Hippo executives and Lennar sell stock
On June 12, 2025, The Baldwin Group’s Westwood Insurance Agency struck a deal to acquire Hippo’s homebuilder distribution network. The transaction included multiple commercial agreements between Westwood, Hippo, and affiliates like Spinnaker and Millennial Specialty Insurance to embed home insurance across 20 of the top 25 US homebuilders—representing over 35% of new single-family homes built annually.
The announcement aligned with Hippo’s 2028 strategy, which targets over $2 billion in gross written premium and $125 million in adjusted net income. As part of the plan, Hippo emphasized its intent to diversify premium, scale through a tech-enabled, multi-line model, and deepen reliance on Spinnaker as its hybrid fronting platform. The $100 million Westwood partnership is a core pillar of its “New Homes” vertical.
What wasn’t in the press release: the executive cash-outs.
Since March, current and former Hippo insiders have cashed in on shares:
Assaf Wand, the co-founder and former CEO of Hippo who resigned from the board on April 21, 2025, sold 49k shares between March and June for $1.23 million and filed a notice to sell an additional 500k shares for $13.9 million. The shares were acquired on May 28, 2019, through a Stock Award from Hippo Holdings Inc.
Ellis Stewart, Hippo’s current Chief Strategy Officer and former CFO, sold 20k shares between March and June for $542,830 and filed a notice to sell an additional 5,125 shares for $155,137. The shares were acquired through Stock Awards from the Issuer – 4,039 shares on August 15, 2024, and 1,085 shares on May 15, 2024, both as compensation.
Torben Ostergaard, President and CEO of Spinnaker Insurance—Hippo’s key fronting carrier—filed a Form 144 to sell 2,444 shares of Hippo Holdings stock around June 12, 2025, for an estimated $66,232, following a prior sale of 4,889 shares on June 4, 2025, that generated $120,316.
Meanwhile, Lennar Corporation—one of Hippo’s earliest distribution partners—reduced its stake in the company to below 10%, selling back $14.5 million worth of shares ($28.17 per share) in a buyback agreement that closed on July 1. Separately, for the six months ended May 31, 2025, Lennar reported a $28.4 million loss related to Hippo.
Bottom Line: On June 12—the day Hippo announced its homebuilder partnership—HIPO closed at $29.56; by July 3, 2025, the stock had dipped to $28.11, falling below Lennar’s selling price.
