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.
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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.
Average reps focus on product features. Top performers are "product agnostic"—they don't care about the specific product they're selling. Instead, they focus entirely on the customer's desired outcome. This allows them to craft bespoke solutions that deliver real value, leading to deeper trust and larger deals.
A sales background teaches more than customer centricity. It instills resilience and the fearlessness to approach anyone in an organization to get things done, a vital skill for navigating the cross-functional demands of product management.
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 sales leader's value isn't in managing from headquarters. It's in being on the front lines, personally engaging in the most challenging deals to figure out the winning sales motion. Only after living in the field and closing landmark deals can they effectively build a playbook and teach the team.
A powerful recruiting tactic is to ask a new customer, "Who would you have bought from if their product was better?" This question identifies competitor reps who excel at selling—persuading buyers despite product disadvantages. These individuals are prime candidates to recruit for your own team.
When direct access to top talent is blocked by competitors, savvy leaders identify other successful companies with strong sales cultures (a "lineage") and strategically recruit from that pool. This allows them to tap into a new vein of proven, high-potential talent.
Technical founders often mistakenly believe the best product wins. In reality, marketing and sales acumen are more critical for success. Many multi-million dollar companies have succeeded with products considered clunky or complex, purely through superior distribution and sales execution.
A sales leader's success is determined less by personal sales ability and more by their capacity to attract a core team of proven performers who trust them. Failing to ask a leadership candidate 'who are you going to bring?' is a major oversight that leads to slow ramps, high recruiting costs, and organizational inefficiency.
