Technical Due Diligence
Clear-eyed technology assessment for acquisitions, investments, and strategic decisions.
Why Technical Due Diligence Matters
When millions of dollars are on the line — whether you’re acquiring a company, investing in a startup, or preparing your own business for sale — the technology underneath matters as much as the balance sheet. Code quality, architecture decisions, security posture, and team capabilities can make or break a deal.
The problem is that most investors, founders, and M&A advisors aren’t equipped to evaluate technology assets with the depth required. A surface-level review misses the risks that surface six months after close — the legacy monolith that can’t scale, the security vulnerabilities that trigger a breach, or the key-person dependency that walks out the door.
I conduct technical due diligence that goes beyond slide decks and self-reported metrics. With over 15 years of technology leadership experience — from enterprise IT at Honeywell to building SaaS products from zero — I know what good looks like, and more importantly, I know where problems hide.
Who Needs Technical Due Diligence?
Private equity firms and investors evaluating technology companies before acquisition or funding. You need an independent assessment of what you’re actually buying — the real state of the codebase, infrastructure, and team, not the polished version presented in the pitch deck.
Founders preparing for fundraising or exit who want to identify and fix issues before investors find them. A pre-diligence assessment gives you time to address gaps and present your technology stack with confidence.
Companies acquiring technology businesses that need to understand integration complexity, hidden technical debt, and ongoing operational costs before finalizing a deal.
Boards and executives seeking an independent assessment of their own technology organisation’s health, capabilities, and risks — particularly during leadership transitions or strategic pivots.
What I Assess
Every technical due diligence engagement is tailored to the specific deal and risk profile, but typically covers these core areas:
Architecture & Code Quality
A deep review of the system architecture, codebase quality, and technical debt. I examine the technology stack choices and their appropriateness for the business, code organisation, test coverage, and development practices. I identify architectural risks that could limit scalability, increase maintenance costs, or create security vulnerabilities. This isn’t a checkbox exercise — it’s an experienced CTO reading the code and understanding what it tells you about the engineering culture.
Infrastructure & Operations
Assessment of cloud infrastructure, deployment pipelines, monitoring, disaster recovery, and operational maturity. I evaluate whether the infrastructure can support projected growth, what the real hosting costs look like at scale, and how resilient the platform is to failures. From Kubernetes clusters to CI/CD pipelines, I assess whether operations are built for reliability or held together by tribal knowledge.
Security & Compliance Posture
A thorough review of security practices, vulnerability management, access controls, data protection, and compliance readiness. With experience leading four consecutive flawless ISO 27001 audits, I bring enterprise-grade security assessment to companies of every size. I evaluate SOC 2 readiness, GDPR compliance, encryption practices, and the overall security culture — not just whether a firewall exists, but whether security is genuinely embedded in how the team builds software.
Team & Capabilities
Technology is built by people, and the team is often the most valuable — and most fragile — asset. I assess team structure, skill levels, key-person dependencies, development processes, and engineering culture. I identify retention risks, hiring gaps, and whether the team can execute the product roadmap without the founder or a single senior engineer holding everything together.
Product & Roadmap Viability
Assessment of the product’s technical roadmap, feature pipeline, and the team’s ability to deliver against it. I evaluate whether the architecture supports planned features, whether timelines are realistic, and where product development risks could impact business projections.
IP & Licensing
Review of intellectual property ownership, open-source license compliance, third-party dependencies, and any licensing risks that could create legal exposure. I verify that the company actually owns what they claim to own and that open-source usage doesn’t create unexpected obligations.
How It Works
Scoping & Alignment — We start with a conversation about the deal context, timeline, and specific risk areas you want investigated. Whether you’re two weeks from close or six months out, I tailor the depth and focus to match your needs.
Document & Access Review — I review available documentation, architecture diagrams, security policies, and team information. For sell-side engagements, this happens internally. For buy-side diligence, I work within whatever data room or access framework has been established.
Technical Deep Dive — Hands-on review of the codebase, infrastructure, deployment processes, and security controls. This includes code review, architecture analysis, infrastructure assessment, and where possible, direct conversations with the engineering team.
Findings & Report — A clear, actionable report that separates critical risks from minor issues, quantifies remediation costs where possible, and provides an honest overall assessment. No jargon-filled documents designed to impress — practical findings that help you make a confident decision.
Executive Briefing — A face-to-face or virtual walkthrough of findings with your deal team, board, or investors. I translate technical findings into business impact and answer questions directly.
Why Choose Selbytech for Due Diligence?
Operator, not just auditor — I’ve built and led the kinds of technology organisations I assess. This means I know the difference between a pragmatic shortcut and a ticking time bomb, and I won’t flag normal startup trade-offs as critical risks.
Enterprise and startup experience — Having directed global teams at Honeywell and built products from zero as a founder, I calibrate my assessment to your context. What’s acceptable for a Series A startup is different from what’s expected of a mature SaaS business.
Security-first perspective — Four consecutive ISO 27001 audits with flawless outcomes means security assessment isn’t an afterthought — it’s woven into every review I conduct.
Speed when it matters — Deal timelines don’t wait. I’ve delivered focused due diligence assessments in as little as one to two weeks when timelines demand it, without sacrificing the depth that makes the assessment valuable.
Independence — I have no incentive to tell you what you want to hear. My reputation depends on accurate, honest assessments — not on closing deals.
Frequently Asked Questions
How long does a technical due diligence assessment take?
A focused assessment typically takes one to three weeks depending on the size and complexity of the technology stack. For time-sensitive deals, I can deliver a rapid assessment covering critical risk areas in five to seven business days, with a deeper follow-up if needed.
Do you work on the buy side or sell side?
Both. For buyers and investors, I provide independent assessment of the target’s technology. For sellers, I conduct pre-diligence reviews that help you identify and address issues before they become deal risks or valuation discounts.
What access do you need?
Ideally, read access to the code repository, infrastructure dashboards, and CI/CD pipelines, plus conversations with key technical team members. I work within whatever access framework has been established for the deal and am comfortable with NDAs and data room protocols.
Can this lead into a longer engagement?
Absolutely. Many due diligence engagements naturally evolve into fractional CTO work — particularly when the assessment identifies areas that need senior technical leadership to remediate. Post-acquisition technology integration is a common next step. See our fractional CTO services and pricing for ongoing engagement options.
What industries do you cover?
I’ve assessed technology across SaaS platforms, fintech, healthcare technology, industrial IoT, e-commerce, and enterprise software. The fundamentals of good architecture, secure code, and reliable infrastructure apply across industries, and my breadth of experience — from industrial SCADA systems to cloud-native microservices — means I can evaluate diverse technology stacks with confidence.
Ready to discuss a technical due diligence engagement?