Technical Due Diligence
Technical due diligence answers one question: is the technology asset actually worth what the deal says it is? One independent investigation changed a nine-figure acquisition decision. That is what rigorous technology review looks like when done correctly.
A nine-figure acquisition that warranted a second look
While serving as Senior Enterprise Architect at First American Title Company — then the world's largest title insurer — I was embedded in the M&A division evaluating nine-figure real-estate acquisitions. A personal review of code, data architecture, and technology infrastructure at one acquisition target led the company to walk away from a roughly $100 million deal. The avoided integration work, which would not have produced sufficient ROI, would have cost millions over three years.
That review covered the dimensions that actually determine whether a technology asset is an asset or a liability: code quality, architecture scalability, data integrity, integration complexity, team capability, and vendor lock-in. These are not checklist items — they are judgment calls that require real enterprise architecture experience to make correctly.
First American at the time was a $5 billion publicly traded conglomerate with 15+ subsidiaries, 770 applications, and 900 engineers. This is what large-scale technology architecture judgment looks like in practice.
Six dimensions of technical due diligence
Code Quality Assessment
Is the codebase maintainable or a liability? Evaluating architecture patterns, technical debt, test coverage, and code quality signals across the full stack.
Data Architecture & Integrity
Can the data be trusted and migrated? Reviewing data models, pipeline architecture, data quality, and the hidden complexity of data integration.
Scalability & Performance
Will it hold under the acquirer's expected load? Bottlenecks are identified and stress-tested against projected growth scenarios before they become your problem.
Security Posture
What vulnerabilities come with the acquisition? Dependency audits, access control review, exposed surface area, and historical security incidents.
Team & Process Assessment
Who actually knows the system? Evaluating key-person risk, documentation quality, development processes, and technical leadership depth.
Integration Complexity
How difficult will it be to absorb? Mapping all third-party dependencies, API contracts, integration points, and the realistic post-close integration timeline.
The intellectual capacity and technical maturity of Shawn Livermore exceeded expectations.
What a technical due diligence engagement looks like
- Scope definition (1–2 days) — Align on deal timeline, access requirements, and the specific risk dimensions the acquirer wants assessed. Every transaction has a different shape; the review scope should reflect it.
- Access and review (1–2 weeks) — Code repository access, database schema review, architecture documentation, team interviews, and dependency audit. This is not a surface-level scan; it is a hands-on technical investigation.
- Investigation and analysis (concurrent) — Identify discrepancies between claimed and actual technical state. Test the critical assumptions in the deal thesis against what the technology can actually support.
- Findings report — Written assessment covering confirmed risks, deal-breakers (if any), remediation paths, and a realistic integration timeline with cost estimates. The report is written for both technical and executive audiences.
- Presentation — Executive-level briefing of findings, with full technical backup documentation for the team that will own integration if the deal proceeds.
If the technology story of an acquisition target has not been independently verified, it has not been verified at all. Reach out to discuss a due diligence engagement.
How Strong Is This Acquisition’s Technology?
A buy-side scorecard for evaluating a target’s codebase, architecture, team, security, technical debt, and data before you sign.
Take the assessment →Ready to evaluate an acquisition target?
Independent technical due diligence from an enterprise architect who has done it at scale — and whose findings have changed nine-figure decisions.
