[144] SHOPIFY INC. SEC Filing

Rhea-AI Filing Summary

Form 144 filed for SHOP discloses proposed sales of Class A Subordinate Voting Shares related to equity vesting. The notice lists two lots scheduled for sale on 09/22/2025: 10,261 shares with an aggregate market value of $1,471,232.69 and 171,145 shares with an aggregate market value of $24,538,770.10, both to be traded on NASDAQ. The securities were acquired on 09/22/2025 through vesting of RSUs and options, with 19,733 and 171,145 shares respectively recorded as vested. The filing also reports multiple prior sales by Harley Finkelstein in the past three months, including a 66,000-share sale on 08/06/2025 generating $9,806,996.20.

Positive

• Rule 144 disclosure provided for planned sales, showing compliance with securities sale notification requirements
• Acquisitions are documented as vesting of RSUs and options, clarifying the source of the shares to be sold

Negative

• Planned sale of 171,145 shares on 09/22/2025 with an aggregate market value of $24,538,770.10
• Multiple recent insider sales by Harley Finkelstein in the past three months, including a 66,000-share sale generating $9,806,996.20

Insights

Securities Analyst

TL;DR: Routine insider sale notice tied to equity vesting; shows meaningful planned liquidation but no new company fundamentals.

The Form 144 documents planned disposition of vested Class A shares totaling 181,406 shares to be sold on 09/22/2025 with stated aggregate market values. These sales arise from RSU and option vesting events rather than open-market purchases, and the shares are to trade on NASDAQ. Prior dispositions by Harley Finkelstein over the past three months are disclosed, including several significant blocks that produced notable gross proceeds. From a market-impact perspective, the combined announced amount is sizable in absolute dollars but the filing contains no operational or financial performance data to change a valuation model.

Corporate Governance Expert

TL;DR: Disclosure complies with Rule 144 mechanics; multiple recent insider sales are transparent but warrant monitoring.

The filing indicates compliance with required notice for proposed sales of securities acquired via vesting. It identifies the nature of acquisition (RSUs and options) and aggregates past sales by the named individual, providing traceability of insider liquidity. While the filing itself is a routine compliance document, the pattern of recurring sales by the same insider over several months is clearly documented here, which is relevant for governance and insider-activity oversight though not inherently a governance violation.

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

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	10261	1471232.69	1220418767	09/22/2025	NASDAQ
Class A Subordinate Voting Shares	Solium Capital Inc. Suite 1500 600-3rd Ave., SW Calgary A0 T2P 0G5	171145	24538770.1	1220418767	09/22/2025	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	09/22/2025	Vesting of RSUs	Issuer			19733	09/22/2025	Vesting of RSUs
Class A Subordinate Voting Shares	09/22/2025	Vesting of RSUs and Options	Issuer			171145	09/22/2025	Vesting of RSUs and Options

* 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
Harley Finkelstein 151 O'Connor St. Ground Floor Ottawa A6 K2P 2L8	Class A Subordinate Voting Shares	06/30/2025	1680	194174.57
Harley Finkelstein 151 O'Connor St. Ground Floor Ottawa A6 K2P 2L8	Class A Subordinate Voting Shares	07/03/2025	1357	156055
Harley Finkelstein 151 O'Connor St. Ground Floor Ottawa A6 K2P 2L8	Class A Subordinate Voting Shares	07/15/2025	19750	2302630.78
Harley Finkelstein 151 O'Connor St. Ground Floor Ottawa A6 K2P 2L8	Class A Subordinate Voting Shares	07/28/2025	1671	213398.73
Harley Finkelstein 151 O'Connor St. Ground Floor Ottawa A6 K2P 2L8	Class A Subordinate Voting Shares	08/04/2025	1357	163541.43
Harley Finkelstein 151 O'Connor St. Ground Floor Ottawa A6 K2P 2L8	Class A Subordinate Voting Shares	08/06/2025	66000	9806996.2
Harley Finkelstein 151 O'Connor St. Ground Floor Ottawa A6 K2P 2L8	Class A Subordinate Voting Shares	08/15/2025	19750	2844784.08
Harley Finkelstein 151 O'Connor St. Ground Floor Ottawa A6 K2P 2L8	Class A Subordinate Voting Shares	08/28/2025	1713	243301.16
Harley Finkelstein 151 O'Connor St. Ground Floor Ottawa A6 K2P 2L8	Class A Subordinate Voting Shares	09/02/2025	1357	185749.42
Harley Finkelstein 151 O'Connor St. Ground Floor Ottawa A6 K2P 2L8	Class A Subordinate Voting Shares	09/09/2025	4873	704724.98
Harley Finkelstein 151 O'Connor St. Ground Floor Ottawa A6 K2P 2L8	Class A Subordinate Voting Shares	09/15/2025	3825	551177.91
Harley Finkelstein 151 O'Connor St. Ground Floor Ottawa A6 K2P 2L8	Class A Subordinate Voting Shares	09/15/2025	19750	2845951.3

144: Remarks and Signature

Remarks

Date of Notice

Date of Plan Adoption or Giving of Instruction, If Relying on Rule 10b5-1

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

What shares does the SHOP Form 144 propose to sell?

The notice proposes sale of 10,261 and 171,145 Class A Subordinate Voting Shares to be sold on 09/22/2025 on NASDAQ.

Why were the securities acquired that are being sold under Rule 144?

The securities were acquired through vesting of RSUs and options on 09/22/2025, as stated in the filing.

Who has sold SHOP shares in the past three months according to the filing?

The filing lists multiple sales by Harley Finkelstein, including sales on dates from 06/30/2025 to 09/15/2025.

What was the largest recent insider sale reported in the filing?

A sale of 66,000 shares on 08/06/2025 produced gross proceeds of $9,806,996.20.

On which exchange will the proposed sales be executed?

The filing states that the proposed sales will be executed on NASDAQ.