Even with a successful playbook from a company like Zoom, a marketing leader must adapt significantly when moving to a new context. Selling a physical product globally introduces complexities like homologation, customs, inventory, and channel sales that require eating 'humble pie' and learning the new business from the ground up.

In the previous SaaS era, emulating giants like Salesforce was a common but flawed strategy for startups. In the new AI era, there is no playbook at all, forcing founders to rethink go-to-market strategies from first principles rather than copying incumbents.

A common failure mode for new CROs is attempting to create the sales playbook in isolation. Core pillars like ICP and value proposition are company-level decisions. The CRO's role is to be interdependent, facilitating this cross-functional creation process, not dictating it.

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.

The traditional sales discovery question "How do they buy?" focused on the procurement process and economic buyers. In a Product-Led Growth (PLG) motion, the crucial question is about the *usage journey*. Sales must analyze user behavior signals within the product—like downloads or manual views—to understand when and how to engage effectively.

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.

First-time leaders often feel pressure to have all the answers. Instead, they should embrace a "beginner's mind," openly admitting what they don't know. This creates a safe environment for the team to share mistakes and learn collaboratively, which is crucial for building a playbook from scratch.

A common PLG pitfall is assuming the user base will naturally springboard into enterprise deals. Often, the enterprise buyer is a different person with different problems. This oversight can cost companies years, as they have to build a second, separate sales motion from scratch.