Senior Payroll Manager

Direct Meds is Growing & Hiring!

Direct Meds is a privately held, high-growth telehealth company on a trajectory toward a $1B valuation. We operate at the intersection of healthcare and technology, prioritizing care, trust, and solutions that focus on the individual patient.

We are a remote-first North American team built around operators who underpromise, overdeliver, and take full ownership of challenges and goals. Our culture is deeply rooted in personal progress and professional development; we believe that when our team members get the most out of their professional experience, our patients receive the highest standard of care. Get ready to climb aboard an absolute rocketship of a company and an elite team.

Role Description

We are seeking a highly capable Senior Payroll Manager who will report to the Controller in our Finance department. This role requires someone who will take extreme ownership of the payroll function, do the heavy lifting in the day-to-day tactical execution, and proactively bring solutions to leadership. You must possess a strong understanding of how payroll data interacts with the general ledger.

What You’ll Do

• Own and execute full-cycle payroll for 250+ employees across Direct Meds LLC and related entities.
• Review and validate time and attendance data, processing all off-cycle payments, corrections, bonuses, and company profit-sharing.

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• Execute payments for offshore teams and 1099 contractors.
• Prepare payroll journal entries, maintaining a strong understanding of GAAP to map multi-entity transactions correctly and explain any variances.
• Tie out all payroll liabilities and expenses to external reporting systems, ensuring alignment with the general ledger.
• Act as the ultimate payroll advisor to the CFO and Controller, providing expert guidance on compliance, multi-state wage and hour regulations, and system optimizations.
• Oversee payroll tax filings, W-2s, statutory reporting, and all required data gathering for annual Workers' Compensation audits.
• Collaborate closely with HR to manage annual benefits enrollments and support the upcoming implementation of the company's 401(k) plan.
• Develop, implement, and maintain comprehensive standard operating procedures (SOPs) for all payroll processes.

What We’re Looking For

• 5+ years of progressive payroll experience, including full-cycle processing and strict compliance management.
• Deep understanding of accounting principles, with hands-on experience mapping complex payroll journal entries to the general ledger.

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• High proficiency with HRIS/Payroll platforms. Hands on experience with Rippling is a HUGE plus.
• Bachelor's degree in Accounting, Finance, Business Administration, or a relevant analytical field.
• A self-starter mentality. You do not wait for executive intervention to identify and resolve discrepancies.

What We Offer

• Base Salary: $85,000 – $115,000 USD
• Profit Sharing: Participation in our company-wide profit-sharing program
• Benefits Package: Medical, Dental, and Vision insurance options
• HSA: Employer contributions to help manage your health-related finances
• Time Off: Flexible Paid Time Off (PTO) and paid company holidays
• Flexibility: A fully remote work environment