Waystar Holding Corp. Insider Trading

WAY

⊜ Compare

Last 12 months

Insiders bought 189K and sold $10.6M on the open market.

All of the selling was scheduled in advance under 10b5-1 plans.

Net open-market

−$10.4M

1 buy · 10 sales

Under a 10b5-1 plan

100%

of the value sold

Insiders who bought / sold

1 / 4

executives and directors

Last open-market buy

Mar 2026

Mar 2, 2026

Get an email when WAY's executives or directors buy, or make a large sale outside a plan.

Trades · last 2 years

Date	Insider	Trade	Shares	Price	Value	Of their stake	Filing
Oct 6	Matthew J. Hawkins Chief Executive Officer	Sold10b5-1 plan	82,500	$26.23	$2.16M	4.4%	Form 4
Sep 2	Matthew J. Hawkins Chief Executive Officer	Sold10b5-1 plan	82,500	$25.97	$2.14M	4.4%	Form 4
Aug 11 – 13	Matthew J. Hawkins Chief Executive Officer	Sold10b5-1 plan 2 parts	82,500	$25.02 average	$2.06M	4.3%	Form 4
Jul 15 – 16	Matthew J. Hawkins Chief Executive Officer	Sold10b5-1 plan 2 parts	70,000	$23.06 average	$1.61M	7.0%	Form 4
Mar 2	Heidi Miller Director	Bought	7,200	$26.25	189K	23%	Form 4
Jan 20	Eric L. (ric) Sinclair III Chief Business Officer	Sold10b5-1 plan	40,225	$30.08	$1.21M	7.8%	Form 4
Dec 22, 2025	Eric L. (ric) Sinclair III Chief Business Officer	Sold10b5-1 plan	9,701	$32.82	318K	2.0%	Form 4
Dec 10, 2025	Christopher L. Schremser Chief Technology Officer	Sold10b5-1 plan	8,623	$30.41	262K	2.0%	Form 4
Nov 25, 2025	Melissa F. (missy) Miller Chief Marketing Officer	Sold10b5-1 plan	3,400	$37.00	126K	1.7%	Form 4
Nov 20, 2025	Eric L. (ric) Sinclair III Chief Business Officer	Sold10b5-1 plan	9,701	$35.27	342K	2.0%	Form 4
Nov 10, 2025	Christopher L. Schremser Chief Technology Officer	Sold10b5-1 plan	8,623	$36.12	311K	2.0%	Form 4
Oct 20, 2025	Eric L. (ric) Sinclair III Chief Business Officer	Sold10b5-1 plan	9,701	$36.94	358K	2.0%	Form 4
Oct 15, 2025	Matthew J. Hawkins Chief Executive Officer	Sold10b5-1 plan	200	$38.00	8K	<0.1%	Form 4
Oct 10, 2025	Christopher L. Schremser Chief Technology Officer	Sold10b5-1 plan	8,623	$36.21	312K	2.0%	Form 4
Sep 22, 2025 – Sep 23, 2025	Matthew J. Hawkins Chief Executive Officer	Sold10b5-1 plan 2 parts	25,000	$38.08 average	952K	3.4%	Form 4
Sep 22, 2025	Eric L. (ric) Sinclair III Chief Business Officer	Sold10b5-1 plan	9,701	$37.63	365K	2.0%	Form 4
Sep 12, 2025	Bain Capital Fund XI, L.p. Large holder	SoldNo plan	4,295,139	$39.21	$168M	24%	Form 4
Sep 12, 2025	Derby Luxco S.a R.l. Large holder	SoldNo plan	7,766,088	$39.21	$305M	24%	Form 4
Sep 12, 2025	CPP Investment Board Private Holdings (4) Inc. Large holder	SoldNo plan	5,938,773	$39.21	$233M	24%	Form 4
Sep 12, 2025	Paul G Moskowitz Director	SoldNo plan	4,295,139	$39.21	$168M	24%	Form 4
Sep 10, 2025	Christopher L. Schremser Chief Technology Officer	Sold10b5-1 plan	8,623	$40.49	349K	2.0%	Form 4
Sep 10, 2025	Steven M Oreskovich Chief Financial Officer	Sold10b5-1 plan	16,666	$40.49	675K	4.5%	Form 4
Sep 8, 2025	T. Craig Bridge Chief Transformation Officer	Sold10b5-1 plan	85,000	$40.06	$3.41M	13%	Form 4
Sep 8, 2025	Eric L. (ric) Sinclair III Chief Business Officer	Sold10b5-1 plan	19,404	$40.03	777K	3.9%	Form 4
Aug 26, 2025	Melissa F. (missy) Miller Chief Marketing Officer	Sold10b5-1 plan	3,400	$37.01	126K	1.7%	Form 4
Aug 20, 2025	Eric L. (ric) Sinclair III Chief Business Officer	Sold10b5-1 plan	9,702	$35.11	341K	1.9%	Form 4
Aug 12, 2025	Matthew J. Hawkins Chief Executive Officer	Sold10b5-1 plan	46,667	$34.66	$1.62M	5.8%	Form 4
Aug 11, 2025	Christopher L. Schremser Chief Technology Officer	Sold10b5-1 plan	8,623	$34.49	297K	1.9%	Form 4
Jul 21, 2025	T. Craig Bridge Chief Transformation Officer	Sold10b5-1 plan	85,000	$37.09	$3.15M	11%	Form 4
Jul 21, 2025	Eric L. (ric) Sinclair III Chief Business Officer	Sold10b5-1 plan	9,702	$37.10	360K	1.9%	Form 4
Jul 15, 2025	Matthew J. Hawkins Chief Executive Officer	Sold10b5-1 plan	46,667	$38.26	$1.79M	5.8%	Form 4
Jul 10, 2025	Christopher L. Schremser Chief Technology Officer	Sold10b5-1 plan	8,623	$37.63	324K	1.9%	Form 4
Jun 25, 2025	Eric L. (ric) Sinclair III Chief Business Officer	Sold10b5-1 plan	9,702	$40.22	390K	1.9%	Form 4
Jun 20, 2025	Eric L. (ric) Sinclair III Chief Business Officer	Sold10b5-1 plan	9,702	$37.79	367K	1.9%	Form 4
Jun 11, 2025	Steven M Oreskovich Chief Financial Officer	Sold10b5-1 plan	16,396	$40.71	667K	4.3%	Form 4
Jun 11, 2025	Melissa F. (missy) Miller Chief Marketing Officer	Sold10b5-1 plan	6,072	$40.71	247K	3.1%	Form 4
Jun 11, 2025	T. Craig Bridge Chief Transformation Officer	Sold10b5-1 plan	15,946	$40.71	649K	2.0%	Form 4
Jun 10, 2025	Christopher L. Schremser Chief Technology Officer	Sold10b5-1 plan	8,623	$40.58	350K	1.9%	Form 4
Jun 10, 2025	Matthew J. Hawkins Chief Executive Officer	Sold10b5-1 plan	2,704	$40.57	110K	0.4%	Form 4
Jun 5, 2025	Matthew J. Hawkins Chief Executive Officer	SoldNo plan	59,836	$40.18	$2.4M	7.3%	Form 4

Oct 610b5-1 plan
Matthew J. Hawkins
Chief Executive Officer · sold 82,500 at $26.23
$2.16M
4.4% of stake
Sep 210b5-1 plan
Matthew J. Hawkins
Chief Executive Officer · sold 82,500 at $25.97
$2.14M
4.4% of stake
Aug 11 – 1310b5-1 plan
Matthew J. Hawkins
Chief Executive Officer · sold 82,500 at avg $25.02
$2.06M
4.3% of stake
Jul 15 – 1610b5-1 plan
Matthew J. Hawkins
Chief Executive Officer · sold 70,000 at avg $23.06
$1.61M
7.0% of stake
Mar 2
Heidi Miller
Director · bought 7,200 at $26.25
189K
23% of stake
Jan 2010b5-1 plan
Eric L. (ric) Sinclair III
Chief Business Officer · sold 40,225 at $30.08
$1.21M
7.8% of stake
Dec 22, 202510b5-1 plan
Eric L. (ric) Sinclair III
Chief Business Officer · sold 9,701 at $32.82
318K
2.0% of stake
Dec 10, 202510b5-1 plan
Christopher L. Schremser
Chief Technology Officer · sold 8,623 at $30.41
262K
2.0% of stake
Nov 25, 202510b5-1 plan
Melissa F. (missy) Miller
Chief Marketing Officer · sold 3,400 at $37.00
126K
1.7% of stake
Nov 20, 202510b5-1 plan
Eric L. (ric) Sinclair III
Chief Business Officer · sold 9,701 at $35.27
342K
2.0% of stake
Nov 10, 202510b5-1 plan
Christopher L. Schremser
Chief Technology Officer · sold 8,623 at $36.12
311K
2.0% of stake
Oct 20, 202510b5-1 plan
Eric L. (ric) Sinclair III
Chief Business Officer · sold 9,701 at $36.94
358K
2.0% of stake
Oct 15, 202510b5-1 plan
Matthew J. Hawkins
Chief Executive Officer · sold 200 at $38.00
8K
<0.1% of stake
Oct 10, 202510b5-1 plan
Christopher L. Schremser
Chief Technology Officer · sold 8,623 at $36.21
312K
2.0% of stake
Sep 22, 2025 – Sep 23, 202510b5-1 plan
Matthew J. Hawkins
Chief Executive Officer · sold 25,000 at avg $38.08
952K
3.4% of stake
Sep 22, 202510b5-1 plan
Eric L. (ric) Sinclair III
Chief Business Officer · sold 9,701 at $37.63
365K
2.0% of stake
Sep 12, 2025No plan
Bain Capital Fund XI, L.p.
Large holder · sold 4,295,139 at $39.21
$168M
24% of stake
Sep 12, 2025No plan
Derby Luxco S.a R.l.
Large holder · sold 7,766,088 at $39.21
$305M
24% of stake
Sep 12, 2025No plan
CPP Investment Board Private Holdings (4) Inc.
Large holder · sold 5,938,773 at $39.21
$233M
24% of stake
Sep 12, 2025No plan
Paul G Moskowitz
Director · sold 4,295,139 at $39.21
$168M
24% of stake
Sep 10, 202510b5-1 plan
Christopher L. Schremser
Chief Technology Officer · sold 8,623 at $40.49
349K
2.0% of stake
Sep 10, 202510b5-1 plan
Steven M Oreskovich
Chief Financial Officer · sold 16,666 at $40.49
675K
4.5% of stake
Sep 8, 202510b5-1 plan
T. Craig Bridge
Chief Transformation Officer · sold 85,000 at $40.06
$3.41M
13% of stake
Sep 8, 202510b5-1 plan
Eric L. (ric) Sinclair III
Chief Business Officer · sold 19,404 at $40.03
777K
3.9% of stake
Aug 26, 202510b5-1 plan
Melissa F. (missy) Miller
Chief Marketing Officer · sold 3,400 at $37.01
126K
1.7% of stake
Aug 20, 202510b5-1 plan
Eric L. (ric) Sinclair III
Chief Business Officer · sold 9,702 at $35.11
341K
1.9% of stake
Aug 12, 202510b5-1 plan
Matthew J. Hawkins
Chief Executive Officer · sold 46,667 at $34.66
$1.62M
5.8% of stake
Aug 11, 202510b5-1 plan
Christopher L. Schremser
Chief Technology Officer · sold 8,623 at $34.49
297K
1.9% of stake
Jul 21, 202510b5-1 plan
T. Craig Bridge
Chief Transformation Officer · sold 85,000 at $37.09
$3.15M
11% of stake
Jul 21, 202510b5-1 plan
Eric L. (ric) Sinclair III
Chief Business Officer · sold 9,702 at $37.10
360K
1.9% of stake
Jul 15, 202510b5-1 plan
Matthew J. Hawkins
Chief Executive Officer · sold 46,667 at $38.26
$1.79M
5.8% of stake
Jul 10, 202510b5-1 plan
Christopher L. Schremser
Chief Technology Officer · sold 8,623 at $37.63
324K
1.9% of stake
Jun 25, 202510b5-1 plan
Eric L. (ric) Sinclair III
Chief Business Officer · sold 9,702 at $40.22
390K
1.9% of stake
Jun 20, 202510b5-1 plan
Eric L. (ric) Sinclair III
Chief Business Officer · sold 9,702 at $37.79
367K
1.9% of stake
Jun 11, 202510b5-1 plan
Steven M Oreskovich
Chief Financial Officer · sold 16,396 at $40.71
667K
4.3% of stake
Jun 11, 202510b5-1 plan
Melissa F. (missy) Miller
Chief Marketing Officer · sold 6,072 at $40.71
247K
3.1% of stake
Jun 11, 202510b5-1 plan
T. Craig Bridge
Chief Transformation Officer · sold 15,946 at $40.71
649K
2.0% of stake
Jun 10, 202510b5-1 plan
Christopher L. Schremser
Chief Technology Officer · sold 8,623 at $40.58
350K
1.9% of stake
Jun 10, 202510b5-1 plan
Matthew J. Hawkins
Chief Executive Officer · sold 2,704 at $40.57
110K
0.4% of stake
Jun 5, 2025No plan
Matthew J. Hawkins
Chief Executive Officer · sold 59,836 at $40.18
$2.4M
7.3% of stake

How to read this. Insiders sell for many reasons: taxes, diversifying, a house. Open-market buys are rarer and say more. A 10b5-1 plan is a trading schedule set up months in advance, so those sales were not timed on news. Large holders (funds and 10% owners) are listed under Everything but not counted as insiders. If you own or watch WAY, we send a push when an executive buys or makes a large sale outside a plan.

Source: SEC Form 4 filings, filed within two business days of each trade and checked for new ones every hour.

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Held by ETFs

WAY is in 73 US ETFs. The largest of them, with WAY's weight in each:

Spot a number that looks wrong? Check it in WAY's SEC filings or

Download this analysis as a PDF (Pro)

Data sourced from SEC EDGAR filings and third-party price providers. Scores, valuations, and metrics are algorithmic estimates. This is not investment advice. See our Terms and Methodology.

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