Target sales leaders who were promoted from an individual contributor role within their current company. Acknowledging this specific achievement shows deep research and helps you build a narrative around consistency and execution, which can then be used as a metaphor for your product's value.
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When interviewing for a leadership role, you must articulate your "leadership tree"—the specific people you developed who succeeded and, in turn, developed others. This lineage of talent, along with who was loyal enough to follow you to new roles, is the most concrete evidence of your leadership impact, far more than personal accolades.
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 sustain sales team hunger, leaders should prioritize small, daily recognitions over waiting for major milestones. A quick Slack message acknowledging good work reinforces positive behavior and connects daily effort to the bigger picture, making people feel their work is appreciated.
Rather than approaching executives first, prospect the individual contributors who will actually use your solution. By creating internal champions at the user level, you generate a 'gravitational pull' that brings you into executive conversations with pre-built support, making decision-makers more receptive to your message.
In enterprise deals, discovery shouldn't stop at company objectives. Ask your champion about a key stakeholder's personal career goals. Are they newly promoted and need to prove themselves? Are they aiming for their next promotion? Aligning your solution to their personal ambitions creates a much stronger motivation to buy.
New salespeople lack personal success stories to use as social proof. Leaders must proactively provide them with a library of stories about other clients or team members. These 'borrowed' narratives are essential for building a value bridge with early prospects.
Instead of asking managers for a checklist to get promoted, focus on delivering significant impact. This approach is more effective and viewed more favorably by leadership. Genuine impact is what gets recognized and rewarded, while simply 'checking boxes' can backfire.
Counterintuitively, the best sales leaders often come from companies with mediocre products. Their ability to hit numbers despite a weak offering demonstrates exceptional sales skills, which are then amplified when they are given a great product to sell.
To move beyond reliance on job ads, structure a career path with three distinct stages: 1) Master selling, 2) Coach one other person to sell, and 3) Recruit and lead a team. This model incentivizes top performers to recruit and train their network, creating a scalable, internal talent pipeline.
Your ideal champion inside a large company is often someone who secretly wishes they'd founded a startup but is too risk-averse. They are drawn to the founders' ambition and will advocate for you because they want to feel part of the startup journey vicariously.
