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Head of M&A

Austin, Texas, United States, Miami, Florida, United States, New York, New York, United States

About Us

  • The insurance broker is a critical, yet underleveraged asset within the healthcare value chain. Despite being the first point of contact for patients and providing critical guidance on everything from insurance plan selection to care navigation, many still rely on manual workflows and spreadsheets to run their business, and are unable to grow at their desired pace.
  • Gyde is building an AI-native brokerage platform by acquiring traditional agencies and supercharging them with workflow automation, voice and chat AI applications, and predictive product and plan selection guidance.
  • Our vision is to be the premier partner for ambitious agencies, streamlining their operations through the Gyde platform to enable their success in the current regulatory and technological paradigm shift. 
  • Our founding team boasts pedigrees from Oscar, Stripe, and Spark. Lightspeed led Gyde’s Seed financing, with participation from Virtue and Crystal Venture Partners, and angels from Oscar, Uber, and more.  

Role Summary

As the Head of M&A, you will oversee the entire 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, & Closing

  • Design transaction structures (asset vs. share deals, earn-outs, rollover equity) that balance seller incentives with investor returns.
  • Negotiate Letters of Intent (LOIs) and definitive agreements in partnership with Legal; manage term-sheet revisions and closing deliverables.
  • Close acquisitions by selling the Gyde vision, convincing owners to partner with us in their next phase of growth.

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 the COO and Value Creation Team, ensuring timely transfer of client relationships, carrier appointments, and staff transition.

Cross-Functional Collaboration

  • Work closely with the Engineering, Product, and Operations teams to identify key 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 the deal pipeline and market intelligence to the executive team and board.

What you bring and who you are

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 that 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

What we offer

Gyde offers a competitive benefits package to all employees.  

  • Top of the market compensation 
  • Flexible (Unlimited) Paid Time Off
  • Remote, or Hybrid Work in Austin or NYC
  • Medical, Dental, and Vision benefits for you and your family
  • Retirement Plan (e.g., 401K) 
  • Parental Leave

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