STILLWELL KENNETH

PrivateCIK: 1680115

Location

WALTHAM, MA

STILLWELL KENNETH (COO, CFO) exercised options at PEGASYSTEMS INC

Option exercise — a mechanical event triggered by vesting or expiry. Not a discretionary conviction trade.

M · 3 exercises

STILLWELL KENNETH

Filed: 9/9/2026ACC: 0001680115-26-000034

InsiderSTILLWELL KENNETHCIK 1680115

→

IssuerPEGASYSTEMS INCCIK 1013857

Officer· COO, CFO

Since Mar 2026

-5.06K

Net shares

Net seller

$189.5K

Total sold

0

Open market trades

0B · 0S

9

Total transactions

12.85K acquired · 17.91K disposed

Non-Derivative Transactions6

Common stock

Direct

M · Option Exercise

Shares

+3.23K

Price / share

—

Trade value

—

% of position

2.5%

9/4/2026

127.06K→130.29K

Common stock

Direct

F · Tax Withholding

Shares

−1.27K

Price / share

$37.72

Trade value

$47.98K

% of position

1.0%

9/4/2026

130.29K→129.02K

Common stock

Direct

M · Option Exercise

Shares

+4.40K

Price / share

—

Trade value

—

% of position

3.4%

9/5/2026

129.02K→133.42K

Common stock

Direct

F · Tax Withholding

Shares

−1.73K

Price / share

$37.36

Trade value

$64.74K

% of position

1.3%

9/5/2026

133.42K→131.69K

Common stock

Direct

M · Option Exercise

Shares

+5.22K

Price / share

—

Trade value

—

% of position

4.0%

9/7/2026

131.69K→136.91K

Common stock

Direct

F · Tax Withholding

Shares

−2.06K

Price / share

$37.36

Trade value

$76.77K

% of position

1.5%

9/7/2026

136.91K→134.85K

Total

Net shares

+7.79K

Net value

-$189.50K

Security	Date	Type	Shares	Price / Share	Trade Value	% of Position	Held Before	Held After
Common stock Direct	9/4/2026	M · Option Exercise	+3.23K	—	—	2.5%	127.06K	130.29K
Common stock Direct	9/4/2026	F · Tax Withholding	−1.27K	$37.72	$47.98K	1.0%	130.29K	129.02K
Common stock Direct	9/5/2026	M · Option Exercise	+4.40K	—	—	3.4%	129.02K	133.42K
Common stock Direct	9/5/2026	F · Tax Withholding	−1.73K	$37.36	$64.74K	1.3%	133.42K	131.69K
Common stock Direct	9/7/2026	M · Option Exercise	+5.22K	—	—	4.0%	131.69K	136.91K
Common stock Direct	9/7/2026	F · Tax Withholding	−2.06K	$37.36	$76.77K	1.5%	136.91K	134.85K
Total			+7.79K		-$189.50K

Derivative Transactions3

Restricted Stock Units

Direct

M · Option Exercise

Converts to

Common stock

3.23K shares

Shares

−3.23K

Strike price

0

Held after

32.31K

Exercisable

—

9/4/2026

Restricted Stock Units

Direct

M · Option Exercise

Converts to

Common stock

4.40K shares

Shares

−4.40K

Strike price

0

Held after

26.41K

Exercisable

—

9/5/2026

Restricted Stock Units

Direct

M · Option Exercise

Converts to

Common stock

5.22K shares

Shares

−5.22K

Strike price

0

Held after

10.44K

Exercisable

—

9/7/2026

Security	Converts To	Date	Type	Shares	Strike Price	Exercisable	Held After
Restricted Stock Units Direct	Common stock3.23K shares	9/4/2026	M · Option Exercise	−3.23K	0	—	32.31K
Restricted Stock Units Direct	Common stock4.40K shares	9/5/2026	M · Option Exercise	−4.40K	0	—	26.41K
Restricted Stock Units Direct	Common stock5.22K shares	9/7/2026	M · Option Exercise	−5.22K	0	—	10.44K

Non-Derivative Holdings (Post-Transaction)1

Common stock

Indirect

Shares owned1.91K

Total

1.91K indirect1.91K

Security Title	Shares Owned	Ownership Type
Common stock	1.91K	Indirect
Total	1.91K	1.91K indirect

Derivative Holdings (Post-Transaction)0

No derivative holdings reported