People Operations Specialist

HappyRobot AI Inc.

Job Overview

Location

San Francisco

Job Type

Full-time

Full Job Description

📋 Description

• As the People Operations Specialist at HappyRobot AI Inc., you will be the second dedicated hire on a growing People team, owning critical operational functions that ensure seamless employee experiences across global teams. This role is foundational to scaling the people function in a high-growth AI startup, where your work directly enables talent to thrive in a mission-driven environment.
• You will own end-to-end immigration program management, serve as the primary liaison with external counsel, track case milestones for H-1B, L-1, O-1, and green card processes, and build scalable tracking systems to ensure compliance and timely support for employees navigating complex visa journeys.
• You will manage the PEO relationship for US-based employees, acting as the go-to for payroll, benefits, and coverage inquiries, handling exceptions and escalations, and ensuring the PEO delivers optimal service aligned with company needs.
• You will support international employees in France, Spain, Switzerland, and other countries by coordinating with EOR partners and local counsel, managing onboarding and offboarding logistics, and proactively identifying compliance risks before they escalate.
• You will maintain data integrity and system hygiene in Rippling as the HRIS administrator, overseeing employee records, status changes, employment eligibility, and supporting broader HRIS workflows as the company scales its people infrastructure.
• You will handle core HR administration including background checks via Checkr, I-9 compliance, onboarding logistics, and offboarding processes, ensuring precision and care in every operational touchpoint that underpins the employee lifecycle.
• You will partner with the People Operations Lead to identify manual inefficiencies and build automations using AI tools, Rippling workflows, and other technologies to eliminate repetitive tasks and increase team leverage.
• You will join a lean, high-impact People team reporting directly to the People Operations Lead and partnering with the Head of People, operating in a startup environment where ownership, initiative, and craftsmanship are valued over hierarchy or bureaucracy.
• You will have the opportunity to shape and scale the people function from the ground up, gaining deep exposure to global HR operations, immigration compliance, HRIS optimization, and AI-driven process innovation in a fast-moving, venture-backed AI startup.

🎯 Requirements

• 3–5 years of HR or People Operations experience at a tech company or fast-scaling startup, with proven ownership of operational responsibilities rather than purely supportive roles.
• Demonstrated proficiency in HRIS systems, with Rippling preferred, and comfort acting as an end-to-end administrator managing employee data, workflows, and system integrity.
• Hands-on experience managing immigration cases (H-1B, L-1, O-1, green card) including coordination with outside counsel, tracking deadlines, and communicating updates to employees.
• Experience supporting international employees across multiple countries, including working with EOR partners, local counsel, or navigating cross-border employment frameworks.
• Strong vendor management skills, with ability to oversee PEO, EOR, immigration counsel, and HRIS partners, ensuring accountability, escalating when needed, and preventing stalled processes.
• AI-native mindset with a habit of building automations—using tools like Claude, Chat GPT, or Rippling workflows—to reduce manual work and improve efficiency.
• High ownership, precision, and low ego: energized by closing loops, maintaining clean processes, and being the reliable teammate others depend on.
• Startup orientation: thrives in ambiguity, resourceful with limited direction, and views building a people function from scratch as an opportunity.

🏖️ Benefits

• Opportunity to work at a high-growth AI startup backed by top-tier investors including a16z, Y Combinator, and Base10, with over $60M in funding.
• Full ownership and autonomy to drive projects from inception to impact, with minimal bureaucracy and direct access to leadership.
• Collaboration with a world-class team of engineers and builders who embody Extreme Ownership, Craftsmanship, and Talent Density as core operating principles.
• Exposure to cutting-edge AI infrastructure and the chance to innovate HR operations using AI tools and automation in a mission-driven environment.
• Professional growth in a rapidly scaling organization where early hires can shape culture, processes, and long-term people strategy.

Skills & Technologies

Onsite

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HappyRobot AI Inc.

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About HappyRobot AI Inc.

HappyRobot AI builds voice AI agents that automate repetitive phone calls for logistics, freight, and supply-chain companies. Its cloud platform lets shippers, brokers, and carriers offload tasks like appointment scheduling, check calls, and rate negotiation to conversational bots that integrate with TMS, ELD, and CRM systems via API. The company targets mid-market and enterprise freight operations seeking to cut labor costs and accelerate data entry without sacrificing accuracy or carrier relationships.

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