WAY

insider transactions

Waystar Holding Corp. — buys & sells by directors, officers and 10% owners (SEC Form 4).

30D 90D 1Y

Net shares · 365d

-33.0K

7.2K buy · 40.2K sell

Net value · 365d

-$1.0M

$189.0K in · $1.2M out

Sentiment · 365d

Net selling

14% buying · 86% selling

Open-market trades · 365d

7.2K buy · 40.2K sell

Net buy / sell volume

Tap or hover the chart for daily net volume. Green = net buying, red = net selling.

All transactions

Other·F
Jun 9, 26

Kimberly S. Wittman

Chief People Officer

$52.5K

2.7K sh · $19.23

Own -1%
Other·F
Jun 9, 26

Christopher L. Schremser

Chief Technology Officer

$283.7K

14.8K sh · $19.23

Own -3%
Other·F
Jun 9, 26

Steven M Oreskovich KEY

Chief Financial Officer

$242.0K

12.6K sh · $19.23

Own -3%
Other·F
Jun 9, 26

Melissa F. (Missy) Miller

Chief Marketing Officer

$55.5K

2.9K sh · $19.23

Own -1%
Other·F
Jun 9, 26

Matthew J. Hawkins KEY

Chief Executive Officer

$918.3K

47.8K sh · $19.23

Own -5%
Other·F
Jun 9, 26

Craig T. Bridge

Chief Transformation Officer

$234.8K

12.2K sh · $19.23

Own -2%
Grant·A
Jun 3, 26

Michael F Roman

Director

$0

9.3K sh

Own +181%
Grant·A
Jun 3, 26

Vivian E. Riefberg

Director

$0

9.3K sh

Own +67%
Grant·A
Jun 3, 26

Heidi Miller

Director

$0

9.3K sh

Own +29%
Grant·A
Jun 3, 26

Aashima Gupta

Director

$0

9.3K sh

Own +181%
Grant·A
Jun 3, 26

Robert Demichiei

Director

$0

9.3K sh

Own +25%
Grant·A
Jun 3, 26

John Patrick Driscoll

Director

$0

9.3K sh

Own +10%
Grant·A
Mar 9, 26

Kimberly S. Wittman

Chief People Officer

$0

61.7K sh

Own +29%
Grant·A
Mar 9, 26

Christopher L. Schremser

Chief Technology Officer

$0

87.4K sh

Own +21%
Grant·A
Mar 9, 26

Gregory R Packer

Chief Legal officer

$0

65.8K sh

Own +50%
Grant·A
Mar 9, 26

Steven M Oreskovich KEY

Chief Financial Officer

$0

82.3K sh

Own +23%
Grant·A
Mar 9, 26

Melissa F. (Missy) Miller

Chief Marketing Officer

$0

61.7K sh

Own +32%
Grant·A
Mar 9, 26

Matthew J. Hawkins KEY

Chief Executive Officer

$0

257.1K sh

Own +36%
Grant·A
Mar 9, 26

William Chan

Chief Product & AI Officer

$0

82.3K sh

Own +5%
Grant·A
Mar 9, 26

Craig T. Bridge

Chief Transformation Officer

$0

87.4K sh

Own +15%
Buy·P
Mar 2, 26

Heidi Miller

Director

$189.0K

7.2K sh · $26.25

Own New
Exercise·M
Jan 20, 26

Eric L. (Ric) Sinclair III

Chief Business Officer · 10b5-1

$0

32.7K sh

Own New
Exercise·M
Jan 20, 26

Eric L. (Ric) Sinclair III

Chief Business Officer · 10b5-1

$0

7.6K sh

Own +5%
Sell·S
Jan 20, 26

Eric L. (Ric) Sinclair III

Chief Business Officer · 10b5-1

$1.2M

40.2K sh · $30.08

Own -8%
Exercise·M
Jan 20, 26

Eric L. (Ric) Sinclair III

Chief Business Officer · 10b5-1

$135.2K

32.7K sh · $4.14

Own +7%
Exercise·M
Jan 20, 26

Eric L. (Ric) Sinclair III

Chief Business Officer · 10b5-1

$137.6K

7.6K sh · $18.19

Own +2%

Date▾	Insider	Role	Type	Shares	Own Δ	Price	Value
Jun 9, 2026	Kimberly S. Wittman	Chief People Officer	Other F	2.7K	-1%	$19.23	$52.5K
Jun 9, 2026	Christopher L. Schremser	Chief Technology Officer	Other F	14.8K	-3%	$19.23	$283.7K
Jun 9, 2026	Steven M Oreskovich KEY	Chief Financial Officer	Other F	12.6K	-3%	$19.23	$242.0K
Jun 9, 2026	Melissa F. (Missy) Miller	Chief Marketing Officer	Other F	2.9K	-1%	$19.23	$55.5K
Jun 9, 2026	Matthew J. Hawkins KEY	Chief Executive Officer	Other F	47.8K	-5%	$19.23	$918.3K
Jun 9, 2026	Craig T. Bridge	Chief Transformation Officer	Other F	12.2K	-2%	$19.23	$234.8K
Jun 3, 2026	Michael F Roman	Director	Grant A	9.3K	+181%	—	$0
Jun 3, 2026	Vivian E. Riefberg	Director	Grant A	9.3K	+67%	—	$0
Jun 3, 2026	Heidi Miller	Director	Grant A	9.3K	+29%	—	$0
Jun 3, 2026	Aashima Gupta	Director	Grant A	9.3K	+181%	—	$0
Jun 3, 2026	Robert Demichiei	Director	Grant A	9.3K	+25%	—	$0
Jun 3, 2026	John Patrick Driscoll	Director	Grant A	9.3K	+10%	—	$0
Mar 9, 2026	Kimberly S. Wittman	Chief People Officer	Grant A	61.7K	+29%	—	$0
Mar 9, 2026	Christopher L. Schremser	Chief Technology Officer	Grant A	87.4K	+21%	—	$0
Mar 9, 2026	Gregory R Packer	Chief Legal officer	Grant A	65.8K	+50%	—	$0
Mar 9, 2026	Steven M Oreskovich KEY	Chief Financial Officer	Grant A	82.3K	+23%	—	$0
Mar 9, 2026	Melissa F. (Missy) Miller	Chief Marketing Officer	Grant A	61.7K	+32%	—	$0
Mar 9, 2026	Matthew J. Hawkins KEY	Chief Executive Officer	Grant A	257.1K	+36%	—	$0
Mar 9, 2026	William Chan	Chief Product & AI Officer	Grant A	82.3K	+5%	—	$0
Mar 9, 2026	Craig T. Bridge	Chief Transformation Officer	Grant A	87.4K	+15%	—	$0
Mar 2, 2026	Heidi Miller	Director	Buy P	7.2K	New	$26.25	$189.0K
Jan 20, 2026	Eric L. (Ric) Sinclair III 10b5-1	Chief Business Officer	Exercise M	32.7K	New	—	$0
Jan 20, 2026	Eric L. (Ric) Sinclair III 10b5-1	Chief Business Officer	Exercise M	7.6K	+5%	—	$0
Jan 20, 2026	Eric L. (Ric) Sinclair III 10b5-1	Chief Business Officer	Sell S	40.2K	-8%	$30.08	$1.2M
Jan 20, 2026	Eric L. (Ric) Sinclair III 10b5-1	Chief Business Officer	Exercise M	32.7K	+7%	$4.14	$135.2K
Jan 20, 2026	Eric L. (Ric) Sinclair III 10b5-1	Chief Business Officer	Exercise M	7.6K	+2%	$18.19	$137.6K

About WAY insider trading

This page tracks insider transactions for Waystar Holding Corp. (WAY) reported to the U.S. Securities and Exchange Commission on Form 4. Corporate insiders — directors, executive officers and beneficial owners of more than 10% of the stock — must disclose their trades within two business days. Open-market purchases (code P) and sales (code S) made at the insider's discretion are the most-watched opportunistic signals, while awards (A), option exercises (M) and tax-withholding (F) reflect compensation rather than conviction. Trades marked 10b5-1 were made under a pre-arranged plan and are considered routine. A cluster buy — several insiders buying within a short window — is historically a stronger bullish indicator than any single trade.