This week on Truth Works, my co-host Jeff Markowitz and I sit down with Judy Gilbert, the Chief People Officer of Oura, the company behind the Oura Ring.

Judy is not a typical HR leader.

She started her career at McKinsey, moved into executive search at Egon Zehnder, and then spent 12 years inside Google's People Operations team, helping scale the company from roughly 3,000 employees to 70,000.

Along the way she ran learning and development, ran performance management, and served as head of HR for both YouTube and Google's moonshot factory, Google X.

After Google, she became Chief People Officer at the biomanufacturing company Zymergen, where she helped build the team, took the company public, and then navigated its sale and wind-down.

She tried to retire. It didn't last. The pull of being on a team trying to do hard things brought her to Oura.

In this episode, we get into the difference between HR as an order-taker and HR as a genuine strategic partner, and why so many chief people officers get "organ rejected" within a year of joining.

We talk about the danger of arriving with a fixed playbook, the chemistry that has to exist between a founder and their people leader, and why the job is really about being the one person willing to tell the emperor he has no clothes.

Judy also shares the exact questions she asks before taking any role, how she pressure-tested Oura's CEO Tom Hale by sparring with him over compensation philosophy, and why a company's soul has to already exist before anyone can help it grow.

In this conversation, we discuss:

- The "I don't want to know" fear that stops people tracking their health
- Whoop vs Oura, and how much data is actually useful
- Why strategic HR is a competitive advantage most companies waste
- The three questions Judy asks before joining any company
- Why chief people officer turnover is so brutally high
- The "toolkit" mistake that gets HR leaders fired
- Being the person who has to tell the CEO he has no clothes
- Glass balls vs rubber balls, and what to drop when you're building
- How to protect a company's soul while running a hard business
- Why clear cultures keep people and confused ones lose them
- Why every CHRO is now the company's AI strategist

This is a candid look at the work behind the work, from someone who has built the people function at three very different companies and seen what separates the ones that scale from the ones that stall.

If this conversation changed how you think about culture, leadership, or the people who quietly hold a company together, share it with someone who needs to hear it.

Full episode of Truth Works with Judy Gilbert out now.