[Hiring] US HR / Payroll Director @Penbrothers

Role Description

The HR & Payroll Director will serve as the strategic and operational lead for all human resources, regulatory compliance, benefits negotiation, 401(k) administration, and multi-state payroll operations across the organization. This senior individual contributor role requires a hands-on leader well-versed in US labor laws, multi-location shift dynamics, and payroll/HRIS system architecture. Reporting directly to US executive leadership, you will:

• Revamp the end-to-end employee lifecycle.
• Execute a seamless payroll/HRIS platform migration (targeted for early 2027).
• Manage broker and vendor partnerships.
• Safeguard organizational compliance across all operational venues.

Work hours: Mid-shift schedule (starting around 4:00 PM PHT) to allow overlap with US business hours for meetings and urgent HR escalation.

Work set-up: Remote / Work from home.

Qualifications

• 10+ years of comprehensive, hands-on experience managing end-to-end HR compliance, strategic benefits, 401(k) administration, and multi-state/multi-site payroll operations for US-based organizations.
• Demonstrated track record of leading end-to-end payroll/HRIS system conversions and data migrations (experience with platforms such as Toast Payroll, ADP, Paylocity, Gusto, or comparable systems is a plus).
• Deep working knowledge of US labor laws (FLSA, ACA, EEOC, FMLA), statutory tax filings, tipped-wage guidelines, and practical experience handling audit inquiries from bodies like the Department of Labor (DOL) or state employment security departments.
• Proven background in managing annual open enrollment cycles, vendor evaluations, and broker package negotiations from initial review to rollout.
• Direct experience in food & beverage, hospitality, craft brewing, retail, or shift-based environments with complex hourly pay structures and tip pools is highly advantageous.
• Ability to operate independently as a senior individual contributor, build standardized HR structures where processes are evolving, and manage sensitive employee relations with discretion and sound judgment.

Requirements

• Extensive Leadership Experience.
• System Migration Expertise.
• Audit & Regulatory Mastery.
• Benefits Negotiation & Open Enrollment.
• Hospitality / Multi-Unit Operational Background.
• Autonomous & Proactive Mindset.

Benefits

• Meaningful work & Growth: We take every opportunity to stretch ourselves and deliver an excellent client experience.
• Employee as our biggest asset: We are genuinely invested in our people’s career and welfare.
• Global reach & local impact: Get to work with high-growth startups and dynamic companies from the comfort of your own home.
• Powering global startups: We’ve created 1,400 Filipino jobs that empower global start-ups to focus on growth.