Four times attending the Transform Conference, and I’ve managed to catch Covid twice— this feels like a pretty steep infection rate. But honestly? I’d still go back. It’s just that good. Every year, I leave excited by the incredible people I meet (but maybe one too many this time, given the viral souvenir). The connections, the conversations, and the sheer energy of the event make it something I genuinely look forward to each spring. That said, as much as I love it, I’m committed to making it even better. It’s becoming the social event of the year, which is great, but it’s also shifting a bit away from creating a great space for learning opportunities—especially for leaders at smaller organizations. Maybe it’s time for the StartupExperts community to step up and create more ways to share knowledge and insights? These things take time, but I’ll be working with the Transform team to refine and enhance the experience next year. We tried a few new programs this time (our expo tour and podcast booth) with mixed success, and we’ll keep iterating!
Coming back from the craziness of Transform, I jumped straight into the massive effort of renewing benefits for all my Sequoia One clients. For the first time since the pandemic, we’re finally seeing normal-looking renewals despite the impact of new GLP-1 drugs and gene therapies driving costs up. Outside of payroll, health insurance is one of the largest line items for any organization, so it’s encouraging to see some cost predictability returning to the medical insurance market.
At the same time, I’ve been learning that some PEOs and in turn, their clients, aren’t faring as well this year. Many PEOs regularly subsidize new business by offering artificially low rates to prospects, and now it’s catching up with them. The truth is, there are no real deals in health insurance—treatments and facilities cost what they cost. So if one PEO’s rates are significantly better than another’s, something is going on behind the scenes. At Sequoia One, we’re seeing high single-digit to low-teen renewals, right in line with large-group benefits trends. I’ve included a chart below that breaks it all down across carriers.

And the juiciest story in the last couple of weeks (okay, there have been a few but I promised myself that despite having a PoliSci degree, I won’t talk about why planning a military attack via text is a bad idea) is the reported espionage lawsuit between Rippling and Deel. If you were too distracted by Transform, renewals, or following how some were launching a “war game” via text, here’s the scoop: Deel is being accused of planting a mole at Rippling and receiving confidential, or at least highly privileged, information from this individual. Likely via text, since one of the accused reportedly tried to flush his phone down the toilet when confronted. Oh, and there was a “honeypot” built to catch them in the act. All entertaining stuff…especially following the very public fight these two had last fall on LinkedIn over “snake oil” and, yet again, text-based chat.
Maybe the takeaway here is simple: we should all put our phones down and stop texting so much. Which, frankly, is the same advice I give my daughters.
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.

