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.

When interviewing salespeople, the biggest red flag is blame. Strong candidates demonstrate humility and self-reflection by taking ownership of lost deals and analyzing their own shortcomings. Weaker candidates deflect, blaming the product, competition, or other external factors, signaling a lack of coachability.

In early-stage sales, candidates asking for quota confidence are a red flag as they seek safety where risk-taking is needed. The ideal hire is hungry, curious, and motivated to build—not just execute a pre-defined playbook. Prioritize these traits over a polished resume. Too much past success can even be a negative indicator.

Senior commercial leaders are professional interviewers who excel at telling you what you want to hear. A hiring process based solely on conversation is flawed. To truly vet a candidate, you must incorporate exercises that force them to demonstrate their abilities and "show you the receipts" of their claims.

When asked about their sales process, weak candidates brainstorm a long list of activities. Strong candidates have a concise checklist for the key "moments of truth" in a deal, like discovery or proposal calls. The brevity and clarity of their answer signal true process discipline.

The most effective way for a salesperson to challenge a perceived unfair quota is not through complaints, but through data. By presenting an analysis of their own average deal size, sales cycle length, and win rates, they can build a logical case for what is achievable and force a more constructive conversation with leadership.

Salespeople are professionally trained to be liked, a skill crucial for their role but often over-weighted in interviews. This rapport doesn't indicate discipline or process-orientation. Hiring managers must test for performance skills beyond mere likability to avoid this trap.

Viewing quota as a lagging indicator, Figma's CRO warns that managing to the number creates "lazy leadership." Performance management should instead center on a detailed framework of inputs: behaviors (e.g., collaboration) and competencies (e.g., discovery skills), giving a real-time view of a rep's effectiveness.

When evaluating talent, the biggest red flag is "hand-waving." If you ask a direct question about their area of responsibility and they can't give a crisp, clear explanation, they likely lack true understanding. Top performers know their craft and can explain the "why" behind their actions.