When hiring remote contractors, the founder learned the critical trait isn't just skill, but genuine care for the product's success. After cycling through 20 contractors, he found success with one who was willing to solve urgent bugs on nights and weekends, demonstrating true ownership and partnership.
Related Insights
Prioritizing a candidate's skills ('capacity') over their fit with the team ('chemistry') is a mistake. To scale culture successfully, focus on hiring people who will get along with their colleagues. The ability to collaborate and integrate is more critical for long-term success than a perfect resume.
Employees at large companies who independently work nights and weekends on projects outside the roadmap, driven by customer obsession, are exhibiting the key traits of a founder. This behavior, while potentially disruptive to their team, signals a strong, innate entrepreneurial drive ready to be unleashed.
Before hiring for a critical function, founders should do the job themselves, even if they aren't experts. The goal isn't mastery, but to deeply understand the role's challenges. This experience is crucial for setting a high hiring bar and being able to accurately assess if a candidate will truly up-level the team.
Chipotle CBO Chris Brandt filters candidates based on a simple, visceral question: 'Would you be willing to walk into a conference room with them at 5 PM on a Friday?' This test prioritizes collaborative spirit and cultural fit over pure skill, ensuring new hires won't disrupt team dynamics, even if they look good on paper.
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.
Sales experience on a resume can be a 'false positive.' When hiring SDRs, prioritize untrainable qualities like work ethic, mindset, and resilience over specific past roles. These character traits are a better predictor of long-term success than skills that can be taught.
To manage the demands of a side-hustle SaaS, Accel Events' co-founders strategically staggered their personal commitments. They scheduled date nights on different days so one founder was always 'on call' for customer support—a crucial tactic since their main customers ran events on nights and weekends.
When a CEO consistently emails on nights and weekends, it's a clear signal of a high-intensity work culture with low work-life balance. For candidates, this isn't just about the CEO's schedule; it's a cultural red flag or green flag depending on their own work preferences and expectations.
