Additional Proxy Soliciting Materials (Form DEFA14A)

UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

SCHEDULE 14A

PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE
SECURITIES EXCHANGE ACT OF 1934

Filed by the Registrant ☒

Filed by a party other than the Registrant ☐

Check the appropriate box:

GLOO HOLDINGS, INC.

(Name of Registrant as Specified In Its Charter)

(Name of Person(s) Filing Proxy Statement, if other than the Registrant)

Payment of Filing Fee (Check all boxes that apply):

Your Vote Counts! GLOO HOLDINGS, INC. 2026 Annual Meeting Vote by July 12, 2026 11:59 PM ET [Alt text was not generated.] GLOO HOLDINGS, INC. 831 PEARL STREET BOULDER, COLORADO 80302 UNITED STATES T00267-P53625 You invested in GLOO HOLDINGS, INC. and it's time to vote! You have the right to vote on proposals being presented at the Annual Meeting. This is an important notice regarding the availability of proxy materials for the stockholder meeting to be held on July 13, 2026. Get informed before you vote View the Proxy Statement and 2025 Annual Report online OR you can receive a free paper or email copy of the material(s) by requesting a copy prior to June 29, 2026. If you would like to request a copy of the material(s) for this and/or future stockholder meetings, you may (1) visit www.ProxyVote.com, (2) call 1-800-579-1639 or (3) send an email to [email protected]. If sending an email, please include your control number (indicated below) in the subject line. Unless requested, you will not otherwise receive a paper or email copy. For complete information and to vote, visit www.ProxyVote.com Control # Vote Virtually at the Meeting* July 13, 2026 10:00 a.m. Mountain Time Smartphone users Point your camera here and vote without entering a control number Virtually at: www.virtualshareholdermeeting.com/GLOO2026 *Please check the meeting materials for any special requirements for meeting attendance.

Vote at www.ProxyVote.com THIS IS NOT A VOTABLE BALLOT This is an overview of the proposals being presented at the upcoming stockholder meeting. Please follow the instructions on the reverse side to vote these important matters. We encourage you to access and review the proxy materials before voting. Voting Items 1. Election of Directors For All Nominees: 01) Bishop Claude Alexander, Jr. 02) John Furst 03) Derek Green 2. The ratification of the appointment of Crowe LLP as our independent registered public accounting firm for our fiscal year ending January 31, 2027. For NOTE: In their discretion, each proxy may also vote upon such other business as may properly come before the meeting or any adjournments or postponements thereof. Prefer to receive an email instead? While voting on www.ProxyVote.com, be sure to click "Delivery Settings". T00268-P53625