Payroll & Benefits
Payroll, benefits, and equity administration
Multi-state payroll, equity compensation, 409A coordination, and the operational work that compounds as you cross 25 employees.
Payroll and benefits look simple at ten employees and get expensive to fix once they are broken at fifty. Every remote hire in a new state creates a registration obligation. Every 401(k) contribution has to be remitted within days, or a founder discovers a fiduciary problem during their first audit. Every equity grant flows through the cap table, the stock comp expense schedule, and the 409A model. And every one of those things has a specific right answer that the market has already figured out.
This section covers the integrated payroll and 401(k) stack we recommend for venture-backed startups, the benefits stack a Series A or B team should actually offer versus what looks good on a recruiting page, multi-state employment compliance and where the operating expense hides, and the mechanics of ISOs, NSOs, and RSUs. It also covers 409A refresh timing, ASC 718 stock comp expense, and how equity administration ties back to the cap-table system of record.
Start with the payroll and 401(k) anchor post and the benefits stack piece, then work outward as your team crosses the thresholds that make each new topic urgent.
Payroll & Benefits
ISO vs NSO vs RSU: a founder's decoder for what you have and what to do with it
How ISOs, NSOs, and RSUs each work, when to use each, the AMT trap, the 83(b) window, and the equity plan we recommend at Series A and B.
13 min read
Payroll & Benefits
Equity compensation 101: ISOs, NSOs, RSUs, and when each one actually makes sense
A practical guide to startup equity comp: when ISOs, NSOs, and RSUs each make sense, the tax implications, and what to grant at Series A and B.
13 min read
Payroll & Benefits
Health insurance for startups: PEO vs. group plan vs. individual stipends
PEO, direct group plan, or individual stipends — a clear-eyed comparison of the three startup health insurance options, with real per-employee costs.
12 min read
Payroll & Benefits
The Series A/B benefits stack: what to offer, what it actually costs, and what employees actually use
An operator's guide to designing a competitive Series A/B benefits package — what to offer, what each component costs per employee, and what your team will actually use.
16 min read
Payroll & Benefits
Payroll tax for the unprepared: federal, state, FICA, FUTA, SUTA, and the deposit schedule that will trip you up
What you actually owe in startup payroll taxes — federal, FICA, FUTA, SUTA — the deposit schedule that trips up founders, and how to stay correct.
11 min read
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