Booth Richard Douglas

SEC source: 0001641054-26-000003 · form4-07202026_090731.xml · nonDerivative · entry 1

Booth Richard Douglas · CIK 0001641054 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 9,924

F1 · shares: The shares vest in four equal annual installments beginning on the first anniversary of the date of grant.

SEC source: 0001415889-25-020059 · form4-07212025_080713.xml · nonDerivative · entry 1

Booth Richard Douglas · CIK 0001641054 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 8,935

F1 · shares: The shares vest in four equal annual installments beginning on the first anniversary of the date of grant.

SEC source: 0001415889-25-011962 · form4-05052025_040504.xml · nonDerivative · entry 1

Booth Richard Douglas · CIK 0001641054 · CHIEF FINANCIAL OFFICER

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 652,630.173

F1 · kind: Represents the withholding of shares by the Issuer to satisfy the Reporting Person's tax withholding obligations in connection with the vesting and settlement of previously reported restricted stock units.

SEC source: 0001415889-25-008398 · form4-03182025_080318.xml · nonDerivative · entry 1

Booth Richard Douglas · CIK 0001641054 · CHIEF FINANCIAL OFFICER

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 660,503.173

F1 · kind: Represents the withholding of shares by the Issuer to satisfy the Reporting Person's tax withholding obligations in connection with the vesting and settlement of previously reported restricted stock units.

SEC source: 0001415889-25-003020 · form4-02042025_110205.xml · nonDerivative · entry 3

Booth Richard Douglas · CIK 0001641054 · CHIEF FINANCIAL OFFICER

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 661,466.173

F3 · kind: Represents the withholding of shares by the Issuer to satisfy the Reporting Person's tax withholding obligations in connection with the vesting and settlement of previously reported restricted stock units.

SEC source: 0001415889-25-003020 · form4-02042025_110205.xml · nonDerivative · entry 2

Booth Richard Douglas · CIK 0001641054 · CHIEF FINANCIAL OFFICER

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 688,546.173

F2 · kind: Represents the withholding of shares by the Issuer to satisfy the Reporting Person's tax withholding obligations in connection with the vesting and settlement of previously reported PSUs.

SEC source: 0001415889-25-003020 · form4-02042025_110205.xml · nonDerivative · entry 1

Booth Richard Douglas · CIK 0001641054 · CHIEF FINANCIAL OFFICER

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 698,738.173

F1 · shares: Reflects the number of performance-based restricted stock units ("PSUs"), each representing a contingent right to receive one share of the Issuer's Class A Common Stock, par value $0.001, earned upon the certification of achievement of certain performance criteria by the Issuer's compensation committee. The PSUs will vest in three substantially equal installments as to 1/3rd on January 21, 2025, 1/3rd on February 1, 2026, and the remaining 1/3rd on February 1, 2027 and will be settled pursuant to the terms of the Issuer's 2021 Equity Incentive Plan (as amended from time to time), in each case subject to the Reporting Person's continued service with the Issuer through each such vesting date.

SEC source: 0001415889-24-029614 · form4-12172024_091257.xml · nonDerivative · entry 1

Booth Richard Douglas · CIK 0001641054 · CHIEF FINANCIAL OFFICER

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 591,258.173

F1 · kind: The transaction reported represents the withholding of shares by the issuer to satisfy the reporting person's tax withholding obligations in connection with the vesting and settlement of previously reported restricted stock units.

SEC source: 0001415889-24-026333 · form4-11072024_041105.xml · nonDerivative · entry 1

Booth Richard Douglas · CIK 0001641054 · CHIEF FINANCIAL OFFICER

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 592,759.173

F1 · shares: Represents restricted stock units ("RSUs"), each representing a contingent right to receive one share of the Issuer's Class A Common Stock, par value $0.001. 100% of the RSUs vest on November 1, 2025, subject to the Reporting Person's continued service with the Issuer through such vesting date.

SEC source: 0001415889-24-026141 · form4-11052024_041108.xml · nonDerivative · entry 1

Booth Richard Douglas · CIK 0001641054 · CHIEF FINANCIAL OFFICER

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 500,380.173

F1 · kind: The transaction reported represents the withholding of shares by the issuer to satisfy the reporting person's tax withholding obligations in connection with the vesting and settlement of previously reported restricted stock units.

SEC source: 0001415889-24-023519 · form4-09172024_040901.xml · nonDerivative · entry 1

Booth Richard Douglas · CIK 0001641054 · CHIEF FINANCIAL OFFICER

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 504,191.173

F1 · kind: The transaction reported represents the withholding of shares by the issuer to satisfy the reporting person's tax withholding obligations in connection with the vesting and settlement of previously reported restricted stock units.

SEC source: 0001415889-24-020792 · form4-08052024_080809.xml · nonDerivative · entry 1

Booth Richard Douglas · CIK 0001641054 · CHIEF FINANCIAL OFFICER

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 505,184.173

F1 · kind: The transaction reported represents the withholding of shares by the issuer to satisfy the reporting person's tax withholding obligations in connection with the vesting and settlement of previously reported restricted stock units.

SEC source: 0001415889-24-019875 · form4-07222024_090743.xml · nonDerivative · entry 1

Booth Richard Douglas · CIK 0001641054 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 8,239

F1 · shares: The shares vest in four equal annual installments beginning on the first anniversary of the date of grant.

SEC source: 0001415889-24-017452 · form4-06182024_090653.xml · nonDerivative · entry 1

Booth Richard Douglas · CIK 0001641054 · CHIEF FINANCIAL OFFICER

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 508,804.173

F1 · kind: The transaction reported represents the withholding of shares by the issuer to satisfy the reporting person's tax withholding obligations in connection with the vesting and settlement of previously reported restricted stock units.

SEC source: 0001415889-24-012176 · form4-05032024_040509.xml · nonDerivative · entry 1

Booth Richard Douglas · CIK 0001641054 · CHIEF FINANCIAL OFFICER

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 509,797.173

F1 · kind: The transaction reported represents the withholding of shares by the issuer to satisfy the reporting person's tax withholding obligations in connection with the vesting and settlement of previously reported restricted stock units.

SEC source: 0001415889-24-008257 · form4-03182024_040306.xml · nonDerivative · entry 1

Booth Richard Douglas · CIK 0001641054 · CHIEF FINANCIAL OFFICER

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 513,417.173

F1 · kind: The transaction reported represents the withholding of shares by the issuer to satisfy the reporting person's tax withholding obligations in connection with the vesting and settlement of previously reported restricted stock units.

SEC source: 0001415889-24-004113 · form4-02162024_040221.xml · nonDerivative · entry 1

Booth Richard Douglas · CIK 0001641054 · CHIEF FINANCIAL OFFICER

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 514,410.173

F1 · shares: Represents restricted stock units ("RSUs"), each representing a contingent right to receive one share of the Issuer's Class A Common Stock, par value $0.001. The RSUs vest over a four-year period, with 25% of the RSUs vesting on February 1, 2025, followed by quarterly vesting of 6.25% every three months thereafter over the subsequent three years, in each case subject to the Reporting Person's continued service with the Issuer through each such vesting date.

SEC source: 0001415889-24-002524 · form4-02052024_040210.xml · nonDerivative · entry 1

Booth Richard Douglas · CIK 0001641054 · CHIEF FINANCIAL OFFICER

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 281,499.173

F1 · kind: The transaction reported represents the withholding of shares by the issuer to satisfy the reporting person's tax withholding obligations in connection with the vesting and settlement of previously reported restricted stock units.

SEC source: 0001415889-24-001882 · form4-01262024_100138.xml · nonDerivative · entry 2

Booth Richard Douglas · CIK 0001641054 · CHIEF FINANCIAL OFFICER

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 295,800.173

F2 · kind: Represents the withholding of shares by the Issuer to satisfy the Reporting Person's tax withholding obligations in connection with the vesting and settlement of previously reported PSUs.

SEC source: 0001415889-24-001882 · form4-01262024_100138.xml · nonDerivative · entry 1

Booth Richard Douglas · CIK 0001641054 · CHIEF FINANCIAL OFFICER

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 301,392.173

F1 · shares: Reflects the number of performance-based restricted stock units ("PSUs"), each representing a contingent right to receive one share of the Issuer's Class A Common Stock, par value $0.001, earned upon the certification of achievement of certain performance criteria by the Issuer's compensation committee. The PSUs will vest in three substantially equal installments as to 1/3rd on January 24, 2024, 1/3rd on February 1, 2025, and the remaining 1/3rd on February 1, 2026 and will be settled pursuant to the terms of the Issuer's 2021 Equity Incentive Plan (as amended from time to time), in each case subject to the Reporting Person's continued service with the Issuer through each such vesting date.

SEC source: 0001209191-23-058964 · doc4.xml · nonDerivative · entry 1

Booth Richard Douglas · CIK 0001641054 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 252,378.173

F1 · kind: The transaction reported represents the withholding of shares by the issuer to satisfy the reporting person's tax withholding obligations in connection with the vesting and settlement of previously reported restricted stock units.

SEC source: 0001209191-23-049768 · doc4.xml · nonDerivative · entry 1

Booth Richard Douglas · CIK 0001641054 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 253,371.173

F1 · kind: The transaction reported represents the withholding of shares by the issuer to satisfy the reporting person's tax withholding obligations in connection with the vesting and settlement of previously reported restricted stock units.

SEC source: 0001415889-23-011181 · form4-07172023_100701.xml · nonDerivative · entry 1

Booth Richard Douglas · CIK 0001641054 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 7,539

F1 · shares: The shares vest in four equal annual installments beginning on the first anniversary of the date of grant.

SEC source: 0001209191-23-037812 · doc4.xml · nonDerivative · entry 1

Booth Richard Douglas · CIK 0001641054 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 254,364.173

F1 · kind: The transaction reported represents the withholding of shares by the issuer to satisfy the reporting person's tax withholding obligations in connection with the vesting and settlement of previously reported restricted stock units.

SEC source: 0001209191-23-019306 · doc4.xml · nonDerivative · entry 1

Booth Richard Douglas · CIK 0001641054 · Chief Financial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 255,357.173

F1 · kind: The transaction reported represents the withholding of shares by the issuer to satisfy the reporting person's tax withholding obligations in connection with the vesting and settlement of previously reported restricted stock units.

SEC source: 0001209191-23-011181 · doc4.xml · nonDerivative · entry 1

Booth Richard Douglas · CIK 0001641054 · Chief Financial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 256,350.173

F1 · shares: Represents restricted stock units ("RSUs"), each representing a contingent right to receive one share of the Issuer's Class A Common Stock, par value $0.001. The RSUs vest over a four-year period, with 25% of the RSUs vesting on February 1, 2024, followed by quarterly vesting of 6.25% every three months thereafter over the subsequent three years, in each case subject to the Reporting Person's continued service with the Issuer through each such vesting date.

F1 · price: Represents restricted stock units ("RSUs"), each representing a contingent right to receive one share of the Issuer's Class A Common Stock, par value $0.001. The RSUs vest over a four-year period, with 25% of the RSUs vesting on February 1, 2024, followed by quarterly vesting of 6.25% every three months thereafter over the subsequent three years, in each case subject to the Reporting Person's continued service with the Issuer through each such vesting date.

SEC source: 0001209191-22-061666 · doc4.xml · nonDerivative · entry 1

Booth Richard Douglas · CIK 0001641054 · Chief Financial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 58,981.173

F1 · kind: The transaction reported represents the withholding of shares by the issuer to satisfy the reporting person's tax withholding obligations in connection with the vesting and settlement of previously reported restricted stock units.

SEC source: 0001209191-22-050286 · doc4.xml · nonDerivative · entry 1

Booth Richard Douglas · CIK 0001641054 · Chief Financial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 59,974.173

F1 · kind: The transaction reported represents the withholding of shares by the issuer to satisfy the reporting person's tax withholding obligations in connection with the vesting and settlement of previously reported restricted stock units.

SEC source: 0001415889-22-007881 · form4-07212022_050701.xml · nonDerivative · entry 1

Booth Richard Douglas · CIK 0001641054 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 6,549

F1 · shares: The shares vest in four equal annual installments beginning on the first anniversary of the date of grant.

SEC source: 0000899243-22-009661 · doc4.xml · nonDerivative · entry 1

Booth Richard Douglas · CIK 0001641054 · Chief Financial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 63,948.173

F1 · kind: The number of securities reported represents an aggregate number of shares purchased in multiple open market transactions over a range of purchase prices. The price reported represents the weighted average price. The Reporting Person undertakes to provide the staff of the SEC, the Issuer, or a stockholder of the Issuer, upon request, the number of shares purchased by the Reporting Person at each separate price within the range.

F2 · price: Purchase prices range from $21.015 to $21.06 per share, inclusive.

SEC source: 0001179110-21-007773 · edgar.xml · nonDerivative · entry 1

Booth Richard Douglas · CIK 0001641054 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 5,469

F1 · shares: The shares vest in four equal annual installments beginning on the first anniversary of the date of grant.

SEC source: 0001073349-21-000044 · primary_doc.xml · nonDerivative · entry 1

Booth Richard Douglas · CIK 0001641054 · Chief Financial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 96,799

F1 · shares: Represents shares automatically sold pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on 8/26/2020.

F2 · price: The price reported represents all shares sold at $45.00

SEC source: 0001073349-21-000019 · primary_doc.xml · nonDerivative · entry 1

Booth Richard Douglas · CIK 0001641054 · Chief Financial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 101,664

F1 · kind: Represents shares automatically sold solely to satisfy tax withholding obligations of reporting person on vesting of restricted stock. Proceeds from the sale were submitted to the Internal Revenue Service.

SEC source: 0001073349-21-000006 · primary_doc.xml · nonDerivative · entry 1

Booth Richard Douglas · CIK 0001641054 · Chief Financial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 102,307

F1 · kind: Represents shares automatically sold solely to satisfy tax withholding obligations of reporting person on vesting of restricted stock. Proceeds from the sale were submitted to the Internal Revenue Service.

SEC source: 0001073349-21-000002 · primary_doc.xml · nonDerivative · entry 1

Booth Richard Douglas · CIK 0001641054 · Chief Financial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 102,965

F1 · kind: Represents shares automatically sold solely to satisfy tax withholding obligations of reporting person on vesting of restricted stock. Proceeds from the sale were submitted to the Internal Revenue Service.

SEC source: 0001073349-20-000141 · primary_doc.xml · nonDerivative · entry 1

Booth Richard Douglas · CIK 0001641054 · Chief Financial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 103,821

F1 · price: The price reported represents the weighted average sale price of the shares sold. The shares were sold at varying prices in the range of $49.07 to $50.01. The reporting person hereby undertakes, upon request of the Staff of the U.S. Securities Exchange Commission, the Issuer or a security holder of the Issuer, to provide full information regarding the number of shares sold at each separate price.

SEC source: 0001073349-20-000107 · primary_doc.xml · nonDerivative · entry 1

Booth Richard Douglas · CIK 0001641054 · Chief Financial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 108,789

F1 · kind: Represents shares automatically sold solely to satisfy tax withholding obligations of reporting person on vesting of restricted stock. Proceeds from the sale were submitted to the Internal Revenue Service

SEC source: 0001073349-20-000102 · primary_doc.xml · nonDerivative · entry 1

Booth Richard Douglas · CIK 0001641054 · Chief Financial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 109,764

F1 · kind: Represents shares automatically sold solely to satisfy tax withholding obligations of reporting person on vesting of restricted stock. All proceeds from the sale were submitted to the Internal Revenue Service.

SEC source: 0001073349-20-000097 · primary_doc.xml · nonDerivative · entry 1

Booth Richard Douglas · CIK 0001641054 · Chief Financial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 110,768

F1 · kind: Represents shares automatically sold solely to satisfy tax withholding obligations of reporting person on vesting of restricted stock. All proceeds from the sale were submitted to the Internal Revenue Service.

F2 · balance_after: Includes 365 shares acquired pursuant to the Bottomline Technologies (de), Inc. Amended and Restated 2000 Employee Stock Purchase Plan on September 30, 2020.

SEC source: 0001073349-20-000090 · primary_doc.xml · nonDerivative · entry 2

Booth Richard Douglas · CIK 0001641054 · Chief Financial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 111,503

F2 · price: The price reported represents the weighted average sale price of the shares sold. The shares were sold at varying prices in the range of $48.29 to $48.35. The reporting person hereby undertakes, upon request of the Staff of the U.S. Securities Exchange Commission, the Issuer or a security holder of the Issuer, to provide full information regarding the number of shares sold at each separate price.

SEC source: 0001073349-20-000090 · primary_doc.xml · nonDerivative · entry 1

Booth Richard Douglas · CIK 0001641054 · Chief Financial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 111,773

F1 · price: The price reported represents the weighted average sale price of the shares sold. The shares were sold at varying prices in the range of $47.27 to $48.27. The reporting person hereby undertakes, upon request of the Staff of the U.S. Securities Exchange Commission, the Issuer or a security holder of the Issuer, to provide full information regarding the number of shares sold at each separate price.

SEC source: 0001073349-20-000086 · primary_doc.xml · nonDerivative · entry 1

Booth Richard Douglas · CIK 0001641054 · Chief Financial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 115,577

F1 · price: The price reported represents the weighted average sale price of the shares sold. The shares were sold at varying prices in the range of $47.48 to $48.11. The reporting person hereby undertakes, upon request of the Staff of the U.S. Securities Exchange Commission, the Issuer or a security holder of the Issuer, to provide full information regarding the number of shares sold at each separate price.

SEC source: 0001073349-20-000080 · primary_doc.xml · nonDerivative · entry 2

Booth Richard Douglas · CIK 0001641054 · Chief Financial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 142,045

F2 · kind: Represents a grant of performance-based restricted stock which will vest in whole or in part to the extent that certain conditions are achieved during the performance period, subject to the recipient's continued service to the Company.

SEC source: 0001073349-20-000080 · primary_doc.xml · nonDerivative · entry 1

Booth Richard Douglas · CIK 0001641054 · Chief Financial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 129,795

F1 · kind: Represents a grant of restricted stock subject to time-based vesting and the recipient's continued service to the Company.

SEC source: 0001073349-20-000069 · primary_doc.xml · nonDerivative · entry 1

Booth Richard Douglas · CIK 0001641054 · Chief Financial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 107,045

F1 · timeliness: Represents shares automatically sold solely to satisfy tax withholding obligations of reporting person on vesting of restricted stock

SEC source: 0001073349-20-000063 · primary_doc.xml · nonDerivative · entry 1

Booth Richard Douglas · CIK 0001641054 · Chief Financial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 110,909

F1 · kind: Represents shares automatically sold solely to satisfy tax withholding obligations of reporting person on vesting of restricted stock.

SEC source: 0001179110-20-008183 · edgar.xml · nonDerivative · entry 1

Booth Richard Douglas · CIK 0001641054 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 4,303

F1 · shares: The shares vest in four equal annual installments beginning on the first anniversary of the date of grant.

SEC source: 0001073349-20-000061 · primary_doc.xml · nonDerivative · entry 1

Booth Richard Douglas · CIK 0001641054 · Chief Financial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 111,559

F1 · kind: Represents shares automatically sold solely to satisfy tax withholding obligations of reporting person on vesting of restricted stock.

SEC source: 0001073349-20-000026 · primary_doc.xml · nonDerivative · entry 1

Booth Richard Douglas · CIK 0001641054 · Chief Financial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 112,633

F1 · kind: Represents shares automatically sold solely to satisfy tax withholding obligations of reporting person on vesting of restricted stock.

SEC source: 0001073349-20-000019 · primary_doc.xml · nonDerivative · entry 1

Booth Richard Douglas · CIK 0001641054 · Chief Financial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 113,271

F1 · kind: Shares withheld by the Company to cover the tax liability due upon vesting of the restricted stock award.

F2 · balance_after: Includes 328 shares acquired pursuant to the Bottomline Technologies (de), Inc. Amended and Restated 2000 Employee Stock Purchase Plan on March 31, 2020.