Bashify’s founder learned to hire not just for skills but for personality-role fit. She seeks extroverted people for client-facing roles, while preferring detail-oriented introverts for back-end tasks like packing kits. This nuanced approach improves job satisfaction and team dynamics.

According to Snowflake's former CRO, salespeople from Salesforce often make poor hires for growing companies because they don't know how to truly sell. Accustomed to massive inbound demand at a market leader, they function as 'order takers' and lack the skills for proactive, competitive selling.

Relying on enthusiastic client reactions as a gauge of success is a trap. Deals can close with quiet, critical clients, while others are lost with overly complimentary ones. This attachment creates unnecessary anxiety and misreads the sales process, revealing a lack of internal grounding.

A sales manager's coaching style directly impacts their team's mindset. Constantly asking 'When will this close?' amplifies a seller's anxiety and negativity bias. In contrast, asking 'How are you helping this person?' reinforces a healthier, customer-centric process that leads to better long-term results.

Sales reps at market leaders often succeed due to brand strength and inbound leads, not individual skill. Instead, recruit talent who proved they could win at the #3 company in a tough market. They possess the grit and creativity needed for an early-stage startup without a playbook.

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.

HubSpot's hiring success improved when they stopped hiring candidates with the fewest weaknesses (e.g., consistent 3/4 scores) and instead chose 'spiky' individuals. These candidates elicit strong positive reactions from some interviewers and weaker reactions from others, indicating exceptional strengths alongside known weaknesses.

Sales experience on a resume can be a 'false positive.' When hiring SDRs, prioritize untrainable qualities like work ethic, mindset, and resilience over specific past roles. These character traits are a better predictor of long-term success than skills that can be taught.