People Operations Generalist

Overland AI•Seattle, WA

14h•$100,000 - $150,000•Onsite

About The Position

Overland AI is at an exciting inflection point. We're growing quickly, adding new contracts, expanding our teams, and building the operational foundation to support what comes next. This is a chance to get in early at a company where your work will have a real, visible impact on how we grow. We're looking for a People Operations Generalist to join as the second hire on our People team and take ownership of the day-to-day HR operations that keep our people supported and our company running smoothly. You'll report directly to our Senior People Ops Manager and play a key role in shaping how we onboard, support, and retain a talented team as we scale. The role covers the full employee lifecycle: onboarding, performance management, manager coaching, employee relations, policy execution, compliance, and offboarding. You'll build scalable processes, improve systems, and use data to drive decisions in a fast-moving environment. You'll be on-site, embedded with the leaders and teams you support across a high-growth organization. The right person for this role brings credibility with technical leaders and knows how to balance strategic thinking with getting things done.

Requirements

4+ years of HR generalist or People Operations experience, ideally at a company that was growing and evolving quickly. You've seen what it takes to support a team through that kind of change.
Solid working knowledge of employment law compliance.
Experienced with HRIS and payroll platforms like Rippling, Gusto, ADP, or similar.
You've managed benefits administration end to end, including open enrollment and working with carriers.
You've handled employee relations with empathy and good judgment: investigations, coaching managers, and navigating sensitive situations thoughtfully.
Proactive and resourceful. You don't need everything mapped out to get started. You're comfortable figuring things out and building as you go.
Strong communicator, both in writing and in person. Whether it's a policy update or a one-on-one conversation, you're clear, approachable, and thoughtful.
Organized and detail-oriented, with the ability to keep multiple workstreams moving without letting things slip.

Nice To Haves

Experience in aerospace, defense, or government contracting. You're familiar with the compliance landscape and what it's like to work in a mission-driven environment.
You’ve built and delivered manager training, whether that's new manager onboarding, performance conversation prep, or ongoing leadership development.
Experience using AI tools like Claude to streamline People Ops workflows, whether that's drafting policies, building templates, analyzing data, or finding ways to work smarter across the employee lifecycle.
PHR, SHRM-CP, or similar certification.

Responsibilities

Own the onboarding experience end to end. From offer letters and I-9 verification to benefits enrollment, systems access, orientation, and check-ins. You'll help make sure every new hire feels welcome and set up for success from day one.
Administer benefits and payroll. Health, dental, vision, 401(k), open enrollment, COBRA, qualifying life events, and vendor relationships. You'll be the knowledgeable, reliable person people turn to when they have questions.
Support employee relations. Serve as a trusted resource for workplace concerns, help managers navigate performance conversations, and handle investigations with care and discretion.
Manage our HRIS (Rippling). Maintain accurate employee records, headcount data, and reporting.
Run offboarding processes. Exit interviews, final pay compliance, systems deprovisioning, and clean handoffs.
Build People Ops infrastructure. Help create and maintain policies, the employee handbook, and company-wide People communications that are clear and useful.
Support performance review cycles. Help coordinate timelines, assist managers with giving effective feedback, and follow through on development and improvement plans.
Partner with the Talent team. Own the recruiting-to-onboarding handoff and help us learn from what's working (and what's not) as we hire.