Jessica Swank: How Box Navigates the New World of Work

Post-pandemic leadership can be challenging. With the current market and increased expectations workers, leaders, and mid-level managers are squeezed, balancing the needs of the business with the demands of their people. This is why I’m excited to talk to a Chief People Officer of a global organization that is doing the work, navigating the journey, and experimenting with ways to better support their people.

Today, I talk with Jessica Swank about how her company’s leaders are navigating the challenges and still taking care of themselves and their people. We discuss the importance of clarity and support when setting high expectations, and how transparency, communication, and listening are vital with hybrid and remote work experimentation. We discuss specific ways Box integrates values into their decisions and develops and enables their managers to be more successful. Whatever your culture, Jessica offers her best advice on where you can start supporting your leaders.


To access the episode transcript, please click on the episode title at

Key Takeaways:

  • In your organization, you cannot be clear enough. Hold high expectations, but also give a clear understanding that you’ll be supporting your team and that you’re available for that support.
  • Actions speak louder than words and other people notice. You continue to show your empathetic culture every time you talk about caring for each other and empathy in service and follow it up with actions.
  • Setting boundaries is both self-care and empathetic. It gives you space to recharge and be more present in the difficult conversations that need to be had in business.
  • Work-life balance is not real. You need to understand priorities and boundaries to ensure you’re healthy with your life in the season you’re in.
  • It is a journey to understanding and managing the needs of your team. Be willing to take that journey and gather information from your employees on what is working and what is not.


“It’s not just up to the business to say, ‘Here’s what I need from you.’ It is incredibly valuable for every person to have that open dialogue with their managers, ask them when they need support, clarification, feedback, not just sitting back and waiting to be told, but also engaging in that dialogue.”

—  Jessica Swank

“It’s all about juggling, and you’re going to drop some balls, just make sure that the balls are going to bounce versus shatter.” —  Jessica Swank


About Jessica Swank, Chief People Officer, Box

Jessica has a proven track record of helping companies define and amplify their people and culture strategy (including diversity, talent development, employee experience, workforce planning, people analytics, and internal communications). She has been with Box since December 2018, and currently leads all People (HR), Belonging, Community (including, Places (workplace services and real estate), and Internal Communications. Prior to Box she led the People team at Blue Bottle Coffee, a high-growth global coffee company. Previously, Jessica led HR for Aruba, a fast-growing subsidiary of HPE, and spent ten years at HP/HPE in a variety of global HR roles. Her early career included executive search and recruiting for CEO’s, CFO’s and other key leadership positions.


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