Senior M&A Associate

About Us

The insurance broker is a critical, yet underleveraged asset within the $5T healthcare value chain, and is ripe for AI-enabled transformation. 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. The broker of the future will become a single source for a member's comprehensive insurance and financial needs, and a longitudinal guide through the healthcare system.

Gyde is an AI-native brokerage platform that enables this transformation, developed through a combination of brokerage acquisitions and an AI platform. The platform will become a chassis to manage a member for their entire lifetime, functioning as a guide for insurance, financial, and healthcare needs. Gyde is assembling the most talented team in the industry to bring this vision to life, and the founding team already boasts pedigrees from Oscar, Stripe, and Spark Advisors. Lightspeed led Gyde’s Seed financing, with participation from Virtue and Crystal Venture Partners.

Role Summary

As the Senior M&A Associate, you will support the entire deal cycle, valuation and negotiation through diligence and closing. You’ll report to the Head of M&A and partner closely with Legal, Market Development, and our outside Counsel and Advisors to develop the M&A strategy, structure transactions that maximize enterprise value for Gyde, own the diligence process, and close deals. The role will have significant ownership and accountability for Gyde’s success, and is a mission-critical function for the business.

Key Responsibilities

• Valuation, Deal Structuring, and Negotiation
• Develop detailed financial models and valuation analyses (DCF, precedent transactions, LBO) to support bid strategy.
• Support financial, operational, and regulatory diligence, evaluating historical performance, book of business composition, commission structures, retention, and profit margins.
• Partner with Head of M&A to establish deal guardrails and design transaction structures that balance partner incentives with Gyde returns.
• Support negotiations of Letters of Intent and definitive agreements in partnership with Legal and Head of M&A.
• Diligence and Closing Support
• Own the post LOI signature diligence, partnering with external advisors (lawyers, accounts, tax) to secure necessary materials for analysis
• Develop updated models and valuations based on materials collected in diligence, and make recommendations to the Head of M&A and CEO
• Lead financial, operational, and commercial diligence across historical performance, customer cohorts, retention, unit economics, and revenue quality.
• Evaluate book-of-business composition, commission structures, margin trends, and operational workflows to identify risks and value-creation levers.
• Surface red flags, quantify exposures, and synthesize diligence findings into clear, actionable recommendations for senior leadership.
• Thought Leadership & Market Insights
• Monitor insurance M&A trends, regulatory changes, and private-market valuations in the SMB brokerage space.
• Support periodic strategic reviews, developing deal pipeline and market intelligence to be reviewed by the Board.
  

What You Bring And Who You Are

• Experience
• 4 years in Banking, Private Equity or Corporate Development, preferably in insurance brokerage, financial services, or healthcare roll-ups, or PE-backed platforms.
• Key members on deal team for 10 deals, ranging in transaction size size from $1-$25M in EBITDA
• Technical Skills
• Advanced financial modeling and the ability to think creatively about deal structure for this segment.
• Hands-on experience with diligence checklists, data rooms, and negotiation.
• Domain Expertise:
• Deep understanding, or willingness to learn quickly, of health insurance distribution economics, carrier appointment processes, and state-by-state regulatory nuances is a nice to have.
• Familiarity with SMB and Medicare Advantage brokerage P&L drivers (commissions, retention, recruiting costs) is a nice to have.
• 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.

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