Waystar Holding Corp.
Waystar Holding Corp. (WAY) Insider Trading
Form 4 buy vs sell counts, ratio, and sentiment — switch this quarter or last 12 months; chart and transactions below.
SEC EDGAR · FMP · WAY · as of Jun 8, 2026
Activity summary
Buy transactions
1
P-Purchase only
Sell transactions
27
12 Months
Buy/Sell ratio
0.04
Buy/Sell (by trades)
Overall sentiment
Waystar Holding Corp. insiders have been primarily selling shares over the past 12 Months. Selling activity is often driven by pre-scheduled Rule 10b5-1 plans rather than negative sentiment toward the company.
▸ Source: SEC EDGAR · Form 3 & 4 · via Financial Modeling Prep · Buy = P-Purchase only · Sell = S-Sale only
As of Jun 8, 2026
WAY insider buying and selling by quarter
WAY insider selling · WAY insider buying stocks · quarterly insider activity
Mobile shows last 4Q · Desktop shows full 8Q
▸ Source: SEC EDGAR · Form 3 & 4 · via Financial Modeling Prep · last 8 quarters
As of Jun 8, 2026
Active insiders
Most active in past 12 months · WAY ceo insider trading
Showing all insiders · Click a card to filter the transactions table below
▸ Aggregated from reportingName · top 5 by trade count (12M) · no extra API
Recent insider transactions
WAY executive sell shares · WAY board member insider trading · WAY insider trading SEC filing
Scroll horizontally to see all columns
| Date | Insider | Type | Shares | Value | Filing |
|---|---|---|---|---|---|
| Jun 3, 2026 | DeMichiei Robert Director | Award | 9,303 | — | Form 4 |
| Jun 3, 2026 | Gupta Aashima Director | Award | 9,303 | — | Form 4 |
| Jun 3, 2026 | Roman Michael F Director | Award | 9,303 | — | Form 4 |
| Jun 3, 2026 | Riefberg Vivian E. Director | Award | 9,303 | — | Form 4 |
| Jun 3, 2026 | MILLER HEIDI Director | Award | 9,303 | — | Form 4 |
| Jun 3, 2026 | Hung Priscilla Director | Award | 9,303 | — | Form 4 |
| Jun 3, 2026 | DRISCOLL JOHN PATRICK Director | Award | 9,303 | — | Form 4 |
| Mar 9, 2026 | Miller Melissa F. (Missy) Chief Marketing Officer | Award | 61,703 | — | Form 4 |
| Mar 9, 2026 | Wittman Kimberly S. CPO | Award | 61,703 | — | Form 4 |
| Mar 9, 2026 | PACKER GREGORY R Chief Legal officer | Award | 65,817 | — | Form 4 |
| Mar 9, 2026 | Chan William Chief Product & AI Officer | Award | 82,271 | — | Form 4 |
| Mar 9, 2026 | Bridge T. Craig Chief Transformation Officer | Award | 87,413 | — | Form 4 |
| Mar 9, 2026 | Schremser Christopher L. CTO | Award | 87,413 | — | Form 4 |
| Mar 9, 2026 | Oreskovich Steven M CFO | Award | 82,271 | — | Form 4 |
| Mar 9, 2026 | Hawkins Matthew J. CEO · Director | Award | 257,096 | — | Form 4 |
| Mar 2, 2026 | MILLER HEIDI Director | Purchase | 7,200 | $189K | Form 4 |
| Jan 20, 2026 | Sinclair III Eric L. (Ric) Chief Business Officer | Option | 32,663 | $135K | Form 4 |
| Jan 20, 2026 | Sinclair III Eric L. (Ric) Chief Business Officer | Option | 7,562 | $138K | Form 4 |
| Jan 20, 2026 | Sinclair III Eric L. (Ric) Chief Business Officer | Sale | 40,225 | $1.21M⚡ | Form 4 |
| Dec 22, 2025 | Sinclair III Eric L. (Ric) Chief Business Officer | Option | 9,701 | $40K | Form 4 |
| Dec 22, 2025 | Sinclair III Eric L. (Ric) Chief Business Officer | Sale | 9,701 | $318K | Form 4 |
| Dec 10, 2025 | Schremser Christopher L. CTO | Option | 8,623 | $36K | Form 4 |
| Dec 10, 2025 | Schremser Christopher L. CTO | Sale | 8,623 | $262K | Form 4 |
| Nov 25, 2025 | Miller Melissa F. (Missy) Chief Marketing Officer | Option | 3,400 | $62K | Form 4 |
| Nov 25, 2025 | Miller Melissa F. (Missy) Chief Marketing Officer | Sale | 3,400 | $126K | Form 4 |
Miller Melissa F. (Missy)
Chief Marketing Officer
Date
Mar 9
Shares
61,703
Price
—
Value
—
Bridge T. Craig
Chief Transformation Officer
Date
Mar 9
Shares
87,413
Price
—
Value
—
Sinclair III Eric L. (Ric)
Chief Business Officer
Date
Jan 20
Shares
32,663
Price
$4.14
Value
$135K
Sinclair III Eric L. (Ric)
Chief Business Officer
Date
Jan 20
Shares
7,562
Price
$18.19
Value
$138K
Sinclair III Eric L. (Ric)
Chief Business Officer
Date
Jan 20
Shares
40,225
Price
$30.08
Value
$1.21M ⚡
Sinclair III Eric L. (Ric)
Chief Business Officer
Date
Dec 22
Shares
9,701
Price
$4.14
Value
$40K
Sinclair III Eric L. (Ric)
Chief Business Officer
Date
Dec 22
Shares
9,701
Price
$32.82
Value
$318K
Miller Melissa F. (Missy)
Chief Marketing Officer
Date
Nov 25
Shares
3,400
Price
$18.19
Value
$62K
Miller Melissa F. (Missy)
Chief Marketing Officer
Date
Nov 25
Shares
3,400
Price
$37.00
Value
$126K
⚡ = value ≥ $1M · Award/Option price shows — · formType=4 · securityName=Common Stock · url → sec.gov/Archives/edgar
▸ Source: SEC EDGAR · Form 4 filings · ⚡ = value ≥ $1M · Award/Option price shows —
About WAY insider trading
WAY insider trades
Waystar Holding Corp. (WAY) insider trading data is sourced from SEC Form 4 filings submitted by corporate insiders, including Sinclair III Eric L. (Ric) (Chief Business Officer), Schremser Christopher L. (CTO), Hawkins Matthew J. (CEO · Director). Over the past 12 months, 5 insiders have filed transactions with the SEC. WAY insiders have been primarily selling, which may reflect pre-scheduled Rule 10b5-1 plan executions.
For Waystar Holding Corp.'s institutional ownership breakdown and insider ownership percentage, see the Ownership tab → Ownership tab →
Frequently asked questions
WAY insider trading · 5 questionsThe insiders of Waystar Holding Corp. (WAY) include executives and directors such as Sinclair III Eric L. (Ric) (Chief Business Officer), Schremser Christopher L. (CTO), Hawkins Matthew J. (CEO · Director), among others. Over the past 12 months, 5 insiders have filed Form 4 transactions with the SEC. Insider transactions are required to be reported within 2 business days of the trade date.
▸ Source: FMP /stable/insider-trading/search · SEC EDGAR Form 3 & 4 · acquisitionOrDisposition A=Buy, D=Sell · RSU vesting (M-Exempt) excluded from sentiment bar · As of Jun 8, 2026