I've spent twenty-five years building software teams and platforms, but my first experience on the inside of technical due diligence came a couple of years ago during a Series A raise. What I expected to be a quick architecture walkthrough turned into a wide-angle examination of security posture, cloud-cost habits, and regulatory readiness.
Today, alongside leading the Cloud Infrastructure, SOC2 Compliance and IT at LiveEO I help founders and VCs gain mutual trust through technical transparency. Tech due diligence isn't about passing an exam - it's about founders proving they understand their own risks.
Why the lens has sharpened
- Regulation is no longer theoretical. The EU AI Act goes live in 2025; GDPR fines are routine. Investors want evidence that founders already grasp data lineage, model governance and customer requirements - not plans to "look at it later".
- The Data Act is next. From 12 September 2025, cloud providers and connected-device manufacturers must enable data portability and even cover switching costs. Due diligence questions now probe cloud-exit plans, shared-data contracts and whether teams understand those obligations.
- LPs push ops to the front. Limited partners press GPs to demonstrate cyber-resilience and vendor hygiene before backing growth curves.
- Cost visibility is strategic. By Series A, investors already ask for burn multiple and early COGS trends; by Series B they expect full FinOps dashboards and proof that margins improve at scale.
Taken together, tech due diligence has become a forward-looking confidence test: can this team run a larger, more regulated business without surprises?
Three opening moves you can expect
- Scalability – "Walk me through what happens to cost and latency if usage jumps 5×."
- Security maturity – "Show me how fast you detect, triage and fix critical vulnerabilities."
- Risk self-awareness – "List your top compliance, regulatory and customer-driven risks. Who owns them and how often are they reviewed?"
Notice the thread: investors aren't just looking for bugs; they're looking for founders who speak plainly about risk, map it to owners, and track progress.
Turning the spotlight into leverage
Bring a one-page living risk register to the very first meeting. Each item lists an owner, an impact score, and a next-review date. The goal isn't to eliminate risk but to frame it. Doing so practically eliminates technical red flags and, more importantly, helps secure a post-deal roadmap that investors will fund rather than discount.
Clarity compounds
Keep the momentum by maintaining your own one-page risk register.
Risk → Owner → Impact (€/%) → Mitigation → Next review. Update it every sprint. In a due diligence call it becomes your talking sheet; outside due diligence it doubles as an internal steering tool.
Ready to Act?
What's been the toughest question you've faced - or asked - during a technical due diligence? Did a hidden risk ever ambush your valuation, or did a well-framed register save the day? Share your stories below - learning from each other is half the battle.
Need a hand building your own risk register or pressure-testing your stack before the next term-sheet call?
Next in the Playbook
Edition 2 looks at right-sizing tech due diligence scope - why a minority stake, a control investment and a carve-out each justify a different depth of review. Subscribe if you'd like it delivered to your inbox, and share your own tech due diligence war stories in the comments.
Originally published on the Tech Due Diligence Playbook newsletter on LinkedIn.