Claude Silver is the world's first Chief Heart Officer at VaynerMedia — one of the largest independent agencies on the planet with over 2,000 employees globally. What started as an unexpected conversation over breakfast with Gary Vaynerchuck turned into a decade-long mission to build what he calls "the greatest human organization in the history of time."
Her only job description? "Touch every single human being and infuse the agency with empathy."
Claude never wanted to be in HR. She started in grocery stores, survived the dot-com boom and bust, built a career as a digital strategist at some of the world's biggest agencies, and stumbled into the most human role in business almost by accident. Today she leads a global people operation and has written the book — literally — on what it means to show up as yourself at work.
In this conversation, Claude and Jessica Neal go deep on why most workplaces are quietly breaking people, why the traditional path to leadership is fundamentally broken, and what it actually takes to build a culture where people don't just perform — they thrive.
In this episode you'll learn:
- Why psychological safety disappears long before performance numbers start dropping
- The difference between culture fit and culture addition — and why mixing them up destroys teams
- The "Lie Exercise" Claude uses to dismantle imposter syndrome in real time
- Why promoting your best people without coaching them is one of the most damaging things a company can do
- How to scale empathy across a 2,000 person organization without losing the human touch
- Why heart-led leadership isn't soft — it's the fastest path to real accountability and zero drama
- What cynicism, politicking and late night Slack messages are really telling you about your culture
- Why the loneliest role in any company might just be the one responsible for everyone else's wellbeing
The moment that changed everything: At 19, Claude left college, strapped 80 pounds onto her back and spent 93 days on an Outward Bound wilderness program in the Colorado Rockies. No tent. No toilet paper. No way out. What she came back with wasn't just confidence — it was a blueprint for servant leadership that still runs through everything she does today.
On the book: Be Yourself At Work is Claude's answer to watching talented people shrink in the workplace — just like she once did. It's a practical, honest, deeply personal guide to self-awareness, team dynamics, and leading with courage. Part memoir, part playbook, part mirror.
Claude Silver's book Be Yourself At Work is available now everywhere books are sold.
