An earnout can look like a fair way to bridge a valuation gap. Then the business misses its targets because the acquired platform cannot support the growth plan. That is the danger in tech debt acquisitions. In mergers and acquisitions, technical debt can undermine the growth plan. Parties may agree on targets before agreeing on […]
Tech Debt Acquisitions: The Earnout Problem Read More »
Your adjusted EBITDA bridge can add millions to a deal’s headline business valuation. It can also fall apart in a single due diligence meeting if you cannot show where each number came from, why it will not recur, and who owns the evidence. The hard part of EBITDA add-backs is not finding expenses. It is
Tech EBITDA Add-Backs That Survive Buyer Scrutiny Read More »
An acquisition can create value quickly, but technology gaps can slow integration, raise cyber risk, disrupt customers, and weaken confidence in the deal. Day one readiness helps limit these risks, while a post acquisition IT integration plan protects the business before it tries to combine every system. The first 100 days are the core phase
The First 100 Days of Tech Integration After an Acquisition Read More »
Trust Debt M&A: What Acquirers See First A deal can look healthy until the buyer starts asking for evidence. That is where trust debt M&A becomes expensive. Trust debt is the gap between what leadership says about technology and what the systems, contracts, reports, and operating habits can prove. Acquirers don’t expect perfection. They do
Trust Debt M&A: What Acquirers See First Read More »
In high-stakes M&A transactions, a deal can look sound on paper and still hand you a technology problem that drains cash, delays integration, and weakens the value you thought you bought. For buy-side deal teams and executives, technology due diligence gives you a clearer view before money changes hands. It tests whether the target’s systems,
Technology Due Diligence Before an Acquisition: What Leaders Need to Know Read More »
Merging two tech stacks is a high-stakes challenge that frequently arrives when you acquire a company, launch a new business unit, or replace a core platform. Whether you are navigating complex mergers and acquisitions or simply consolidating internal systems, you suddenly find two teams relying on different infrastructure, data models, vendors, and workflows. Everyone expects
Merging Two Tech Stacks Without Wasting Time Read More »
The first budget surprise in a deal is usually not the purchase price. It is the cleanup that follows. If you wait until after the letter of intent, you are often negotiating with the clock against you. Skipping thorough IT due diligence early in the process creates blind spots that threaten your total deal value.
How to Negotiate Acquisition Integration Costs in the LOI Read More »
A deal can look clean until you ask the wrong questions. The seller has a polished deck, the demo runs fine, and everyone sounds confident. Then you start digging and find technical debt, vendor dependence, shaky security, and a roadmap held together by hope. That is where technology due diligence matters. Whether you are leading
Technology Due Diligence Questions CEOs Should Ask Before Buying Read More »
In the fast-paced world of M&A transactions, a mid-market deal rarely falls apart because of one ugly system. Instead, these acquisitions typically collapse because the buyer identifies a pattern they do not trust. That pattern emerges quickly during the evaluation phase. Weak ownership, messy reporting, rising cyber exposure, and heavy vendor dependence all tell the
Technology Due Diligence Red Flags That Kill Mid-Market Deals Read More »
You can close the deal and still lose the value in the first 90 days. That happens when systems stay split, vendors keep pulling in different directions, and nobody owns the real decisions. Poor post-merger integration often leaves companies struggling with duplicate tools, fragmented data, and a team that loses momentum. When PMI is poorly
Post-Acquisition Technology Integration Checklist Every CEO Needs Read More »
