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STILLWELL KENNETH

Disclosed activity across 1 company

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SEC CIK
0001680115

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Reported relationships

Latest disclosed role at each company.

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 11, 2026 Filed Sep 15, 2026 20:21 UTC PEGASYSTEMS INC PEGA · Entity 309 SaleCommon stock 39,627 $35.77 $1,417,437.98
Disclosure

SEC source: 0001680115-26-000036 · wk-form4_1789503659.xml · nonDerivative · entry 1

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 95,225

F1 · price: 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.

Read SEC document
September 07, 2026 Filed Sep 9, 2026 21:38 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionRestricted Stock Units · Derivative 5,220 $0.00 Strike: $0.00 $0.00
Disclosure

SEC source: 0001680115-26-000034 · wk-form4_1788989919.xml · derivative · entry 10

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 10,442

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

F2 · derivative.exercise_date: 25% of the restricted stock units vested on the Date Exercisable in Table II, and the remaining 75% vest in equal quarterly installments over the following three years.

Read SEC document
September 07, 2026 Filed Sep 9, 2026 21:38 UTC PEGASYSTEMS INC PEGA · Entity 309 Tax withholdingCommon stock 2,055 $37.36 $76,774.80
Disclosure

SEC source: 0001680115-26-000034 · wk-form4_1788989919.xml · nonDerivative · entry 6

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 134,852

Read SEC document
September 07, 2026 Filed Sep 9, 2026 21:38 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionCommon stock 5,220 $0.00 $0.00
Disclosure

SEC source: 0001680115-26-000034 · wk-form4_1788989919.xml · nonDerivative · entry 5

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 136,907

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
September 05, 2026 Filed Sep 9, 2026 21:38 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionRestricted Stock Units · Derivative 4,402 $0.00 Strike: $0.00 $0.00
Disclosure

SEC source: 0001680115-26-000034 · wk-form4_1788989919.xml · derivative · entry 9

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 26,414

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

F2 · derivative.exercise_date: 25% of the restricted stock units vested on the Date Exercisable in Table II, and the remaining 75% vest in equal quarterly installments over the following three years.

Read SEC document
September 05, 2026 Filed Sep 9, 2026 21:38 UTC PEGASYSTEMS INC PEGA · Entity 309 Tax withholdingCommon stock 1,733 $37.36 $64,744.88
Disclosure

SEC source: 0001680115-26-000034 · wk-form4_1788989919.xml · nonDerivative · entry 4

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 131,687

Read SEC document
September 05, 2026 Filed Sep 9, 2026 21:38 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionCommon stock 4,402 $0.00 $0.00
Disclosure

SEC source: 0001680115-26-000034 · wk-form4_1788989919.xml · nonDerivative · entry 3

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 133,420

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
September 04, 2026 Filed Sep 9, 2026 21:38 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionRestricted Stock Units · Derivative 3,232 $0.00 Strike: $0.00 $0.00
Disclosure

SEC source: 0001680115-26-000034 · wk-form4_1788989919.xml · derivative · entry 8

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 32,308

Underlying: Common stock · 3,232 shares

Expires 2029-03-04

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: 25% of the restricted stock units vested on the Date Exercisable in Table II, and the remaining 75% vest in equal quarterly installments over the following three years.

Read SEC document
September 04, 2026 Filed Sep 9, 2026 21:38 UTC PEGASYSTEMS INC PEGA · Entity 309 Tax withholdingCommon stock 1,272 $37.72 $47,979.84
Disclosure

SEC source: 0001680115-26-000034 · wk-form4_1788989919.xml · nonDerivative · entry 2

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 129,018

Read SEC document
September 04, 2026 Filed Sep 9, 2026 21:38 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionCommon stock 3,232 $0.00 $0.00
Disclosure

SEC source: 0001680115-26-000034 · wk-form4_1788989919.xml · nonDerivative · entry 1

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 130,290

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
September 01, 2026 Filed Sep 2, 2026 20:12 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionRestricted Stock Units · Derivative 2,350 $0.00 Strike: $0.00 $0.00
Disclosure

SEC source: 0001680115-26-000032 · wk-form4_1788379926.xml · derivative · entry 4

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 4,702

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
September 01, 2026 Filed Sep 2, 2026 20:12 UTC PEGASYSTEMS INC PEGA · Entity 309 Tax withholdingCommon stock 925 $36.81 $34,049.25
Disclosure

SEC source: 0001680115-26-000032 · wk-form4_1788379926.xml · nonDerivative · entry 2

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 127,058

Read SEC document
September 01, 2026 Filed Sep 2, 2026 20:12 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionCommon stock 2,350 $0.00 $0.00
Disclosure

SEC source: 0001680115-26-000032 · wk-form4_1788379926.xml · nonDerivative · entry 1

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 127,983

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 10, 2026 Filed Aug 11, 2026 20:10 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionStock Options · Derivative 25,920 $0.00 Strike: $16.95 $0.00
Disclosure

SEC source: 0001680115-26-000030 · wk-form4_1786479056.xml · derivative · entry 4

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 25,920

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 a four-year period beginning on the Date Exercisable in Table II.

Read SEC document
August 10, 2026 Filed Aug 11, 2026 20:10 UTC PEGASYSTEMS INC PEGA · Entity 309 Tax withholdingCommon stock 18,292 $32.93 $602,355.56
Disclosure

SEC source: 0001680115-26-000030 · wk-form4_1786479056.xml · nonDerivative · entry 2

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 125,633

Read SEC document
August 10, 2026 Filed Aug 11, 2026 20:10 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionCommon stock 25,920 $16.95 $439,344.00
Disclosure

SEC source: 0001680115-26-000030 · wk-form4_1786479056.xml · nonDerivative · entry 1

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 143,925

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
June 07, 2026 Filed Jun 9, 2026 20:22 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionRestricted Stock Units · Derivative 5,222 $0.00 Strike: $0.00 $0.00
Disclosure

SEC source: 0001680115-26-000028 · wk-form4_1781036556.xml · derivative · entry 4

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 15,662

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.

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.

Read SEC document
June 07, 2026 Filed Jun 9, 2026 20:22 UTC PEGASYSTEMS INC PEGA · Entity 309 Tax withholdingCommon stock 2,055 $34.71 $71,329.05
Disclosure

SEC source: 0001680115-26-000028 · wk-form4_1781036556.xml · nonDerivative · entry 2

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 117,752

Read SEC document
June 07, 2026 Filed Jun 9, 2026 20:22 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionCommon stock 5,222 $0.00 $0.00
Disclosure

SEC source: 0001680115-26-000028 · wk-form4_1781036556.xml · nonDerivative · entry 1

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 119,807

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
June 05, 2026 Filed Jun 8, 2026 20:07 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionRestricted Stock Units · Derivative 4,402 $0.00 Strike: $0.00 $0.00
Disclosure

SEC source: 0001680115-26-000026 · wk-form4_1780949224.xml · derivative · entry 7

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 30,816

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: 25% of the restricted stock units vested on the Date Exercisable in Table II, and the remaining 75% vest in equal quarterly installments over the following three years.

Read SEC document
June 05, 2026 Filed Jun 8, 2026 20:07 UTC PEGASYSTEMS INC PEGA · Entity 309 Tax withholdingCommon stock 1,733 $35.44 $61,417.52
Disclosure

SEC source: 0001680115-26-000026 · wk-form4_1780949224.xml · nonDerivative · entry 4

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 114,585

Read SEC document
June 05, 2026 Filed Jun 8, 2026 20:07 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionCommon stock 4,402 $0.00 $0.00
Disclosure

SEC source: 0001680115-26-000026 · wk-form4_1780949224.xml · nonDerivative · entry 3

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 116,318

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
June 04, 2026 Filed Jun 8, 2026 20:07 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionRestricted Stock Units · Derivative 3,230 $0.00 Strike: $0.00 $0.00
Disclosure

SEC source: 0001680115-26-000026 · wk-form4_1780949224.xml · derivative · entry 6

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 35,540

Underlying: Common stock · 3,230 shares

Expires 2029-03-04

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: 25% of the restricted stock units vested on the Date Exercisable in Table II, and the remaining 75% vest in equal quarterly installments over the following three years.

Read SEC document
June 04, 2026 Filed Jun 8, 2026 20:07 UTC PEGASYSTEMS INC PEGA · Entity 309 Tax withholdingCommon stock 1,272 $35.11 $44,659.92
Disclosure

SEC source: 0001680115-26-000026 · wk-form4_1780949224.xml · nonDerivative · entry 2

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 111,916

Read SEC document
June 04, 2026 Filed Jun 8, 2026 20:07 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionCommon stock 3,230 $0.00 $0.00
Disclosure

SEC source: 0001680115-26-000026 · wk-form4_1780949224.xml · nonDerivative · entry 1

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 113,188

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
June 01, 2026 Filed Jun 2, 2026 20:53 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionRestricted Stock Units · Derivative 2,352 $0.00 Strike: $0.00 $0.00
Disclosure

SEC source: 0001680115-26-000024 · wk-form4_1780433619.xml · derivative · entry 4

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 7,052

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.

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
June 01, 2026 Filed Jun 2, 2026 20:53 UTC PEGASYSTEMS INC PEGA · Entity 309 Tax withholdingCommon stock 926 $35.73 $33,085.98
Disclosure

SEC source: 0001680115-26-000024 · wk-form4_1780433619.xml · nonDerivative · entry 2

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 109,958

Read SEC document
June 01, 2026 Filed Jun 2, 2026 20:53 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionCommon stock 2,352 $0.00 $0.00
Disclosure

SEC source: 0001680115-26-000024 · wk-form4_1780433619.xml · nonDerivative · entry 1

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 110,884

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 05, 2026 Filed May 6, 2026 20:06 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionStock Options · Derivative 25,920 $0.00 Strike: $16.95 $0.00
Disclosure

SEC source: 0001680115-26-000022 · wk-form4_1778097995.xml · derivative · entry 5

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 51,840

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
May 05, 2026 Filed May 6, 2026 20:06 UTC PEGASYSTEMS INC PEGA · Entity 309 SaleCommon stock 8,383 $36.45 $305,560.35
Disclosure

SEC source: 0001680115-26-000022 · wk-form4_1778097995.xml · nonDerivative · entry 3

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 108,532

Read SEC document
May 05, 2026 Filed May 6, 2026 20:06 UTC PEGASYSTEMS INC PEGA · Entity 309 Tax withholdingCommon stock 17,537 $36.32 $636,943.84
Disclosure

SEC source: 0001680115-26-000022 · wk-form4_1778097995.xml · nonDerivative · entry 2

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 116,915

Read SEC document
May 05, 2026 Filed May 6, 2026 20:06 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionCommon stock 25,920 $16.95 $439,344.00
Disclosure

SEC source: 0001680115-26-000022 · wk-form4_1778097995.xml · nonDerivative · entry 1

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 134,452

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, 2026 Filed Apr 3, 2026 20:02 UTC PEGASYSTEMS INC PEGA · Entity 309 SaleCommon stock 1,000 $43.17 $43,170.00
Disclosure

SEC source: 0001680115-26-000020 · wk-form4_1775246547.xml · nonDerivative · entry 1

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 108,532

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 10, 2026 Filed Mar 12, 2026 20:04 UTC PEGASYSTEMS INC PEGA · Entity 309 SaleCommon stock 44,000 $44.81 $1,971,640.00
Disclosure

SEC source: 0001680115-26-000018 · wk-form4_1773345867.xml · nonDerivative · entry 1

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 109,123

F1 · price: Represents the weighted average of sale prices, ranging from $44.52 to $45.42 . 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
March 07, 2026 Filed Mar 10, 2026 20:24 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionRestricted Stock Units · Derivative 5,220 $0.00 Strike: $0.00 $0.00
Disclosure

SEC source: 0001680115-26-000016 · wk-form4_1773174240.xml · derivative · entry 4

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 20,884

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.

Read SEC document
March 07, 2026 Filed Mar 10, 2026 20:24 UTC PEGASYSTEMS INC PEGA · Entity 309 Tax withholdingCommon stock 2,055 $47.24 $97,078.20
Disclosure

SEC source: 0001680115-26-000016 · wk-form4_1773174240.xml · nonDerivative · entry 2

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 153,123

Read SEC document
March 07, 2026 Filed Mar 10, 2026 20:24 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionCommon stock 5,220 $0.00 $0.00
Disclosure

SEC source: 0001680115-26-000016 · wk-form4_1773174240.xml · nonDerivative · entry 1

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 155,178

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
March 05, 2026 Filed Mar 9, 2026 20:25 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionRestricted Stock Units · Derivative 4,402 $0.00 Strike: $0.00 $0.00
Disclosure

SEC source: 0001680115-26-000014 · wk-form4_1773087926.xml · derivative · entry 4

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 35,218

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

F2 · derivative.exercise_date: 25% of the restricted stock units vest on the Date Exercisable in Table II, and the remaining 75% vest in equal quarterly installments over the following three years.

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March 05, 2026 Filed Mar 9, 2026 20:25 UTC PEGASYSTEMS INC PEGA · Entity 309 Tax withholdingCommon stock 1,733 $47.05 $81,537.65
Disclosure

SEC source: 0001680115-26-000014 · wk-form4_1773087926.xml · nonDerivative · entry 2

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 149,958

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March 05, 2026 Filed Mar 9, 2026 20:25 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionCommon stock 4,402 $0.00 $0.00
Disclosure

SEC source: 0001680115-26-000014 · wk-form4_1773087926.xml · nonDerivative · entry 1

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 151,691

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.

Read SEC document
March 04, 2026 Filed Mar 5, 2026 21:23 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionRestricted Stock Units · Derivative 6,668 $0.00 Strike: $0.00 $0.00
Disclosure

SEC source: 0001680115-26-000012 · wk-form4_1772745802.xml · derivative · entry 10

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common stock · 6,668 shares

Expires 2026-03-04

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.

F5 · derivative.exercise_date: This restricted stock unit award vested 100% based on the achievement of performance conditions under the Company's CICP related to the Company's financial results for the year ended December 31, 2025.

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March 04, 2026 Filed Mar 5, 2026 21:23 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionRestricted Stock Units · Derivative 12,924 $0.00 Strike: $0.00 $0.00
Disclosure

SEC source: 0001680115-26-000012 · wk-form4_1772745802.xml · derivative · entry 9

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 38,770

Underlying: Common stock · 12,924 shares

Expires 2029-03-04

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.

F3 · derivative.exercise_date: 25% of the restricted stock units vest on the Date Exercisable in Table II, and the remaining 75% vest in equal quarterly installments over the following three years.

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March 04, 2026 Filed Mar 5, 2026 21:23 UTC PEGASYSTEMS INC PEGA · Entity 309 Tax withholdingCommon stock 2,624 $45.01 $118,106.24
Disclosure

SEC source: 0001680115-26-000012 · wk-form4_1772745802.xml · nonDerivative · entry 4

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 147,289

Read SEC document
March 04, 2026 Filed Mar 5, 2026 21:23 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionCommon stock 6,668 $0.00 $0.00
Disclosure

SEC source: 0001680115-26-000012 · wk-form4_1772745802.xml · nonDerivative · entry 3

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 149,913

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.

Read SEC document
March 04, 2026 Filed Mar 5, 2026 21:23 UTC PEGASYSTEMS INC PEGA · Entity 309 Tax withholdingCommon stock 4,195 $45.01 $188,816.95
Disclosure

SEC source: 0001680115-26-000012 · wk-form4_1772745802.xml · nonDerivative · entry 2

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 143,245

Read SEC document
March 04, 2026 Filed Mar 5, 2026 21:23 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionCommon stock 12,924 $0.00 $0.00
Disclosure

SEC source: 0001680115-26-000012 · wk-form4_1772745802.xml · nonDerivative · entry 1

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 147,440

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.

Read SEC document
March 03, 2026 Filed Mar 5, 2026 21:23 UTC PEGASYSTEMS INC PEGA · Entity 309 GrantRestricted Stock Units · Derivative 6,469 $0.00 Strike: $0.00 $0.00
Disclosure

SEC source: 0001680115-26-000012 · wk-form4_1772745802.xml · derivative · entry 8

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 6,469

Underlying: Common stock · 6,469 shares

Expires 2027-03-03

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

F4 · derivative.exercise_date: This award represents the election by the individual, as part of the Company's Corporate Incentive Compensation Plan (CICP), to receive half of their annual bonus in restricted share units. This restricted stock unit award vests 100% on the Date Exercisable in Table II, subject to attainment of the CICP performance threshold funding for the year ending December 31, 2026.

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March 03, 2026 Filed Mar 5, 2026 21:23 UTC PEGASYSTEMS INC PEGA · Entity 309 GrantRestricted Stock Units · Derivative 44,683 $0.00 Strike: $0.00 $0.00
Disclosure

SEC source: 0001680115-26-000012 · wk-form4_1772745802.xml · derivative · entry 7

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 44,683

Underlying: Common stock · 44,683 shares

Expires 2030-03-03

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

F3 · derivative.exercise_date: 25% of the restricted stock units vest on the Date Exercisable in Table II, and the remaining 75% vest in equal quarterly installments over the following three years.

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March 03, 2026 Filed Mar 5, 2026 21:23 UTC PEGASYSTEMS INC PEGA · Entity 309 GrantStock Option · Derivative 113,896 $0.00 Strike: $45.01 $0.00
Disclosure

SEC source: 0001680115-26-000012 · wk-form4_1772745802.xml · derivative · entry 6

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 113,896

Underlying: Common stock · 113,896 shares

Expires 2036-03-03

F2 · derivative.exercise_date: This stock option vests as to 25% of the shares subject thereto on the Date Exercisable in Table II, with the remaining 75% vesting in equal quarterly amounts over the following three years.

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March 02, 2026 Filed Mar 3, 2026 21:12 UTC PEGASYSTEMS INC PEGA · Entity 309 Exercise / conversionRestricted Stock Units · Derivative 1,152 $0.00 Strike: $0.00 $0.00
Disclosure

SEC source: 0001680115-26-000010 · wk-form4_1772572343.xml · derivative · entry 8

STILLWELL KENNETH · CIK 0001680115 · COO, CFO

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 0

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.

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.

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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.