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Comprehensive due diligence: Conduct thorough technical due diligence. Evaluate system architecture, cybersecurity, application code quality and development processes. Prioritizing remediation efforts: Remediation efforts must start as soon as technical debt is identified. Prioritizing these efforts based on their impact on the business can help manage costs and ensure that critical issues are addressed first. Start with the Minimum Viable Controls (MVCs). Strategic planning for integration or separation: Developing a strategic plan for integrating the acquired company’s technology (or moving to a standalone model) is vital. This plan should include steps for addressing technical debt, application rationalization, standardizing processes, documenting code and ensuring compatibility with existing systems. Ongoing monitoring and management: Technical debt should not be viewed as a one-time issue but rather as an ongoing challenge that requires continuous monitoring and management. Implementing robust governance frameworks and regular audits can help keep technical debt in check and prevent it from accumulating to problematic levels.

IT Integration – Due Diligence Questionnaire 7. Over-reliance on one or two “IT heroes” Strategic Discovery & Mitigation Once you know where to look, methodical IT discovery and assessments bring hidden costs and immature processes and systems to light. Correct inefficiencies and build roadmaps aligned with your portfolio strategy with these steps: holdings that have a planned 5-to-10-year exit; they have a shorter runway to create value than firms that retain tail investments. The latter case is not exempt however; as part of exit preparedness, it’s wise to avoid lingering technical debt that could affect post-close earnings. Signs of Technical Debt in PortCos: These warning signs can point to the issues behind an inability to quickly grow and scale with the existing tech stack, internal resources, and partners:. 1. Compliance or cybersecurity audit failures 2. Lack of multi-site IT standardization 3. On-prem systems with inconsistent backups 4. Resistance to cloud migration 5. Partially understood or mapped dependencies 6. Limited integration with other business systems

Category

Requested Item

Priority Status Notes

P1 P2 P1 P2 P2 P1 P1 P1 P1 P2 P2 P2 P1 P1 P2 P2 P1 P2 P1 P2 P1 P1

Organization & Spend Organization & Spend Organization & Spend Strategy & Governance Strategy & Governance Strategy & Governance Strategy & Governance Infrastructure & Hosting Infrastructure & Hosting Infrastructure & Hosting

IT spend by category (people, software, hardware, cloud, telecom, services)

Capitalization policy for IT and current capitalized IT assets

Planned/committed IT projects and capital requests (next 12 – 24 months)

IT strategy, roadmap, or board materials referencing technology

IT policies (acceptable use, access, data handling) with revision dates

Any prior IT, cyber, or technical assessments, audits, or pen tests (with findings)

IT-related insurance policies (cyber, tech E&O) with limits and claim history

Inventory of servers/VMs with OS, role, age, and location (on-prem/cloud/colo)

Hardware age profile and refresh plan; known end-of-life systems

Hypervisor/storage platform details and support status

Network & Facilities Applications & Data

Firewall and core network equipment inventory with age/support status

Data flow/integration map between core systems

Cloud & SaaS Cybersecurity

SaaS application list with owner, seats, and annual cost

Security incident history – breaches, ransomware, significant events (past 5 years)

Backup, DR, & Continuity

Disaster recovery/business continuity plans with stated RTO/RPO for critical systems

Vendors & Contracts People & Key-Person People & Key-Person Compliance & Legal

Telecom/connectivity contracts with termination dates and ETFs

Identification of key IT personnel and single points of knowledge

Documentation state – what runbooks/system docs exist

Applicable regulatory obligations (CMMC, HIPAA, PCI, GDPR/CCPA, etc.)

M&A / Structural M&A / Structural M&A / Structural

Known technical debt register or deferred maintenance list

Prior acquisitions and their integration state (any un-integrated environments)

Any systems, domains, tenants, or licenses shared with entities outside the deal perimeter

Sample IT integration due diligence questionnaire to guide the process.

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