As we turn the page into May, I’m filled with gratitude and pride reflecting on the incredible progress we’ve made together at StartupExperts. We recently welcomed our 2,000th member — an achievement that feels especially meaningful because of how we got here.

Our leadership team is 100% volunteer. Every bit of programming, connection, and value our community delivers happens thanks to the generosity of leaders who show up not to transact, but to give. It’s rare these days to find a group so committed to sharing without expectation of return, and it’s one of the things that makes StartupExperts truly special. We’ve built a culture of contribution — a place where leaders across HR, Finance, and Operations come together to support one another, simply because we believe in the power of community. It’s inspiring to witness, and I couldn’t be prouder of what we’re building together.

On a personal note, I’m also wrapping up renewal season at Sequoia One PEO, which, as always, has been both a challenging and rewarding experience. This season gives me the chance to connect with so many HR, Finance, and Ops leaders across the amazing companies I support — and every conversation reminds me just how deeply these leaders care about their teams.

One thing that always stands out to me: great people leaders know their people. They’re tuned into not just the professional challenges, but often the personal ones too. It’s interesting — companies that experience larger renewal increases often aren’t surprised. They understand the story behind the numbers because they live it every day: employees navigating health issues, supporting families, and simply being human. In many ways, during renewal season, I’m the messenger of both good news and hard news. Ironically, it’s sometimes the companies with the smallest renewal increases who seem the most caught off guard — an interesting phenomenon that speaks to how connected (or disconnected) leaders are to the everyday realities of their teams.

Both StartupExperts and my work at Sequoia continue to reinforce a simple but powerful truth: Leadership isn’t about transactions. It’s about relationships. And when we lead with heart — when we truly show up for others — the impact ripples far beyond any single moment or metric.

With warmest wishes, Jesse

DISCLAIMER

The opinions in this newsletter are solely my own and don't represent any affiliated organization's views. Information is provided for general purposes only without warranties regarding accuracy or completeness.