Senior HR Generalist

Unstructured is defining the standard for enterprise data transformation in the age of LLMs and generative AI. In just two years, we've raised over $65M from world-class investors, including Menlo Ventures, Bain Capital, Databricks, NVIDIA, Microsoft, and IBM. Our open-source toolkit has been downloaded 83M+ times and is used by 90% of the Fortune 1000. We power production AI workflows across commercial and federal sectors — transforming PDFs, HTML, Word docs, images, emails, and more into AI-ready data pipelines that scale. We're not just building tools, we're building the backbone of generative AI and the infrastructure that unlocks intelligence across industries. ABOUT THE ROLE 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. WHAT YOU'LL OWN HR Operations & Compliance - 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 Total Rewards & Compensation - Support offer letter creation and compensation benchmarking using Pave - Partner with People, Finance and Legal on total rewards program design and administration Employee Relations & Performance - 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 Recruiting Support & People Programs - 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 WE'RE LOOKING FOR Must-haves - 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 Strong plusses - Experience supporting pre-litigation HR matters or working alongside employment attorneys - Comfort using AI tools — particularly Claude — to accelerate drafting, research, and HR workflows - Comfort with light automation or scripting for HR workflows (Google Apps Script, Zapier, or similar) - Experience building or overhauling folder structures and HR documentation in Google Drive - PHR or SHRM-CP certification - Exercises sound risk judgment on when to escalate vs. close independently. 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 WHY JOIN - Real ownership: this isn't a support role buried in a large People org — you'll shape how HR works at a critical stage - Equity that matters: we're past the high-risk phase and heading toward a liquidity event on a realistic timeline - Smart, low-ego team: we move fast, but we're deliberate about culture and doing things right - Founder-accessible: you'll have direct lines to the leadership team and your work wi