How to Spot the Tech Skeletons That Sink SaaS Deals

Lessons from software audits that looked fine until they weren’t


Most software deals are closed on a deck.
Most delivery failures start with silence.

Everything seems solid  until someone asks:

  • How fast can the team deploy?
  • What’s the trend in cloud cost per active user?
  • Who owns this service?

That silence isn’t deception. It’s risk no one traced. Engineering scale doesn’t break at the code level, it breaks at the seams between speed, cost, and responsibility.


What Actually Gets Assessed

In short-cycle audits (~10 days), what matters falls into five structural categories:

  • Architecture 
    Modularity, boundary clarity, scale ceilings
  • Codebase
    Complexity, churn hotspots, testability
  • CI/CD
    Deployment frequency, rollback safety, release friction
  • Cloud
    Waste patterns, cost dynamics, FinOps maturity
  • Day-2
    Operations

    Incident load, on-call resilience, recovery playbooks

These aren’t about blame. They’re about surfacing the truth: What’s working, what’s brittle, and what’s blocking scale.


The Trust Layer

Technical audits aren’t pitch reviews.
They expose shortcuts, tradeoffs, and path-dependent systems. They require trust  especially when the architecture reflects speed over process.

Done right, this process stays founder-aligned:

  • Findings are shared in full context  not in isolation
  • No red flag is raised without a clear solution path
  • No surprises get surfaced without prior validation

Good diligence doesn’t erode trust. It earns it  by turning assumptions into shared clarity.


Questions Every Founding Team Should Face

  • Can we deploy safely, without ceremony?
  • Where is cloud spend leaking  and why?
  • What happens if two senior engineers leave next month?
  • What’s our actual release velocity  not the aspirational one?

None of these need perfect answers. But they do need honest ones  before scale pressure makes them unavoidable.


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