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OVERVIEW

 

Alera Group is looking for an Associate Director, Finance to join our team! This position is fully remote. 

 

About Alera Group

Alera Group was founded in 2017 and has grown to become the 14th largest broker of U.S. business. We are passionate about our clients’ success in the areas of Employee Benefits, Property and Casualty Insurance, and Financial Services. With a network of offices nationwide, our commitment to collaboration allows us to offer national resources combined with local service.

Why Alera Group

• Make an Impact: Your work supports businesses and individuals in protecting what matters most.

• Grow With Us: We invest in development, mentorship, and long-term career growth.

• The Collaborative Way: We believe in accountability, teamwork, and shared success across all offices and lines of business.

• National Strength. Local Heart: Scale, resources, and expertise — with relationships that feel personal.

 

Role Summary:

We’re looking for a highly capable Associate Director of Finance to lead the financial operations of our Benefits Administration Technology Center of Excellence (COE) while remaining deeply hands-on in daily execution.

 

This role owns the end-to-end financial operations of the department, including client billing and accounts receivable, cash management, banking, accounts payable, and financial reporting. This is a hands-on position responsible for executing core accounting functions while leading a small team and ensuring accuracy, timeliness, and accountability across all financial workflows.

 

You will be expected to scale critical finance operations, be a key steward of our operating and trust accounts, and maintain rock-solid financial controls and reporting.

RESPONSIBILITIES

What You’ll Own

Billing, Revenue, & Cash Flow

• Oversee and actively support client billing and invoicing processes, ensuring accuracy and timeliness
• Manage AR, collections visibility, and cash application
• Identify and resolve billing discrepancies and process gaps
• Improve billing workflows to support scale and reduce leakage

General Ledger Oversight & Month-End Close

• Own the monthly close process, ensuring accurate and timely submission of materials to national finance team
• Maintain integrity of the general ledger and ensure clean financials with clear supporting documentation
• Conduct account reconciliations, submit intercompany transactions, book adjusting journal entries, and review GL detail

AP & Banking

• Oversee AP processes, approvals, and payment execution
• Monitor cash movement, account balances, and exceptions
• Ensure operational discipline across all transaction flows

Team Leadership

• Maintain internal controls and oversight of financial operations
• Manage and develop a small team (2–4 associates)
• Set clear expectations, review output, and ensure accountability
• Step in and execute when needed - this is not a purely supervisory role

Budgeting & Financial Planning and Reporting

• Support budgeting and forecasting processes
• Partner on financial reporting and variance analysis
• Provide financial intelligence through preparing and submitting monthly financial commentary, providing insight into revenue, cash flow, and operational performance
• Lead the annual budgeting process, collaborating with COE leadership to align financial planning with organizational goals

 

Is this role for you?

This role IS:

• Hands-on and execution-oriented
• Responsible for getting the work done, not just reviewing it
• Highly operational, requiring the ability to navigate complex environments
• A critical owner of financial accuracy and process discipline

This role IS NOT:

• A large-team leadership position
• A purely strategic or FP&A role
• A position removed from day-to-day accounting operations

 

What Success Looks Like

• Clean, accurate financials delivered on time - every month
• Billing goes out correctly and on schedule
• Cash is visible, applied, and reconciled without surprises
• Processes improve over time (not just maintained)
• Your team is accountable, supported, and effective

QUALIFICATIONS

What We’re Looking For

• 5+ years of recent, hands-on accounting or financial operations experience across billing, AR, AP, reconciliations, banking, cash activity, and month-end close.
  
• Experience personally managing or overseeing a complex, recurring client-invoicing process with meaningful volume, multiple data sources, billing rules, or client-specific exceptions.
  
• Experience leading direct reports in a working-manager role while continuing to execute detailed accounting or financial operations work personally.
  
• Advanced Excel proficiency, including XLOOKUP/VLOOKUP, SUMIFS, pivot tables, large-data reconciliations, and system-import preparation.
  
• Hands-on experience with ACH processing, cash application, multi-account bank reconciliations, returned payments, and resolving banking exceptions.
  
• Experience managing overlapping billing, AP, banking, reporting, and month-end deadlines while maintaining accuracy, strong financial controls, and attention to detail.
  
• Demonstrated ability to analyze large volumes of financial data, identify discrepancies, and drive timely resolution of issues.
  
• Strong process-management and problem-solving skills, with the ability to work through complex client requirements and operational challenges.
  
• Excellent organizational and communication skills, with the ability to collaborate across teams and balance both strategic oversight and day-to-day execution.

Strongly Preferred:

• Experience in benefits administration, insurance, SaaS, or a similar services model
• Experience managing multi-entity environments
• Track record of improving processes (not just maintaining them)

ADDITIONAL INFORMATION

Compensation:
$85,000 - $95,000/year, depending on experience  

 

Benefits:
Alera Group offers comprehensive benefits including medical, dental, vision, life and disability coverage, 401(k), generous PTO, and more.

 

Work Model:
This role is Remote

 

Professional Development – Alera Group Academy

At Alera Group, growth isn’t left to chance. Through Alera Group Academy, we provide structured development opportunities designed to help you expand your expertise and build a meaningful career.

You’ll have access to:

• Role-specific learning paths

• Leadership development programs

• Technical and compliance training

• Industry certifications and continuing education support

• Peer learning and knowledge-sharing communities

Whether you’re deepening technical expertise or preparing for leadership, we’re invested in helping you grow.

 

We're an equal opportunity employer. All applicants will be considered for employment without attention to race, color, religion, sex, sexual orientation, gender identity, national origin, veteran or disability status, or any other protected class.

Alera Group is committed to protecting your privacy. Please review our Privacy Policy to understand what personal information we may collect and use as part of your application process.

 

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Location Type

Remote