Shopify CEO Files $49M Stock Sale Plan|SHOP Executive Lutke Discloses Rule 144 Trading Plan|Shopify Insider Trading Notice - 464K Share Sale

Rhea-AI Filing Summary

Shopify CEO Tobias Lutke filed Form 144 indicating intent to sell 464,469 shares worth approximately $48.9M. The sale comprises 446,584 shares from vested options and 17,885 shares from vested RSUs, with transactions planned for NASDAQ execution on June 23, 2025. The filing reveals Lutke's recent sales of 677,331 shares in May-June 2025, generating about $73.7M in proceeds. Sales will be conducted under a Rule 10b5-1 trading plan established on June 12, 2024. Share price calculation based on $105.34 closing price as of June 13, 2025, with total outstanding shares at 1.22B. The planned transactions represent approximately 0.038% of Shopify's total outstanding shares.

Positive

• CEO Tobias Lutke's planned sales are part of a pre-arranged 10b5-1 trading plan established in June 2024, indicating compliance with regulatory requirements and proper corporate governance
• Large outstanding share base of 1.2 billion Class A Subordinate Voting Shares indicates strong market capitalization and liquidity
• Current share price of $105.34 (as of June 13, 2025) suggests strong market valuation

Negative

• Significant insider selling: CEO plans to sell 464,469 shares (combined options and RSUs) worth approximately $48.9 million
• Recent large sale by CEO: Sold 659,478 shares for $71.8 million on June 16, 2025
• Total insider sales in past 3 months amount to 677,331 shares worth approximately $73.7 million, indicating substantial insider liquidation

Form 144 Filer Information	UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 144 NOTICE OF PROPOSED SALE OF SECURITIES PURSUANT TO RULE 144 UNDER THE SECURITIES ACT OF 1933
FORM 144

144: Filer Information

Filer CIK
Filer CCC
Is this a LIVE or TEST Filing?	LIVE TEST
Submission Contact Information
Name
Phone
E-Mail Address

144: Issuer Information

Name of Issuer

SEC File Number

Address of Issuer

Phone

Name of Person for Whose Account the Securities are To Be Sold

See the definition of "person" in paragraph (a) of Rule 144. Information is to be given not only as to the person for whose account the securities are to be sold but also as to all other persons included in that definition. In addition, information shall be given as to sales by all persons whose sales are required by paragraph (e) of Rule 144 to be aggregated with sales for the account of the person filing this notice.

Relationship to Issuer

Relationship to Issuer

144: Securities Information

Title of the Class of Securities To Be Sold	Name and Address of the Broker	Number of Shares or Other Units To Be Sold	Aggregate Market Value	Number of Shares or Other Units Outstanding	Approximate Date of Sale	Name the Securities Exchange
Class A Subordinate Voting Shares	Solium Capital Inc. Suite 1500 600-3rd Ave., SW Calgary A0 T2P 0G5	446584	47043158.56	1218135388	06/23/2025	NASDAQ
Class A Subordinate Voting Shares	Solium Capital Inc. Suite 1500 600-3rd Ave., SW Calgary A0 T2P 0G5	17885	1883972.19	1218135388	06/23/2025	NASDAQ

Furnish the following information with respect to the acquisition of the securities to be sold and with respect to the payment of all or any part of the purchase price or other consideration therefor:

144: Securities To Be Sold

Title of the Class	Date you Acquired	Nature of Acquisition Transaction	Name of Person from Whom Acquired	Is this a Gift?	Date Donor Acquired	Amount of Securities Acquired	Date of Payment	Nature of Payment *
Class A Subordinate Voting Shares	06/23/2025	Vesting of options	Issuer			446584	06/23/2025	Exercise of options
Class A Subordinate Voting Shares	06/23/2025	Vesting of RSUs	Issuer			17885	06/23/2025	Exercise of RSUs

* If the securities were purchased and full payment therefor was not made in cash at the time of purchase, explain in the table or in a note thereto the nature of the consideration given. If the consideration consisted of any note or other obligation, or if payment was made in installments describe the arrangement and state when the note or other obligation was discharged in full or the last installment paid.

Furnish the following information as to all securities of the issuer sold during the past 3 months by the person for whose account the securities are to be sold.

144: Securities Sold During The Past 3 Months

Name and Address of Seller	Title of Securities Sold	Date of Sale	Amount of Securities Sold	Gross Proceeds
Tobias Lutke 151 O'Connor St. Ground Floor Ottawa A6 K2P 2L8	Class A Subordinate Voting Shares	05/30/2025	17853	1910717.33
Tobias Lutke 151 O'Connor St. Ground Floor Ottawa A6 K2P 2L8	Class A Subordinate Voting Shares	06/16/2025	659478	71781682.86

144: Remarks and Signature

Remarks

Date of Notice

ATTENTION:

The person for whose account the securities to which this notice relates are to be sold hereby represents by signing this notice that he does not know any material adverse information in regard to the current and prospective operations of the Issuer of the securities to be sold which has not been publicly disclosed. If such person has adopted a written trading plan or given trading instructions to satisfy Rule 10b5-1 under the Exchange Act, by signing the form and indicating the date that the plan was adopted or the instruction given, that person makes such representation as of the plan adoption or instruction date.

Signature

ATTENTION: Intentional misstatements or omission of facts constitute Federal Criminal Violations (See 18 U.S.C. 1001)

FAQ

How many SHOP shares is Tobias Lutke selling on June 23, 2025?

Tobias Lutke is selling a total of 464,469 shares, consisting of 446,584 shares from vested options and 17,885 shares from vested RSUs.

What is the total value of SHOP shares being sold by Lutke in this Form 144 filing?

The total aggregate market value of shares to be sold is $48,927,130.75, calculated using the June 13, 2025 closing price of $105.34 per share.

How many SHOP shares has Tobias Lutke sold in the past 3 months before this filing?

In the past 3 months, Lutke sold 677,331 shares: 17,853 shares on May 30, 2025 for $1,910,717.33 and 659,478 shares on June 16, 2025 for $71,781,682.86.

Is Tobias Lutke's SHOP stock sale part of a 10b5-1 trading plan?

Yes, the sales are being made pursuant to a Rule 10b5-1(c) trading plan that became effective on June 12, 2024, when Lutke was not aware of material non-public information.

What positions does Tobias Lutke hold at SHOP according to the Form 144?

According to the filing, Tobias Lutke serves as both an Officer and Director of Shopify Inc.