📜 What This Document Is 📄

This document is a definitive Proxy Statement (DEF 14A). Think of it as a massive instruction manual and proposal booklet that Hippo Holdings Inc. is providing to its stockholders ahead of its annual meeting. 👉 Instead of simply reporting financial results, this filing is asking you, the owner, to vote on key decisions that govern the company’s future—from who should be on the Board to how executive pay should be structured. The annual meeting is set for Tuesday, June 2, 2026, and it will be conducted completely virtually via live webcast.

🏛️ Company Overview 🏢

Hippo Holdings Inc. is the company issuing this proxy statement. While the document is highly technical and focused on governance, it confirms the Company is actively managing its corporate structure and governance. 👉 As a Delaware corporation, the company is structured to govern its affairs through its Board of Directors.

📅 Annual Meeting Logistics 🗓️

This section tells stockholders when and how they must exercise their voting rights. The annual meeting is scheduled for Tuesday, June 2, 2026, at 11:00 a.m. Central Time, and it will be virtual.

• Record Date: Stockholders must be "holders of record" as of the close of business on April 7, 2026, to be entitled to vote.
• Shares Outstanding: As of the Record Date, there were 26,031,227 shares of common stock outstanding and entitled to vote at the Annual Meeting.
• Quorum: A quorum (the minimum number of shares needed for business to be conducted) requires the presence of a majority in voting power of the stock issued and outstanding.
• Voting Mechanism: Stockholders are strongly encouraged to vote promptly via the Internet, phone, or mail. If shares are held in "street name" (by a bank or broker), the stockholder must follow the instructions provided by that bank or broker to ensure their votes are counted.

✅ Board Proposals & Votes 🗳️

The primary function of this document is to present several critical proposals for the stockholders to approve. Voting on these matters is essential because they determine the legal and operational framework of the company for the coming year. The Board of Directors recommends voting FOR all the proposals listed below.

• Proposal 1: Electing Directors 🧑‍⚖️
  • Stockholders will vote to elect Lori Dickerson Fouché, Hugh R. Frater, and Richard McCathron as Class II directors for a three-year term.
  • Why it matters: Directors guide the Board’s oversight of the company. Electing new members determines the company's strategic guidance and accountability for the next three years.
• Proposal 2: Ratifying the Auditor 💰
  • Stockholders are asked to ratify the appointment of Deloitte & Touche LLP as the independent registered public accounting firm for the fiscal year ending December 31, 2026.
  • Why it matters: The auditor is the third-party expert that verifies the company’s financial books. While ratification is not legally required, it is a "good corporate governance practice" that the Board wants the owners to support.
• Proposal 3: Advisory Say-On-Pay Vote 💸
  • This proposal allows stockholders to provide an advisory vote on the overall compensation of the Named Executive Officers (NEOs).
  • Why it matters: This gives owners a public voice on whether they feel the pay structure for top executives is appropriate and aligns with creating shareholder value. The vote is advisory (non-binding), but the Board stated they will consider the result.
• Proposal 4: Advisory Vote on Frequency ⏳
  • Stockholders vote on how often future "say-on-pay" votes should occur: every 1 year, 2 years, or 3 years.
  • Board Recommendation: The Board recommends choosing a frequency of 1 year (an annual vote).

💎 Corporate Governance and Leadership Structure 🌐

Corporate governance refers to the system of rules, controls, and practices by which a company is directed and controlled. This extensive section outlines the rules and structures in place to maintain oversight, ensuring the company is managed responsibly.

• Board Composition and Changes: The Board of Directors currently consists of ten members, including Richard McCathron, Laura Hay, and Susan Holliday. Notably, Eric Feder announced his resignation from the Board effective June 3, 2026. In his place, the Board appointed Stewart Ellis effective June 3, 2026.
• Board Structure: The Board operates with a three-class structure, which is a common governance mechanism that can help delay or prevent a change of management or control.
• Separation of Roles: The Board affirms that separating the roles of Chair of the Board (Sandra Wijnberg) and Chief Executive Officer (Richard McCathron) is in the best interest of the Company.
• Committee Charters: The Board operates three standing committees:
  • Audit, Risk, and Compliance: This committee's role is highly technical and critical. It reviews the company's financial statements, oversees risk management (including cybersecurity and financial risks), and pre-approves all services related to the independent auditor.
  • Compensation: This committee oversees all compensation policies, ensuring they are designed to reward performance and avoid encouraging "excessive risk-taking."
  • Nominating and Corporate Governance: This committee is responsible for identifying and recommending qualified candidates for the Board of Directors.

💼 Executive Officers and Director Profiles 🧑‍💼

The filing provides detailed professional histories for the people running the company and guiding the Board. This gives stockholders insight into the experience and expertise driving the business.

• Executive Officers:
  • Richard McCathron: President, CEO & Director.
  • Guy Zeltser: CFO. He took over as CFO in March 2025 and previously served as VP of Finance.
  • Torben Ostergaard: President & CEO, Spinnaker.
  • Michael Stienstra: Chief Insurance Officer and General Manager, HHIP.
  • Note: Stewart Ellis stepped down as CFO and transitioned to EVP & Chief Strategy Officer in March 2025.
• Board Skills: The Board uses a "Skills Matrix" to track diverse expertise, including Technology/Cybersecurity, Financial Literacy, and Insurance Industry Experience, ensuring the Board has comprehensive tools for oversight.

💵 Compensation and Incentives 📈

The compensation section is very detailed, outlining exactly how the company plans to pay its top executives and why. It details both cash incentives and equity-based grants.

• Shift to Performance Focus: The Compensation Committee is shifting toward a "more performance-based executive compensation model."
• Equity Grants (2025): In 2025, the company granted Restricted Stock Units (RSUs) to all NEOs. The Board is also reintroducing Performance Restricted Stock Units (PRSUs) for the CEO, splitting the award 25% as PRSUs and 75% as RSUs.
• RSU Details: Each RSU award vests ratably over a three-year period following the February 15, 2025 commencement date, meaning 100% vests on February 15, 2028.
• CEO Performance Targets (2025): The Board determined that the CEO achieved 100% of the annual cash incentive payout for 2025 for three key metrics:
  • 2025 Net Income (Payout: 100% / Achievement: $(33)M for $69M).
  • CEO Performance (Payout: 100% / Achievement: Board discretion).
  • TSR Performance (Payout: 100% / Achievement: 75th percentile).
• HSCM Insurtech Index: Mr. McCathron’s PRSUs vest based on the company's Total Shareholder Return (TSR) compared to the HSCM Insurtech Index over a three-year period, from March 1, 2025 to February 28, 2028.

📊 Independent Auditor Fees 🔎

This section provides transparency regarding how much the company spent to ensure its financial reports were accurate. These fees are crucial for understanding the total cost of compliance and oversight.

Fee Category	2025 Amount	2024 Amount
Audit Fees	$2,500,000	$1,860,000
Audit-Related Fees	$130,500	$110,000
Tax Fees	$344,000	$145,000
All Other Fees	$2,000	—
Total Fees	$2,976,500	$2,115,000

• Observation: Total fees increased significantly from $2,115,000 in 2024 to $2,976,500 in 2025.
• Key Oversight: All services were approved by the Audit, Risk, and Compliance Committee.

📞 Contact & Investor Relations Info ℹ️

For stockholders with questions, Hippo provides clear channels to communicate, emphasizing the online portal for the meeting.

• Online Voting/Participation: Use www.proxydocs.com/HIPO.
• Advance Question Submission: Use www.proxyvote.com before 11:59 p.m. Eastern Time on June 1, 2026.
• General Inquiries (Secretary): Hippo Holdings Inc., 1 Almaden Blvd., Ste 400, San Jose, CA 95113.

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🧠 The Analogy

Think of the Annual Meeting Proxy Statement as the ultimate shareholder group decision meeting. Hippo Holdings Inc. is not just presenting its score card (its financial results); it's asking the owners for their vote on the referees (the auditors), the coach (the CEO), the coaching staff (the Board), and the rulebook (the governance rules). The company needs the owners to agree on these structures and payments to keep running smoothly.

🧩 Final Takeaway

The annual proxy statement is a complex governance document, but the core message is that the company is seeking stockholder approval for its fundamental operating structures, notably strengthening its focus on performance-based executive pay and ratifying Deloitte & Touche LLP as its auditor for 2026.