When direct access to top talent is blocked by competitors, savvy leaders identify other successful companies with strong sales cultures (a "lineage") and strategically recruit from that pool. This allows them to tap into a new vein of proven, high-potential talent.
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.
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.
Successful sales leaders don't just copy-paste their old playbook. They adapt it using first principles, considering the new company's specific product, user behavior, and GTM motion (like PLG). Rigidity is a common mistake that leads to failure.
A powerful recruiting tactic is to ask a new customer, "Who would you have bought from if their product was better?" This question identifies competitor reps who excel at selling—persuading buyers despite product disadvantages. These individuals are prime candidates to recruit for your own team.
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.
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.
Instead of just celebrating a win, use that moment to learn. Ask the new customer two key questions: "Where were we better than we thought?" and "Where are we not as good as we think?" The champion is now invested in your success and will provide candid feedback to ensure their decision pays off.
Even successful PLG companies like Figma eventually burn through their early adopter market. To avoid hitting an asymptotic growth curve, they must proactively build a traditional outbound sales team to tackle the enterprise market before the PLG engine stalls. Don't wait until you need it.