INSIGHT

Due diligence red flags in tech deals: What to look for and how to navigate them effectively

Craig Hamm • May 20, 2025

Services: Due Diligence

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When acquiring or investing in technology companies, thorough due diligence can prevent costly mistakes and protect your investment from unexpected pitfalls. Identifying warning signs early allows potential buyers to address issues before finalizing a transaction or adjust terms accordingly.  

7 due diligence red flags found in tech deals 

This article discusses the most common due diligence red flags in tech deals and how to navigate them effectively. 

1. Financial discrepancies 

Unusual financial patterns merit close scrutiny during due diligence. Watch for revenue recognition practices that don’t align with industry standards, unexpected cash flow fluctuations or significant differences between reported metrics and audited financials. 

Other warning signs include excessive founder compensation, related-party transactions or deferred maintenance on critical systems to artificially inflate short-term profitability. 

2. Customer concentration risk 

When a small number of clients account for a large percentage of revenue, this creates significant business risk. A healthy tech company typically maintains a diverse customer base without excessive dependence on any single client. 

Review customer contracts carefully, examining renewal rates, churn patterns and the stability of top customers. Be particularly cautious if more than 20 percent of revenue comes from a single customer, as losing that relationship could devastate the business financially. 

3. Technical debt accumulation 

Many tech companies, particularly startups, accumulate technical debt while rushing products to market. This manifests as poorly documented code, outdated technologies or systems that won’t scale with growth. 

During code reviews, watch for signs including frequent system crashes, slow performance under load testing or excessive manual processes that should be automated. Outdated technologies can create security vulnerabilities and make it difficult to attract talent to maintain these systems. 

4. People and knowledge concentration 

The value of many tech companies resides primarily in their people. Software development relies heavily on the knowledge of developers who build and maintain systems. High turnover rates, particularly among key technical staff, should raise concerns about company culture and leadership. 

Evaluate whether knowledge is concentrated in just a few individuals, creating operational risk. Companies without proper knowledge transfer processes may face significant challenges if key team members depart after acquisition. 

5. Compliance and regulatory gaps 

Tech companies operate in an increasingly complex regulatory environment. Failure to comply with data privacy regulations, industry-specific requirements or security standards can lead to significant penalties and reputation damage. 

Request documentation of all compliance measures and third-party audits. Red flags include the absence of formal policies, lack of regular security assessments or history of data breaches that weren’t properly addressed. 

6. Integration challenges 

Successful tech acquisitions require thorough planning for integration. Misalignment between the acquirer and target company in areas like development methodologies, technology stacks or company culture can severely impact post-deal success. 

Inconsistencies in terminology, processes and problem-solving approaches between organizations can indicate potential integration difficulties that might prevent achieving the expected synergies. 

7. Intellectual property vulnerabilities 

One critical area to scrutinize involves intellectual property rights and protection. Companies that cannot clearly demonstrate ownership of their technology present a significant risk factor. This includes situations where developers may have created code while employed elsewhere or where open-source components have been incorporated without proper compliance. 

Insufficient documentation regarding patents, trademarks or copyright registrations should prompt deeper investigation. The absence of proper IP protection can substantially diminish a company’s value and create future legal complications. 

How BPM can help 

Identifying red flags during tech due diligence requires a multi-disciplinary approach that examines technical, financial, legal and operational aspects of the target company. BPM provides you with a team that understands the nuances of technology transactions and who can help navigate potential pitfalls before they derail your investment. 

To ensure your next tech acquisition undergoes comprehensive due diligence that protects your interests and maximizes the value of your technology investments, contact us.