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.
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Your best reps are often "unconsciously competent" and can't explain their own success. Before an SKO, leaders must help these individuals deconstruct their process and build a prescriptive presentation, translating their individual "art" into a replicable science for the entire sales team.
Stop trying to convince executives to adopt your priorities. Instead, identify their existing strategic initiatives—often with internal code names—and frame your solution as an accelerator for what they're already sold on doing. This dramatically reduces friction and speeds up deals.
Some CEOs encourage tension between sales and marketing. A more effective model is for the CRO and CMO to build enough trust to handle all disagreements—like lead quality or follow-up—behind closed doors. This prevents a culture of finger-pointing and presents a united front to leadership.
A key, often overlooked, function of leaders in high-growth groups is to act as a shield against internal company interference. This allows their teams to focus on innovation and execution rather than navigating organizational friction, which is a primary driver of top talent attrition.
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.
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.
Founders and CEOs can develop an inflated sense of their contribution by focusing only on the final executive meeting. They often overlook the months of prospecting, relationship-building, and deal choreography done by the sales rep, leading to unfair perceptions about who truly 'closed the deal.'
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.
Don't be afraid to surface problems to executives, as their job is almost entirely focused on what's not working. Withholding a problem is unhelpful; clarifying and framing it is incredibly valuable. Your champion isn't offending their boss by raising an issue, they're demonstrating strategic awareness.
The traditional definition of a champion (power, influence, vested interest) is incomplete. The most critical, and often overlooked, criterion is their proven willingness to actively sell on your behalf when you are not present. Without evidence of them taking action, you don't have a champion, regardless of their position.
