Waystar Holding WAY Insider Ownership

NASDAQ WAY

$27.99 +0.63 (+2.30%)

At close: Oct 19, 2026 · 4:00 PM EDT

Insider Holdings by Owner

106.04Mn Shares

Insider Ownership Statistics

as of 30 Sep, 2026

Insider Ownership

33.73%

▲+1.07% pp QoQ

Shares Held by Insiders

64.74Mn

filed for Sep 2026

▲+3.27% QoQ

Shares Outstanding

191.92Mn

191,923,976 shares

Direct Holdings

7.59Mn

Indirect: 57.16Mn

Net Shares Traded (QoQ)

+2.05Mn

net buying in Sep 2026

Insiders Holding Shares

with Form 4 holdings on file

Shares Owned by Insiders

Shares held % of outstanding

Latest —

Average ownership —

Peak ownership —

Shares Purchased/Sold by Insiders

Bought Sold

Latest quarter —

Net over range —

Buying quarters —

Insider Ownership Summary

Updated Oct 11, 2026

Across the past 12 months, open-market trades by Waystar Holding insiders totaled $188,986 in purchases (7.2K shares) and $10.92 million in sales (407.67K shares).

By number of insiders, Waystar Holding saw one insider buy and 4 insiders sell on the open market over the past 12 months.
Among Waystar Holding's insiders, the largest open-market purchases in the past 12 months were by Heidi Miller (Director), totaling $188,986 (7.2K shares), most recently on March 2, 2026.
On the selling side, Matthew J. Hawkins (Chief Executive Officer) was the top open-market seller of Waystar Holding over the past 12 months, with $7.99 million sold (317.7K shares) and the latest sale on October 6, 2026.
Beyond open-market trades, insiders at Waystar Holding received 2.32Mn shares in stock awards, acquired 407.67K shares through option exercises and conversions and gave up 170.31K shares to cover taxes or exercise prices in the last 12 months.
Per Business Quant data, Waystar Holding insiders hold 64.74Mn shares in total based on their latest Form 4 filings, or 33.73% of the 191.92Mn shares outstanding; that total is up 3.25% from 62.7Mn shares at the end of Q2 2026 and up 6.67% from 60.69Mn shares at the end of Q3 2025.
Indirect holdings, through trusts, partnerships, family members and other entities, make up 88.29% (57.16Mn shares) of Waystar Holding's insider total, with the other 11.71% (7.58Mn shares) held directly.
WAY's insider total is spread across 22 insiders who have filed a Form 4 in the past two years.
WAY's largest insider holders by reported holdings are Derby Luxco S.A R.L. (10% owner, 24.88Mn shares), Pension Plan Investment Board Canada (10% owner, 19.03Mn shares) and Bain Capital Investors LLC (10% owner, 13.24Mn shares).
Derby Luxco S.A R.L. alone accounts for 38.43% of the shares held by Waystar Holding insiders.
In the last 12 months, 43 Form 4 filings with transactions in WAY stock came from 19 insiders.
Insider figures for WAY include Form 4 filings through October 7, 2026.

Form 4 Holdings

Insiders Holding WAY

Insiders 24

Shares held 106.04Mn

Of outstanding 55.25%

#	Insider	Position	Direct	Indirect	Total	Share of Insiders	Last Filed
1	Capital Investors Llc Bain	TenPercentOwner	0	41,223,956	41,223,956	38.9%	16 Sep, 2025
2	Luxco S.A R.L. Derby	TenPercentOwner	0	24,879,437	24,879,437	23.5%	16 Sep, 2025
3	Pension Plan Investment Board Canada	TenPercentOwner	0	19,025,452	19,025,452	17.9%	16 Sep, 2025
4	Paul G Moskowitz	Director, TenPercentOwner	0	13,243,539	13,243,539	12.5%	16 Sep, 2025
5	Matthew J. Hawkins	Chief Executive Officer	1,804,794	0	1,804,794	1.7%	07 Oct, 2026
6	William Chan	Chief Product Ai Officer	1,571,252	0	1,571,252	1.5%	06 Oct, 2026
7	T. Craig Bridge	Chief Transformation Officer	833,234	0	833,234	0.8%	03 Sep, 2026
8	Christopher L. Schremser	Chief Technology Officer	495,033	0	495,033	0.5%	09 Jun, 2026
9	Iii Eric L. (Ric) Sinclair	Chief Business Officer	474,826	0	474,826	0.4%	22 Jan, 2026
10	Steven M Oreskovich	Chief Financial Officer	424,200	0	424,200	0.4%	09 Jun, 2026
11	Gregory R Packer	Chief Legal Officer	418,255	0	418,255	0.4%	03 Sep, 2026
12	Amit Khanna	Chief Prod. Tech. Officer	390,625	0	390,625	0.4%	08 Sep, 2026
13	Kimberly S. Wittman	Chief People Officer	270,233	0	270,233	0.3%	09 Jun, 2026
14	Melissa F. (Missy) Miller	Chief Marketing Officer	252,077	0	252,077	0.2%	09 Jun, 2026
15	Todd Charles Woods	Chief Commercial Officer	220,506	0	220,506	0.2%	10 Aug, 2026
16	Alpana Wegner	Chief Financial Officer	162,112	0	162,112	0.2%	14 Aug, 2026
17	John Patrick Driscoll	Director, Other	100,060	0	100,060	0.1%	03 Jun, 2026
18	Matthew R. A. Heiman	Officer	86,956	0	86,956	0.1%	12 Jun, 2024
19	Robert Demichiei	Director	46,199	0	46,199	0.0%	03 Jun, 2026
20	Heidi Miller	Director	40,917	0	40,917	0.0%	03 Jun, 2026
21	Vivian E. Riefberg	Director	23,132	0	23,132	0.0%	03 Jun, 2026
22	Priscilla Hung	Director	23,132	0	23,132	0.0%	03 Jun, 2026
23	Michael F Roman	Director	14,437	0	14,437	0.0%	03 Jun, 2026
24	Aashima Gupta	Director	14,437	0	14,437	0.0%	03 Jun, 2026

Each row is that insider’s most recently reported position, from Form 4 filings over the last 60 months — which is why this total does not tie to the quarterly series above, where a quarter counts only the insiders who filed in it. Shares held through a fund or institutional portfolio are counted on the institutional ownership page instead.

Form 4 Filings

251 Insider Transactions

Source SEC Form 4

Latest quarter Sep 2026

Date	Insider	Position	Transaction	Shares	Price	Value	Shares Held After	Ownership
06 Oct, 2026	Matthew J. Hawkins	Chief Executive Officer	Acquired M	82,500	$4.14	$341.55K	1,887,294	Direct
06 Oct, 2026	Matthew J. Hawkins	Chief Executive Officer	Disposed S	82,500	$26.23	$2.16Mn	1,804,794	Direct
06 Oct, 2026	Matthew J. Hawkins	Chief Executive Officer	Disposed M	82,500	$0.00	$0	1,427,598	Direct
05 Oct, 2026	William Chan	Chief Product Ai Officer	Disposed F	9,560	$26.07	$249.23K	1,571,252	Direct
17 Aug, 2026	Amit Khanna	Chief Prod. Tech. Officer	Acquired A	390,625	$0.00	$0	390,625	Direct
01 Sep, 2026	Matthew J. Hawkins	Chief Executive Officer	Disposed F	30,287	$25.73	$779.28K	1,804,794	Direct
01 Sep, 2026	Gregory R Packer	Chief Legal Officer	Disposed F	6,754	$25.73	$173.78K	418,255	Direct
01 Sep, 2026	T. Craig Bridge	Chief Transformation Officer	Disposed F	30,792	$25.73	$792.28K	833,234	Direct
02 Sep, 2026	Matthew J. Hawkins	Chief Executive Officer	Acquired M	82,500	$4.14	$341.55K	1,887,294	Direct
02 Sep, 2026	Matthew J. Hawkins	Chief Executive Officer	Disposed S	82,500	$25.97	$2.14Mn	1,804,794	Direct
02 Sep, 2026	Matthew J. Hawkins	Chief Executive Officer	Disposed M	82,500	$0.00	$0	1,510,098	Direct
24 Jul, 2026	Alpana Wegner	Chief Financial Officer	Acquired A	162,112	$0.00	$0	162,112	Direct
11 Aug, 2026	Matthew J. Hawkins	Chief Executive Officer	Acquired M	22,462	$4.14	$92.99K	1,857,543	Direct
11 Aug, 2026	Matthew J. Hawkins	Chief Executive Officer	Disposed S	22,462	$25.04	$562.35K	1,835,081	Direct
13 Aug, 2026	Matthew J. Hawkins	Chief Executive Officer	Acquired M	60,038	$4.14	$248.56K	1,895,119	Direct
13 Aug, 2026	Matthew J. Hawkins	Chief Executive Officer	Disposed S	60,038	$25.01	$1.50Mn	1,835,081	Direct
11 Aug, 2026	Matthew J. Hawkins	Chief Executive Officer	Disposed M	22,462	$0.00	$0	1,375,875	Direct
13 Aug, 2026	Matthew J. Hawkins	Chief Executive Officer	Disposed M	60,038	$0.00	$0	1,315,837	Direct
01 Aug, 2026	Todd Charles Woods	Chief Commercial Officer	Acquired A	90,827	$0.00	$0	220,506	Direct
01 Aug, 2026	Matthew J. Hawkins	Chief Executive Officer	Acquired A	908,265	$0.00	$0	1,835,081	Direct

Showing 1 to 20 of 251 transactions