The ideal sales hire changes dramatically across scaling stages. Initially, you need a "product manager" type who can handle ambiguity and provide product feedback. A top rep from a large company would fail because they rely on established processes and support systems that don't yet exist.
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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.
Vercel COO Jean Grosser's litmus test for a great salesperson is that engineers shouldn't be able to tell they aren't a PM for at least 10 minutes. This requires deep product knowledge, enabling sales to act as an R&D function by translating customer feedback into valuable product signals.
Sales coaches excel at turning a functional, founder-led sales process into a scalable machine. They are not equipped to solve the fundamental problem of figuring out your initial case study and factory from scratch. Hiring one before you have a repeatable motion is premature and will likely fail.
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.
In the pre-product-market fit stage (the first ~20 deals), the sales leader's primary role is not just closing revenue, but acting as a product manager. They must be in every meeting to gather objections, find pockets of value, and translate raw market feedback into actionable insights for the engineering team.
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.
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.
When making your first sales hires, never hire just one person. Hire two. This instantly creates healthy competition and camaraderie. More importantly, it provides a crucial benchmark. If one succeeds and the other fails, you know the problem is the rep. If both fail, the problem is likely your product or market.
Peets identifies a critical hiring error: founders hire sales leaders with experience managing a large, scaled organization for their future goals. This backfires because those leaders often lack the essential skills to build a sales function from the ground up, preventing the company from ever reaching that future state.
ElevenLabs' CEO realized his first sales leader hire was monumental not just for revenue, but for culture. Sales leaders tend to hire people in their own image, meaning that first hire dictates the approach and values of the entire future sales organization.
