"Mercenaries" are transactional reps who perform well but leave when conditions change. "Patriots" are mission-driven team members who build a winning culture. While startups may need mercenaries for early traction, long-term success requires actively cultivating and hiring for patriot-like qualities.
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The most motivated employees ("freedom fighters") offer unparalleled commitment, but only if the company's mission is authentic. Unlike mercenaries (paid) or conscripts (obligated), they demand integrity and will quickly expose any disconnect between the stated mission and reality, making them a high-reward but high-maintenance talent segment.
Organizational success depends less on high-profile 'superstars' and more on 'Sherpas'—generous, energetic team players who handle the essential, often invisible, support work. When hiring, actively screen for generosity and positive energy, as these are the people who enable collective achievement.
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 resilient sales culture is built on pride. This pride doesn't appear organically; it's the result of a specific sequence. Effective training and development equip reps to win. Consistent winning fosters genuine pride in their work, team, and company, which in turn builds a loyal, high-retention culture.
To scale from 100 to 1,000+ employees, you must stop interviewing everyone. Success depends entirely on the cultural foundation built with the first 100 people. By personally hiring and imbuing them with the company's core values, you create a group of leaders who can replicate that culture as the organization expands.
When evaluating sales leaders, prioritize their track record in recruiting above all else. Exceptional leaders are talent magnets who build scalable teams through strong hiring and enablement. Their ability to attract A-players is the foundation of a predictable revenue machine.
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.
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.
A founder's ability to sell is not proof of a scalable business. The real litmus test for repeatability is when a non-founder sales hire can close a deal from start to finish. This signals that the value proposition and process are teachable, which is the first true sign of a scalable go-to-market motion.
