I recently sat down with Jeff Epstein, an operating partner at Bessemer Venture Partners and former CFO of Oracle. The aim of Pinpoint is to use data science to answer questions about engineering performance, in a language the business can understand. So I wanted to hear directly from a longtime business leader—what, in Jeff’s own experience, would a CTO ideally be able to tell him?

That’s how we framed the discussion: if CFO Jeff were sitting across the table from the CTO, what would he ask? Here in condensed form are his questions:

  1. Can you show me how efficiently we’re using our current engineering resources? How has our efficiency changed over time?
  2. How many days does it take for a new hire engineer to become productive? How has this changed over time?
  3. What percentage of our engineering team are at risk to leave in a given year? Is our churn getting better or worse?
  4. What percent of our work effort is keeping the lights on versus innovation? How has this changed over time?
  5. Which of our delivery locations returns the most for money spent?
  6. Which of our outsource software development vendors returns the most for money spent?
  7. How long on average does it take to deliver high priority features, from start of work to deployment? If you could reduce that by 10 percent, how much more could we deliver in a year?
  8. What’s our average variance between delivery date and the original due date? How has this changed over time?
  9. What’s our average variance between delivered scope (features, etc.) and original scope? How has this changed over time?
  10. How do you evaluate the performance of your organization? What are the top areas you’d like to improve?

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