Payroll and Benefits Associate

Obra Capital Payroll & Benefits Associate

Obra Capital is seeking a detail-oriented and highly reliable Payroll & Benefits Associate to oversee U.S. payroll operations and administer employee benefits for Obra Capital Inc.'s subsidiaries and to back up Obra Capital's investment firm as needed. Reporting to Obra Capital's Director of Benefits and HR Operations, this role will serve as a key partner to Finance, Human Resources, and external service providers, ensuring accurate payroll processing, strong internal controls, and a high-quality employee experience.

The ideal candidate has experience supporting both exempt and non-exempt employees in the insurance industry with complex organizational structures in a fast-paced, high-standards environment.

Key Responsibilities

• Manage end-to-end payroll processing for Obra Capital's various entities, including salary, bonus, and commissions.
• Ensure payroll accuracy, compliance, and timeliness across all employee populations
• Coordinate with Finance on payroll funding, accruals, bonus payments, and reporting
• Maintain payroll records, audits, reconciliations, and year-end processes (W-2s, state filings)
• Serve as primary point of contact in conjunction with the Director of Benefits and HR Operations with payroll vendors and tax providers
• Ensure compliance with federal, state, and local wage and hour regulations across multiple states
• Support the administration of employee benefits programs including health, dental, vision, life, disability, FSA/HSA, commuter benefits, earned wage access provider, leave management and retirement plans
• Manage employee enrollments, changes, terminations, and annual open enrollment
• Act as liaison in conjunction with the Director of Benefits and HR Operations with benefits brokers, carriers, and plan administrators
• Respond to employee benefit inquiries with discretion, clarity, and professionalism
• Support benefits compliance including COBRA, ERISA, and required filings and notices
• Ensure payroll and benefits practices comply with applicable laws and regulations
• Assist with internal and external audits related to payroll and benefits
• Prepare and maintain documentation, controls, and process improvements
• Support compensation-related reporting and ad-hoc requests from senior management
• Partner closely with HR on onboarding, offboarding, and employee data changes
• Contribute to continuous improvement of payroll and benefits processes and systems

Education and Qualifications

• Bachelor's degree in Accounting, Finance, Human Resources, or a related field
• 5+ years of experience in payroll and benefits administration, preferably with extensive experience in non-exempt populations within the insurance industry.
• Demonstrated experience supporting payroll for mixed employee populations (hourly, salaried, exempt, and non‑exempt) in compliance with wage and hour laws.
• Strong working knowledge of U.S. payroll tax regulations and benefits compliance
• Experience with ADP is required, experience with Rippling is a plus.
• Experience with company acquisitions, and new workforce integrations.
• High level of accuracy, discretion, and attention to detail
• Strong communication and organizational skills
• Experience supporting bonus-heavy or commission compensation structures
• Exposure to multi-state payroll
• Experience working in a lean or growing organization

In accordance with New York pay transparency laws, the expected base salary range for this position is $90,000.00 - $120,000.00 This range represents the good‑faith estimate of base compensation the firm expects to pay for this role at the time of posting and does not include other forms of compensation, which may include performance‑based bonuses, incentive compensation, or other discretionary compensation. Actual compensation will be determined based on experience, skills, and qualifications.