Jessica Swank didn’t set out to be a Chief People Officer—but when the opportunity found her, she said yes. Now CPO at Box, Jessica joins Rob to share her unconventional career journey and how she’s helping lead the company into its next era as an AI-first organization. She explains why AI is more about change management than tech, what it means to build cross-functional partnerships that work, and why every Boxer (even the CEO) has to pass an AI quiz. Jessica also reveals how Box rolled out an internal AI agent that writes job descriptions in seconds, and why “return on time” is her new favorite metric. Plus: a cameo from Jeep, her 7-year-old’s favorite GPT agent.
Jessica’s journey from recruiter to Chief People Officer
Why she nearly said no to the CPO role at Box
What it’s really like to lead HR during a global shutdown
How Box is approaching AI as a cross-functional, people-first initiative
Why HR should lead AI strategy—not just adoption
Box’s three-pillar framework for AI: Optimize, Elevate, Amplify
The ROI of AI? Try ROT—Return on Time
How Box built an AI agent that drafts JDs from intake calls
Why every employee at Box is required to pass an AI enablement course
How to grow with a company instead of being outgrown by it
Why “get comfortable being uncomfortable” is still the best career advice
