TECHNICAL DUE DILIGENCE — SERVICE SPEC v2025
The financials tell you what a company earned. The technology tells you what it will cost to keep earning it. Undisclosed technical debt, fragile architecture, and undocumented systems are material risks — and they don't appear on any balance sheet. A technical audit does.
A structural engineer doesn't just look at a building's blueprints before a sale closes. They inspect the foundation, test the load-bearing walls, check for concealed damage behind the finished surfaces. The building can look pristine from the outside and be quietly failing from within. Software systems work exactly the same way. The product demo looks clean. The revenue numbers are growing. But underneath: undocumented dependencies, a decade of accumulated technical debt, a codebase that three engineers maintain and nobody else can read, and infrastructure one failed server away from a critical outage. These risks are real, quantifiable — and discoverable before you sign.
Every software company carries technical debt. The question is how much, how concentrated, and how expensive to service. Short-cuts taken to hit launch deadlines compound into systemic liabilities. The cleanup cost is real — and it belongs in your valuation model.
One engineer knows how the payment system works. One architect wrote the core data model and never documented it. If those people leave post-acquisition — and they often do — what you paid for begins to degrade immediately. Key-person risk is a structural liability, not a personnel footnote.
The current architecture handles the current load. But can it handle 10x users? What breaks first, and how much does it cost to fix? Growth is the plan. If the infrastructure can't support it, the plan requires unplanned capital — which changes the deal math.
Data handling, access controls, encryption standards, and third-party dependency licenses don't always get disclosed in a data room. Undiscovered compliance gaps become acquirer liability the moment the deal closes. Pre-close discovery is exponentially cheaper than post-close remediation.
The question isn't whether the technology works today. The question is what it will cost to keep it working, scale it, and secure it after the deal closes. That number belongs in the LOI, not in the first post-acquisition engineering sprint.
No independent technical assessment. The target's engineering team self-reports health. That's not an audit — it's a reference check written by the candidate.
Architecture quality not represented in financial models. Rebuild or migration costs are omitted from integration budgets. Post-close surprises erode deal value and damage stakeholder confidence.
Licensing and open-source compliance unreviewed. GPL-licensed components in commercial software, expired vendor contracts, and undocumented SaaS dependencies are material risks that don't surface in legal DD alone.
Integration complexity underestimated. Connecting the target's systems to your existing stack takes longer and costs more than expected — every time — when the target's architecture is undocumented and untested.
I conduct technical due diligence the way a structural engineer inspects a building before a sale: systematically, independently, and with full documentation of findings. Not a surface-level walkthrough — a load-bearing assessment of architecture, codebase quality, infrastructure, team, and operational risk.
My 25 years of enterprise web architecture experience means I know what healthy systems look like at scale — and I recognize the patterns of systems that are quietly failing. My MBA gives me the framework to translate technical findings into financial language: remediation cost estimates, integration risk factors, and valuation adjustments that belong in a deal model.
The deliverable is a Technical Due Diligence Report: a structured, risk-rated assessment across all material technical domains, with executive summary, detailed findings, and quantified remediation estimates. Written for both the boardroom and the engineering team. No jargon substituting for substance.
Timeline and depth are scoped to your deal requirements — from a rapid pre-LOI flag check to a full pre-close architecture inspection.
| PACKAGE | DELIVERABLES | SCOPE & ENGAGEMENT | STRUCTURAL OUTCOME |
|---|---|---|---|
|
DD-01
RAPID FLAG ASSESSMENT
Pre-LOI Technical Scan
RAPID
|
|
Fixed engagement. Remote review of provided documentation, codebase
samples, and architecture diagrams. Delivered in 5–7 business days. Designed for pre-LOI
decision gates.
|
You know whether there are material deal-breakers before investing in
full diligence. High-confidence go / proceed-with-caution / walk-away signal in under a
week.
|
|
DD-02
FULL TECHNICAL AUDIT
Pre-Close Due Diligence Report
FULL AUDIT
|
|
Project-based engagement. Requires data room access, codebase access, and
interviews with target's technical leads. Timeline: 2–3 weeks. NDA required.
|
Every material technical risk is identified, rated, and cost-quantified
before closing. You negotiate from fact, not assumption. Post-close surprises are minimized
by design.
|
|
DD-03
POST-CLOSE INTEGRATION
Technical Integration Advisory
ADVISORY
|
|
Monthly retainer. Activated post-close. Typically follows Full Technical
Audit engagement. Minimum 3-month term, scoped to integration timeline.
|
The risks identified in the audit are actively managed, not just
documented. Integration stays on schedule, on budget, and governed by someone who knows
exactly what was found before close.
|
"You can't negotiate what
you haven't inspected."
Technical due diligence is only as useful as the examiner's ability to recognize what they're looking at. I've spent 15 years architecting and maintaining enterprise-scale web applications — which means I've seen what good architecture looks like under production load, and I've also seen what accumulated technical debt looks like from the inside. I know the difference between a codebase that's mature and a codebase that's been held together with workarounds for three years. That distinction matters in a deal.
A decade of civil engineering and land surveying trained me to inspect physical infrastructure before it's transferred, built upon, or load-tested. That discipline — systematic inspection, objective measurement, documented findings, stamped report — maps directly onto software due diligence. I don't deliver opinions. I deliver findings with evidence, ratings with justification, and cost estimates grounded in real remediation experience.
Most technical auditors produce reports that investors can't parse and engineers can't act on. My MBA gives me the framework to translate architecture findings into financial terms: what this costs to fix, what it costs to operate, and what it does to the deal model. My engineering background means the technical findings are precise, not superficial. You get a report that closes the loop between the technical data room and the financial model.
The Rapid Flag Assessment is the right starting point for most deals — a fast, focused review that tells you whether there are material technical deal-breakers before you invest in full diligence. Delivered in 5–7 days. Scoped to your timeline. NDA-protected.
If you're already in the full diligence phase, the Full Technical Audit delivers a complete risk register with cost-quantified findings ready for the deal model.
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