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.

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.

CROs are often blamed for missed targets, but the root cause is often a flawed hiring plan from the CEO. Rushing to hire reps without adequate ramp time leads to B-player hires, immense pressure from managers, a toxic "horse whipping" culture, and ultimately, missed numbers.

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.

To make a hire "weird if they didn't work," don't hire for potential or vibe. Instead, find candidates who have already succeeded in a nearly identical role—selling a similar product to a similar audience at a similar company stage. This drastically reduces performance variables.

A common failure mode for new CROs is attempting to create the sales playbook in isolation. Core pillars like ICP and value proposition are company-level decisions. The CRO's role is to be interdependent, facilitating this cross-functional creation process, not dictating it.

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.

Teopo Capital prioritizes rigorous post-hire evaluation. They believe the true assessment of a candidate's fit and capability occurs on the job. The greatest risk is not making the wrong hire, but failing to act swiftly when they underperform, making quick termination crucial for risk management.

Peets argues the most crucial, untrainable skill for a startup sales rep is the demonstrated ability to generate pipeline and close net new accounts. He dismisses the common founder obsession with hiring from competitors, stating domain knowledge can be taught, but the grit to land new business cannot.