Senior HR Generalist

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About the Job

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. From medical, dental, and vision coverage effective the 1st of the month following your start date, life and disability insurance, unlimited PTO, and flexible parental leave, to a 401(k) with company match, equity, a $500 work from home stipend, $70/month internet reimbursement, and team/company offsites throughout the year - we want you focused on building, growing, and staying energized for the long haul.

If you're excited about what we're building, we'd love to meet you.

Location: United States (Remote)