STOCK TITAN

PEGASYSTEMS (PEGA) CFO Stillwell exercises options, covers taxes and sells shares

Filing Impact
(Neutral)
Filing Sentiment
(Neutral)
Form Type
4

Rhea-AI Filing Summary

PEGASYSTEMS INC COO and CFO Kenneth Stillwell reported a combination of option exercises, tax withholding, and share sales in company stock. He exercised stock options for 25,920 shares of common stock at $16.95 per share, then 17,537 shares were disposed of to cover tax obligations at $36.32 per share. He also sold 8,383 shares in an open-market transaction at $36.45 per share. After these transactions, he directly holds 108,532 common shares, with an additional 1,908 shares reported as indirectly held for his children.

Positive

  • None.

Negative

  • None.
Insider STILLWELL KENNETH
Role COO, CFO
Sold 8,383 shs ($306K)
Type Security Shares Price Value
Exercise Stock Options 25,920 $0.00 --
Exercise Common stock 25,920 $16.95 $439K
Tax Withholding Common stock 17,537 $36.32 $637K
Sale Common stock 8,383 $36.45 $306K
holding Common stock -- -- --
Holdings After Transaction: Stock Options — 51,840 shares (Direct, null); Common stock — 134,452 shares (Direct, null); Common stock — 1,908 shares (Indirect, Reporting Person's children)
Footnotes (1)
  1. [object Object]
Options exercised 25,920 shares Stock options exercised into common stock on May 5, 2026 at $16.95
Exercise price $16.95/share Exercise price of stock options converted into common stock
Tax-withholding shares 17,537 shares Shares disposed as tax-withholding at $36.32 per share
Open-market sale 8,383 shares at $36.45 Common stock sold in open-market transaction on May 5, 2026
Direct holdings after 108,532 shares PEGASYSTEMS common stock directly owned after reported transactions
Indirect holdings 1,908 shares Common stock held indirectly for reporting person’s children
Option expiration November 2, 2032 Expiration date of stock options with $16.95 exercise price
open-market sale financial
"transaction_action": "open-market sale""
An open-market sale is when a shareholder sells existing shares directly on a public exchange to any willing buyer, rather than through a private deal. Think of it like putting goods on a busy market stall where price is set by supply and demand; for investors it matters because such sales increase available supply, can put short-term downward pressure on the stock price, and signal changes in liquidity or investor confidence.
tax-withholding disposition financial
"transaction_action": "tax-withholding disposition""
A tax-withholding disposition is an event or transaction—such as selling or transferring securities, exercising options, or receiving compensation—that triggers a requirement to hold back part of the payment and remit it to tax authorities. It matters to investors because it reduces the cash they receive immediately and can change the timing and amount of taxable income, like a cashier taking a portion of your sale proceeds to pay taxes before you get the rest.
derivative exercise/conversion financial
"transaction_action": "derivative exercise/conversion""
stock option financial
"This stock option vests in 16 equal quarterly installments"
A stock option is a contract that gives you the right to buy or sell a company's stock at a specific price within a certain time frame. People use them to potentially make money if the stock's price moves favorably or to protect against losses. It's like holding a coupon that can be used to buy or sell stock at a set price later on.
derivative security financial
"transaction_code_description": "Exercise or conversion of derivative security""
A derivative security is a financial contract whose value comes from the price or performance of something else, such as a stock, bond, commodity, or market index. For investors it acts like an insurance policy or a wager: it can be used to protect against losses, lock in prices, or amplify gains and losses, so it can change a portfolio’s risk and potential return without owning the underlying asset directly.
SEC Form 4
FORM 4UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940
OMB APPROVAL
OMB Number:3235-0287
Estimated average burden
hours per response:0.5
Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).
Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.
1. Name and Address of Reporting Person*
STILLWELL KENNETH

(Last)(First)(Middle)
C/O PEGASYSTEMS INC.
225 WYMAN STREET, STE 300

(Street)
WALTHAM MASSACHUSETTS 02451

(City)(State)(Zip)

UNITED STATES

(Country)
2. Issuer Name and Ticker or Trading Symbol
PEGASYSTEMS INC [ PEGA ]
5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)
Director10% Owner
XOfficer (give title below)Other (specify below)
COO, CFO
2a. Foreign Trading Symbol
3. Date of Earliest Transaction (Month/Day/Year)
05/05/2026
6. Individual or Joint/Group Filing (Check Applicable Line)
XForm filed by One Reporting Person
Form filed by More than One Reporting Person
4. If Amendment, Date of Original Filed (Month/Day/Year)

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3) 2. Transaction Date (Month/Day/Year)2A. Deemed Execution Date, if any (Month/Day/Year)3. Transaction Code (Instr. 8) 4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5) 5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4) 6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) 7. Nature of Indirect Beneficial Ownership (Instr. 4)
CodeVAmount(A) or (D)Price
Common stock05/05/2026M25,920A$16.95134,452D
Common stock05/05/2026F17,537D$36.32116,915D
Common stock05/05/2026S8,383D$36.45108,532D
Common stock1,908IReporting Person's children
Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned
(e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3) 2. Conversion or Exercise Price of Derivative Security 3. Transaction Date (Month/Day/Year)3A. Deemed Execution Date, if any (Month/Day/Year)4. Transaction Code (Instr. 8) 5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5) 6. Date Exercisable and Expiration Date (Month/Day/Year)7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4) 8. Price of Derivative Security (Instr. 5) 9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4) 10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) 11. Nature of Indirect Beneficial Ownership (Instr. 4)
CodeV(A)(D)Date ExercisableExpiration DateTitleAmount or Number of Shares
Stock Options$16.9505/05/2026M25,92002/02/2023(1)11/02/2032Common stock25,920$051,840D
Explanation of Responses:
1. This stock option vests in 16 equal quarterly installments over four years beginning on the Date Exercisable in Table II.
Remarks:
/s/Kathryn Leach, Attorney-in-Fact for Kenneth Stillwell05/06/2026
** Signature of Reporting PersonDate
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.
* Form 4: SEC 1474 (03-26)

FAQ

What insider transactions did PEGASYSTEMS INC (PEGA) report for Kenneth Stillwell?

Kenneth Stillwell reported an option exercise, tax withholding, and a share sale. He exercised 25,920 stock options, had 17,537 shares withheld to cover taxes, and sold 8,383 shares in an open-market trade, all involving PEGASYSTEMS common stock.

How many PEGASYSTEMS (PEGA) shares did Kenneth Stillwell sell in this Form 4 filing?

Kenneth Stillwell sold 8,383 PEGASYSTEMS common shares. The sale was reported as an open-market transaction at $36.45 per share, separate from additional shares disposed of to satisfy tax obligations related to an option exercise.

What stock options did PEGASYSTEMS (PEGA) executive Kenneth Stillwell exercise?

He exercised stock options covering 25,920 PEGASYSTEMS common shares. The options had an exercise price of $16.95 per share and were part of a grant that vests in 16 equal quarterly installments over four years from the stated exercisable date.

How many PEGASYSTEMS (PEGA) shares does Kenneth Stillwell hold after these transactions?

After the reported transactions, Kenneth Stillwell directly holds 108,532 PEGASYSTEMS common shares. The filing also reports 1,908 additional shares as indirectly owned, attributed to his children, reflecting both direct and indirect ownership positions.

Why were 17,537 PEGASYSTEMS (PEGA) shares disposed of by Kenneth Stillwell?

17,537 shares were disposed of to cover tax obligations. The Form 4 classifies this as a tax-withholding disposition at $36.32 per share, connected to the exercise of stock options rather than an open-market sale decision.

What is the exercise price and expiration for Kenneth Stillwell’s PEGASYSTEMS stock options?

The exercised PEGASYSTEMS stock options have a $16.95 exercise price. According to the filing, these options are scheduled to expire on November 2, 2032, and vest in 16 equal quarterly installments beginning on the stated exercisable date.