A raw win rate on its own says little — a 20% hit rate on negotiated work with repeat customers and a 20% hit rate on open public bids are very different businesses. The useful version is segmented: win rate by customer, by job type, by estimator, and by bid size.
Segmented win rates answer real staffing questions. A customer you never win with is costing estimating hours every time they invite you to bid; a job type you win half the time deserves more of the bench's attention. Contractors who track outcomes with dates and reasons can see these patterns; contractors who track wins in their heads usually cannot.
The prerequisite is recording every outcome (won, lost, or no-bid) with a date and a reason. That record-keeping is a core function of bid management software.