Senior HR Generalist - US Benefits/Leave of Absence

San Mateo, California, United States

The Role

We are seeking a Senior HR Generalist who brings deep expertise in U.S. and global benefits strategy and administration, leave of absence (LOA) and accommodations, and compliance across multiple jurisdictions. This role is a strategic partner and operational leader who will play a pivotal role in harmonizing our employee programs globally and supporting our diverse workforce—including our office staff and factory team members.

This position is ideal for someone who thrives in fast-paced, high-growth environments and has a passion for building scalable, equitable, and compliant people programs.

Location

• Minimum 3 days a week out of our HQ in San Mateo, CA 94402 as well as occasional travel to our Manufacturing Facility in Hayward, CA.

Key Responsibilities

Global Benefits Strategy, Administration & Compliance

• Manage and optimize U.S. health & welfare benefits, and wellness programs, with an eye on scalability and cost-effectiveness.
• Analyze current benefits and broker partners and create a long term strategy to implement over time that will achieve global harmonization and optimization.  Own the implementation of the multi-year global strategy.
• Design and implement supplementary and harmonized global benefits programs across existing and future expansion entities.
• Serve as the primary point of contact for brokers and vendors, ensuring accountability, effective service delivery, and regular benchmarking.
• Time & Attendance maintenance and compliance.
• Run Open Enrollment and annual compliance activities.
• Employee Onboarding and other HR Generalist knowledge and duties.

Leave of Absence & Accommodations

• Oversee LOA processes for U.S. and international employees, ensuring compliance with federal, state, and local leave laws (including CFRA, FMLA, and ADA).
• Oversee and manage all accommodation requests and interactive process in compliance with ADA.
• Partner with internal stakeholders to ensure seamless integration of leave, accommodations and benefits continuation.
• Coordinate with worker’s compensation, disability, state paid leave benefits and third-party leave administrators and develop playbooks for consistency and employee support.

Training, Compliance & Reporting

• Ensure compliance and complete required reporting for all U.S. and international labor and benefits laws, including, but not limited to, I-9/E-verify, Meal & Rest Break compliance, Worker’s Compensation/OSHA, ACA, EEO-1, VETS-4212, COBRA, Non-Discrimination Testing,  mandatory trainings, and OFCCP obligations as a federal contractor.
• Ownership of audits, policy development, and employee handbook updates for global compliance.
• Using Learning & Development best practices, principals and models, build employee and manager enablement training for non-standard content and ownership of administration and training planning within our training platform.
• Maintain required notices and filings (ERISA, 5500, ACA, etc.) and act as a subject matter expert for employment and benefits law changes.

Cross-Functional Collaboration

• Embrace a collaborative and team-oriented environment by participating in cross-training and flexing across HR functions such as onboarding, terminations, immigration, etc. as needed to support team goals and ensure seamless employee experiences.
• Partner with People Operations teammates to ensure comprehensive HR support and shared backup responsibilities across functions including People Partners, Workplace Experience, Facilities and Recruiting.
• Partner with EHS teams to manage workplace injuries, worker’s compensation and OSHA reporting.
• Adept at creating and maintaining business processes and workflows; recognizing gaps and changes as the business scales.  Partner with People Systems teams for complex system implementations to automate and streamline.
• Research and ongoing education related to changes in HR related laws and compliance in all regions where we operate.
• Provide guidance and tailored support to both exempt and non-exempt workers, recognizing and responding to unique population needs.
• Mentor and train junior team members.
• Payroll resource for resolution of time and attendance related questions.
• Partner with People Managers, Finance and Legal as needed.

Qualifications

Required

• 8+ years of progressive HR experience, with a strong focus on global benefits, LOA and compliance.
• 3+ years of demonstrated experience managing full-life cycle, end-to-end Employee Programs including concept, executive approval, resource/time line planning, implementation, testing, roll out communications, documentation,operationalization, day-to-day management, ROI, impact analysis, program maintenance and continuous incremental improvement.
• Demonstrated experience in U.S. and global benefits strategy and administration, including working with international vendors and harmonizing plans across geographies.
• In-depth understanding of U.S. employment laws and compliance obligations (ACA, COBRA, FMLA, ADA, ERISA, etc.).
• Keep up with changes in compliance, legislation and regulations that impact your scope of programs and responsibilities and prepare action plans and recommendations to prepare the company for necessary impacts and changes.
• Experience working with and optimizing relationships with brokers, carriers, and third-party administrators.
• Previous experience standing up a foreign company entity including statutory & voluntary benefits, employee management and foreign compliance.
• Strong HR systems, reporting, analytical and project management skills; strong preference for 3+ years Workday hands on experience.
• Demonstrated mastery of AI tools to optimize and simplify day-to-day operations and work flows.
• Proactively explore and utilize AI tools and automation to streamline HR operations, enhance employee support, and improve program efficiency and scalability.
• We are a highly collaborative team that values curiosity, critical analysis, ongoing education, knowledge sharing, candidness, caring, humor, and a mindset of urgency, kindness & respect with good intent. We thrive in a fast-paced environment where launching, learning, and iterating is part of how we work. The successful candidate will add to our team and not detract.
  
  

Preferred

• Experience working in a dual-use hardware/software or manufacturing environment.
• Familiarity with OFCCP and affirmative action compliance for federal contractors.
• Prior experience supporting non-exempt and exempt employee populations.
• Working knowledge of immigration processes and I-9 requirements.
• Systems preferences: Workday, Traliant, Optum, WEX, various global benefit portals
• CPE certified for general ergonomics and experience providing assessments/integrating into accommodation requests

Physical Requirements

• Prolonged periods sitting at a desk and working on a computer.
• Must be able to travel locally between office locations and walk through a factory environment with appropriate PPE.

Compensation & Benefits

At Skydio, our compensation packages for regular, full-time employees include competitive base salaries, equity in the form of stock options, and comprehensive benefits packages. Compensation will vary based on factors, including skill level, proficiencies, transferable knowledge, and experience. Relocation assistance may also be provided for eligible roles. The annual base salary range for this position is $130,000 - 170,000*. Fundamentally, we believe that equity is the key to long-term financial growth, and we ensure all regular, full-time employees have the opportunity to significantly benefit from the company's success. Regular, full-time employees are eligible to enroll in the Company’s group health insurance plans. Regular, full-time employees are eligible to receive the following benefits: Paid vacation time, sick leave, holiday pay and 401K savings plan. This position and all associated benefits are subject to applicable federal, state, and local laws, as well as the Company’s policies and eligibility criteria.

*Compensation for certain positions may vary based on the position’s location.

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