Head of M&A

Role Overview

As Head of M&A, you will own the full deal cycle, from sourcing and diligence through negotiation and closing. You’ll partner closely with our CEO, Legal, and our Operations teams to structure accretive transactions that maximize enterprise value and seamlessly integrate acquired agencies into our AI-powered platform.

Key Responsibilities

• Deal Sourcing & Origination

  • Build and maintain a robust pipeline of 100+ qualified agency targets in the Southern states  (e.g. TX, GA, FL, TN, NC, SC).

  • Cultivate relationships with agency owners, brokers, and intermediaries; attend regional trade events and PE network forums.

• Due Diligence & Valuation

  • Lead financial, operational, and regulatory diligence—evaluate historical performance, book of business composition, commission structures, retention, and profit margins.

  • Develop detailed financial models and valuation analyses (DCF, precedent transactions, LBO) to support bid strategy.

• Deal Structuring & Negotiation

  • Design transaction structures (asset vs. share deals, earn-outs, rollover equity) that balance seller incentives with investor returns.

  • Negotiate LOIs and definitive agreements in partnership with Legal; manage term-sheet revisions and closing deliverables.

• Execution & Integration Planning

  • Own the transaction closing process—coordinate external advisors (lawyers, accountants, tax), manage data-room Q&A, and drive sign-off.

  • Hand off to Head of Operations and Integration, ensuring timely transfer of client relationships, carrier appointments, and staff transition.

• Cross-Functional Collaboration

  • Work closely with Engineering, Product, and Ops teams to identify integration levers (e.g., lead-gen overlay, portfolio analytics).

  • Partner with Finance to track post-close performance against value-creation KPIs and refine acquisition criteria.

• Thought Leadership & Market Insights

  • Monitor insurance M&A trends, regulatory changes, and private-market valuations in the SMB brokerage space.

  • Lead periodic strategic reviews, presenting deal pipeline and market intelligence to the executive team and board.

Qualifications

• Experience

  • 8+ years in M&A or Corporate Development, preferably in insurance brokerage, financial services or healthcare roll-ups, or PE-backed platforms.

  • Proven deal lead on 10+ closed transactions ranging from $2–$25 million EBITDA.

• Technical Skills

  • Advanced financial modeling (LBO, DCF, accretion/dilution).

  • Hands-on experience with diligence checklists, data rooms, and SPA/APA negotiation.

• Domain Expertise:

  • Deep understanding of health insurance distribution economics, carrier appointment processes, and state-by-state regulatory nuances in the Southeast.

  • Familiarity with SMB brokerage P&L drivers (commissions, retention, recruiting costs).

• Leadership & Communication:

  • Strong project management skills and able to lead cross-functional teams under tight timelines.

  • Exceptional written and verbal communication; comfortable presenting to C-suite and board.

• Personal Attributes:

  • Entrepreneurial mindset; thrives in high-growth, fast-paced environments.

  • High integrity, self-starter, relationship-builder, and highly organized under ambiguity.

  • Would enjoy sharing a cold beer at a baseball game with SMB owners