(b) without overwhelming them so balls start dropping. A common number for a SaaS rep doing low­five­figure deals to juggle is 25­30 opportunities. Yours may or may not be different. For yours, look to your own history. How many have your best reps juggled? Does it vary much by segment, type of customer or average deal size? When was it too many? This metric also gives you a sanity check if you need to grow your open opportunities a lot (by cranking up lead generation), or if your team is overwhelmed (and you need to hire more salespeople). 2) Number of Closed Opportunities in total and per rep: Measure total opportunities closed including both closed­won and closed­lost opportunities. What to do with it: Your reps should be closing a certain number of sales deals each month (whether won or lost). It’’ s a form of “throughput”. If they’re not closing enough total opportunities, drill down: Are they light on deals? Not closing effectively? Is their pipeline full of “hope” that never goes anywhere? Are they not updating the sales system? 3) $ deal size: Measure the average value of your closed­won deals. What to do with it: Knowing this metric will make it easy for you to spot opportunities that fall outside the normal deal size (say 3x greater than average) and flag them for special attention. Also, if the trend shows an increase in smaller deals won, perhaps some reps are focusing on small fish. Or perhaps your reps are increasing discounts. If you see a new trend in average deal size, then you need to dig into your pipeline mix or discounting practices to understand why. 4) Win rate: Measure the number of closed opportunities, in a specific closing period, that you won (Closed Won Opportunities)/(Total Opportunities: both Closed­Won + Closed­Lost). This won’t mean much unless you can watch it trend, or use it to A/B test reps with similar segments, or compare against companies similar to yours. What to do with it: “High” win rates aren’t good; “low” ones aren’t bad –– either one gives you a chance to get smart about your sales system, to spot areas of success or problems. For example, if your win rate is high, maybe your pricing is too low! The simplest way to start increasing your team’’ s win rate is to find the one or two most problematic steps in your process, and then look both “inside” (e.g., a better demo process) and “outside” the team (e.g. an easier free trial, or simpler pricing)... It’s common for sales teams beginning to scale up to see win rates drop. Is it because of the new people? Has lead quality or management quality changed? Or because of packaging, pricing or website changes? You need to drill down and see exactly where opportunities are falling off, in order to get to the root cause. Look at your sales funnel and understand conversions through every stage through to closed­won. If most reps are struggling in the same area, then don’t blame them; it might be something outside their control. Nominate an investigator to find the truth of what’s going on. If specific individuals consistently have much higher or lower win rates, don’t be too quick to jump to conclusions and criticize or compliment them. First look at their data first to find out why and learn from it. A sales rep with highest consistent win rate may be talented at sales –– or talented at sandbagging/cherry picking. Don’t assume –– investigate. Look at win rates with other data to get the whole story.