Gloo Holdings, Inc.

Item 2. Unregistered Sales of Equity Securities and Use of Proceeds.

Corporate Reorganization Transactions

On November 19, 2025, as part of the Corporate Reorganization, we issued (1) 38,822,616 shares of Class B common stock in exchange for 116,468,006 Series A preferred units of Gloo Holdings, LLC; (2) 8,345,221 shares of our Class

B common stock in exchange for 25,035,689 common units of Gloo Holdings, LLC; and (3) 29,649 shares of our Class B common stock in exchange for 7,490,000 incentive units of Gloo Incentives, LLC.

These issuances that were part of the Corporate Reorganization were exempt from registration in reliance on Section 4(a)(2) of the Securities Act and Rule 506 promulgated thereunder.

XRI Transaction

On November 19, 2025, we issued 346,244 shares of our Class A common stock to XRI Global, Inc. (“XRI”), pursuant to a securities purchase agreement by and among the Company, Gloo Holdings, LLC, XRI and Daniel Wilson dated August 30, 2025, as amended on November 19, 2025.

This issuance was exempt from registration in reliance on Section 4(a)(2) of the Securities Act and Rule 506 promulgated thereunder.

Notes Conversion

In connection with the closing of our IPO, the Senior Secured Convertible Notes automatically converted into shares of Class B common stock. Pursuant to the terms of the Senior Secured Convertible Notes, all outstanding accrued and unpaid interest owed under the Senior Secured Convertible Notes was to convert into Class B common stock immediately prior to the closing of the IPO. An aggregate of $143.1 million of outstanding principal and accrued interest under the A&R Senior Secured Note was converted to Class B common stock on November 20, 2025, resulting in the issuance of an aggregate of 22,363,700 shares of our Class B common stock, based on a conversion price of $6.40 per share, as set forth in the Senior Secured Convertible Notes.

These issuances that were part of the Corporate Reorganization were exempt from registration in reliance on Section 4(a)(2) of the Securities Act and Rule 506 promulgated thereunder.

Equity Plan-Related Issuances

On November 18, 2025, we granted stock options to purchase an aggregate of 7,649,678 shares of our Class A common stock to certain directors, executive officers, employees and other service providers under our 2025 Equity Incentive Plan, at an exercise price of $8.00 per share.

These equity plan-related issuances were exempt from registration in reliance on Section 4(a)(2) of the Securities Act or Rule 701 promulgated under Section 3(b) of the Securities Act.

Use of Proceeds from the IPO

On November 18, 2025, the Registration Statement on Form S-1 (File No. 333-290930) for our IPO (the “Registration Statement”) became effective, pursuant to which we sold an aggregate of 9,784,688 shares of Class A common stock, including the exercise of the underwriters’ option to purchase 684,688 additional shares (the “Option Closing”), in each case at a public offering price of $8.00 per share. Roth Capital Partners, LLC acted as representative for the underwriters in the IPO. Upon completion of the IPO on November 20, 2025, we received net proceeds of $67.2 million, after deducting underwriting discounts and commissions of $5.1 million and underwriting offering expenses of $0.5 million. Upon completion of the Option Closing, we received net proceeds of $5.1 million, after deducting underwriting discounts and commissions of $0.4 million. No other payments for such offering expenses were made directly or indirectly to (1) any of our officers or directors or their associates, (2) any persons owning 10% or more of any class of our equity securities or (3) any of our affiliates. The offering commenced on November 19, 2025 and terminated after the sale of all shares registered pursuant to the Registration Statement.

There has been no material change in our planned use of the net proceeds from our IPO as described in the Prospectus.