We're a small, fully remote B2B company. We don't have an HR employee so we need a sharp, senior HR generalist who can spend 10–20 hours a month keeping us compliant and giving our CEO clear answers to various people-related questions.
About usFully remote 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 part of this job.
Employees concentrated in New York and California, plus global contractors.
We run on EOS. We're comfortable with structure and documented decisions.
Our stack: Gusto (payroll/benefits), Remote.com, Dover (ATS), Google Workspace, Slack, HubSpot.
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 classification1099 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 offboardingOffer 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 benefitsParental 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 relationsHandbook 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 forYou'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.
Lead with the recommendation and show the reasoning.
Are proactive. We won't always know what to ask you, so 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."
Skills Required
- Experience running HR for small, remote, multi-state US companies
- Knowledge of New York and California labor laws, payroll tax registrations, leave requirements, notices, postings, and pay rules
- Experience determining 1099 versus W-2 classification under federal and state tests, including California’s ABC test
- Experience managing contractor agreements and agency or staff-augmentation relationships to prevent co-employment issues
- Experience with onboarding and offboarding, including offer letters, I-9s, background checks, state-specific new-hire paperwork, access removal, final pay, and documentation
- Experience administering parental leave, New York DBL/PFL, disability carriers, and benefits brokers
- Ability to maintain handbooks and policies and coach managers on employee-relations matters
- Ability to provide accurate, proactive HR guidance and clearly distinguish known information from items requiring verification
- Ability to communicate concise recommendations and cost models directly to a CEO
- Responsiveness within one business day
- Startup HR experience
