Schaffer Ryan 4

What Happened
Ryan Schaffer, Chief Financial Officer of Expensify, reported a mix of acquisitions and disposals in mid‑March 2026. On March 13 he purchased 28,141 shares under the Expensify 2021 Stock Purchase & Matching Plan (SPMP) for $0.82/share ($23,076) and received 8,705 matched shares (no cash paid). On March 15 he recorded the exercise/conversion of a derivative for 3,922 shares (listed at $0.00). He later sold 3,333 shares on March 17 at $0.76 ($2,533) and 2,700 shares on March 24 at $0.84 ($2,268). Net acquired (gross) in these entries = 40,768 shares acquired; total cash proceeds from the two reported sales = $4,801. Several derivative entries at $0.00 appear related to the exercise/settlement process.

Key Details

• Transaction dates: March 13–24, 2026; Form 4 filed June 11, 2026 (covering period of report 2026-03-13). The filing was submitted well after the March transactions.
• Prices and amounts: 28,141 shares @ $0.82 (purchase, $23,076); 8,705 shares @ $0.00 (matched grant); exercise/conversion of 3,922 derivative shares at $0.00; sales of 3,333 @ $0.76 ($2,533) and 2,700 @ $0.84 ($2,268).
• Shares owned after the transactions: not disclosed in the supplied filing excerpt.
• Notable footnotes: purchases under the SPMP (F1), matched share grant (F2), RSU/derivative settlements referenced (F3, F9), sales to cover tax obligations and weighted‑average sale price ranges noted (F4–F7), LT50 share conversion/restrictions (F10), and deposit into the Expensify Voting Trust while retaining voting/investment control (F11).
• Filing timeliness: the Form 4 was filed roughly three months after the March transactions (appears late relative to the usual two‑business‑day reporting window).

Context

• The activity combines a planned employee purchase/matching plan and derivative/RSU settlement mechanics with small open‑market sales (likely tax withholding or covering exercise costs). The sales reported are small in dollar terms (~$4.8k) relative to the purchases and awards.
• For derivative/RSU items: the filing shows exercise/conversion entries at $0.00 and matching/grant entries — these often reflect vesting/settlement mechanics rather than a market directional bet; some shares were then sold (consistent with tax withholding).
• No inference about motivation should be drawn beyond the transactional facts; the late filing may be relevant for compliance review by investors tracking insider activity.