Why Box's VP of Product Strategy Wants to See Your Side Projects

Wacker argues that the era of theoretical interviewing is over. He prefers candidates who treat AI as a sandbox rather than a shortcut, specifically looking for those who have launched mobile apps or monetized niche projects. These ventures signal a level of grit and practical intuition that a resume alone cannot convey. By building and shipping their own tools, applicants prove they can navigate the entire development lifecycle, even if their side work remains entirely unrelated to Box’s core enterprise software.

This "builder" mindset is one Wacker applies to his own routine. After thirty years in software and product management, he found himself drifting away from hands-on engineering, but recent AI advancements have lowered the barrier to entry for solo projects. To combat the decision fatigue inherent in modern streaming, he used the AI-powered code editor Cursor to build a custom Apple TV application. The tool bypasses massive content libraries by selecting a random movie from his collection and starting it at an arbitrary point, effectively mimicking the unpredictable experience of legacy cable television.

Wacker is part of a growing cohort of executives returning to the command line to stay relevant. By experimenting with AI coding, these leaders are reconnecting with the role of an individual contributor, keeping their intuition sharp as the landscape of software development undergoes a fundamental shift.