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.

In a collaborative sales environment, a candidate's ability to be a good teammate is more valuable than their contact list. A difficult personality with a great rolodex can harm team productivity, whereas a collaborative person can be supported in building their own network.

At the $1-10M ARR stage, avoid junior reps or VPs from large companies. The ideal first hire can "cosplay a founder"—they sell the vision, craft creative deals, and build trust without a playbook. Consider former founders or deep product experts, even with no formal sales experience.

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.

Where the SDR/BDR team reports has significant cultural and career-pathing consequences. When Snowflake moved SDRs under marketing, they began aspiring to be marketers, not salespeople. This created a hiring bottleneck for the sales organization, which needed that talent pipeline to fuel its growth.

A startup's initial salesperson should prioritize mirroring the founder's successful sales approach. Their job is to deconstruct the founder's "hook" through observation and trial-and-error, not to immediately implement formal sales processes, metrics, or a CRM. Success comes from successful knowledge transfer, not premature system building.

Chris Degnan got rid of the Customer Success function at Snowflake because he wasn't willing to give the "B team" access to his "A accounts." He made the sales team responsible for the entire customer lifecycle, including upsells and renewals, to ensure top talent handled high-stakes competitive situations.

Counterintuitively, the best sales leaders often come from companies with mediocre products. Their ability to hit numbers despite a weak offering demonstrates exceptional sales skills, which are then amplified when they are given a great product to sell.

Chris Degnan reflects that financial success made him a worse leader because he lost the desire to do the "hard things" required at scale, like constant global travel and endless internal operations meetings. His passion was for selling and competing, not the operational grind of a multi-billion dollar CRO role.