A founder's real boss is their customer base. While keeping a board happy is important, some CEOs become so consumed with managing up that they lose sight of the product and customer needs, ultimately driving the company off a cliff despite running perfect board meetings.

A sales manager's coaching style directly impacts their team's mindset. Constantly asking 'When will this close?' amplifies a seller's anxiety and negativity bias. In contrast, asking 'How are you helping this person?' reinforces a healthier, customer-centric process that leads to better long-term results.

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.

Fixating on closing a deal triggers negativity bias and creates a sense of desperation that prospects can detect. To counteract this, salespeople should shift their primary objective from 'How do I close this?' to 'How do I help this person?'. This simple reframe leads to better questions, stronger rapport, and more natural closes.

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.

Securing executive buy-in is its own sales stage, distinct from champion agreement. Don't just repeat the demo for the boss. Use executive-level tactics like reference calls with their peers, exec-to-exec meetings to build relationships, or roadmap presentations to sell the long-term vision and partnership.

Founder-led selling is essential for the first 6-12 months but becomes a critical growth bottleneck if it continues. Founders who can't let go create a self-fulfilling prophecy where the business can't scale beyond them. They must be coached to transition from being the primary seller to an enabler of the sales team.

Prospects often express interest to gather information but lack a commitment to solve the problem. Sellers must differentiate by probing for concrete timelines and stakeholder involvement to avoid chasing deals that won't close, rather than hoping to convert interest into commitment on the call.