Senior HR Generalist, Unstructured.io

• 5–8 years of HR generalist experience, with at least 2 years at a startup or high-growth tech company (Series A–C preferred and/or upward growth from 100 employees)
• Hands-on experience with a PEO environment (Justworks, Rippling, or equivalent)
• Solid grounding in US employment law; comfort navigating multi-state complexity
• Excellent written communication — you draft clearly, document carefully, and know when to loop in counsel
• High degree of discretion and emotional intelligence; people trust you with sensitive information

Desirable

• We're at a pivotal moment — post-Series B with Series C on the horizon, scaling headcount fast and building the people infrastructure to match. This is a hands-on, high-ownership role at the center of everything that keeps our people systems running: compliance, onboarding, HR ops, employee relations, and cross-functional support for Legal, Finance, and Ops leaders
• You'll be a true partner to the Head of People — owning the operational work that keeps the people function running while also having a seat at the table on strategy. This role spans both ends deliberately: you'll handle the nuts-and-bolts of HR ops and be expected to shape how we build programs, not just run them
• The person who thrives here shows up with energy, brings a solutions-first mindset to hard conversations, and makes the people around them feel supported — even on a tough day
• Maintain the employee lifecycle in our PEO (Justworks) — onboarding, offboarding, status changes, leaves
• Own compliance calendars: state registrations, required training, policy updates
• Administer and audit benefit programs; serve as primary liaison to benefits brokers and PEO
• Ensure handbook and policy documentation stays current across jurisdictions
• Support offer letter creation and compensation benchmarking using Pave
• Partner with People, Finance and Legal on total rewards program design and administration
• Handle day-to-day ER issues — PIPs, accommodations, conflict resolution — with discretion and good judgment
• Draft and manage separation agreements, including release language and severance
• Partner with legal counsel on pre-litigation matters; maintain clean documentation trails
• Support managers through performance cycles, calibrations, and difficult conversations
• Offer logistics, and own onboarding handoffs
• Run or support people programs: engagement surveys, manager effectiveness, new-hire check-ins
• Own HRIS data integrity and HR reporting cadence (headcount, attrition, time-to-fill)
• What Success Looks Like:
• 90 days: You own the Justworks queue, HR documentation is clean and current, and you've closed at least one ER matter independently
• 6 months: HR compliance calendar is systematized, separation agreement process is templated and reliable, and you're a trusted resource for managers company-wide
• 12 months: You've materially reduced post-termination legal activity, people programs are running on a repeatable cadence, and leadership considers you a strategic partner — not just an operator