Early jobs without direct sales quotas, like retail, can build stronger foundational selling skills. When not pressured by a number, reps learn to conduct discovery and upsell based on genuine belief in a product's value, fostering a more customer-centric and authentic approach.
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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.
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.
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.
Beyond personal or financial goals, the most sustainable motivation can be an intrinsic desire to help clients succeed. This "helper's carrot" shifts the focus from your product to the customer's achievement, creating a genuine belief that powers you through challenges and builds long-term success.
The moment a customer buys, they signal maximum trust. This is the optimal time for a salesperson to be assertive with upsells, cross-sells, or referral requests. Many reps mistakenly push too hard at the beginning of the sale when trust has not yet been established.
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.
Newcomers to sales often fail when they fixate on immediate outcomes. The key is to embrace the learning process—making dials, fumbling through conversations, and learning from mistakes. Competence and results are byproducts of consistent effort over time.
Instead of failing with hard-to-reach C-suite targets, new reps should engage easier-to-access, adjacent personas (like insurance brokers). These conversations serve as low-stakes training, rapidly building the specific industry language and knowledge needed to credibly approach senior decision-makers.
Like Picasso mastering fundamental techniques before developing his style, elite salespeople develop their "art" only after mastering the "science"—the structure and process of selling. True artistry is built upon a foundation of discipline, not just natural talent.
Junior reps can leverage their inexperience by approaching lower-level employees with a humble "Teach me" or "Help me understand" posture. This disarms prospects, turning a sales pitch into a collaborative learning session that builds rapport and extracts valuable internal intelligence for later use.