Kayla Marty
Why Healthcare M&A Deals Succeed or Fail: Lessons from the Deal Table
Kayla Marty
Partner, McGuireWoods

Why Healthcare M&A Deals Succeed or Fail: Lessons from the Deal Table

With Kayla Marty
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Selling a healthcare organization is often viewed primarily as a financial event, but as my conversation with Kayla Marty makes clear, it’s just as much an operational and human one. Drawing on her experience advising healthcare transactions at McGuireWoods, Marty explains that the deals most likely to succeed begin long before a letter of intent is signed. Organizations that understand their financials, prepare for diligence, establish realistic expectations, and think carefully about life after closing consistently navigate the process more successfully than those focused solely on valuation.

We talked about what those expectations actually involve. Price matters, of course, but so do payment structure, risk allocation, governance, control, restrictive covenants, the founder’s role after closing, and how the organization will ultimately be integrated. As Kayla points out, founders also need to think seriously about whether they’re actually ready to give up control. That can be much harder once a transaction becomes real than it seemed at the beginning.

Another major theme was preparation. Kayla explained why diligence can be overwhelming for founders, who suddenly find themselves answering detailed questions about everything from financials and billing and coding to benefits, IT, cybersecurity, and compliance. Buyers aren’t necessarily criticizing the business or expecting perfection. They’re trying to understand the risks, determine what additional investment may be necessary, and plan for the organization after closing.

I was particularly interested in Kayla’s perspective on what makes a good deal. Her advice is not to assume that the buyer offering the highest price is automatically the right buyer. The structure of the deal, strategic fit, post-closing integration, and level of control can ultimately matter just as much. She recommends identifying the five issues that are truly non-negotiable before entering the process and making sure your advisors understand them.

We also talked about life after closing, an issue I see frequently in our work with multi-location healthcare organizations. Branding, EHR systems, technology, leadership, and operational integration can determine whether an acquisition becomes part of a cohesive organization or what I jokingly call a “bag of bolts,” where the individual pieces never quite come together.

For anyone considering a transaction, Kayla offers a practical roadmap for what to do well before going to market: understand your financials, address known problems rather than kicking them down the road, define what matters most to you, and start learning from potential buyers, investment bankers, and experienced healthcare M&A advisors.

The timing of our conversation is especially relevant with McGuireWoods’ 19th Annual Healthcare Growth & Operations Conference (HealthcareGO), coming up September 15–16, 2026, in Charlotte, North Carolina. The conference brings together healthcare executives, founders, investors, operators, consultants, and advisers to discuss many of the same strategic and operational issues Kayla and I explore in this episode.

Whether you’re actively considering a transaction or simply want to understand what you should be doing now to prepare for one in the future, I think you’ll find Kayla’s perspective extremely useful.

Why Listen?

If you own, lead, acquire, or invest in healthcare organizations, understanding what happens before, during, and after a transaction can help you make better decisions long before a deal is on the table. In this episode, Kayla offers a candid look at what she’s learned from working on hundreds of healthcare transactions.

You’ll learn:

  • Why setting expectations early can prevent problems later in the transaction.
  • What founders should do before entering the M&A process.
  • Why diligence can feel overwhelming and what buyers are actually trying to learn.
  • How to think beyond purchase price when evaluating a potential buyer or partner.
  • Why control, governance, branding, technology, and integration need to be considered before closing.

Key Insights and Takeaways

  1. Set expectations before negotiations get complicated. Kayla sees mismatched expectations as one of the biggest threats to a transaction. Buyers and sellers should be clear about the issues that could cause them to walk away, including price, risk allocation, employee retention, control, and post-closing operations.
  2. The highest price isn’t necessarily the best deal. Purchase price is only one component of a transaction. Deal structure, strategic fit, governance, post-closing control, and integration can make a lower-priced offer a better long-term choice for a seller.
  3. Know whether you’re truly ready to sell. Founders sometimes enter a majority transaction without fully considering what giving up majority ownership means for governance and control. That realization can become both an emotional and practical obstacle once negotiations are underway.
  4. Prepare for diligence to become a second job. Founders are often surprised by the sheer volume of financial, legal, regulatory, billing and coding, insurance, benefits, technology, and cybersecurity questions. Kayla describes the resulting “deal fatigue” as one reason prolonged transactions become increasingly difficult to complete.
  5. Buyers aren’t expecting perfection. Diligence isn’t simply an exercise in finding fault. Buyers need to understand existing risks, future capital requirements, operational opportunities, and what will be required to integrate the organization after closing.

6. Choose advisors who understand healthcare transactions. Healthcare’s regulatory and tax complexities create risks that may not be obvious to attorneys without deep industry and transactional experience. Kayla particularly emphasizes the importance of experienced transactional tax counsel.

7. Decide what really matters before you start negotiating. Kayla recommends identifying the five issues that are most important to you and communicating them clearly to your attorneys, investment banker, and business partners. That allows your team to spend its negotiating capital on the points that can truly determine whether the deal works for you.

8. Don’t wait until closing to think about integration. Branding, EHR systems, technology, leadership, governance, and operating models can look very different from one buyer to another. Understanding a potential partner’s philosophy before the transaction can help prevent unpleasant surprises afterward.

“The highest price is often good. But it's really important that you drill down beyond pricing and make sure that the buyer, partner, or fit is right for you."
Kayla Marty

Kayla Marty

Partner, McGuireWoods

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Note: The following AI-generated transcript is provided as an additional resource for those who prefer not to listen to the podcast recording. It has been lightly edited and reviewed for readability and accuracy.

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