The short version
We're a small, fully remote B2B company. We don't have an HR employee and we don't need one — we need a sharp, senior HR generalist who can spend 10–20 hours a month keeping us compliant, keeping our people paperwork clean, and giving our CEO straight answers to questions like "what does this actually cost us, and what are our options?"
This is not a coordinator role. You will be the most senior HR voice in the company. Your work goes directly to the CEO.
About us
Fully remote, US-based team, under 10 employees — which means a lot of the big-employer thresholds don't apply to us. Knowing exactly which ones do is a meaningful part of this job.
Employees concentrated in New York and California, plus global contractors.
We run on EOS (Rocks, Scorecard, L10s). We're comfortable with structure and documented decisions.
Our stack: Gusto (payroll/benefits), , Dover (ATS), Google Workspace, Slack, HubSpot.
What you'll own
Multi-state compliance for a remote team
State payroll tax registrations, NY and CA labor law (leave, sick time, pay transparency, final pay, meal/rest rules), required notices and postings, and telling us early when a new hire in a new state creates a new obligation.
Contractor vs. employee classification
1099 vs. W-2 determinations under both federal and state tests (including CA's ABC test), contractor agreements, and clean management of an agency/staff-aug relationship so we don't drift into co-employment.
Onboarding and offboarding
Offer letters, I-9s, background checks, state-specific new-hire paperwork, and an offboarding checklist that holds up — including the access, final-pay, and documentation pieces that a SOC 2 audit will eventually ask about.
Leave and benefits
Parental leave policy administration, NY DBL/PFL, disability carrier and broker coordination, and clear cost modelling so the CEO can make informed calls.
General HR admin and employee relations
Handbook and policy maintenance, manager coaching on the awkward conversations, documentation when something needs documenting, and a calm second opinion when we're not sure whether something is a problem.
Who this is for
You'll do well here if you:
Have run HR for small, remote, multi-state US companies — ideally startups.
Get the details right. We've been burned by confident-sounding guidance that turned out to be wrong. If you're not sure, we'd much rather hear "here's what I know, here's what I need to verify, here's how I'll verify it."
Write for a CEO, not for HR. Lead with the recommendation and the number. Show the reasoning underneath, not on top. One page beats five.
Are proactive. We won't always know what to ask you. Part of the value is you telling us what's coming.
Are responsive within a business day, even if the answer is "on it, full answer by Thursday."
Probably not a fit if: you need a lot of direction, you work primarily through existing templates, or you're looking for the volume of work.
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