Shopify Executive's $26.2M Stock Sale Adds to $7.9M Sold in Past 3 Months

Rhea-AI Filing Summary

Shopify insider Harley Finkelstein has filed Form 144 indicating a proposed sale of 249,408 Class A subordinate voting shares with an aggregate market value of approximately $26.27 million. The shares were acquired through vesting of RSUs and Options on June 23, 2025.

The filing reveals significant recent trading activity by Finkelstein over the past 3 months, including:

• Multiple sales between March and June 2025 totaling 77,233 shares
• Largest single transaction was 23,575 shares sold on June 16, 2025 for $2.55 million
• Total gross proceeds from previous sales amount to approximately $7.97 million

The proposed sale represents approximately 0.02% of Shopify's total outstanding Class A shares (1.22 billion shares). The transactions are to be executed through Solium Capital Inc. on the NASDAQ exchange.

Positive

• None.

Negative

• Significant insider selling: Harley Finkelstein has sold approximately 77,233 shares totaling over $7.9M in the past 3 months, showing a consistent pattern of share disposals
• New proposed sale of additional 249,408 shares (combined from two transactions) worth approximately $26.2M indicates continued selling pressure from insider

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	10262	1080956.24	1218135388	06/23/2025	NASDAQ
Class A Subordinate Voting Shares	Solium Capital Inc. Suite 1500 600-3rd Ave., SW Calgary A0 T2P 0G5	239146	25191639.64	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 RSUs	Issuer			19734	06/23/2025	Vesting of RSUs
Class A Subordinate Voting Shares	06/23/2025	Vesting of RSUs and Options	Issuer			239146	06/23/2025	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	03/28/2025	1713	170938.04
Harley Finkelstein 151 O'Connor St. Ground Floor Ottawa A6 K2P 2L8	Class A Subordinate Voting Shares	04/02/2025	1357	128773.88
Harley Finkelstein 151 O'Connor St. Ground Floor Ottawa A6 K2P 2L8	Class A Subordinate Voting Shares	04/14/2025	12250	1073644.35
Harley Finkelstein 151 O'Connor St. Ground Floor Ottawa A6 K2P 2L8	Class A Subordinate Voting Shares	04/23/2025	7500	693415
Harley Finkelstein 151 O'Connor St. Ground Floor Ottawa A6 K2P 2L8	Class A Subordinate Voting Shares	04/28/2025	1700	166838
Harley Finkelstein 151 O'Connor St. Ground Floor Ottawa A6 K2P 2L8	Class A Subordinate Voting Shares	05/05/2025	1357	129471.37
Harley Finkelstein 151 O'Connor St. Ground Floor Ottawa A6 K2P 2L8	Class A Subordinate Voting Shares	05/15/2025	19750	2190806.28
Harley Finkelstein 151 O'Connor St. Ground Floor Ottawa A6 K2P 2L8	Class A Subordinate Voting Shares	05/28/2025	1720	182777.18
Harley Finkelstein 151 O'Connor St. Ground Floor Ottawa A6 K2P 2L8	Class A Subordinate Voting Shares	06/02/2025	1356	144102.12
Harley Finkelstein 151 O'Connor St. Ground Floor Ottawa A6 K2P 2L8	Class A Subordinate Voting Shares	06/09/2025	4955	541399.16
Harley Finkelstein 151 O'Connor St. Ground Floor Ottawa A6 K2P 2L8	Class A Subordinate Voting Shares	06/16/2025	23575	2546741.24

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 Class A shares is Harley Finkelstein planning to sell in June 2025?

According to the Form 144 filing, Harley Finkelstein plans to sell a total of 249,408 Class A subordinate voting shares (10,262 + 239,146 shares) through Solium Capital Inc., with an approximate sale date of June 23, 2025.

What is the total market value of SHOP shares being sold in this Form 144?

The total aggregate market value of the shares to be sold is $26,272,595.88 (calculated as $1,080,956.24 + $25,191,639.64) according to the Form 144 filing.

How did Harley Finkelstein acquire the SHOP shares being sold?

The shares were acquired through two transactions on June 23, 2025: 19,734 shares from vesting of RSUs and 239,146 shares from vesting of RSUs and Options, both acquired directly from the issuer (Shopify).

What is the total value of SHOP shares Harley Finkelstein sold in the past 3 months?

Between March 28, 2025, and June 16, 2025, Harley Finkelstein sold a total of 77,233 Class A subordinate voting shares for gross proceeds of approximately $7,968,906.62 through multiple transactions.

What percentage of SHOP's outstanding shares are being sold in this Form 144?

The 249,408 shares being sold represent approximately 0.02% of Shopify's total outstanding Class A subordinate voting shares, which currently stand at 1,218,135,388 shares.