Technology Due Diligence in Mergers and Acquisitions: Comprehensive M&A Guide

When companies merge or get bought, buyers need to check the target company’s technology before closing the deal. Technology due diligence is the analysis of technology products, architecture, and processes of an organization that helps buyers understand what they’re purchasing.

This process reveals critical technology risks, security gaps, and hidden costs that could make or break a deal’s success.

A group of business professionals collaborating around a table with laptops and digital screens displaying technology data in a modern office.

The stakes are high in today’s digital business world. Companies rely heavily on technology systems, software, and data to operate.

Without proper technology review, buyers could inherit outdated systems, security problems, or expensive technology debt they never saw coming. That’s a headache no one wants.

Smart buyers dig into everything from software licenses and cybersecurity measures to system architecture and compliance issues. This deep dive helps them make better decisions, negotiate fair prices, and plan for smoother technology integration after the acquisition.

They also check intellectual property rights, evaluate the current technology teams, and look for roadblocks that could hurt the combined company’s future.

Understanding Technology Due Diligence in Mergers and Acquisitions

A group of business professionals in a conference room reviewing data on laptops and documents during a technology evaluation meeting.

Technology due diligence works as a comprehensive evaluation process, examining a target company’s technical assets, infrastructure, and capabilities. The assessment focuses on risks, technological value, and figuring out if integration is even feasible within the bigger M&A picture.

Definition and Purpose

Technology due diligence is a comprehensive evaluation of a target company’s technology stack, operational infrastructure, and ability to scale. This process digs into the technical foundation behind business operations.

The evaluation covers several areas. Software systems, hardware infrastructure, and digital assets all get a thorough look.

Technical teams check code quality, system architecture, and operational stability. They’re looking for cracks before things go wrong.

Key components include:

  • Software applications and databases
  • IT infrastructure and cloud systems
  • Cybersecurity measures and protocols
  • Intellectual property assets
  • Technical team capabilities

The purpose isn’t just risk assessment. Buyers want insights into the tech that drives business performance.

This understanding helps them see if the target’s technology lines up with their acquisition goals. Technical due diligence also flags integration challenges early, so teams can plan for compatibility issues and resource needs.

Getting ahead of these problems cuts down post-acquisition chaos and helps everyone realize value faster.

Role in the M&A Process

Tech due diligence fits right into the bigger M&A evaluation, alongside financial and legal reviews. Companies eyeing a merger or acquisition want to know what they’re really buying through this deep dive into the target’s tech, systems, and potential risks.

Usually, this process kicks in once there’s serious acquisition interest. Initial business case validation leads, then the technical assessment follows.

Timeline integration:

  1. Business strategy alignment
  2. Technical infrastructure review
  3. Detailed system analysis
  4. Integration planning begins

Only one in four CEOs report conducting technology due diligence for most of their deals, even though 74% call technology a growth enabler. That’s a pretty big gap—and a risky one.

The technical review shapes valuation talks. Infrastructure costs, upgrade needs, and integration complexity all affect pricing. Security flaws or compliance gaps can push prices down.

Sometimes, critical technical flaws even kill deals. On the flip side, strong tech assets can justify a premium.

Key Objectives and Benefits

The main goal? Identify and mitigate risks. The due diligence process helps uncover potential risks and liabilities associated with the target company’s technology assets.

This means spotting security vulnerabilities, compliance gaps, and technical debt. Teams also check if tech assets actually justify the asking price.

Hidden costs like infrastructure upgrades or new security measures can change the true price tag. No one likes surprises there.

Strategic benefits include:

  • Risk reduction through early problem identification
  • Value validation of technological assets
  • Integration planning for smoother transitions
  • Synergy identification for enhanced capabilities

Technical due diligence provides insights into scalability and future-proofing of tech assets. Teams want to know if the tech can grow and adapt.

They also look for competitive advantages—proprietary technologies, unique algorithms, or specialized systems that set the company apart. These can justify paying more and fuel future growth.

Weaknesses give buyers leverage to negotiate a better price. Strong tech? That supports higher valuations.

Core Components of Technology Due Diligence

A group of business professionals having a meeting around a conference table, reviewing data and technology documents on laptops and a large screen in a modern office.

Technology due diligence digs into four main areas that can make or break acquisition success. These include infrastructure, software reliability, data protection, and team expertise.

IT Infrastructure and Systems Assessment

The IT infrastructure evaluation is the backbone of tech due diligence. Here, buyers look at hardware capacity, network architecture, and cloud systems.

Hardware and Network Systems

  • Server capacity and performance
  • Network bandwidth and reliability
  • Storage systems and backup setups
  • Disaster recovery infrastructure

Cloud infrastructure often brings surprises. Buyers need to know about hosting costs, scalability limits, and vendor lock-in.

Many companies run into unexpected bills when their cloud systems can’t handle more demand. It happens more than you’d think.

System Integration Capabilities
IT systems have to play nice together. Legacy systems can cause integration nightmares (and cost millions to fix).

The assessment spots compatibility issues between platforms and databases before they get out of hand.

Performance and Reliability Metrics
System uptime, response times, and error rates show infrastructure quality. If performance lags now, it’ll probably get worse after the deal.

Software and Applications Review

Software is the engine of business and customer experience. The technology stack assessment checks code quality, licensing, and maintenance needs.

Application Portfolio Analysis

  • Custom vs. third-party software
  • Software licensing costs and restrictions
  • Application dependencies and integrations
  • User adoption and satisfaction

Code quality matters. Clean, well-documented code means faster innovation and fewer headaches.

Poor code quality? That’s technical debt that can drag down growth and rack up expenses.

Technology Stack Evaluation
Modern tech stacks let teams move faster and deliver better experiences. Outdated tech slows feature development and makes hiring a pain.

The review highlights upgrade needs and what they’ll cost.

Software Licensing and Compliance
Software licenses can trip up an acquisition. Some restrict business operations or force expensive upgrades if ownership changes.

Data Security and Protection Evaluation

Data security vulnerabilities can lead to breaches, fines, and reputation hits. This part looks at security measures, compliance status, and data handling practices.

Security Framework Assessment

  • Access controls and user permissions
  • Encryption standards for data storage
  • Network security and firewall setups
  • Security monitoring and incident response

Compliance and Regulatory Requirements
Companies need to meet industry regs like GDPR, HIPAA, or PCI DSS. Failing here means legal headaches and operational restrictions.

The review checks compliance status and flags any gaps.

Data Management Practices
Bad data practices create risk and missed opportunities. Teams look at data quality, backup processes, and recovery plans.

If data is scattered or inconsistent, decision-making gets tough.

Organizational Structure and Team Capabilities

A company’s tech team determines how well things run and how fast they can innovate. The technical team evaluation looks at skills, processes, and how well knowledge gets shared.

Team Skills and Experience

  • Technical chops in key areas
  • Development process maturity
  • Documentation and knowledge transfer
  • Team retention and hiring challenges

Development Processes and Practices
Solid development processes mean better quality and faster delivery. Teams without good testing, code review, or deployment practices create risk.

Knowledge Management
If only a couple people know how things work, that’s dangerous. Good documentation and sharing protect against talent loss and make transitions less painful.

Evaluating Intellectual Property and Compliance

Intellectual property assets can be a huge part of a company’s value. Software licenses and regulatory requirements create legal obligations that can make or break a deal.

Buyers need to verify ownership rights, check licensing agreements, and see if the company complies with data protection laws.

Intellectual Property Ownership

Identifying and cataloging all intellectual property rights is fundamental to IP due diligence. Companies need to confirm ownership of patents, trademarks, copyrights, and trade secrets.

Patent portfolios require checking filing dates, expiration, and where they’re valid. Buyers verify that patents are assigned to the target company and look for any licensing obligations.

Trademark ownership means confirming registration and renewal dates. Are trademarks actually used in commerce? Expired or abandoned ones lose protection.

Key steps:

  • Review assignment agreements
  • Check government databases
  • Confirm employee invention agreements
  • Identify jointly owned assets

Trade secrets are tricky since there’s no formal registration. Companies need to show they’ve kept secrets safe with confidentiality agreements and access controls.

Software Licensing and Agreements

Software licensing is a legal maze. Third-party licenses might restrict how software gets used after an acquisition.

Open source licenses sometimes require source code disclosure or restrict distribution. Some, like GPL, force derivative works to use the same license.

Companies need to inventory all open source components and their license requirements.

Commercial software agreements may have change-of-control clauses that end licenses if the company is acquired. Enterprise licenses might not transfer automatically.

Critical areas to check:

  • License transferability after an ownership change
  • Usage restrictions and user limits
  • Maintenance and support terms
  • Compliance obligations and audit rights

Custom development agreements with contractors need clear proof that IP transfers to the company. Work-for-hire clauses should be in writing.

Regulatory and Legal Compliance

Technology companies face more and more regulatory requirements. Data protection laws, in particular, are strict.

GDPR compliance affects any company processing EU resident data, no matter where it’s based. Violations can mean fines up to 4% of annual revenue.

Companies need a lawful basis for processing and must keep detailed records.

HIPAA requirements apply to healthcare data and call for specific security safeguards. Business associate agreements are a must with vendors.

CCPA regulations cover California resident data and require disclosure and deletion rights. Companies must be able to respond to consumer requests quickly.

Essential compliance checks:

Regulation Key Requirements Penalty Risk
GDPR Consent management, data mapping Up to 4% revenue
HIPAA Security controls, breach reporting Criminal charges possible
CCPA Privacy notices, deletion processes $7,500 per violation

Industry-specific regulations can add more hoops, depending on the company’s sector. Financial services, healthcare, and telecom have especially tough rules.

Cybersecurity and Technology Risk Management

Good cybersecurity risk management during M&A means thoroughly checking the target company’s security infrastructure. Teams look for existing vulnerabilities and assess how the company handles incidents.

They also review business continuity plans to make sure operations can keep running after the deal closes.

Current Security Posture Assessment

The security posture evaluation forms the foundation of cybersecurity due diligence in M&A.

Companies need to dig into existing security protocols, governance frameworks, and control implementations across all their technology systems.

Key assessment areas include:

  • Access controls and user authentication systems

  • Firewall configurations and network segmentation

  • Intrusion detection and monitoring capabilities

  • Encryption standards for data at rest and in transit

  • Security policies and employee training programs

Organizations should check compliance with industry standards like ISO 27001 and any regulations that apply to their sector.

This assessment often uncovers gaps between what’s in place and what’s actually required.

The evaluation process means reviewing security documentation, talking with IT folks, and running technical assessments.

Companies frequently find outdated security protocols or weak monitoring systems at this stage.

Identification of Security Vulnerabilities

Technology due diligence teams have to systematically hunt for vulnerabilities that could hurt deal value or mess with post-merger operations.

This process digs deeper than just ticking boxes on security checklists—it’s about finding hidden risks.

Critical vulnerability categories include:

Vulnerability Type Risk Level Common Issues
Unpatched systems High Outdated software, missing security updates
Network security Medium-High Weak firewall rules, unsegmented networks
Access management Medium Excessive user privileges, weak passwords
Data protection High Unencrypted sensitive data, inadequate backups

Companies should also look at their external digital footprint and check if anything’s popped up on the dark web.

Sometimes, previous security breaches slip right past the target company’s radar.

Teams need to examine third-party vendor relationships and supply chain security risks.

A lot of breaches actually come through compromised vendor systems, not direct hits on the main infrastructure.

Incident Response and Disaster Recovery

Incident response capabilities show how fast a company can contain and bounce back from security breaches.

M&A cybersecurity teams need to evaluate current response plans and recovery procedures.

Essential incident response components:

  • Detection systems for spotting security events

  • Response team structure and communication protocols

  • Containment procedures to limit breach impact

  • Evidence collection and forensic analysis capabilities

  • Recovery timelines and system restoration processes

Disaster recovery plans should cover both cybersecurity incidents and bigger IT failures.

Companies really need tested backup systems and alternate processing facilities.

The evaluation covers how previous incidents were handled and what the company learned from them.

Weak incident response usually means longer recovery times and higher costs after a breach.

Business Continuity Planning

Business continuity frameworks keep things running during and after security incidents.

Companies have to figure out how tech disruptions might hit critical business functions and revenue.

Key continuity elements include:

  • Critical system identification and priority rankings

  • Recovery time objectives for essential operations

  • Alternate workflow procedures during outages

  • Communication plans for stakeholders and customers

  • Supply chain backup arrangements

The assessment looks at integration headaches between acquiring and target company systems.

Cybersecurity protocols need to mesh across merged organizations to keep protection levels steady.

Risk mitigation strategies need to cover both immediate post-merger vulnerabilities and long-term security integration.

This planning helps reduce chaos during technology system consolidation.

Technology Due Diligence Checklist and Process

A structured approach to technology due diligence takes careful planning, team coordination, and a methodical process spread over several phases.

The process kicks off with assembling specialized teams, setting up secure data environments, building evaluation frameworks, and generating findings that actually help during negotiations.

Preliminary Planning and Team Assembly

The first phase sets the stage for technical due diligence.

Organizations define the scope based on deal size, industry quirks, and strategic goals.

Team composition usually brings together technical architects, cybersecurity specialists, data analysts, and project managers.

Everyone brings their own expertise to the table.

The planning phase flags critical risk areas like:

  • Legacy system dependencies

  • Scalability limitations

  • Security vulnerabilities

  • Compliance gaps

Timeline development lines up with the broader M&A schedule.

Technical reviews often take 4-6 weeks, but that depends on the size and complexity of the target company.

Getting stakeholders on the same page early helps avoid scope creep.

Clear communication protocols set expectations for how findings get escalated and resolved.

Document Collection and Data Room Management

Secure document management is crucial for smooth due diligence.

Virtual data rooms (VDRs) give controlled access to sensitive technical info and keep audit trails.

Essential document categories include:

  • System architecture diagrams

  • Security policies and procedures

  • Software licenses and contracts

  • Infrastructure inventories

  • Compliance certifications

Data room organization sticks to standardized folder structures that mirror IT due diligence checklists.

This makes reviews systematic and saves time hunting for files.

Access controls make sure only the right people see the right stuff.

Technical team members get permissions based on what they’re supposed to evaluate.

Document version control keeps everyone from getting confused when multiple people leave comments.

Regular updates keep the info current as diligence moves along.

Checklist Development and Execution

Comprehensive due diligence checklists give teams a systematic way to evaluate technology assets.

Each checklist item ties back to specific risk factors or value drivers from the planning stage.

Core evaluation areas include:

Category Focus Areas
Infrastructure Cloud deployment, scalability, disaster recovery
Security Access controls, vulnerability management, compliance
Software Code quality, technical debt, licensing
Data Architecture, governance, privacy controls

Execution means running structured interviews with the target’s technical leaders.

These sessions help validate what’s in the documents and highlight any gaps needing further digging.

Risk assessment matrices let teams score issues by likelihood and potential impact.

That way, remediation planning and negotiation strategies get prioritized.

Progress tracking makes sure teams cover every checklist item on schedule.

Regular status updates keep stakeholders in the loop about new findings and possible deal impacts.

Reporting and Negotiation

Final deliverables pull together technical findings into business insights that people can actually use.

Reports emphasize critical risks, integration needs, and value creation opportunities that can sway deal terms.

Executive summaries distill key points into plain language for non-technical folks.

These sections focus on financial impacts, not just technical details.

Risk categorization splits immediate concerns from longer-term optimization opportunities.

Critical issues might mean price adjustments or tweaks to the deal structure.

Integration planning lays out what needs to be consolidated, how long it’ll take, and what resources it’ll eat up.

This info supports post-acquisition planning and budgeting.

Negotiation support includes recommendations for contract terms, warranties, and indemnification.

Technical teams back up final deal talks to make sure risks get allocated properly.

Post-Acquisition Technology Integration

Technology integration starts right after the deal closes.

It takes careful execution to actually deliver on the promised synergies.

Success hinges on solid planning, tackling challenges head-on, and tweaking systems to match the new organization’s goals.

Integration Planning and Strategy

Technology integration planning usually starts during due diligence and keeps going post-close.

Companies need a tech roadmap that fits with their overall business strategy.

The first step is to set up a Technology Integration Management Office (Tech IMO).

This team drives the integration strategy and coordinates all the moving parts.

Key planning elements include:

  • System compatibility assessment – Do the platforms even play nice together?

  • Data migration strategy – How will you securely move critical business info?

  • Timeline development – Set realistic milestones for each integration phase

  • Resource allocation – Assign technical staff and budget to the right tasks

Organizations should grab some quick wins but also map out long-term consolidation.

That way, business keeps humming during the transition.

Addressing Integration Challenges

Technology integration is one of the biggest headaches in M&A.

Plenty can go sideways if you don’t manage it well.

Common integration challenges include:

Challenge Impact Solution
Legacy system incompatibility Data silos, workflow disruption Phased migration approach
Security vulnerabilities Data breaches, compliance issues Security audits and updates
Staff resistance Productivity loss, turnover Training and change management
Budget overruns Delayed timelines, reduced ROI Detailed cost planning

Data security gets even more critical during integration.

Companies have to protect sensitive info while merging systems and databases.

Technology consulting firms can step in with specialized expertise for tricky integrations.

They’ve seen it before and can speed things up.

Monitoring and Optimization Post-Merger

Post-merger integration isn’t a “set it and forget it” deal.

Companies need to track performance metrics and adjust as needed.

Key performance indicators include:

  • System uptime and reliability

  • User adoption of new technologies

  • Data accuracy across integrated platforms

  • Cost savings from system consolidation

Regular assessments help teams spot areas that need improvement.

Quarterly reviews of integration progress and system performance are a solid idea.

Optimization focuses on cutting out redundant systems and streamlining processes.

This usually ramps up 6-12 months after initial integration.

Companies should stay flexible and tweak their tech roadmap as business needs change.

Market shifts and strategy pivots are inevitable.

A well-executed integration creates a unified tech platform that actually supports growth.

It’s rarely perfect, but patience and ongoing adjustments go a long way.

Additional Considerations and Best Practices

Companies really need to tackle technical debt and legacy systems early to avoid nasty surprises later.

Smart ROI planning, vendor contract reviews, and future-ready tech strategies build lasting value beyond just closing the deal.

Technical Debt and Legacy Systems

Technical debt is basically the hidden cost of keeping outdated software and systems alive.

It’s something acquirers should address right away.

Companies often run into legacy systems on unsupported platforms or custom code written years ago without decent documentation.

Legacy systems create all sorts of headaches.

They might lack security patches, need rare skills to maintain, or just refuse to play nice with modern tools.

Outdated software can slow things down and block growth.

Assessment priorities include:

  • Code quality reviews for custom apps

  • Documentation gaps in legacy systems

  • Security holes in old platforms

  • Integration capabilities with modern tools

Companies should budget for system upgrades or outright replacements.

The costs to bring technology up to snuff hit deal valuations and post-acquisition results directly.

Migration timelines can stretch from 6 to 18 months, depending on how gnarly the systems are.

Organizations often run parallel operations for a while to smooth the transition.

ROI and Cost Optimization

Tech investments during M&A need clear ROI calculations.

You’ve got to justify the spend and measure if it’s working.

Key ROI factors include:

  • License consolidation savings

  • Lower IT support costs

  • Improved operational efficiency

  • Better data analytics capabilities

Automation tools can slash costs.

Cloud platforms like AWS often cut infrastructure expenses by 20-40% compared to old-school on-prem setups.

Companies get economies of scale by standardizing platforms.

Modern project management tools like Jira or Trello can boost delivery times by 15-25% versus legacy systems.

Cost optimization strategies:

  • Kill duplicate software licenses

  • Consolidate vendor relationships

  • Automate manual processes

  • Standardize dev tools

Organizations should track these metrics monthly during the first year after the deal.

That’s the only way to know if the savings are real.

Vendor and SLA Management

Vendor contracts need a hard look during tech due diligence.

Service level agreements (SLAs) can make or break operations and must fit the merged company’s needs.

Critical contract elements:

  • Termination clauses and penalties

  • Data ownership and portability rights

  • Price escalation terms

  • Performance guarantees

SLA reviews focus on uptime, response times, and penalty structures.

Companies often find mismatched service levels that need to be standardized.

Vendor consolidation gives you more leverage.

Organizations typically cut vendor count by 30-50% after M&A and get better contracts.

Best practices include:

  • Map out all critical vendor relationships

  • Check contract renewal dates

  • Assess vendor financial health

  • Negotiate unified pricing structures

Getting vendors involved early helps avoid service hiccups while you’re integrating everything.

Continuous Improvements and Future Readiness

Technology integration isn’t just about connecting systems at the start. It’s about building platforms that can actually handle what’s coming next.

Companies really need infrastructure that scales with their plans and keeps up with new tech. Otherwise, they’ll just keep playing catch-up.

Future readiness factors:

  • Cloud-native architectures
  • API-first system design
  • Scalable data storage solutions
  • Modern development frameworks

If your company’s eyeing more acquisitions, you’ve got to pick flexible platforms. Nobody wants to rip out half their systems every time they buy a new team.

Standardizing the software development lifecycle across teams makes a big difference. When everyone uses the same tools and processes, collaboration speeds up and training gets less painful.

Implementation priorities:

  • Establish coding standards
  • Deploy unified project management tools
  • Create shared development environments
  • Implement automated testing procedures

It’s smart to plan technology roadmaps at least 3-5 years ahead. That way, you’re not scrambling for replacements every time the business grows.

Frequently Asked Questions

Technology due diligence is about digging into a company’s infrastructure, code quality, security, and how well everything connects. Buyers need solid checklists for architecture, team skills, and compliance risks before making a call.

What are the essential components of an IT due diligence checklist during a merger or acquisition?

An IT due diligence checklist covers the target’s technology stack, infrastructure, and security. You’ll want to look at hardware, software, network setup, and data management.

Assessing code quality is key—check coding standards, documentation, and automated tests. If those are a mess, you’ll have headaches later.

Security? You’ve got to look at access controls, encryption, and whether they follow rules like GDPR or PCI DSS. Don’t skip checking for vulnerabilities or their incident response plan.

Scalability is another must. Teams should review cloud services, server capacity, and network performance to see if the company can actually grow.

Team skills matter too. Look at development processes, documentation, and figure out if there are risky knowledge gaps.

How is technical due diligence typically conducted for a software company acquisition?

Technical due diligence for software companies usually starts with a deep dive into the codebase and architecture. Teams go through source code, documentation, and system design patterns.

The process can take anywhere from two to four weeks, depending on how complex things are. Evaluators check development and testing practices, plus deployment processes.

Security checks involve vulnerability scans and sometimes penetration testing. They look for common flaws and see how data’s protected.

Performance testing puts the system under load—think database speed, API response, and how snappy the user interface feels.

Integration analysis comes last. Teams see how easily the software connects to other systems, checking APIs, data formats, and communication protocols.

What key factors are assessed in a technical due diligence report for M&A?

Technical due diligence reports focus on system architecture and whether it matches business goals. They ask if the current setup can support future growth.

Technical debt gets a close look. Reports call out legacy code, outdated components, and what’s needed for maintenance or upgrades.

Scalability gets tested—can the system handle more users and data? If not, expect to see bottlenecks and limits flagged.

Security compliance is another biggie. Reports check if the company meets industry standards for privacy, access, and audits.

Finally, they assess team skills and processes. It’s important to spot key-person risks and training needs early.

Which critical items should be included in a technical due diligence checklist in Excel format?

A comprehensive technical due diligence checklist in Excel should break down infrastructure, security, and development processes. Each area needs clear criteria and scoring.

Infrastructure covers servers, cloud services, databases, and networks. Make sure to include performance benchmarks and capacity metrics.

For security, list out access management, encryption, vulnerability checks, and compliance certifications. Each line item should have a way to verify and document findings.

Development processes? Check code review practices, testing, deployment automation, and version control. Don’t forget to evaluate team workflows and quality checks.

Data management should include backup routines, disaster recovery, and governance policies. You want to know how well business continuity is handled.

In what ways does tech due diligence differ when conducted by major consulting firms like Bain & Company?

Major consulting firms like Bain & Company take a strategic approach to tech due diligence. They’re looking at how technology links to market opportunities and competitive edges.

These firms send in teams with sector-specific know-how. They get the regulations, trends, and competition better than most.

They put a lot of weight on financial modeling and ROI for tech investments. It’s not just about what works—it’s about what pays off.

Benchmarking against industry standards and competitors is a big deal for them. It helps put the company’s tech maturity in context.

And unlike some, they tie tech findings directly to business strategy. It’s all about connecting tech strengths to revenue and efficiency.

What are the typical responsibilities of an IT due diligence professional within the context of mergers and acquisitions?

IT due diligence professionals dig into technology assessments to spot technical risks and opportunities in companies up for acquisition.

They look at system architecture, security, and how easily things might integrate.

You’ll find them reviewing code quality, peeking at development practices, and flipping through technical documentation.

They want to know if the current tech stack can actually handle the company’s business goals or if it’ll buckle under pressure.

Risk identification sits at the heart of their job. They hunt for security holes, compliance issues, and piles of technical debt that could tank a deal.

Cost estimation isn’t just a guess—they calculate upgrade costs, what it’ll take to merge systems, and the price tag for ongoing maintenance.

This all helps buyers see the real technology investment ahead.

When it comes time to report, they pull together detailed technical assessments for deal teams and execs.

Their reports translate all that tech jargon into business impact and practical recommendations.

Jeff Barrington is the Managing Director of Windsor Drake, a specialized M&A advisory firm focused on strategic sell-side mandates for founder-led and privately held businesses in the lower middle market.

Known for operating with discretion, speed, and institutional precision, Jeff advises owners on maximizing exit value through a disciplined, deal-driven process. His work spans sectors, but his approach is consistent: trusted counsel, elite execution, and outcomes that outperform market benchmarks.