Operational due diligence checklist

Twenty-four questions, and where each answer lives.

The checklist a deal team actually works from, organized by dimension. Each line names the question, the system that answers it, and whether the answer is a document request or a metadata read.

01

Delivery & Execution

6 questions
  • Is deploy frequency keeping pace with engineering headcount?
  • What is cycle time, and has it drifted over four quarters?
  • What proportion of work is reopened after review?
  • Is there a documented release process, and is it followed?document
  • How much work-in-progress is older than 90 days?
  • What is the current known-defect backlog?document
02

Culture & People

6 questions
  • Which functions have stopped communicating, and when?
  • What is response latency between engineering and product?
  • What is voluntary attrition by function over eight quarters?document
  • How concentrated is the meeting load on the leadership group?
  • Is there a single point of failure in any critical system?
  • What is the current org chart, dated?document
03

Go-to-Market

6 questions
  • What share of ARR is closed by the top rep?
  • How has pipeline velocity moved across four quarters?
  • What is the stage-transition timing distribution?
  • What are the top-ten customer contracts and their terms?document
  • Is win rate moving, and against whom?
  • What is the renewal calendar for the next twelve months?
04

Financial Vitality & Risk

6 questions
  • How many days after period end do the books close?
  • How are receivables aging, and is it drifting?
  • What share of revenue sits with the top three accounts?
  • Which systems have a single administrator?
  • What are the outstanding contingent liabilities?document
  • What insurance is in force, and at what limits?document

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