Waystar Holding Corp (WAY) insider trading

Recent insider transactions reported to the SEC on Form 4 — directors and officers buying or selling their own company’s stock. Sourced directly from public SEC filings, latest filed Oct 7, 2026.

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Filings shown
42
Open-market buys
1
Open-market sells
13
Buys, 10b5-1 box not checked
1 of 1

Counts cover the 42 most recent Form 4 filings Tradune holds for WAY (filed Oct 21 – Oct 7, 2026); the score below covers only the trailing 90 days (0 buys, 4 sells). No completed check of WAY's Form 4 list on SEC EDGAR is on record yet; the latest WAY filing Tradune holds was filed Oct 7, 2026. This is not guaranteed to be the complete record — see WAY's full Form 4 filing history on SEC EDGAR.

Open-market activity, last 90 days

Purchases (Form 4 code P) and sales (code S) on the 12 filings Tradune holds for WAY filed Aug 3 – Oct 7, 2026. Grants, exercises, tax withholding and the other Form 4 transaction codes are left out.

4 open-market sales by Rule 10b5-1 checkbox

On filings with the 10b5-1 box checked
4 sales· 247,500 sh
checkbox disclosed
On filings with the box not checked
0 sales· 0 sh
not proof that no plan exists
Not comparable
0 sales· 0 sh
filed before Apr 1, 2023, or no checkbox value in the filing data

Counts are Form 4 lines as filed. The checkbox is one per filing, so every sale on a filing with the box checked is counted there even if only some of its transactions were under a plan; it records what the filer disclosed, and the three categories are not a judgement about why a sale was made.

Open-market purchases and sales by insider
Insider Buys Sells Shares bought Shares sold Value
Matthew J. HawkinsChief Executive Officer 0 4 — 247,500 −$6,370,481

Value = shares × the price reported on each Form 4 (+ purchases, − sales); every open-market line in this window disclosed a price.

Insider-activity score
0/ 100
Net insider sales
0 distinct buyers0 buy · 4 sell tx

Summarises ~90 days of public SEC Form 4 activity — more distinct buyers, officer involvement and net buying score higher. A description of filing activity, not a rating or buy signal. How this score is computed →

How to read this: an open-market purchase (Form 4 code P) is a buy at the market price with the insider’s own money, as opposed to a grant, award or option exercise; an open-market sale is code S. When two or more distinct insiders report open-market purchases in the same 90-day window, this site labels that a cluster — a definition, not a forecast; see insider cluster buying. “Held after” is Form 4 Table I column 5; “Change” = shares ÷ holdings before the trade (held after − shares for an acquisition, held after + shares for a disposition).

Insider Buying at WAY

Insiders reported 1 open-market purchase of WAY between Oct 21, 2025 and Oct 7, 2026, across 1 distinct buyer. The most recent purchase was reported by Heidi Miller (Director) on Mar 2, 2026. Grants, option exercises, and tax-withholding transactions are excluded from these counts.

Recent Form 4 filings

Source: SEC EDGAR Form 4 · transaction codes explained

Matthew J. Hawkins Chief Executive Officer · filed Oct 7, 2026 · SEC ↗
TransactionSharesPriceHeld afterChange†Date
Open-market sale 10b5-1 box checked 82,500 $26.23 1,804,794 −4.4% Oct 6, 2026
Option exercise 82,500 $4.14 1,887,294 +4.6% Oct 6, 2026
Option exercise Stock Options (right to buy) 82,500 — — — Oct 6, 2026

† change in this filer’s own reported holding line (Form 4 Table I, col. 5), not of total company ownership; small prior holdings produce large percentages, so under 100 shares the prior holding is shown instead.

“10b5-1 box checked” = the filer checked the Form 4 box stating that a transaction on the filing was made under a plan intended to satisfy Rule 10b5-1(c); “10b5-1 box not checked” = the box was left blank, which does not prove that no plan exists. The box applies to Form 4s filed from April 1, 2023; older filings, and boxes we could not read, carry no tag. What the 10b5-1 box means.

William Chan Chief Product & AI Officer · filed Oct 6, 2026 · SEC ↗
TransactionSharesPriceHeld afterChange†Date
Tax withholding 9,560 $26.07 1,571,252 −0.6% Oct 5, 2026
Amit Khanna Chief Prod. & Tech. Officer · filed Sep 8, 2026 · SEC ↗
TransactionSharesPriceHeld afterChange†Date
Grant / award 390,625 — 390,625 — Aug 17, 2026
Matthew J. Hawkins Chief Executive Officer · filed Sep 3, 2026 · SEC ↗
TransactionSharesPriceHeld afterChange†Date
Open-market sale 10b5-1 box checked 82,500 $25.97 1,804,794 −4.4% Sep 2, 2026
Option exercise Stock Options (right to buy) 82,500 — — — Sep 2, 2026
Option exercise 82,500 $4.14 1,887,294 +4.6% Sep 2, 2026
Tax withholding 30,287 $25.73 1,804,794 −1.7% Sep 1, 2026
T. Craig Bridge Chief Transformation Officer · filed Sep 3, 2026 · SEC ↗
TransactionSharesPriceHeld afterChange†Date
Tax withholding 30,792 $25.73 833,234 −3.6% Sep 1, 2026
Gregory R. Packer Chief Legal officer · filed Sep 3, 2026 · SEC ↗
TransactionSharesPriceHeld afterChange†Date
Tax withholding 6,754 $25.73 418,255 −1.6% Sep 1, 2026
Alpana Wegner Chief Financial Officer · filed Aug 14, 2026 · SEC ↗
TransactionSharesPriceHeld afterChange†Date
Grant / award 162,112 — 162,112 — Jul 24, 2026
Matthew J. Hawkins Chief Executive Officer · filed Aug 13, 2026 · SEC ↗
TransactionSharesPriceHeld afterChange†Date
Option exercise Stock Options (right to buy) 60,038 — — — Aug 13, 2026
Option exercise 60,038 $4.14 1,895,119 +3.3% Aug 13, 2026
Open-market sale 10b5-1 box checked 60,038 $25.01 1,835,081 −3.2% Aug 13, 2026
Open-market sale 10b5-1 box checked 22,462 $25.04 1,835,081 −1.2% Aug 11, 2026
Option exercise Stock Options (right to buy) 22,462 — — — Aug 11, 2026
Option exercise 22,462 $4.14 1,857,543 +1.2% Aug 11, 2026
Todd Charles Woods Chief Commercial Officer · filed Aug 10, 2026 · SEC ↗
TransactionSharesPriceHeld afterChange†Date
Grant / award 90,827 — 220,506 +70% Aug 1, 2026
T. Craig Bridge Chief Transformation Officer · filed Aug 3, 2026 · SEC ↗
TransactionSharesPriceHeld afterChange†Date
Grant / award 205,470 — 864,026 +31% Aug 1, 2026
Matthew J. Hawkins Chief Executive Officer · filed Aug 3, 2026 · SEC ↗
TransactionSharesPriceHeld afterChange†Date
Grant / award 908,265 — 1,835,081 +98% Aug 1, 2026
Gregory R. Packer Chief Legal officer · filed Aug 3, 2026 · SEC ↗
TransactionSharesPriceHeld afterChange†Date
Grant / award 232,061 — 425,009 +120% Aug 1, 2026
Tax withholding 4,016 $23.69 192,948 −2.0% Apr 6, 2026
Matthew J. Hawkins Chief Executive Officer · filed Jul 17, 2026 · SEC ↗
TransactionSharesPriceHeld afterChange†Date
Option exercise 36,901 $4.14 963,717 +4.0% Jul 16, 2026
Open-market sale 10b5-1 box checked 36,901 $23.09 926,816 −3.8% Jul 16, 2026
Option exercise Stock Options (right to buy) 36,901 — — — Jul 16, 2026
Option exercise Stock Options (right to buy) 33,099 — — — Jul 15, 2026
Open-market sale 10b5-1 box checked 33,099 $23.02 926,816 −3.4% Jul 15, 2026
Option exercise 33,099 $4.14 959,915 +3.6% Jul 15, 2026
Kimberly S. Wittman Chief People Officer · filed Jun 9, 2026 · SEC ↗
TransactionSharesPriceHeld afterChange†Date
Tax withholding 2,731 $19.23 270,233 −1.0% Jun 9, 2026
Christopher L. Schremser Chief Technology Officer · filed Jun 9, 2026 · SEC ↗
TransactionSharesPriceHeld afterChange†Date
Tax withholding 14,751 $19.23 495,033 −2.9% Jun 9, 2026
T. Craig Bridge Chief Transformation Officer · filed Jun 9, 2026 · SEC ↗
TransactionSharesPriceHeld afterChange†Date
Tax withholding 12,212 $19.23 658,556 −1.8% Jun 9, 2026
Matthew J. Hawkins Chief Executive Officer · filed Jun 9, 2026 · SEC ↗
TransactionSharesPriceHeld afterChange†Date
Tax withholding 47,754 $19.23 926,816 −4.9% Jun 9, 2026
Melissa F. (Missy) Miller Chief Marketing Officer · filed Jun 9, 2026 · SEC ↗
TransactionSharesPriceHeld afterChange†Date
Tax withholding 2,887 $19.23 252,077 −1.1% Jun 9, 2026
Steven M. Oreskovich Chief Financial Officer · filed Jun 9, 2026 · SEC ↗
TransactionSharesPriceHeld afterChange†Date
Tax withholding 12,583 $19.23 424,200 −2.9% Jun 9, 2026
Aashima Gupta Director · filed Jun 3, 2026 · SEC ↗
TransactionSharesPriceHeld afterChange†Date
Grant / award 9,303 — 14,437 +181% Jun 3, 2026
Robert DeMichiei Director · filed Jun 3, 2026 · SEC ↗
TransactionSharesPriceHeld afterChange†Date
Grant / award 9,303 — 46,199 +25% Jun 3, 2026
Vivian E. Riefberg Director · filed Jun 3, 2026 · SEC ↗
TransactionSharesPriceHeld afterChange†Date
Grant / award 9,303 — 23,132 +67% Jun 3, 2026
Michael F. Roman Director · filed Jun 3, 2026 · SEC ↗
TransactionSharesPriceHeld afterChange†Date
Grant / award 9,303 — 14,437 +181% Jun 3, 2026
Priscilla Hung Director · filed Jun 3, 2026 · SEC ↗
TransactionSharesPriceHeld afterChange†Date
Grant / award 9,303 — 23,132 +67% Jun 3, 2026
John Patrick Driscoll Director · filed Jun 3, 2026 · SEC ↗
TransactionSharesPriceHeld afterChange†Date
Grant / award 9,303 — 100,060 +10% Jun 3, 2026

Listing the 25 most recent of 42 Form 4 filings held for WAY; the 17 older filings (filed Oct 21 – Jun 3, 2026) are counted above but not listed here — see WAY's full Form 4 filing history on SEC EDGAR.

Insider filings reported around the same time

Other companies whose most recent Form 4 was filed closest to WAY's (Oct 7, 2026).

Frequently asked about WAY insider activity

How many insiders bought WAY stock in these Form 4 filings?

1 distinct insider at Waystar Holding Corp reported 1 open-market purchase (Form 4 code P) of WAY shares between Oct 21, 2025 and Oct 7, 2026, the most recent filed by Heidi Miller (Director) on Mar 2, 2026. Grants, option exercises, and tax-withholding transactions are excluded from these counts.

Who filed the most recent Form 4 for WAY?

The most recent Form 4 on this page was filed by Matthew J. Hawkins (Chief Executive Officer) on Oct 7, 2026, reporting 3 transactions. The original document is linked from the filing list above on SEC EDGAR. Amended filings (Form 4/A) may later revise reported figures.

What was the largest open-market WAY insider sale shown?

The largest open-market sale among the filings shown was 82,500 WAY shares at $26.23 (about $2,163,868) by Matthew J. Hawkins (Chief Executive Officer) on Oct 6, 2026. Value is shares × the price reported on the Form 4; that Form 4 has the Rule 10b5-1 box checked.

Do the recent WAY insider purchases have the Form 4 10b5-1 box checked?

No. The one WAY open-market purchase shown was reported with the Rule 10b5-1 box not checked. A blank box records what the filer disclosed; it does not prove that no plan exists. Latest: Heidi Miller (Director) on Mar 2, 2026, 7,200 shares.

New to Form 4s? The transaction codes, the 90-day window and the 0–100 score are defined on the insider-activity score methodology page.

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This score summarizes SEC Form 4 filing activity over the trailing 90 days. It is descriptive, not predictive — not a rating, recommendation, or investment advice. Data: SEC EDGAR (public domain), as filed; amendments may revise figures. Tradune is not a registered investment adviser.

Data as filed; amended filings (Form 4/A) may revise figures. Sales may occur under prearranged Rule 10b5-1 trading plans.