M&A · Technology Diligence
The Technology Due Diligence Checklist
The 7-section checklist Pineapples runs for PE operating partners and mid-market acquirers. Every item is structured so findings translate directly into the deal model — not narrative risks that get filed and forgotten.
Working a specific deal?
We run this in 10 days, fixed-fee.
1. Usual Checks (Table Stakes)
Necessary, not sufficient. If diligence stops here, you have a stack inventory — not a decision.
- Stack inventory: languages, frameworks, databases, cloud services, current versions, EOL dates
- Infrastructure: hosting, redundancy, backup cadence, RTO/RPO, DR tested in last 12 months
- Security & compliance: SOC 2 / HIPAA / PCI status, last pen test, dependency scan
- License audit: commercial licenses for every paid dependency, no GPL-tainted proprietary paths
- Code quality signals: test coverage, build/deploy frequency, MTTR for production incidents (12mo)
2. Leadership Execution Capability
Single biggest predictor of integration success. Different from general competence.
- Has the current CTO managed an integration of THIS scale before? (References from prior integrations.)
- Retention risk profile for top 5 technical contributors: comp, equity vest, tenure, pending moves
- Engineering team structure today vs the structure the integration plan assumes
- Architecture decision-making: one person or distributed?
- Capacity planning: integration backlog + committed roadmap, FTEs at burnout risk in months 3-9
3. Knowledge Concentration Risk
In mid-market companies, knowledge is concentrated. The question is how bad.
- Map each critical system to engineers who can modify it without breaking it. Flag <2 engineers per system.
- Ask the CTO: if your top engineer left tomorrow, which systems are immediately at risk?
- Inspect runbooks for every critical system. Count systems with current runbook vs without.
- On-call history: same two people primary for 80% of incidents over 12mo = concentration risk
4. Integration Surface Area
Architecture diagrams show shape. They do not show how hard connection is.
- Every external API: documented, versioned, actively maintained — could a 3rd party integrate without asking?
- Data model alignment: can target entities map to acquirer model without loss?
- Authentication / identity: SSO compatible? Migration path for existing accounts?
- Observability: will logs / metrics / traces flow into acquirer monitoring or rebuild from scratch?
5. Technical Debt That Actually Matters
Not "how much debt" — "what does the debt prevent you from doing."
- Identify the 3-5 pieces of debt that block the integration plan. Not all debt — the blocking debt.
- For each blocking item: remediation cost in weeks of senior engineering time. Compare to integration timeline. >20% of capacity = unrealistic timeline.
- Flag any dependency more than two major versions behind
- Identify any custom-patched OSS dependency — every patch is a tax on every future upgrade
6. Vendor and Supply Chain Risk
Mid-market companies run on a handful of third-party services. Vendor problem = deal problem.
- List every vendor in the critical path: payment, email, auth, primary cloud, anything that causes outage
- Review contract renewal dates — vendors renewing in the 12 months after close are opportunity OR risk
- Flag single-vendor dependencies without a documented migration plan
7. Deal-Thesis Alignment
The section diligence usually skips. The one that determines whether tech supports or undermines the return model.
- What does the value-creation plan require the technology to do?
- Can the current architecture support that requirement — or is it structured in a way that requires ground-up rebuild?
- Rebuild-vs-remediate calculation: if remediation is 60% of rebuild cost, rebuild usually wins on time-to-value
Want a second set of eyes on a specific deal?
We run this assessment on a compressed timeline for mid-market acquirers and PE operating teams. 10-14 days, fixed fee, deliverable that translates directly into the deal model.
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