Controller

Howard Enterprise is on a mission to build generational wealth through education, empowerment, and community-driven brands like From the Trap to Wall Street and Wall Street Looks Like Us Now. At the heart of our vision is The Freedom Center, a dynamic hub for learning, creating, and collaboration. Join us to be part of a purpose-driven team shaping the future of financial empowerment.

As Controller, you will serve as a strategic financial leader, ensuring the integrity and accuracy of payroll, accounting systems, and financial reporting. You will be the critical quality control point between bookkeeping, outsourced payroll, and financial leadership, driving compliance, clarity, and cost-efficiency aligned with our company’s financial goals. This role focuses on overseeing financial processes — not day-to-day execution.

Payroll Oversight & Strategic Review

• Own the payroll schedule and ensure timely, accurate processing aligned with company policies.
• Review payroll cycles for accuracy—validating bonuses, raises, commissions, deductions, and employee status changes.
• Track and report payroll costs as a percentage of revenue, ensuring alignment with headcount and budget goals.
  

Accounting System Integration

• Manage seamless integration between payroll platforms (e.g., Gusto) and accounting software (e.g., QuickBooks).
• Verify payroll journal entries are accurately posted and reconciled in collaboration with the Bookkeeper.
  

Risk Management & Compliance

• Ensure payroll complies fully with tax regulations and employee classification laws.
• Identify and escalate financial risks, such as payroll overages, benefit cost spikes, or misclassifications.
• Provide regular updates and insights to the CEO and Director of Operations to mitigate risk.
  

Strategic Financial Support

• Deliver data-driven insights and metrics to aid the Fractional CFO’s strategic planning and forecasting.
• Assist in preparing labor cost dashboards, variance analyses, and other financial reports for executive decision-making
  

• Bachelor’s degree in Accounting, Finance, or related field; CPA or equivalent certification a plus.
• 5+ years in accounting or financial control roles, preferably in fast-growing, mission-driven, or subscriber-based businesses.
• Strong knowledge of payroll oversight, financial reporting, tax compliance, and accounting integrations (Gusto and QuickBooks preferred).
• Ability to analyze financial data and provide strategic insights related to subscriber acquisition and scaling.
• Detail-oriented with proven accuracy in payroll reconciliation and financial controls.
• Comfortable as a strategic partner with a clear path to evolving into a CFO role.
• Excellent communication and collaboration skills across teams and external vendors.
• Skilled at managing priorities in a fast-paced environment while maintaining quality and compliance.
• Proficient in financial dashboards, variance analysis, and labor cost forecasting.
• Proactive problem-solver focused on identifying and mitigating financial risks.
• Oversees processes without manual payroll execution responsibility.

Ready to build something that lasts?
Complete the following Job Fit Assessment today and help shape the future of Howard Enterprise—from the inside out:

https://TeamArchitects.asmt.io/XAA63WC76/CFOFinancialControllerJob-Assessment