"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.

To transition from working 'in the business' to 'on the business,' Snowflake's CRO was told his hands-on, 'deal hound' approach wouldn't work at scale. The solution was to hire other capable 'drivers,' trust them to do their jobs, and hold them accountable. If a leader has to do their team's job, it's a problem with the team member.

The best reps don't complain about lacking resources; they attract them. Internal teams like product and engineering gravitate towards these reps because they trust their time will be well-spent on a deal that is more likely to close, effectively making them the deal's 'quarterback.'

The founder of Bending Spoons describes himself as "perennially unhappy." While personally challenging, this constant state of discontent is framed as a professional superpower. It fuels a relentless drive to identify flaws and push for improvement across the organization, serving as the engine for the company's high standards.

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.

As a technical founder, Sanjit Biswas initially avoided sales. He embraced it only after reframing it as a systems engineering problem—a necessary challenge to solve in order to get his product out into the world and achieve real impact.

The company's leadership philosophy, borrowed from Palantir, is to hire highly opinionated and sometimes difficult talent. While this feels chaotic, these individuals are essential for innovation and adaptation, unlike talent that merely optimizes existing, stable systems.

Unlike corporate roles where activity can be mistaken for success, sales provides direct, visceral feedback. This "winning" mentality, born from the pain of losing a customer, keeps product leaders grounded in the ultimate goal: winning the customer, not just executing processes.

After years selling a "nice-to-have" edtech product, Drata's founder knew how rare it was to have customers desperate for a solution. This perspective created an intense appreciation that fueled the team's aggressive, execution-focused culture from day one.