Understanding what buyers and their advisers focus on during technology due diligence is the most direct way to prepare for a sale process. Sophisticated investors, and the specialists they engage, are looking for specific things. Knowing what those are, before the process starts, is a material advantage.
Architecture and scalability
The first question buyers ask about a software platform is whether it can support the growth thesis.
They are looking for evidence that the architecture can scale, in terms of load, geography, and feature complexity, without a costly rewrite. Specific concerns include:
- Monolith vs. modular: Is the platform structured in a way that allows parts to be scaled, replaced, or extended independently? Tightly coupled monolithic architectures are not disqualifying, but they need to be understood and the cost of evolution needs to be quantified.
- Infrastructure choices: Cloud-native platforms running on managed infrastructure are generally easier to assess positively. Significant on-premise infrastructure, or deep dependency on niche hosting providers, introduces questions about portability and migration cost.
- Single points of failure: Are there architectural bottlenecks or dependencies (third-party integrations, data pipelines, internal services) that represent fragility? Buyers want to understand what breaks, and how quickly it can be fixed.
- Integration complexity: For businesses that acquire other businesses, or that sell into enterprise environments requiring deep integration, how complex is the integration layer, and what is the cost of adding new integrations?
Security posture
Security findings are among the most deal-sensitive outcomes of technology due diligence. A serious finding can affect price, deal structure, and completion. In some cases it surfaces a liability that was not visible in the commercial or financial diligence.
Buyers are specifically looking for:
- Known exploitable vulnerabilities in the application, infrastructure, or third-party dependencies
- Data handling and privacy compliance: GDPR, SOC 2, ISO 27001, and relevant sector-specific regulations
- Access controls: are credentials managed properly, and is there a risk of insider access or credential theft?
- Security incident history: has the business had incidents, how were they handled, and what changed as a result?
- Third-party risk: is the security of the supply chain (SaaS tools, vendors, APIs) understood and managed?
A business with no security certifications and no evidence of a security programme will attract scrutiny. A business with clear policies, completed certifications, and a documented response to any historical incidents will not.
Technical debt
Every technology business carries technical debt. Buyers are not looking for a platform with zero debt. They are looking for a management team that understands what they have, has a credible plan to address the most material items, and has quantified the cost.
Vague statements about “legacy code” or “some areas that need updating” are not reassuring. A specific, prioritised assessment of what the debt is, where it sits, what it will cost to address, and what happens if it isn’t, is.
The key outputs buyers want to see on technical debt:
- What are the material items? (Not an exhaustive list, the ones that actually matter)
- What is the remediation cost and timeline?
- What is the risk of not addressing them within the investment horizon?
- Has anything been addressed already, and what is the evidence?
Engineering team
Key-person risk in engineering is one of the most frequently underestimated deal risks, and one of the hardest to discover from a financial or commercial review. It surfaces in tech DD.
Buyers are asking:
- Who are the critical individuals, and what happens if they leave post-close?
- Is the team sized and structured to execute the business plan?
- Is there capability depth, or is the team thin below the founder/CTO level?
- What does attrition look like, and what are the causes?
A business where a small number of individuals hold all the critical technical knowledge, and where that knowledge is not documented, transferred, or hedged, carries real execution risk post-acquisition.
AI readiness
For software businesses, AI is now a standard area of due diligence scrutiny, not an optional extra. Buyers are asking:
- Is AI embedded in the product as a genuine value driver, or is it a recent addition to the narrative?
- What is the model infrastructure: proprietary models, fine-tuned open-source, or API-based? What are the cost, dependency, and risk implications of each?
- Is there an AI governance framework? How are outputs validated, monitored, and audited?
- What is the data quality underpinning AI features? Is the training or retrieval data well-managed?
- What are the regulatory risks, particularly for AI in regulated sectors such as financial services and health?
A business that can answer these questions clearly, with evidence, is in a stronger position than one that cannot.
Product and roadmap
Buyers are investing in the future, not the current state. They want to understand whether the product has the legs to support the growth thesis, and whether the team can deliver it.
Specific questions:
- Is the roadmap credible? Are features resourced, sequenced, and validated against market demand?
- Does delivery velocity match the stated plan?
- Is there evidence of product-market fit beyond early customers?
- Are there competitive threats, from AI-native alternatives or better-resourced incumbents, that are not reflected in the narrative?
What a well-prepared business looks like
A business that has done the preparation work presents very differently from one that has not. The differences are usually visible immediately:
- Architecture documentation is clear and current
- Security posture is evidenced, not asserted
- Technical debt is quantified and prioritised
- The engineering team’s structure and capability are explained clearly
- AI capability is described with specifics, not vague claims
- The roadmap is backed by evidence of delivery capability
This preparation reduces friction, reduces buyer uncertainty, and reduces the number of reasons to chip the price. It is the work that a Technology Health Check and Sell-Side Technology Report combination is designed to produce.