1. The AI shift isn’t just technical — it’s organizational

At Box, the move to AI is being led as a company-wide transformation, not just a product update. Jessica framed it as a three-part focus for the People team:

• Optimize: Use AI to streamline the employee lifecycle.
• Elevate: Rethink job design, org structure, and the skills that matter most.
• Amplify: Become a use case for customers by showing what’s possible.

"We're still at the beginning of massive change on every single dimension."​

2. Every role is changing — and so is what "qualified" means

AI is rewriting job expectations across the board. Jessica shared how Box has had to recalibrate what makes someone a good fit for a leadership role.

"Someone with just a year of AI experience might be the most knowledgeable person in the room — and now they're the ones educating people with 20 years of experience."

It’s not about tenure anymore. It’s about adaptability, curiosity, and the ability to lead in ambiguity.

3. HR doesn’t own AI — but we do shape how it shows up

Instead of treating AI as an HR-vs-IT turf war, Box created an AI council that includes their CIO, COO, CPO, and others across the business. HR brings the people lens, but it’s a shared strategy.

"It’s not about slapping AI onto your existing workflows. It’s about reimagining how work gets done."

And when the work changes, so do the people systems: training, performance, and team design all have to evolve.

4. Leading hybrid teams now means humans + agents

One of the most forward-thinking moves Box has made? Training managers to lead hybrid teams that include both people and AI agents.

That means new questions like:

• How do you give feedback to an agent?
• What does performance management look like?
• How do you evaluate which agents are working and which ones should be sunset?

"We’re piloting, learning, and sharing best practices — and some of our best agents are being built by ICs and scaled to whole teams."

5. Not every AI agent is worth keeping — and that’s okay

Box is already seeing the consequences of what Jessica calls "agent sprawl" — where too many custom agents get created without a strategy. That leads to messy handoffs, unclear ROI, and duplicate effort.

Their solution? Start tracking agent performance just like people performance. Align agents to team OKRs. Share what’s working. And don’t be afraid to deprecate the ones that aren’t.

"We need to treat agent management like team management. That means feedback, iteration, and knowing when to let go."

6. Start small. And give the scary stuff a hug.

Jessica’s advice for HR teams just getting started:

• Start with personal use. Play with the tools.
• Set up an AI council or designate champions inside your team.
• Get skeptics involved so you’re solving real concerns.

"This is an era of 'think again' — every assumption is worth reexamining."

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