Shopify Officer Harley Finkelstein Files Form 144 for $22.8M Share Sale

Executive Summary

On September 18, 2026, Harley Finkelstein, Officer (President) of Shopify Inc., filed Form 144 indicating the proposed sale of up to 177,318 Class A Subordinate Voting Shares, representing an aggregate market value of approximately $22.84 million.

Transaction Details

• Security: Class A Subordinate Voting Shares
• Proposed Sale Size: 177,318 shares across two tranches:
  • Tranche 1: 5,268 shares ($678,481.17)
  • Tranche 2: 172,050 shares ($22,158,319.50)
• Approximate Sale Date: September 19, 2026
• Broker: Solium Capital Inc.
• Securities Outstanding: 1,208,570,347 shares as of July 31, 2026

Origin & Nature of Transaction

• Acquisition Sources: Vesting of RSUs (10,131 shares) and exercise/vesting of RSUs and Options (172,050 shares), scheduled for September 19, 2026.
• Trading Plan / Mechanism: Sales are executed pursuant to a pre-arranged Rule 10b5-1 trading plan established on November 14, 2025, along with sell-to-cover transactions for taxes and fees associated with RSU vesting.

Historical Context

Over the preceding three months, the filer reported gross proceeds of approximately $12.44 million from several sales totaling 77,390 shares, reflecting regular structured dispositions under established plans.