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STILLWELL KENNETH

Disclosed activity across 1 company

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SEC CIK
0001680115

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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
September 02, 2025 Filed Sep 4, 2025 20:56 UTC PEGASYSTEMS INC PEGA · Entity 309 Tax withholdingCommon stock 454 $54.21 $24,611.34
Disclosure

SEC source: 0001680115-25-000008 · wk-form4_1757019359.xml · nonDerivative · entry 4

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 121,992

Read SEC document
September 02, 2025 Filed Sep 4, 2025 20:56 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionCommon stock 1,152 $0.00 $0.00
Disclosure

SEC source: 0001680115-25-000008 · wk-form4_1757019359.xml · nonDerivative · entry 3

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 122,446

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: 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.

Read SEC document
September 01, 2025 Filed Sep 4, 2025 20:56 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionRestricted Stock Units · Derivative 2,352 $0.00 Strike: $0.00 $0.00
Disclosure

SEC source: 0001680115-25-000008 · wk-form4_1757019359.xml · derivative · entry 5

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 14,104

Underlying: Common stock · 2,352 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.

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

F1 · shares: Represents a 5% vesting on September 1, 2025, with a release date of September 2, 2025, the first business day following vesting. The original grant was 23,508 restricted stock units, with 20% vesting on March 1, 2023, 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.

Read SEC document
September 01, 2025 Filed Sep 4, 2025 20:56 UTC PEGASYSTEMS INC PEGA · Entity 309 Tax withholdingCommon stock 926 $54.21 $50,198.46
Disclosure

SEC source: 0001680115-25-000008 · wk-form4_1757019359.xml · nonDerivative · entry 2

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 121,294

Read SEC document
September 01, 2025 Filed Sep 4, 2025 20:56 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionCommon stock 2,352 $0.00 $0.00
Disclosure

SEC source: 0001680115-25-000008 · wk-form4_1757019359.xml · nonDerivative · entry 1

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 122,220

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: Represents a 5% vesting on September 1, 2025, with a release date of September 2, 2025, the first business day following vesting. The original grant was 23,508 restricted stock units, with 20% vesting on March 1, 2023, and the remaining 80% vesting in equal quarterly installments over the remaining four years.

Read SEC document
August 04, 2025 Filed Aug 5, 2025 21:09 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionStock Options · Derivative 25,920 $0.00 Strike: $16.95 $0.00
Disclosure

SEC source: 0001680115-25-000006 · wk-form4_1754428157.xml · derivative · entry 6

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 129,600

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.

F4 · shares: All share amounts and price data 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.

F5 · derivative.exercise_date: Option vests in 16 equal quarterly installments over four years beginning on the Date Exercisable in Table II.

Read SEC document
August 04, 2025 Filed Aug 5, 2025 21:09 UTC PEGASYSTEMS INC PEGA · Entity 309 SaleCommon stock 11,147 $58.19 $648,643.93
Disclosure

SEC source: 0001680115-25-000006 · wk-form4_1754428157.xml · nonDerivative · entry 5

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 119,868

F3 · price: Represents the weighted average of sale prices, ranging from $58.17 to $58.27. 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
August 04, 2025 Filed Aug 5, 2025 21:09 UTC PEGASYSTEMS INC PEGA · Entity 309 Tax withholdingCommon stock 14,773 $58.27 $860,822.71
Disclosure

SEC source: 0001680115-25-000006 · wk-form4_1754428157.xml · nonDerivative · entry 4

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 131,015

Read SEC document
August 04, 2025 Filed Aug 5, 2025 21:09 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionCommon stock 25,920 $16.95 $439,344.00
Disclosure

SEC source: 0001680115-25-000006 · wk-form4_1754428157.xml · nonDerivative · entry 3

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 145,788

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
August 01, 2025 Filed Aug 5, 2025 21:09 UTC PEGASYSTEMS INC PEGA · Entity 309 SaleCommon stock 100 $58.24 $5,824.00
Disclosure

SEC source: 0001680115-25-000006 · wk-form4_1754428157.xml · nonDerivative · entry 2

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 119,868

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
August 01, 2025 Filed Aug 5, 2025 21:09 UTC PEGASYSTEMS INC PEGA · Entity 309 SaleCommon stock 3,900 $57.70 $225,030.00
Disclosure

SEC source: 0001680115-25-000006 · wk-form4_1754428157.xml · nonDerivative · entry 1

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 119,968

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 $57.20 to $58.14. 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
July 28, 2025 Filed Jul 29, 2025 21:03 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionStock Options · Derivative 220,000 $0.00 Strike: $26.24 $0.00
Disclosure

SEC source: 0001680115-25-000004 · wk-form4_1753823013.xml · derivative · entry 3

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common stock · 220,000 shares

Expires 2032-06-05

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 · shares: All share amounts and price data 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.

F2 · derivative.exercise_date: Options vested 33% on the Date Exercisable in Table II, with the remaining 67% vesting in equal quarterly amounts over the next two years.

Read SEC document
July 28, 2025 Filed Jul 29, 2025 21:03 UTC PEGASYSTEMS INC PEGA · Entity 309 Tax withholdingCommon stock 145,482 $59.42 $8,644,540.44
Disclosure

SEC source: 0001680115-25-000004 · wk-form4_1753823013.xml · nonDerivative · entry 2

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 123,868

Read SEC document
July 28, 2025 Filed Jul 29, 2025 21:03 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionCommon stock 220,000 $26.24 $5,772,800.00
Disclosure

SEC source: 0001680115-25-000004 · wk-form4_1753823013.xml · nonDerivative · entry 1

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 269,350

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
July 01, 2025 Filed Jul 3, 2025 21:10 UTC PEGASYSTEMS INC PEGA · Entity 309 SaleCommon stock 1,000 $53.64 $53,640.00
Disclosure

SEC source: 0001013857-25-000195 · wk-form4_1751577032.xml · nonDerivative · entry 2

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 49,350

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.

F3 · price: Represents the weighted average of sale prices, ranging from $53.05 to $53.94. 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.

F4 · balance_after: Total shares beneficially owned reflect a 2-for-1 stock split effectuated on June 20, 2025. Includes shares acquired on June 30, 2025 pursuant to the employee stock purchase plan.

Read SEC document
July 01, 2025 Filed Jul 3, 2025 21:10 UTC PEGASYSTEMS INC PEGA · Entity 309 SaleCommon stock 3,000 $52.31 $156,930.00
Disclosure

SEC source: 0001013857-25-000195 · wk-form4_1751577032.xml · nonDerivative · entry 1

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 50,350

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 $51.88 to $52.67. 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
June 09, 2025 Filed Jun 10, 2025 21:11 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionRestricted Stock Units · Derivative 2,611 $0.00 Strike: $0.00 $0.00
Disclosure

SEC source: 0001013857-25-000178 · wk-form4_1749589887.xml · derivative · entry 3

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 18,273

Underlying: Common stock · 2,611 shares

Expires not disclosed

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.

F4 · security: Each restricted stock unit represents the right to receive, following vesting, one share of the issuer's common stock.

F1 · shares: Represents a 5% vesting on June 7, 2025, with a release date of June 9, 2025, the first business day following vesting. The original grant was 41,768 restricted stock units, with a 25% vesting on March 7, 2024. The remaining 75% will vest in equal quarterly installments over the remaining three years.

F5 · derivative.expiration_date: Once vested, the shares of common stock are not subject to expiration.

Read SEC document
June 09, 2025 Filed Jun 10, 2025 21:11 UTC PEGASYSTEMS INC PEGA · Entity 309 Tax withholdingCommon stock 1,028 $102.46 $105,328.88
Disclosure

SEC source: 0001013857-25-000178 · wk-form4_1749589887.xml · nonDerivative · entry 2

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 26,605

F2 · shares: Tendered to issuer to satisfy tax withholding obligations of the reporting person, exempted pursuant to Rule 16b-3(e).

F3 · balance_after: Does not include shares of common stock subject to unvested restricted stock units and/or options awards.

Read SEC document
June 09, 2025 Filed Jun 10, 2025 21:11 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionCommon stock 2,611 $0.00 $0.00
Disclosure

SEC source: 0001013857-25-000178 · wk-form4_1749589887.xml · nonDerivative · entry 1

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 27,633

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: Represents a 5% vesting on June 7, 2025, with a release date of June 9, 2025, the first business day following vesting. The original grant was 41,768 restricted stock units, with a 25% vesting on March 7, 2024. The remaining 75% will vest in equal quarterly installments over the remaining three years.

Read SEC document
June 05, 2025 Filed Jun 9, 2025 21:27 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionRestricted Stock Units · Derivative 2,201 $0.00 Strike: $0.00 $0.00
Disclosure

SEC source: 0001013857-25-000168 · wk-form4_1749504441.xml · derivative · entry 3

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 24,212

Underlying: Common stock · 2,201 shares

Expires not disclosed

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.

F4 · security: Each restricted stock unit represents the right to receive, following vesting, one share of the issuer's common stock.

F1 · shares: Represents a 5% vesting on June 5, 2025. The original grant was 35,218 restricted stock units, with 25 % vesting on March 5, 2025, and the remaining 75% vesting in equal quarterly installments over the next three years.

F5 · derivative.expiration_date: Once vested, the shares of common stock are not subject to expiration.

Read SEC document
June 05, 2025 Filed Jun 9, 2025 21:27 UTC PEGASYSTEMS INC PEGA · Entity 309 Tax withholdingCommon stock 867 $101.41 $87,922.47
Disclosure

SEC source: 0001013857-25-000168 · wk-form4_1749504441.xml · nonDerivative · entry 2

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 25,022

F2 · shares: Tendered to issuer to satisfy tax withholding obligations of the reporting person, exempted pursuant to Rule 16b-3(e).

F3 · balance_after: Does not include shares of common stock subject to unvested restricted stock units and/or options awards.

Read SEC document
June 05, 2025 Filed Jun 9, 2025 21:27 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionCommon stock 2,201 $0.00 $0.00
Disclosure

SEC source: 0001013857-25-000168 · wk-form4_1749504441.xml · nonDerivative · entry 1

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 25,889

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: Represents a 5% vesting on June 5, 2025. The original grant was 35,218 restricted stock units, with 25 % vesting on March 5, 2025, and the remaining 75% vesting in equal quarterly installments over the next three years.

Read SEC document
June 02, 2025 Filed Jun 3, 2025 21:25 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionRestricted Stock Units · Derivative 576 $0.00 Strike: $0.00 $0.00
Disclosure

SEC source: 0001013857-25-000152 · wk-form4_1748985930.xml · derivative · entry 7

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 1,729

Underlying: Common stock · 576 shares

Expires not disclosed

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

F3 · shares: Represents a 5% vesting on June 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.

F7 · derivative.expiration_date: Once vested, the shares of common stock are not subject to expiration.

Read SEC document
June 02, 2025 Filed Jun 3, 2025 21:25 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionRestricted Stock Units · Derivative 1,175 $0.00 Strike: $0.00 $0.00
Disclosure

SEC source: 0001013857-25-000152 · wk-form4_1748985930.xml · derivative · entry 6

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 8,228

Underlying: Common stock · 1,175 shares

Expires not disclosed

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

F1 · shares: Represents a 5% vesting on June 1, 2025, with a release date of June 2, 2025, the first business day following vesting. The original grant was 23,508 restricted stock units, with 20% vesting on March 1, 2023, and the remaining 80% vesting in equal quarterly installments over the remaining four years.

F7 · derivative.expiration_date: Once vested, the shares of common stock are not subject to expiration.

Read SEC document
June 02, 2025 Filed Jun 3, 2025 21:25 UTC PEGASYSTEMS INC PEGA · Entity 309 SaleCommon stock 2,000 $97.48 $194,960.00
Disclosure

SEC source: 0001013857-25-000152 · wk-form4_1748985930.xml · nonDerivative · entry 5

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 23,688

F4 · 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.

F5 · balance_after: Does not include shares of common stock subject to unvested restricted stock units and/or options awards.

Read SEC document
June 02, 2025 Filed Jun 3, 2025 21:25 UTC PEGASYSTEMS INC PEGA · Entity 309 Tax withholdingCommon stock 227 $98.15 $22,280.05
Disclosure

SEC source: 0001013857-25-000152 · wk-form4_1748985930.xml · nonDerivative · entry 4

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 25,688

F2 · shares: Tendered to issuer to satisfy tax withholding obligations of the reporting person, exempted pursuant to Rule 16b-3(e).

Read SEC document
June 02, 2025 Filed Jun 3, 2025 21:25 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionCommon stock 576 $98.15 $56,534.40
Disclosure

SEC source: 0001013857-25-000152 · wk-form4_1748985930.xml · nonDerivative · entry 3

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 25,915

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 · shares: Represents a 5% vesting on June 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.

Read SEC document
June 02, 2025 Filed Jun 3, 2025 21:25 UTC PEGASYSTEMS INC PEGA · Entity 309 Tax withholdingCommon stock 463 $98.15 $45,443.45
Disclosure

SEC source: 0001013857-25-000152 · wk-form4_1748985930.xml · nonDerivative · entry 2

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 25,339

F2 · shares: Tendered to issuer to satisfy tax withholding obligations of the reporting person, exempted pursuant to Rule 16b-3(e).

Read SEC document
June 02, 2025 Filed Jun 3, 2025 21:25 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionCommon stock 1,175 $98.15 $115,326.25
Disclosure

SEC source: 0001013857-25-000152 · wk-form4_1748985930.xml · nonDerivative · entry 1

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 25,802

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: Represents a 5% vesting on June 1, 2025, with a release date of June 2, 2025, the first business day following vesting. The original grant was 23,508 restricted stock units, with 20% vesting on March 1, 2023, and the remaining 80% vesting in equal quarterly installments over the remaining four years.

Read SEC document
May 14, 2025 Filed May 15, 2025 21:26 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionStock Options · Derivative 12,960 $0.00 Strike: $33.90 $0.00
Disclosure

SEC source: 0001013857-25-000134 · wk-form4_1747344391.xml · derivative · entry 3

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 77,760

Underlying: Common stock · 12,960 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.

F3 · derivative.exercise_date: Options will vest in equal quarterly installments over a four year period. The first vest occurred on February 2, 2023.

Read SEC document
May 14, 2025 Filed May 15, 2025 21:26 UTC PEGASYSTEMS INC PEGA · Entity 309 Tax withholdingCommon stock 7,828 $97.70 $764,795.60
Disclosure

SEC source: 0001013857-25-000134 · wk-form4_1747344391.xml · nonDerivative · entry 2

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 24,627

F1 · price: Represents the exercise price of the stock options referenced in Table II and Mr. Stillwell's tax liability, which were paid by way of the Company withholding shares of equal value.

F2 · balance_after: Does not include shares of common stock subject to unvested restricted stock units and/or options awards.

Read SEC document
May 14, 2025 Filed May 15, 2025 21:26 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionCommon stock 12,960 $33.90 $439,344.00
Disclosure

SEC source: 0001013857-25-000134 · wk-form4_1747344391.xml · nonDerivative · entry 1

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 32,455

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
May 01, 2025 Filed May 5, 2025 21:14 UTC PEGASYSTEMS INC PEGA · Entity 309 SaleCommon stock 300 $94.17 $28,251.00
Disclosure

SEC source: 0001013857-25-000130 · wk-form4_1746479666.xml · nonDerivative · entry 2

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 19,495

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.

F3 · price: Represents the weighted average of sale prices, ranging from $93.76 to $94.55. 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.

F4 · balance_after: Does not include shares of common stock subject to unvested restricted stock units and/or options awards.

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May 01, 2025 Filed May 5, 2025 21:14 UTC PEGASYSTEMS INC PEGA · Entity 309 SaleCommon stock 1,700 $92.71 $157,607.00
Disclosure

SEC source: 0001013857-25-000130 · wk-form4_1746479666.xml · nonDerivative · entry 1

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 19,795

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 $92.14 to $93.05. 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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April 25, 2025 Filed Apr 29, 2025 21:09 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionStock Options · Derivative 31,326 $0.00 Strike: $47.27 $0.00
Disclosure

SEC source: 0001013857-25-000121 · wk-form4_1745960978.xml · derivative · entry 8

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common stock · 31,326 shares

Expires 2033-03-07

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.

F5 · shares: On March 7, 2023, the reporting person was granted an option to purchase 41,768 shares of common stock. The option vested in two installments: 25% vested on the first anniversary of the date of grant, and 75% vested on the second anniversary of the date of grant.

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April 25, 2025 Filed Apr 29, 2025 21:09 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionStock Options · Derivative 30,000 $0.00 Strike: $47.27 $0.00
Disclosure

SEC source: 0001013857-25-000121 · wk-form4_1745960978.xml · derivative · entry 7

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common stock · 30,000 shares

Expires 2033-03-07

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.

F4 · shares: On March 7, 2023, the reporting person was granted an option to purchase 40,000 shares of common stock. The option vested in two installments: 25% vested on the first anniversary of the date of grant, and 75% vested on the second anniversary of the date of grant.

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April 25, 2025 Filed Apr 29, 2025 21:09 UTC PEGASYSTEMS INC PEGA · Entity 309 SaleCommon stock 9,048 $89.36 $808,529.28
Disclosure

SEC source: 0001013857-25-000121 · wk-form4_1745960978.xml · nonDerivative · entry 6

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 21,495

F2 · price: Represents the weighted average of sale prices, ranging from $89.33 to $89.49. 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.

F3 · balance_after: Does not include shares of common stock subject to unvested restricted stock units and/or options awards.

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April 25, 2025 Filed Apr 29, 2025 21:09 UTC PEGASYSTEMS INC PEGA · Entity 309 Tax withholdingCommon stock 22,278 $90.25 $2,010,589.50
Disclosure

SEC source: 0001013857-25-000121 · wk-form4_1745960978.xml · nonDerivative · entry 5

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 30,543

F1 · price: Represents the exercise price of the stock options referenced in Table II and Mr. Stillwell's tax liability, which were paid by way of the Company withholding shares of equal value.

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April 25, 2025 Filed Apr 29, 2025 21:09 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionCommon stock 31,326 $47.27 $1,480,780.02
Disclosure

SEC source: 0001013857-25-000121 · wk-form4_1745960978.xml · nonDerivative · entry 4

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 52,821

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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April 25, 2025 Filed Apr 29, 2025 21:09 UTC PEGASYSTEMS INC PEGA · Entity 309 SaleCommon stock 8,665 $89.36 $774,304.40
Disclosure

SEC source: 0001013857-25-000121 · wk-form4_1745960978.xml · nonDerivative · entry 3

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 21,495

F2 · price: Represents the weighted average of sale prices, ranging from $89.33 to $89.49. 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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April 25, 2025 Filed Apr 29, 2025 21:09 UTC PEGASYSTEMS INC PEGA · Entity 309 Tax withholdingCommon stock 21,335 $90.25 $1,925,483.75
Disclosure

SEC source: 0001013857-25-000121 · wk-form4_1745960978.xml · nonDerivative · entry 2

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 30,160

F1 · price: Represents the exercise price of the stock options referenced in Table II and Mr. Stillwell's tax liability, which were paid by way of the Company withholding shares of equal value.

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April 25, 2025 Filed Apr 29, 2025 21:09 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionCommon stock 30,000 $47.27 $1,418,100.00
Disclosure

SEC source: 0001013857-25-000121 · wk-form4_1745960978.xml · nonDerivative · entry 1

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 51,495

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
April 01, 2025 Filed Apr 3, 2025 22:48 UTC PEGASYSTEMS INC PEGA · Entity 309 SaleCommon stock 2,000 $69.75 $139,500.00
Disclosure

SEC source: 0001013857-25-000089 · wk-form4_1743720353.xml · nonDerivative · entry 1

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 21,245

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 $69.49 to $70.00. The individual has provided the Company, and undertakes to provide to the staff of the Securities and Exchange Commission or any security holder of the Company, upon request, full information regarding the number of shares sold at each separate price.

F3 · balance_after: Does not include shares of common stock subject to unvested restricted stock units and/or options awards.

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March 07, 2025 Filed Mar 11, 2025 21:18 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionRestricted Stock Units · Derivative 2,610 $0.00 Strike: $0.00 $0.00
Disclosure

SEC source: 0001013857-25-000079 · wk-form4_1741727917.xml · derivative · entry 3

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 20,884

Underlying: Common stock · 2,610 shares

Expires not disclosed

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.

F4 · security: Each restricted stock unit represents the right to receive, following vesting, one share of the issuer's common stock.

F1 · shares: Represents a 5% vesting on March 7, 2025. The original grant was 41,768 restricted stock units, with a 25% vesting on March 7, 2024. The remaining 75% will vest in equal quarterly installments over the remaining three years.

F5 · derivative.expiration_date: Once vested, the shares of common stock are not subject to expiration.

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March 07, 2025 Filed Mar 11, 2025 21:18 UTC PEGASYSTEMS INC PEGA · Entity 309 Tax withholdingCommon stock 1,028 $76.86 $79,012.08
Disclosure

SEC source: 0001013857-25-000079 · wk-form4_1741727917.xml · nonDerivative · entry 2

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 23,245

F2 · shares: Tendered to issuer to satisfy tax withholding obligations of the reporting person, exempted pursuant to Rule 16b-3(e).

F3 · balance_after: Does not include shares of common stock subject to unvested restricted stock units and/or options awards.

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March 07, 2025 Filed Mar 11, 2025 21:18 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionCommon stock 2,610 $0.00 $0.00
Disclosure

SEC source: 0001013857-25-000079 · wk-form4_1741727917.xml · nonDerivative · entry 1

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 24,273

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: Represents a 5% vesting on March 7, 2025. The original grant was 41,768 restricted stock units, with a 25% vesting on March 7, 2024. The remaining 75% will vest in equal quarterly installments over the remaining three years.

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March 05, 2025 Filed Mar 6, 2025 22:41 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionRestricted Stock Units · Derivative 8,805 $0.00 Strike: $0.00 $0.00
Disclosure

SEC source: 0001013857-25-000065 · wk-form4_1741300893.xml · derivative · entry 9

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 26,413

Underlying: Common stock · 8,805 shares

Expires not disclosed

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

F3 · shares: Represents a 25% vesting on March 5, 2025. The original grant was 35,218 restricted stock units, with the remaining 75% vesting in equal quarterly installments over the next three years.

F7 · derivative.expiration_date: Once vested, the shares of common stock are not subject to expiration.

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March 05, 2025 Filed Mar 6, 2025 22:41 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionRestricted Stock Units · Derivative 3,522 $0.00 Strike: $0.00 $0.00
Disclosure

SEC source: 0001013857-25-000065 · wk-form4_1741300893.xml · derivative · entry 8

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common stock · 3,522 shares

Expires not disclosed

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

F1 · shares: Represents a 100% vesting on March 5, 2025. The original grant was 3,522 restricted stock units, which were granted on March 5, 2024. As part of the Company's Corporate Incentive Compensation Plan (CICP), Mr. Stillwell elected to receive half of his annual bonus in RSUs.

F7 · derivative.expiration_date: Once vested, the shares of common stock are not subject to expiration.

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March 05, 2025 Filed Mar 6, 2025 22:41 UTC PEGASYSTEMS INC PEGA · Entity 309 Tax withholdingCommon stock 3,465 $77.63 $268,987.95
Disclosure

SEC source: 0001013857-25-000065 · wk-form4_1741300893.xml · nonDerivative · entry 4

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 21,663

F2 · shares: Tendered to issuer to satisfy tax withholding obligations of the reporting person, exempted pursuant to Rule 16b-3(e).

F4 · balance_after: Does not include shares of common stock subject to unvested restricted stock units and/or options awards.

Read SEC document
March 05, 2025 Filed Mar 6, 2025 22:41 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionCommon stock 8,805 $0.00 $0.00
Disclosure

SEC source: 0001013857-25-000065 · wk-form4_1741300893.xml · nonDerivative · entry 3

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 25,128

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 · shares: Represents a 25% vesting on March 5, 2025. The original grant was 35,218 restricted stock units, with the remaining 75% vesting in equal quarterly installments over the next three years.

Read SEC document

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