Founders can assess their Head of Sales using two core metrics: 1) Can they hire reps who consistently close over $250k in new ACV per quarter within six months? 2) How many sales calls are they personally conducting each week? These are the ultimate measuring sticks of effectiveness.

Counterintuitively, Peets argues that very low sales team attrition (e.g., 2%) is a red flag indicating a lack of accountability. For a scaling company, he models 25% annual attrition, comprising performance-based terminations (~10%), promotions, and voluntary departures, as a sign of a healthy, high-performance environment.

Instead of focusing on a large quota, leaders should reverse engineer it. Calculate the number of deals needed based on win rate and average contract value, then break that down into weekly opportunity creation goals for reps.

Don't hire more reps until your current team hits its productivity target (e.g., generating 3x their OTE). Scaling headcount before proving the unit economics of your sales motion is a recipe for inefficient growth, missed forecasts, and a bloated cost structure.

Don't use static KPIs. Every month, analyze the activity metrics of reps who successfully hit quota. Use this data to set the new KPIs for the entire team for the upcoming month. This ensures targets are based on proven success and increases team buy-in.

At a small company, one or two big deals can significantly inflate the average productivity per rep. This hides the fact that the majority of the team may be underperforming. As the team grows and these outliers have less impact, the true, often flatlining, productivity of the sales force is exposed.

Sales reps often feel overwhelmed by their large annual number. The key is to break it down, subtract predictable existing business, and focus solely on the smaller, incremental revenue needed. This makes the goal feel achievable and maintains motivation.

The cost of setting quotas too high is catastrophic: you demoralize and lose your A-player sales team. The cost of setting them too low is manageable: you overspend on commissions but exceed targets and retain a motivated team. The latter can be adjusted; the former is an unrecoverable error.

A sales organization has truly scaled when leadership stops talking about individual deals and starts managing based on predictable capacity. This means knowing that a certain number of ramped sellers will predictably generate a specific amount of revenue each quarter, turning sales into a machine.