Episode SummaryWhat does it really take to lead through uncertainty—and stay true to yourself while doing it? In this episode of Built by People, host Dave D’Angelo sits down with Jessica Swank, Chief People Officer at Box, to explore her unconventional journey from recruiting to executive leadership. Jess opens up about the personal and professional turning points that shaped her path, including being thrust into a CPO role just weeks before the COVID-19 shutdown.

She shares how mentors played a critical role in her growth, what courageous leadership really means, and how she's redefining success by focusing on energy—not just time. From building resilience to embracing vulnerability at the top, Jess offers honest, actionable insights for leaders at every level.

Whether you’re navigating your first leadership role or leading through transformation, this episode will inspire you to lead with more empathy, clarity, and authenticity.

Key Timestamps

• [00:52] – Jess's nonlinear career journey into HR leadership

• [03:35] – The power of mentorship and having champions in your corner

• [04:43] – Navigating the challenges of becoming CPO just as COVID hit

• [07:30] – How remote work reshaped leadership and brought authenticity forward

• [08:38] – Advice for emerging leaders on showing up authentically

• [10:38] – Where C-level leaders find support and keep growing

• [12:00] – The legacy Jess hopes to leave as a people leader

• [12:54] – Rethinking productivity through the lens of “return on energy”

Takeaways

• Embrace the unexpected: Career-defining opportunities often arise from unplanned moments.

• Lean into mentorship: The right mentors can see potential in you before you see it yourself.

• Lead with humility and courage: Especially in moments of crisis, authenticity and adaptability matter more than perfection.

• Know your energy sources: Being intentional about how and where you spend your energy is key to sustainable leadership.

• Authenticity is your superpower: You don’t need to fit a mold to be an effective leader—lead by being more of yourself.

• Create your support system: Even in the C-suite, learning from peers and asking for help is essential.

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