Non-sales founders often don't know how to evaluate or support their first sales leader. The advice is to hire a sales-focused board member or advisor whose primary role is to mentor and care for that new sales leader, providing crucial guidance and a dedicated advocate.

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.

Snowflake's initial high-velocity sales model hit a wall with large enterprises. New CEO Frank Slootman mandated a change, forcing CRO Chris Degnan to "rip the bandaid off" and restructure the entire GTM organization in the middle of a fiscal year to create a dedicated enterprise sales motion.

Snowflake hired its first salesperson pre-revenue not to sell, but to get the product into customers' hands to break it. This person acted as a de facto product manager, gathering critical feedback that led to a core architectural change, proving the value of a GTM hire before product-market fit.

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.

Snowflake's first CRO, Chris Degnan, joined two years before the product launched. His primary role was not selling but gathering customer feedback to guide engineering, acting as a "shadow CTO." This redefined the initial sales function as a product discovery and validation role.

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.

Early-stage companies need experienced executives not just for their skills, but for their 'borrowed credibility.' A well-respected leader like former CEO Bob Muglia lent Snowflake instant legitimacy, which inspired belief in the team, reassured customers, and empowered the young founders.

Most VCs fail at talent support by simply matching logos on a resume to a portfolio company. A better model is to first embed operators (e.g., fractional sales leaders) into the startup. This provides the deep, nuanced context required to find candidates who fit the specific business and culture, leading to better hiring outcomes.