Executives don't care about tactical benefits like 'five fewer clicks'. A crucial skill for modern sellers is to extrapolate that tactical user-level gain into a strategic business outcome. You must translate efficiency into revenue, connecting the dots from a daily task to the company's bottom line.

New SDRs get overwhelmed when forced to learn industry nuances first. A better approach is to prioritize mechanics (CRM, scripts), then knowledge (personas), and finally the 'art' of sales, which develops over time. This builds confidence and allows them to execute quickly while they learn.

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.

Insecure reps often avoid involving their own executives, fearing it makes them look weak. In contrast, top performers demonstrate confidence by strategically bringing in their leadership (even the CEO) to help close major deals. This is a sign of strategic maturity, not a weakness to be hidden.

Sellers often adopt an overly formal, academic persona when speaking to executives, which creates distance. In reality, executive conversations are simple, direct, and unpretentious. Drop the jargon and complicated words. Your goal is clear communication, not demonstrating your vocabulary.

New salespeople lack personal success stories to use as social proof. Leaders must proactively provide them with a library of stories about other clients or team members. These 'borrowed' narratives are essential for building a value bridge with early prospects.

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.

Discomfort with concepts like income statements or margins causes salespeople to shy away from conversations with CFOs and other executives. This self-imposed limitation prevents them from connecting their solution to core business metrics like cost, revenue, and profit, trapping them in lower-level discussions.

Bypass C-suite gatekeepers by interviewing lower-level employees who experience the problem daily. Gather their stories and pain points. Then, use this internal "insight" to craft a highly relevant pitch for executives, showing them a problem their own team is facing that they are unaware of.