What does a chief of staff do for a visionary founder?
Most people have heard the title in a political context. In the startup and founder world, it means something different, and according to Jeremy Bergeron, it looks different depending on who you're talking to. Jeremy describes his version of the role as three people having a baby: Rick Rubin, who holds space for greatness without getting in the way; Brené Brown, who brings vulnerability and trust as table stakes; and Matt Mochary, the strategist who coaches fast-growth business athletes. "It looks and feels different depending on the day," Jeremy says. "Different businesses, different challenges, different needs."
For Leor Weinstein, serial polymath, founder of CTO X, and what Ben Laws calls "the Willy Wonka of the technology world", the chief of staff role had never existed. Leor had operators, teams, and deal flow. What he didn't have was a trusted number two who could go in front of him, behind him, and beside him across a portfolio of ten-plus businesses.
How to become a chief of staff without the job title
Jeremy didn't apply for the role. He invented it. After meeting Leor at a conference in Austin, staying in touch, and eventually spending a day at his house listening to back-to-back meetings, Jeremy noticed something: "He had no one in that seat." When Leor said hiring for the role was too hard, Jeremy's response was immediate. "Why don't I just jump into that role? I've never been a chief of staff. Admittedly, you've never hired for it. So we're already batting a hundred there."
He asked for 30 days, unpaid, with access to every meeting. Leor said okay. Within two weeks, Jeremy knew the role was his. At the end of the month, Leor paid him retroactively and texted: "Let's do this for a couple decades."
What a chief of staff does in a startup or founder-led company
The practical answer: throughput. Jeremy describes himself as a who-not guy, someone who knows enough people across enough industries to find the right Avenger for any problem. He filters candidates not by resume but by heart connection. "We laughingly say we're hiring for a lifetime," he says. "We only want to work with people that we love."
Beyond recruiting, he's in vendor meetings, C-suite conversations, and all-hands calls, representing Leor when Leor isn't there, and building trust on his behalf. The result is that Leor can take on more risk, more ventures, and more complexity than he could alone. The portfolio has crossed 100 million in revenue under management across ten-plus businesses, and Jeremy projects tens of billions within a decade.
Chief of staff vs. executive assistant vs. COO
Jeremy is careful to separate the roles. An executive assistant manages logistics. A COO runs operations. A chief of staff, in his framing, does something harder to define: they expand the founder's nervous system. "It's a much different energy," he says. "Founders won't even know the value it can bring to their nervous system, to their team's nervous system." He's sat in meditation with Leor. He's been in raw accounting meetings where his own nervous system was stretched. He's the person who knows what Leor needs before Leor knows it.
Why empathy and compassion beat the resume in the age of AI
As AI accelerates every category of business, Jeremy and Leor are doubling down on something AI can't replicate: empathetic leadership. Leor doesn't ask candidates about their experience. He has a heart-centered conversation and listens for specific things. "The resume, he doesn't even care about it," Jeremy says. "It's almost secondary."
The result is a core team where everyone is wired with empathy and compassion alongside high performance. That combination creates safety, and safety creates the conditions for people to build things without being asked. "Because we have safety, because we have trust, from that place, watch what we can create," Jeremy says. "Watch what can bubble to the surface."
How to hire a chief of staff, or become one
For founders considering the role, Jeremy's advice is practical: use an LLM to build a job description based on your actual challenges, your team, and your vision. Put it out there. The people you attract will surprise you. You might find someone like Jeremy, someone who's never held the title but is wired for it, or you might find a seasoned operator. Either way, the filter is the same: frequency match, heart connection, and the ability to see yourself working with this person for years. "You might even find a Jeremy," he says. "Someone who's like, look, I've never done this, but I'm wired for this, and here's why."
