Payroll and Benefits Senior Manager

Who We Are:

Archipelago Companies, a portfolio of highly successful consumer lifestyle brands, is seeking a talented and passionate individual with an entrepreneurial mindset to join our team. Our brands, including OluKai, Melin, Roark, and Tradewind Services are leaders in their respective markets, offering high-quality products and authentic marketing stories direct to consumers. At Archipelago Companies, we pride ourselves on our commitment to integrity, and we strive to create a culture of excellence in everything we do. If you are a driven and innovative individual with a passion for consumer brands, we invite you to apply for our open position and become a part of our dynamic and growing team.

About the Role:

The Tradewind Services Payroll and Benefits Senior Manager is responsible for overseeing payroll processing, benefits programs and administration, and compliance with all applicable federal, state and local regulations to ensure employees are paid accurately and receive the appropriate benefits. This role works closely with HR, Payroll, Finance, and external vendors to manage payroll operations, optimize benefits programs, and maintain compliance with all regulatory requirements.

Key responsibilities in the following areas include but are not limited to:
Payroll Administration:

• Maintain accurate payroll records for new hires, terminations, salary adjustments,  leave of absence, bonus, commissions and other supplemental compensation in HR and Payroll systems.
• Manage payroll schedules, state tax registrations, take ownership of communication with state tax agencies, tax filings, deductions, and direct deposits.
• Partner with Finance to reconcile payroll transactions and support budget planning.
• Oversee end-to-end payroll processing, ensuring accuracy, timeliness, and compliance with federal, state, and local regulations.
• Ensure compliance with wage and hour laws, including FLSA, overtime calculations, and payroll tax reporting.
• Manager 401K audit and internal control/annual audit, prepare 401K and payroll-related documentation for audits and assist auditors in resolving discrepancies.
• Manage the annual workers compensation audit, providing support as needed

Benefits Administration:

• Manage company benefits programs, including health insurance, retirement plans, FSA, life insurance, disability, and wellness initiatives.
• Partner with Human Resources for benefits enrollment, renewals, and changes, ensuring employees understand their options.
• Communicate with employees and management about benefits options and usage.
• Ability to audit monthly payments and resolve enrollment issues.
• Work with benefits providers and brokers to evaluate and improve plan offerings.
• Ensure compliance with ACA, COBRA, ERISA, and other benefits-related regulations.
• Address employee inquiries related to benefits and payroll, providing guidance on plan options, deductions, and eligibility.
• Collaborate with external vendors to negotiate benefits contracts and evaluate cost-effectiveness.
• Lead annual benefits open enrollment campaigns and wellness initiatives

Compliance & Reporting:

• Ensure payroll and benefits programs adhere to all applicable laws and regulations.
• Register to new states for new hires, if applicable.
• Prepare and submit payroll tax filings, W-2s, 1095-Cs, and other required government reports.
• Conduct internal audits of payroll and benefits data to maintain accuracy and compliance.
• Stay informed of changes in labor laws, tax codes, and benefits regulations to implement necessary adjustments.
• Adhoc and Payroll Analytics reporting compliance reports, including, but not limited to ACA, BLS, EEO, PCORI, EEO-1, CA Pay Reports, etc.
• Contractor Compliance & 1099 Management: Ensure accurate and timely processing of 1099 forms, reviewing vendor and contractor payments for compliance with IRS regulations and company standards.

Process Improvement, Systems Management, Misc:

• Optimize payroll and benefits processes to enhance efficiency and reduce errors.
• Maintain and improve payroll and benefits systems, collaborating with HRIS and IT teams.
• Automate reporting and workflows to streamline payroll and benefits administration.
• Implement best practices for payroll and benefits management.
• Oversee new system implementation, upgrades, testing, and integration of new technologies to improve operational efficiency.

• Acquisition Support: Play a key role in integrating payroll processes during acquisitions or mergers, ensuring a seamless transition for all employees.
• Ramp Expense Report Employee Setup for new hires
• Retail Operations Support: Coordinate accounting-related needs for retail locations, including Loomis cash-handling setup, business license requirements, and ongoing compliance to support smooth store operations.

Employee Support & Communication:

• Serve as the primary point of contact for employee payroll and benefits inquiries.
• Provide clear communication and training on payroll procedures and benefits options.

Minimum Qualifications:

• Bachelor’s degree in accounting, finance, human resources, business administration, or a related field preferred or equivalent experience.
• Minimum 8  years of experience in payroll and benefits administration.
• Strong knowledge of payroll and benefits multi-state laws, including FLSA, ACA, COBRA, ERISA, and IRS regulations.
• Experience with payroll and HRIS systems (e.g., ADP, Paychex, BambooHR, Full Circle).
• Excellent attention to detail, problem-solving skills, and ability to manage confidential information.
• Professional Certifications such as: Certified Payroll Professional (CPP)
• Strong organizational and time management abilities to meet deadlines in a fast-paced environment.
• Actively seeks out AI-enabled tools and emerging technologies, adapting quickly to leverage them for improved productivity, deeper insights, and more effective processes, while exercising sound judgment and maintaining compliance with organizational standards

Location & Office Structure: This is an in-office hybrid position, mandatory 4 days per week in office in Irvine, CA with the option to work from home 1 day per week.  Subject to change without notice as per company guidelines.

Compensation: The salary range for this position is $111,000 to $130,000 plus opportunity for annual bonus; salary is based on the experience that you bring to the position.

Benefits and Perks:

• Complimentary chef prepared breakfast and lunch provided Monday - Thursday
• Generous product gift program and all brand discounts
• Company bonus program
• 5 year and 10 year Milestone Anniversary travel gifts
• Medical, Dental, Vision insurance in accordance with plan guidelines
• Company paid life insurance in accordance with plan guidelines
• 401k with employer match in accordance with plan guidelines
• 15 Days of PTO accrued annually, plus one additional day of PTO every year on your anniversary, and 3 Floating Holidays per year
• Paid beach and giveback days, bi-annual team building events and other in-person celebrations
• Work with talented and great people who share a love of the ocean lifestyle

Archipelago Companies values a diverse, inclusive, and entrepreneurial workforce and culture, and we provide equal employment opportunity for all applicants and employees. All qualified applicants for employment will be considered without regard to an individual’s race, color, sex, gender identity, gender expression, religion, age, national origin or ancestry, citizenship, physical or mental disability, medical condition, family care status, marital status, domestic partner status, sexual orientation, genetic information, military or veteran status, or any other basis protected by federal, state or local laws. If you are unable to submit your application because of incompatible assistive technology or a disability, please contact us at hr@arch-cos.com. Archipelago will reasonably accommodate qualified individuals with disabilities to the extent required by applicable law.