US HR / Payroll Director

About Penbrothers 

Penbrothers is an HR & remote talent management partner and one of the fastest growing companies in the Philippines. We provide talented Filipinos with global opportunities in high-growth startups and dynamic companies, from the comfort of their own homes.

About the Client

Our client is a multi-location craft brewing and hospitality business based in the United States. Driven by a commitment to community, hospitality, and quality products, they operate multiple bustling taprooms, production facilities, and full-service kitchens. 

About the Role

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, and 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

What you’ll do

• Payroll Operations & Tax Oversight: Direct end-to-end payroll operations for multi-site hourly, salaried, tipped, and overtime-eligible staff. Conduct routine checks and reconciliations on multi-state payroll tax withholdings, deductions, and statutory filings to ensure absolute accuracy and compliance.

• HRIS & Payroll System Implementation: Lead the evaluation, selection, data migration, and full implementation of a modern, scalable payroll/HRIS system (e.g., evaluating Toast Payroll or alternative solutions), targeting go-live in early 2027.

• Benefits & 401(k) Administration: Oversee the day-to-day administration, onboarding, and offboarding of employees across health insurance plans and the 401(k) retirement program.

• Annual Open Enrollment & Broker Negotiations: Drive the annual benefits strategy and open enrollment process (beginning planning in January for April enrollment). Evaluate plan options, compare competitive packages, and negotiate rates directly with insurance brokers.

• Audits & Regulatory Defense: Serve as the subject matter expert on federal, state, and local labor standards. Lead reporting defense, documentation extraction, and compliance reviews for routine and agency inquiries, including the Department of Labor (DOL) and Department of Employment Security (DES).

• Employee Lifecycle & Workplace Policies: Design, formalize, and maintain core HR documentation from the ground up—including updating employee handbooks, onboarding flows, arbitration agreements, and SOPs for venue general managers.

• Cross-Functional Strategy & Workforce Analytics: Partner with venue operations and financial leadership to analyze labor metrics, compensation structures, turnover trends, and headcount plans as the organization scales.

What You Bring 

• Extensive Leadership Experience: 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.

• System Migration Expertise: 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).

• Audit & Regulatory Mastery: 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.

• Benefits Negotiation & Open Enrollment: Proven background in managing annual open enrollment cycles, vendor evaluations, and broker package negotiations from initial review to rollout.

• Hospitality / Multi-Unit Operational Background: Direct experience in food & beverage, hospitality, craft brewing, retail, or shift-based environments with complex hourly pay structures and tip pools is highly advantageous.

• Autonomous & Proactive Mindset: 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.

Don't meet every single requirement? At Penbrothers we are committed to building a diverse, inclusive, and authentic workplace, so if you're excited about this role but you don't feel 100% aligned with the qualifications, we encourage you to apply anyway. You may just be the right fit for this or other roles.

Our Hiring Process & AI Disclaimer

We use AI tools to streamline our application process—including an initial conversation with an AI Interviewer. All hiring decisions are made entirely by humans: our Talent Acquisition team guides your full candidate journey and makes all evaluation decisions.

You are welcome to use AI for CV refinement and research, but real-time AI assistance during interviews or skill assessments is strictly prohibited to ensure an authentic evaluation. 

Read our full AI Disclaimer to learn more

What You’ll Get

At Penbrothers, we are obsessed with creating positive employee experiences. Here you’ll find an environment that nurtures learning and provides opportunities for growth. You’ll have the opportunity to make an impact on fast-growing startups and dynamic companies.  

• 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.