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STILLWELL KENNETH

Disclosed activity across 1 company

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SEC CIK
0001680115

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Reported relationships

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CompanyLast reported asReport datePublished
PEGASYSTEMS INCPEGA · Entity 309COO, CFOSeptember 11, 2026September 15, 2026

Disclosed balances

About these balances

Latest available filing per company, not a reconstructed current portfolio. Matching sequences show the last reported balance with all source rows expandable; grouping alone does not establish account ownership. Do not add unresolved positions together. Filings may omit unchanged positions, and amendments may correct only part of an older disclosure. Jointly reported shares are not necessarily this owner's personal holdings.

PEGASYSTEMS INC

Report date September 11, 2026 · Filed September 15, 2026

Security / awardOwnership accountDisclosed shares / unitsDisclosure context
Common stockSEC Table I · non-derivativeDirect95,225 Reported balance After 2026-09-11 transaction · row 1
1 source row

Row 1 · 2026-09-11 · Sale · Disposed 39,627 · Balance 95,225

F1: Represents the weighted average of sale prices, ranging from $35.7400 to $35.8350. The individual has provided the Company, and undertakes to provide to the staff of the Security and Exchange Commission or any security holder of the Company, upon request, full information regarding the number of shares sold at each separate price.

Common stockSEC Table I · non-derivativeIndirectReporting Person's children1,908 Reported balance Holding disclosure · report date 2026-09-11 · row 2 Holding and transaction disclosures are not merged.
1 source row

Row 2 · Balance 1,908

Filing footnotes · ownership attribution and instrument terms

F1: Represents the weighted average of sale prices, ranging from $35.7400 to $35.8350. The individual has provided the Company, and undertakes to provide to the staff of the Security and Exchange Commission or any security holder of the Company, upon request, full information regarding the number of shares sold at each separate price.

Transaction history

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Purchases/sales include open-market and private transactions. Plan disclosure applies to the filing; individual rows may differ. “Not disclosed” is not “unplanned.”

The cutoff filters transaction history only. Company summaries and owner relationships show the latest available disclosures. Parser corrections can improve historical records.

Transaction dateCompanyActivity / securityShares / unitsReported priceReported valueDetails
March 02, 2026 Filed Mar 3, 2026 21:12 UTC PEGASYSTEMS INC PEGA · Entity 309 SaleCommon stock 1,000 $43.37 $43,370.00
Disclosure

SEC source: 0001680115-26-000010 · wk-form4_1772572343.xml · nonDerivative · entry 5

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 134,516

F1 · shares: Sold pursuant to a pre-arranged trading plan adopted by Mr. Stillwell August 12, 2025 under Rule 10b5-1 of the Securities Exchange Act of 1934, as amended.

Read SEC document
March 02, 2026 Filed Mar 3, 2026 21:12 UTC PEGASYSTEMS INC PEGA · Entity 309 Tax withholdingCommon stock 281 $43.73 $12,288.13
Disclosure

SEC source: 0001680115-26-000010 · wk-form4_1772572343.xml · nonDerivative · entry 4

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 135,516

Read SEC document
March 02, 2026 Filed Mar 3, 2026 21:12 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionCommon stock 1,152 $0.00 $0.00
Disclosure

SEC source: 0001680115-26-000010 · wk-form4_1772572343.xml · nonDerivative · entry 3

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 135,797

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

Read SEC document
March 01, 2026 Filed Mar 3, 2026 21:12 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionRestricted Stock Units · Derivative 2,350 $0.00 Strike: $0.00 $0.00
Disclosure

SEC source: 0001680115-26-000010 · wk-form4_1772572343.xml · derivative · entry 7

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 9,404

Underlying: Common stock · 2,350 shares

Expires 2027-03-01

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F2 · shares: Each restricted stock unit represents the right to receive, following vesting, one share of common stock.

F3 · derivative.exercise_date: 20% of the restricted stock units vested on the Date Exercisable in Table II, and the remaining 80% vest in equal quarterly installments over the following four years.

Read SEC document
March 01, 2026 Filed Mar 3, 2026 21:12 UTC PEGASYSTEMS INC PEGA · Entity 309 Tax withholdingCommon stock 573 $43.73 $25,057.29
Disclosure

SEC source: 0001680115-26-000010 · wk-form4_1772572343.xml · nonDerivative · entry 2

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 134,645

Read SEC document
March 01, 2026 Filed Mar 3, 2026 21:12 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionCommon stock 2,350 $0.00 $0.00
Disclosure

SEC source: 0001680115-26-000010 · wk-form4_1772572343.xml · nonDerivative · entry 1

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 135,218

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

Read SEC document
February 12, 2026 Filed Feb 17, 2026 21:06 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionStock Options · Derivative 25,920 $0.00 Strike: $16.95 $0.00
Disclosure

SEC source: 0001680115-26-000008 · wk-form4_1771362396.xml · derivative · entry 4

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 77,760

Underlying: Common stock · 25,920 shares

Expires 2032-11-02

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_date: This stock option vests in 16 equal quarterly installments over four years beginning on the Date Exercisable in Table II.

Read SEC document
February 12, 2026 Filed Feb 17, 2026 21:06 UTC PEGASYSTEMS INC PEGA · Entity 309 Tax withholdingCommon stock 14,932 $39.29 $586,678.28
Disclosure

SEC source: 0001680115-26-000008 · wk-form4_1771362396.xml · nonDerivative · entry 2

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 132,868

Read SEC document
February 12, 2026 Filed Feb 17, 2026 21:06 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionCommon stock 25,920 $16.95 $439,344.00
Disclosure

SEC source: 0001680115-26-000008 · wk-form4_1771362396.xml · nonDerivative · entry 1

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 147,800

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

Read SEC document
February 10, 2026 Filed Feb 12, 2026 21:12 UTC PEGASYSTEMS INC PEGA · Entity 309 GrantStock Options · Derivative 96,000 $0.00 Strike: $31.05 $0.00
Disclosure

SEC source: 0001680115-26-000006 · wk-form4_1770930746.xml · derivative · entry 1

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 96,000

Underlying: Common stock · 96,000 shares

Expires 2034-03-05

F1 · shares: On March 5, 2024, the reporting person was granted an option to purchase shares of Pegasystems common stock. The option vests in two installments, with 25% to vest on the first anniversary of the date of grant based on the Pegasystems' satisfaction of certain performance criteria for the fiscal year ended December 31, 2024, and 75% to vest on the second anniversary of the date of grant based on Pegasystems' satisfaction of certain performance criteria for the fiscal year ended December 31, 2025. Pegasystems overachieved the performance criteria for the fiscal year ended December 31, 2025 at 160%, resulting in vesting of the option as to 96,000 shares.

Read SEC document
February 02, 2026 Filed Feb 3, 2026 21:12 UTC PEGASYSTEMS INC PEGA · Entity 309 SaleCommon stock 1,000 $43.69 $43,690.00
Disclosure

SEC source: 0001680115-26-000004 · wk-form4_1770153152.xml · nonDerivative · entry 1

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 121,880

F1 · shares: Sold pursuant to a pre-arranged trading plan adopted by Mr. Stillwell August 29, 2024 under Rule 10b5-1 of the Securities Exchange Act of 1934, as amended.

Read SEC document
January 02, 2026 Filed Jan 6, 2026 21:05 UTC PEGASYSTEMS INC PEGA · Entity 309 SaleCommon stock 4,000 $59.99 $239,960.00
Disclosure

SEC source: 0001680115-26-000002 · wk-form4_1767733536.xml · nonDerivative · entry 1

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 122,880

F1 · shares: Sold pursuant to a pre-arranged trading plan adopted by Mr. Stillwell August 29, 2024 under Rule 10b5-1 of the Securities Exchange Act of 1934, as amended.

F2 · price: Represents the weighted average of sale prices, ranging from $59.98 to $60.00. The individual has provided the Company, and undertakes to provide to the staff of the Security and Exchange Commission or any security holder of the Company, upon request, full information regarding the number of shares sold at each separate price.

Read SEC document
December 12, 2025 Filed Dec 16, 2025 21:49 UTC PEGASYSTEMS INC PEGA · Entity 309 GiftCommon stock 1,908 $0.00 $0.00
Disclosure

SEC source: 0001680115-25-000022 · wk-form4_1765921749.xml · nonDerivative · entry 2

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Indirect · Reporting Person's children

Disclosed balance after: 1,908

F1 · shares: These transactions reflect Mr. Stillwell's gift of shares to his children. Mr. Stillwell disclaims beneficial ownership of the shares held by his children except to the extent of his pecuniary interest therein.

Read SEC document
December 12, 2025 Filed Dec 16, 2025 21:49 UTC PEGASYSTEMS INC PEGA · Entity 309 GiftCommon stock 1,908 $0.00 $0.00
Disclosure

SEC source: 0001680115-25-000022 · wk-form4_1765921749.xml · nonDerivative · entry 1

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 126,880

F1 · shares: These transactions reflect Mr. Stillwell's gift of shares to his children. Mr. Stillwell disclaims beneficial ownership of the shares held by his children except to the extent of his pecuniary interest therein.

Read SEC document
December 10, 2025 Filed Dec 12, 2025 21:28 UTC PEGASYSTEMS INC PEGA · Entity 309 GiftCommon stock 6,000 $0.00 $0.00
Disclosure

SEC source: 0001680115-25-000020 · wk-form4_1765574887.xml · nonDerivative · entry 1

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 128,788

Read SEC document
December 07, 2025 Filed Dec 9, 2025 21:53 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionRestricted Stock Units · Derivative 5,222 $0.00 Strike: $0.00 $0.00
Disclosure

SEC source: 0001680115-25-000018 · wk-form4_1765317182.xml · derivative · entry 14

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 26,104

Underlying: Common stock · 5,222 shares

Expires 2027-03-07

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · security: Each restricted stock unit represents the right to receive, following vesting, one share of the issuer's common stock.

F4 · derivative.exercise_date: This restricted stock unit award vested 25% on the Date Exercisable in Table II, with the remaining 75% vesting in equal quarterly amounts over the remaining 3 years.

Read SEC document
December 07, 2025 Filed Dec 9, 2025 21:53 UTC PEGASYSTEMS INC PEGA · Entity 309 Tax withholdingCommon stock 2,055 $60.11 $123,526.05
Disclosure

SEC source: 0001680115-25-000018 · wk-form4_1765317182.xml · nonDerivative · entry 10

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 134,788

Read SEC document
December 07, 2025 Filed Dec 9, 2025 21:53 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionCommon stock 5,222 $0.00 $0.00
Disclosure

SEC source: 0001680115-25-000018 · wk-form4_1765317182.xml · nonDerivative · entry 9

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 136,843

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · shares: Each restricted stock unit represents the right to receive, following vesting, one share of the issuer's common stock.

Read SEC document
December 05, 2025 Filed Dec 9, 2025 21:53 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionStock Options · Derivative 20,000 $0.00 Strike: $31.05 $0.00
Disclosure

SEC source: 0001680115-25-000018 · wk-form4_1765317182.xml · derivative · entry 13

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common stock · 20,000 shares

Expires 2034-03-05

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F6 · derivative.exercise_date: On March 5, 2024, the reporting person was granted an option to purchase 80,000 shares of common stock. The option vests in two installments, with up to 25% to vest on the Date Exercisable in Table II based on Pegasystems' satisfaction of certain performance criteria for the fiscal year ended December 31, 2024, and with up to 75% to vest on the second anniversary of the date of grant based on Pegasystems' satisfaction of certain performance criteria for the fiscal year ended December 31, 2025. The performance criteria for the fiscal year ended December 31, 2024 were met in full, resulting in vesting of the option as to 20,000 shares.

Read SEC document
December 05, 2025 Filed Dec 9, 2025 21:53 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionStock Options · Derivative 29,240 $0.00 Strike: $32.18 $0.00
Disclosure

SEC source: 0001680115-25-000018 · wk-form4_1765317182.xml · derivative · entry 12

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common stock · 29,240 shares

Expires 2029-03-06

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F5 · derivative.exercise_date: This stock option is fully vested.

Read SEC document
December 05, 2025 Filed Dec 9, 2025 21:53 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionRestricted Stock Units · Derivative 4,402 $0.00 Strike: $0.00 $0.00
Disclosure

SEC source: 0001680115-25-000018 · wk-form4_1765317182.xml · derivative · entry 11

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 39,620

Underlying: Common stock · 4,402 shares

Expires 2028-03-05

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · security: Each restricted stock unit represents the right to receive, following vesting, one share of the issuer's common stock.

F4 · derivative.exercise_date: This restricted stock unit award vested 25% on the Date Exercisable in Table II, with the remaining 75% vesting in equal quarterly amounts over the remaining 3 years.

Read SEC document
December 05, 2025 Filed Dec 9, 2025 21:53 UTC PEGASYSTEMS INC PEGA · Entity 309 SaleCommon stock 998 $57.75 $57,638.39
Disclosure

SEC source: 0001680115-25-000018 · wk-form4_1765317182.xml · nonDerivative · entry 8

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 131,621

F3 · price: Represents the weighted average of sale prices, ranging from $57.70 to $57.80. The individual has provided the Company, and undertakes to provide to the staff of the Security and Exchange Commission or any security holder of the Company, upon request, full information regarding the number of shares sold at each separate price.

Read SEC document
December 05, 2025 Filed Dec 9, 2025 21:53 UTC PEGASYSTEMS INC PEGA · Entity 309 SaleCommon stock 5,586 $57.86 $323,205.96
Disclosure

SEC source: 0001680115-25-000018 · wk-form4_1765317182.xml · nonDerivative · entry 7

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 132,619

F2 · price: Represents the weighted average of sale prices, ranging from $57.86 to $57.89. The individual has provided the Company, and undertakes to provide to the staff of the Security and Exchange Commission or any security holder of the Company, upon request, full information regarding the number of shares sold at each separate price.

Read SEC document
December 05, 2025 Filed Dec 9, 2025 21:53 UTC PEGASYSTEMS INC PEGA · Entity 309 SaleCommon stock 7,821 $57.89 $452,757.69
Disclosure

SEC source: 0001680115-25-000018 · wk-form4_1765317182.xml · nonDerivative · entry 6

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 138,205

Read SEC document
December 05, 2025 Filed Dec 9, 2025 21:53 UTC PEGASYSTEMS INC PEGA · Entity 309 Tax withholdingCommon stock 35,833 $57.56 $2,062,547.48
Disclosure

SEC source: 0001680115-25-000018 · wk-form4_1765317182.xml · nonDerivative · entry 5

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 146,026

Read SEC document
December 05, 2025 Filed Dec 9, 2025 21:53 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionCommon stock 20,000 $31.05 $621,000.00
Disclosure

SEC source: 0001680115-25-000018 · wk-form4_1765317182.xml · nonDerivative · entry 4

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 181,859

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

Read SEC document
December 05, 2025 Filed Dec 9, 2025 21:53 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionCommon stock 29,240 $32.18 $940,943.20
Disclosure

SEC source: 0001680115-25-000018 · wk-form4_1765317182.xml · nonDerivative · entry 3

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 161,859

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

Read SEC document
December 05, 2025 Filed Dec 9, 2025 21:53 UTC PEGASYSTEMS INC PEGA · Entity 309 Tax withholdingCommon stock 1,733 $57.00 $98,781.00
Disclosure

SEC source: 0001680115-25-000018 · wk-form4_1765317182.xml · nonDerivative · entry 2

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 132,619

Read SEC document
December 05, 2025 Filed Dec 9, 2025 21:53 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionCommon stock 4,402 $0.00 $0.00
Disclosure

SEC source: 0001680115-25-000018 · wk-form4_1765317182.xml · nonDerivative · entry 1

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 134,352

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · shares: Each restricted stock unit represents the right to receive, following vesting, one share of the issuer's common stock.

Read SEC document
December 02, 2025 Filed Dec 3, 2025 21:30 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionRestricted Stock Units · Derivative 1,154 $0.00 Strike: $0.00 $0.00
Disclosure

SEC source: 0001680115-25-000016 · wk-form4_1764797412.xml · derivative · entry 6

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,152

Underlying: Common stock · 1,154 shares

Expires 2026-03-02

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · shares: Each restricted stock unit represents the right to receive, following vesting, one share of common stock.

F2 · derivative.exercise_date: 20% of the restricted stock units vested on the Date Exercisable in Table II, and the remaining 80% vest in equal quarterly installments over the following four years.

Read SEC document
December 02, 2025 Filed Dec 3, 2025 21:30 UTC PEGASYSTEMS INC PEGA · Entity 309 Tax withholdingCommon stock 455 $54.85 $24,956.75
Disclosure

SEC source: 0001680115-25-000016 · wk-form4_1764797412.xml · nonDerivative · entry 4

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 129,950

Read SEC document
December 02, 2025 Filed Dec 3, 2025 21:30 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionCommon stock 1,154 $0.00 $0.00
Disclosure

SEC source: 0001680115-25-000016 · wk-form4_1764797412.xml · nonDerivative · entry 3

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 130,405

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

Read SEC document
December 01, 2025 Filed Dec 3, 2025 21:30 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionRestricted Stock Units · Derivative 2,350 $0.00 Strike: $0.00 $0.00
Disclosure

SEC source: 0001680115-25-000016 · wk-form4_1764797412.xml · derivative · entry 5

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 11,754

Underlying: Common stock · 2,350 shares

Expires 2027-03-01

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · shares: Each restricted stock unit represents the right to receive, following vesting, one share of common stock.

F2 · derivative.exercise_date: 20% of the restricted stock units vested on the Date Exercisable in Table II, and the remaining 80% vest in equal quarterly installments over the following four years.

Read SEC document
December 01, 2025 Filed Dec 3, 2025 21:30 UTC PEGASYSTEMS INC PEGA · Entity 309 Tax withholdingCommon stock 925 $54.77 $50,662.25
Disclosure

SEC source: 0001680115-25-000016 · wk-form4_1764797412.xml · nonDerivative · entry 2

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 129,251

Read SEC document
December 01, 2025 Filed Dec 3, 2025 21:30 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionCommon stock 2,350 $0.00 $0.00
Disclosure

SEC source: 0001680115-25-000016 · wk-form4_1764797412.xml · nonDerivative · entry 1

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 130,176

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

Read SEC document
November 03, 2025 Filed Nov 5, 2025 22:03 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionStock Options · Derivative 25,920 $0.00 Strike: $16.95 $0.00
Disclosure

SEC source: 0001680115-25-000014 · wk-form4_1762380232.xml · derivative · entry 4

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 103,680

Underlying: Common stock · 25,920 shares

Expires 2032-11-02

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F2 · derivative.exercise_date: This option vests in equal quarterly installments over a four-year period, with the first installment vesting on the Date Exercisable set forth in Table II.

Read SEC document
November 03, 2025 Filed Nov 5, 2025 22:03 UTC PEGASYSTEMS INC PEGA · Entity 309 SaleCommon stock 11,442 $62.18 $711,463.56
Disclosure

SEC source: 0001680115-25-000014 · wk-form4_1762380232.xml · nonDerivative · entry 3

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 127,826

F1 · price: Represents the weighted average of sale prices, ranging from $62.07 to $62.31. The individual has provided the Company, and undertakes to provide to the staff of the Security and Exchange Commission or any security holder of the Company, upon request, full information regarding the number of shares sold at each separate price.

Read SEC document
November 03, 2025 Filed Nov 5, 2025 22:03 UTC PEGASYSTEMS INC PEGA · Entity 309 Tax withholdingCommon stock 14,478 $62.29 $901,834.62
Disclosure

SEC source: 0001680115-25-000014 · wk-form4_1762380232.xml · nonDerivative · entry 2

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 139,268

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November 03, 2025 Filed Nov 5, 2025 22:03 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionCommon stock 25,920 $16.95 $439,344.00
Disclosure

SEC source: 0001680115-25-000014 · wk-form4_1762380232.xml · nonDerivative · entry 1

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 153,746

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

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October 24, 2025 Filed Oct 28, 2025 20:23 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionStock Options · Derivative 52,828 $0.00 Strike: $31.05 $0.00
Disclosure

SEC source: 0001680115-25-000012 · wk-form4_1761683035.xml · derivative · entry 4

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 88,044

Underlying: Common stock · 52,828 shares

Expires 2034-03-05

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F2 · derivative.exercise_date: Option vested 25% on the Date Exercisable in Table II, with the remaining 75% vesting in equal quarterly installments over the following three years.

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October 24, 2025 Filed Oct 28, 2025 20:23 UTC PEGASYSTEMS INC PEGA · Entity 309 SaleCommon stock 17,171 $66.40 $1,140,154.40
Disclosure

SEC source: 0001680115-25-000012 · wk-form4_1761683035.xml · nonDerivative · entry 3

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 127,826

F1 · price: Represents the weighted average of sale prices, ranging from $66.37 to $66.60 . The individual has provided the Company, and undertakes to provide to the staff of the Security and Exchange Commission or any security holder of the Company, upon request, full information regarding the number of shares sold at each separate price.

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October 24, 2025 Filed Oct 28, 2025 20:23 UTC PEGASYSTEMS INC PEGA · Entity 309 Tax withholdingCommon stock 35,657 $66.91 $2,385,809.87
Disclosure

SEC source: 0001680115-25-000012 · wk-form4_1761683035.xml · nonDerivative · entry 2

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 144,997

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October 24, 2025 Filed Oct 28, 2025 20:23 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionCommon stock 52,828 $31.05 $1,640,309.40
Disclosure

SEC source: 0001680115-25-000012 · wk-form4_1761683035.xml · nonDerivative · entry 1

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 180,654

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

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September 07, 2025 Filed Sep 9, 2025 20:08 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionRestricted Stock Units · Derivative 5,220 $0.00 Strike: $0.00 $0.00
Disclosure

SEC source: 0001680115-25-000010 · wk-form4_1757448523.xml · derivative · entry 6

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 31,326

Underlying: Common stock · 5,220 shares

Expires 2027-03-07

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · security: Each restricted stock unit represents the right to receive, following vesting, one share of the issuer's common stock.

F2 · derivative.exercise_date: This restricted stock unit award vested 25% on the Date Exercisable in Table II, with the remaining 75% vesting in equal quarterly amounts over the remaining 3 years.

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September 07, 2025 Filed Sep 9, 2025 20:08 UTC PEGASYSTEMS INC PEGA · Entity 309 Tax withholdingCommon stock 2,055 $55.51 $114,073.05
Disclosure

SEC source: 0001680115-25-000010 · wk-form4_1757448523.xml · nonDerivative · entry 4

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 127,826

Read SEC document
September 07, 2025 Filed Sep 9, 2025 20:08 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionCommon stock 5,220 $0.00 $0.00
Disclosure

SEC source: 0001680115-25-000010 · wk-form4_1757448523.xml · nonDerivative · entry 3

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 129,881

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · shares: Each restricted stock unit represents the right to receive, following vesting, one share of the issuer's common stock.

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September 05, 2025 Filed Sep 9, 2025 20:08 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionRestricted Stock Units · Derivative 4,402 $0.00 Strike: $0.00 $0.00
Disclosure

SEC source: 0001680115-25-000010 · wk-form4_1757448523.xml · derivative · entry 5

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 44,022

Underlying: Common stock · 4,402 shares

Expires 2028-03-05

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · security: Each restricted stock unit represents the right to receive, following vesting, one share of the issuer's common stock.

F2 · derivative.exercise_date: This restricted stock unit award vested 25% on the Date Exercisable in Table II, with the remaining 75% vesting in equal quarterly amounts over the remaining 3 years.

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September 05, 2025 Filed Sep 9, 2025 20:08 UTC PEGASYSTEMS INC PEGA · Entity 309 Tax withholdingCommon stock 1,733 $53.81 $93,252.73
Disclosure

SEC source: 0001680115-25-000010 · wk-form4_1757448523.xml · nonDerivative · entry 2

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 124,661

Read SEC document
September 05, 2025 Filed Sep 9, 2025 20:08 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionCommon stock 4,402 $0.00 $0.00
Disclosure

SEC source: 0001680115-25-000010 · wk-form4_1757448523.xml · nonDerivative · entry 1

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 126,394

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · shares: Each restricted stock unit represents the right to receive, following vesting, one share of the issuer's common stock.

Read SEC document
September 02, 2025 Filed Sep 4, 2025 20:56 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionRestricted Stock Units · Derivative 1,152 $0.00 Strike: $0.00 $0.00
Disclosure

SEC source: 0001680115-25-000008 · wk-form4_1757019359.xml · derivative · entry 6

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 2,306

Underlying: Common stock · 1,152 shares

Expires 2026-03-02

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F3 · security: Each restricted stock unit represents the right to receive, following vesting, one share of the issuer's common stock.

F2 · shares: Represents a 5% vesting on September 2, 2025. The original grant was 11,527 restricted stock units, with 20% vesting on March 2, 2022, and the remaining 80% vesting in equal quarterly installments over the remaining four years.

F4 · balance_after: All share amounts in this Form 4 have been restated to reflect a 2-for-1 forward stock split of Pegasystems Inc.'s common stock effectuated on June 20, 2025.

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Value uses the disclosed total when available, otherwise shares × reported transaction price. It is not an estimate of exercise cash cost or investment performance.