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Job Type   /   Job Level
Full-time   /   Senior Executive
Job Location
Boston, MA
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Firm Summary:

Winged Keel Group is the premier national platform for the structuring, implementation, and administration of high-end life insurance solutions. With ten offices nationwide, the firm specializes in Traditional Life Insurance, Business Continuation Insurance, Private Placement Life Insurance and Annuities, and Corporate-Owned Life Insurance portfolios.

Position Summary:

The Controller will lead the company’s accounting operations and ensure the integrity of financial reporting as the firm continues its rapid growth. This role is critical in ensuring accuracy, transparency, and discipline across all financial operations, with a strong emphasis on private equity standards, EBITDA focus, and scalable structures.

The ideal candidate brings deep technical accounting expertise and experience operating in a private equity-backed environment. There will be a targeted focus on the ability to build processes that support continued expansion and M&A activity.

Position Responsibilities:

Financial Reporting & Accounting Operations

  • Oversee all accounting operations including general ledger, accounts payable, accounts receivable, payroll accounting, and revenue recognition
  • Manage the monthly, quarterly, and annual close process
  • Prepare accurate and timely financial statements in accordance with GAAP
  • Maintain and improve internal controls and accounting policies
  • Ensure compliance with all regulatory and reporting requirements
  • Ensure clear visibility into EBITDA, margins, and key financial metrics
  • Deliver executive-ready reporting packages for leadership and private equity stakeholders

Private Equity & Investor Reporting

  • Partner with executive leadership and investors to support board reporting and financial insights
  • Prepare and analyze reporting aligned with private equity expectations (EBITDA adjustments, add-backs, KPI tracking)
  • Support financial modeling and performance analysis tied to value creation

Process Improvement & Scalability

  • Build and refine scalable accounting processes to support rapid growth and M&A integration
  • Drive automation and system improvements to enhance efficiency and reporting accuracy
  • Evaluate and optimize current financial systems and workflows

M&A Support

  • Support financial due diligence, integration planning and post-acquisition reporting
  • Ensure alignment and standardization of accounting practices across acquired entities

Leadership & Team Management

  • Lead and mentor accounting staff
  • Provide guidance on accounting best practices and internal controls
  • Foster a high-performance culture within the finance team
  • Assist with budgeting, forecasting, and financial analysis
  • Provide financial insight to support strategic initiatives and growth

Compliance & Audit

  • Manage relationships with external auditors, tax advisors, and regulatory bodies
  • Lead the annual audit process
  • Ensure compliance with tax regulations and financial reporting standards

Qualifications

  • Bachelor’s degree in Accounting or Finance required
  • CPA strongly preferred
  • 10+ years of accounting experience including leadership roles
  • Prior experience in private equity-backed company
  • Experience in financial services, insurance brokerage, wealth management, or professional services preferred
  • Deep knowledge of GAAP accounting principles
  • Demonstrated experience with EBITDA analysis, financial modeling, and KPI reporting
  • Experience supporting M&A activity
  • Strong experience with financial systems and accounting software
  • Excellent analytical and problem-solving skills
  • Highly effective communication and leadership capabilities
  • Ability to operate both strategically and hands-on
  • Strong organizational skills with exceptional attention to detail
  • Ability to manage multiple priorities and deadlines in a fast-paced environment
  • Excellent written and verbal communication skills

Working Conditions/Demands/Complexity:

  • Required to work on a computer for a substantial part of the day
  • A strong fundamental skillset in the above areas from the outset. Candidate will have a unique opportunity to apply and grow these skills in a highly productive, successful, and challenging environment
  • Interaction with multiple internal and external stakeholders including registered representatives, broker-dealer personnel, insurance carriers, and regulatory bodies

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