and Form 300A posting (February 1) are required.
At Series A: Investor Due Diligence Compliance
- Clean entity records: All Delaware annual reports current, all state registrations current, registered agent relationships maintained.
- BOI reports current: Initial report filed and all changes reflected within 30 days.
- IP assignment confirmed: All employees and contractors have executed IP assignment agreements — typically surfaced in the due diligence questionnaire.
- Cap table governance: All equity grants properly documented, 83(b) elections filed, options properly priced at FMV (409A valuation).
At Series B: Scale-Stage Obligations
- Multi-state sales tax: Revenue growth has likely created economic nexus in multiple states. Confirm registrations are current for all nexus states.
- EEO-1 Report: Required for employers with 100+ employees or federal contractors. Filed annually with the EEOC.
- Benefits plan governance: ERISA plan documents, SPDs, and Form 5500 obligations for health, retirement, and welfare benefit plans.
- Board governance: D&O insurance, board meeting minutes, consent resolutions — all part of Series B compliance posture.
Compliance Singularity's Role
Compliance Singularity tracks your company's compliance state against this checklist in real time. As you hire employees, cross revenue thresholds, and form new entities, the system automatically generates the new obligations triggered by each change and adds them to your compliance calendar. The checklist is never something you consult manually — it executes itself.