Associate Director, Finance

OVERVIEW

Alera Group is looking for an Associate Director, Finance to join our North Haven, CT office.

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

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

In this role, you will be expected to own and scale critical finance operations across cash management, payables, and receivables, be a key steward of our operating and trust accounts, and maintain rock-solid financial controls and reporting.

• Accounting & Financial Operations
  • Manage day‑to‑day financial operations for the COE, including client invoicing, accounts receivable, cash management, banking, and accounts payable
  • Ensures billing accuracy, and timely collection and reconciliation of transactions
• Month‑End Close & General Ledger Oversight
  • Manage the month‑end close process in accordance with parameters and deadlines set by the national finance team
  • Conduct account reconciliations, submit intercompany transactions, book adjusting journal entries, and review general ledger detail to ensure financial accuracy
• Budgeting & Financial Reporting and Analysis
  • Provide financial intelligence through preparing and submitting monthly financial commentary
  • Conduct financial analysis and forecasting to support data‑driven decision making
  • Lead the annual budgeting process, collaborating with COE leadership to align financial planning with organizational goals
• Process Management & Internal Controls
  • Maintain internal controls and oversight of financial operations
  • Identify opportunities and implement processes to streamline workflows, enhance efficiency, accuracy, and internal controls, and ensure compliance with accounting best practices
  • Identify and solve risks, breakdowns, and inefficiencies, and partner cross functionally to resolve discrepancies quickly and clearly
• Leadership & Team Management
  • Act as the go‑to contact for questions and escalations from colleagues and clients regarding finance operations
  • Manage performance and provide coaching and mentorship to direct reports

This is a true player‑coach role: you’ll own the function end‑to‑end, set direction and priorities, and personally execute critical workflows. This isn’t a role with a large team beneath it — you’ll be expected to lead from the front and stay in the weeds when needed.

This role is hands‑on and highly operational, requiring the ability to efficiently navigate complex environments, and is responsible for leading budgeting, financial planning, reporting, and analysis for the department. You’ll partner closely with operations, leadership, and external vendors to ensure accurate cash movement, strong controls, and clear financial insights that drive decision‑making.

• 6‑8+ years of progressive experience in finance or accounting operations (experience in employee benefits administration, insurance, or multi‑entity environments a plus)
• Bachelor’s degree in Accounting, Finance, or a related field preferred, or equivalent experience
• Proven ability to own financial operations while also leading planning, reporting, and analysis
• Hands‑on experience with ACH processing, multi‑account cash management, and reconciliations
• Strong understanding of AP/AR fundamentals, P&L management, budgeting, and forecasting
• Comfort working independently without a large team; confident being both strategic and tactical
• Highly organized, detail‑oriented, and reliable in high‑volume, time‑sensitive environments
• Clear communicator who can coordinate effectively with operations, leadership, clients, and vendors
• Strong critical thinking, problem solving, and decision‑making skills, with the ability to thrive in a complex and ambiguous, fast‑paced…