Senior HR Generalist

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.

Responsibilities

• 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)

Requirements

• 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

Benefits

Additional Information

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.

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