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Technical Due Diligence Checklist

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1. Intellectual Property & Legal Ownership

Focus: Ensuring the seller has clean, transferable title to the code and assets without legal encumbrances.

Inspection Examples

  • Open Source Compliance: Scanning for copyleft licenses (GPL, AGPL) that legally mandate open-sourcing proprietary code.
  • Contributor Rights: Verifying IP assignment agreements are signed by all past contractors and agencies.
  • Asset Registration: Checking that domains, cloud accounts (AWS/GCP), and app store accounts are registered to the company entity, not personal emails.
  • Critical Dependencies: Identifying third-party APIs or data sources that could halt operations if they changed terms.

Common Tools

  • Snyk / FOSSA: Automated scanning of package managers (NPM, Pip, Maven) to identify license risks.
  • GitHub Dependency Graph: Native view in GitHub to quickly spot GPL-licensed libraries.
  • Whois / ICANN Lookup: Verifying domain registrant details.

2. Team & Key Person Dependency

Focus: Assessing if the technology can operate and evolve without the current founders or lead engineers.

Inspection Examples

  • Knowledge Silos: Identifying critical system components understood by only one individual.
  • Admin Access Control: Checking for shared root passwords or lack of individual identity management for critical infrastructure.
  • Deployment Independence: Verifying the team can deploy code and manage releases without the founder's physical hardware or input.
  • Retention Criticality: Identifying specific engineers who hold institutional knowledge not documented elsewhere.

Common Tools

  • Git Shortlog / GitExtras: CLI tools to visualize code contribution percentages by author (identifies "Bus Factor").
  • AWS IAM / GCP IAM: Auditing user lists to identify shared accounts (e.g., "admin@company.com" used by five people).
  • Pluralsight Flow (formerly GitPrime): Advanced visualization of engineering impact (optional for larger teams).

3. Architecture & Scalability

Focus: Determining if the current technology stack supports the investment thesis and growth targets.

Inspection Examples

  • Stack Standardisation: Evaluating if core programming languages and frameworks are widely used to ensure easy hiring.
  • Technical Debt Hotspots: Locating modules with high cyclomatic complexity or legacy code that typically require rewriting.
  • Database Performance: Checking for unoptimized queries, lack of indexing, or architectural bottlenecks that limit concurrent users.
  • API Architecture: Assessing if the system uses modern patterns (REST/GraphQL) versus legacy methods that hinder performance.

Common Tools

  • SonarQube / SonarCloud: Automated code quality scanning to identify complexity hotspots and technical debt.
  • Cloudcraft: Auto-generating architecture diagrams from live AWS environments to visualize complexity.
  • Locust.io / JMeter: Load testing tools to simulate traffic spikes and measure system response.

4. Infrastructure, Security & Costs

Focus: Validating the operational balance sheet, security posture, and true cost of delivery.

Inspection Examples

  • Cloud Waste: Auditing for idle servers, unattached storage, or inefficient resource provisioning.
  • Unit Economics: Calculating the actual hosting and compute cost per user or transaction.
  • Sensitive Data Handling: Verifying encryption methods for PII (Personally Identifiable Information) both at rest and in transit.
  • Disaster Recovery: Checking for automated backups and evidence of recent restoration tests.

Common Tools

  • Prowler: Open-source command line tool for AWS security best practice assessments (CIS Benchmarks).
  • AWS Trusted Advisor / Cost Explorer: Native cloud tools to identify idle resources and cost-saving opportunities.
  • OWASP ZAP: Scanning web applications for basic security vulnerabilities (SQL Injection, XSS).

5. Data Integrity & Analytics

Focus: Confirming that the data in the pitch deck matches the technical reality in the database.

Inspection Examples

  • Metric Reconciliation: Comparing reported active user counts against raw database login timestamps.
  • Traffic Quality: Filtering analytics for internal traffic, scrapers, and bot activity to find true user volume.
  • Conversion Tracking: Verifying that marketing pixels fire on confirmed events rather than page views or clicks.
  • Revenue Matching: Cross-referencing payment gateway logs (Stripe/PayPal) with internal database records.

Common Tools

  • Google Tag Assistant: Browser extension to verify firing triggers for Google Analytics and Ads tags.
  • Segment Inspector: Debugging tool to view the raw JSON payload of data events in real-time.
  • DBeaver / Postico: SQL clients for querying the production database to verify raw row counts.

6. Code Hygiene & Development Lifecycle

Focus: Evaluating the maturity of the engineering process and the maintainability of the codebase.

Inspection Examples

  • Secrets Management: Scanning the repository for hardcoded API keys, passwords, or credentials.
  • Automated Testing: Checking for the presence and coverage of unit and integration tests.
  • Documentation Quality: Reviewing the existence of API documentation, setup guides, and architecture diagrams.
  • Repository Health: Assessing commit frequency, branch management, and code review processes.

Common Tools

  • Trivy / GitGuardian: Scanning repositories specifically for hardcoded secrets and keys.
  • ESLint / Pylint: Linters that check for adherence to coding standards.
  • Swagger / Postman Collections: Checking for auto-generated API documentation.

7. Integration Readiness

Focus: Measuring the technical friction involved in merging the asset with another company or system.

Inspection Examples

  • Data Portability: Assessing the difficulty of exporting all customer and transaction data programmatically.
  • API Write Capabilities: Checking if external systems can create or update records via API.
  • Authentication Support: Verifying if the platform supports Single Sign-On standards (SAML, OIDC) for enterprise integration.
  • Webhooks: Checking for automated event notification systems to sync data with third-party tools.

Common Tools

  • Postman: Testing API endpoints for latency, structure, and write capabilities.
  • SchemaSpy: Generating visual Entity Relationship Diagrams (ERD) of the database to plan data migrations.

8. Remediation Guide (Optional)

Focus: Standard corrective actions for the most common issues found during LMM diligence.

Intellectual Property

  • Issue: High-risk GPL library detected.
  • Remedy: Replace with a permissive alternative (MIT/Apache) or purchase a commercial license wrapper pre-close.
  • Issue: Missing IP assignment for past contractor.
  • Remedy: Execute a retroactive "Confirmatory Assignment Deed" before signing.

Security & Infrastructure

  • Issue: Shared root credentials / No MFA.
  • Remedy: Enforce MFA on all root accounts and implement individual Identity & Access Management (IAM) users immediately.
  • Issue: PII stored in plain text.
  • Remedy: Implement database-level encryption or application-level hashing for sensitive fields.

Team & Knowledge

  • Issue: Undocumented "Black Box" algorithm.
  • Remedy: Condition of Closing: CTO must record a comprehensive code walkthrough video explaining the logic.
  • Issue: Manual deployment from a laptop.
  • Remedy: Containerize the application (Docker) and set up a basic CI/CD pipeline (GitHub Actions) to automate releases.

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Tech Due Diligence Checklist - this example will vary by project

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