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 will be visible

• We actually have fun: team offsites, real camaraderie, and a culture where people genuinely like working here — not just say they do

Why You’ll Love It Here

You'll be surrounded by smart, kind, low-ego people who genuinely enjoy building together. We invest in our team with company offsites, best-in-tech swag, and the tools you need to do your best work, wherever you're based.

We support you holistically, not just at work.