For a new product, don't choose between targeting executives or end-users; do both simultaneously. While mapping the C-suite (top-down), engage lower-level employees to gather intel and build internal champions (bottom-up). This dual approach creates pressure and relevance from both directions.

Avoid pursuing prosumer and enterprise motions simultaneously. The optimal sequence is to first build massive bottoms-up love and brand trust with individual users. This creates internal champions within target companies, providing crucial momentum and turning a cold B2B sale into a pull-based motion.

Elite salespeople understand that closing deals requires a team. They actively cultivate advocates within their own company—in operations, support, and finance—by treating them well and recognizing their contributions. This internal support system is critical for smooth deal execution and ensures they can deliver on client promises.

To sell into bureaucratic organizations like schools, adopt a "bottoms-up" strategy. Instead of pitching directors, focus on getting individual teachers to use and love the product. This creates internal demand and pressure on decision-makers to adopt it organization-wide.

Directly approaching large organizations is often ineffective. Instead, emulate Slack's growth model by getting individual employees to use and love the product. This creates internal champions who advocate for wider organizational adoption, pulling the product in rather than pushing it from the outside.

Instead of waiting years to develop industry expertise, new salespeople should call lower-level end-users at target accounts. By simply asking about their roles, challenges, and industry, reps can quickly learn the specific language and patterns needed to speak credibly with executive buyers, bypassing a long learning curve.

Executives are inherently skeptical of salespeople and product demos. To disarm them, frame the initial group meeting as a collaborative "problem discussion" rather than a solution pitch. The goal is to get the buying group to agree that a problem is worth solving *now*, before you ever present your solution. This shifts the dynamic from a sales pitch to a strategic conversation.

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.

Instead of approaching leaders first, engage end-users to gather 'ammunition' about their daily pains. They may not have buying power, but their firsthand accounts create a powerful internal case (groundswell) that you can then present to management, making the approach much warmer and more relevant.