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In a major process reversal, potential buyers of software companies now conduct technical diligence first. They assess tech debt and engineering modernity upfront, often leading to price reductions to account for necessary rebuilds—a stark change from when tech was a later-stage confirmation item.

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AI diligence has replaced cybersecurity as the modern, high-stakes technical hurdle in M&A. Buyers now focus on a company's AI defensibility and roadmap. A lack of a clear AI strategy or a perceived vulnerability to AI disruption can be an existential risk that either kills the deal or severely impacts the valuation.

To maintain speed in a high-volume M&A environment, you sacrifice the luxury of sequential processes. The key is to front-load diligence by identifying the five to ten critical items that could kill a deal and immediately testing for them.

In a sale process with multiple potential PE buyers, vendor due diligence acts as a critical shield. An external firm can handle initial tech workshops for all bidders, protecting the internal development team from being distracted and unproductive for months.

When Corp Dev runs diligence and hands it off to integration, it creates information gaps. Having the integration leader run diligence provides irreplaceable firsthand context, preventing misinterpretations and avoiding the need to 're-diligence' the deal later.

For PE firms buying founder-owned software companies, AI is a game-changer. It dramatically accelerates paying down the technical debt and modernizing the tech stack—often the biggest hurdles to growth post-acquisition. This allows firms to unlock value faster and more efficiently than ever before.

Tech due diligence is no longer a post-LOI, checkbox "IT audit." In the AI era, it has "shifted left" to become a critical, pre-LOI analysis of a company's strategic defensibility, AI maturity, and ability to innovate, often starting with outside-in signal gathering.

Despite rapid growth, AI-native SaaS companies are seen as more vulnerable to disruption by acquirers. Buyers are wary of the business's long-term defensibility, leading to harder questions and higher hurdles during the M&A process compared to traditional SaaS.

Dealmakers often fear that bringing integration teams into diligence early will kill deals. The proper framing is that their job is to make the deal better by stress-testing assumptions and arming dealmakers with the right questions, leading to a better outcome.

The ultimate goal for portfolio management is shifting from episodic due diligence to a continuous process. By constantly assessing and improving a company's tech posture, a future sale becomes a "non-event" where a comprehensive vendor fact book can be generated on demand.

Valuation multiples aren't just about growth. Acquirers actively discount multiples for specific, identified risks. Common penalties are applied for poor cybersecurity, high technical debt, or being stuck in a business model transition (e.g., from on-prem to SaaS), using them as negotiation leverage to lower the price.

Tech Diligence Has Shifted from Mid-Process Check to Day-One Priority in Software M&A | RiffOn