RPD

SEC source: 0000899243-17-016378 · doc4.xml · derivative · entry 2

Holzman Benjamin · CIK 0001647255 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 12,384

Underlying: Common Stock · 12,384 shares

Expires 2027-06-12

F3 · derivative.exercise_date: This option vests in full on the earlier of: (i) the date of the Issuer's next annual meeting of stockholders held after the date of the grant or (ii) the first anniversary of the date of grant, in each case subject to the Reporting Person's continued service with the Issuer through the applicable vesting date.

SEC source: 0000899243-17-016378 · doc4.xml · nonDerivative · entry 1

Holzman Benjamin · CIK 0001647255 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 12,756

F1 · security: This security represents restricted stock units. Each restricted stock unit represents a contingent right to receive one share of common stock of the Issuer.

F2 · shares: This restricted stock unit grant vests in full on the earlier of: (i) the date of the Issuer's next annual meeting of stockholders held after the date of the grant or (ii) the first anniversary of the date of grant, in each case subject to the Reporting Person's continued service with the Issuer through the applicable vesting date.

SEC source: 0000899243-17-016383 · doc4.xml · derivative · entry 3

Nye Benjamin · CIK 0001427438 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 12,384

Underlying: Common Stock · 12.384 shares

Expires 2027-06-12

F3 · derivative.exercise_date: This option vests in full on the earlier of: (i) the date of the Issuer's next annual meeting of stockholders held after the date of the grant or (ii) the first anniversary of the date of grant, in each case subject to the Reporting Person's continued service with the Issuer through the applicable vesting date.

SEC source: 0000899243-17-016383 · doc4.xml · nonDerivative · entry 1

Nye Benjamin · CIK 0001427438 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 12,756

F1 · security: This security represents restricted stock units. Each restricted stock unit represents a contingent right to receive one share of common stock of the Issuer.

F2 · shares: This restricted stock unit grant vests in full on the earlier of: (i) the date of the Issuer's next annual meeting of stockholders held after the date of the grant or (ii) the first anniversary of the date of the grant, in each case subject to the Reporting Person's continued service with the Issuer through the applicable vesting date.

SEC source: 0000899243-17-016373 · doc4.xml · derivative · entry 2

BERRY MICHAEL J · CIK 0001269088 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 12,384

Underlying: Common Stock · 12,384 shares

Expires 2027-06-12

F3 · derivative.exercise_date: This option vests in full on the earlier of: (i) the date of the Issuer's next annual meeting of stockholders held after the date of the grant or (ii) the first anniversary of the date of grant, in each case subject to the Reporting Person's continued service with the Issuer through the applicable vesting date.

SEC source: 0000899243-17-016373 · doc4.xml · nonDerivative · entry 1

BERRY MICHAEL J · CIK 0001269088 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 12,756

F1 · security: This security represents restricted stock units. Each restricted stock unit represents a contingent right to receive one share of common stock of the Issuer.

F2 · shares: This restricted stock unit grant vests in full on the earlier of: (i) the date of the Issuer's next annual meeting of stockholders held after the date of the grant or (ii) the first anniversary of the date of grant, in each case subject to the Reporting Person's continued service with the Issuer through the applicable vesting date.

SEC source: 0000899243-17-016372 · doc4.xml · derivative · entry 2

Schodorf Thomas E · CIK 0001547258 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 12,384

Underlying: Common Stock · 12,384 shares

Expires 2027-06-12

F3 · derivative.exercise_date: This option vests in full on the earlier of: (i) the date of the Issuer's next annual meeting of stockholders held after the date of the grant or (ii) the first anniversary of the date of grant, in each case subject to the Reporting Person's continued service with the Issuer through the applicable vesting date.

SEC source: 0000899243-17-016372 · doc4.xml · nonDerivative · entry 1

Schodorf Thomas E · CIK 0001547258 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 21,417

F1 · security: This security represents restricted stock units. Each restricted stock unit represents a contingent right to receive one share of common stock of the Issuer.

F2 · shares: This restricted stock unit grant vests in full on the earlier of: (i) the date of the Issuer's next annual meeting of stockholders held after the date of the grant or (ii) the first anniversary of the date of grant, in each case subject to the Reporting Person's continued service with the Issuer through the applicable vesting date.

SEC source: 0000899243-17-016379 · doc4.xml · derivative · entry 2

Brown Marc Evan · CIK 0001679724 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 12,384

Underlying: Common Stock · 12,384 shares

Expires 2027-06-12

F3 · derivative.exercise_date: This option vests in full on the earlier of: (i) the date of the Issuer's next annual meeting of stockholders held after the date of the grant or (ii) the first anniversary of the date of grant, in each case subject to the Reporting Person's continued service with the Issuer through the applicable vesting date.

SEC source: 0000899243-17-016379 · doc4.xml · nonDerivative · entry 1

Brown Marc Evan · CIK 0001679724 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 21,417

F1 · security: This security represents restricted stock units. Each restricted stock unit represents a contingent right to receive one share of common stock of the Issuer.

F2 · shares: This restricted stock unit grant vests in full on the earlier of: (i) the date of the Issuer's next annual meeting of stockholders held after the date of the grant or (ii) the first anniversary of the date of grant, in each case subject to the Reporting Person's continued service with the Issuer through the applicable vesting date.

SEC source: 0000899243-17-016371 · doc4.xml · derivative · entry 2

Matthews Alan · CIK 0001647460 · Director · Chairman of the Board

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 12,384

Underlying: Common Stock · 12,384 shares

Expires 2027-06-12

F3 · derivative.exercise_date: This option vests in full on the earlier of: (i) the date of the Issuer's next annual meeting of stockholders held after the date of the grant or (ii) the first anniversary of the date of grant, in each case subject to the Reporting Person's continued service with the Issuer through the applicable vesting date.

SEC source: 0000899243-17-016371 · doc4.xml · nonDerivative · entry 1

Matthews Alan · CIK 0001647460 · Director · Chairman of the Board

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,204,947

F1 · security: This security represents restricted stock units. Each restricted stock unit represents a contingent right to receive one share of common stock of the Issuer.

F2 · shares: This restricted stock unit grant vests in full on the earlier of: (i) the date of the Issuer's next annual meeting of stockholders held after the date of the grant or (ii) the first anniversary of the date of grant, in each case subject to the Reporting Person's continued service with the Issuer through the applicable vesting date.

SEC source: 0001082906-17-000014 · edgar.xml · nonDerivative · entry 3

HOAG JAY C · CIK 0001082906 · 10% owner · May be part of a 13(d) group

KIMBALL RICK · CIK 0001197937 · 10% owner · May be part of a 13(d) group

DREW JOHN · CIK 0001188456 · 10% owner · May be part of a 13(d) group

REYNOLDS JON Q JR · CIK 0001188444 · 10% owner · May be part of a 13(d) group

Yuan David · CIK 0001406509 · 10% owner · May be part of a 13(d) group

Trudeau Robert · CIK 0001343722 · 10% owner · May be part of a 13(d) group

Marshall Christopher P · CIK 0001440008 · 10% owner · May be part of a 13(d) group

Rosenberg John C. · CIK 0001406576 · May be part of a 13(d) group

TCV VII LP · CIK 0001420295 · 10% owner · May be part of a 13(d) group

TCV VII(A) L P · CIK 0001419272 · 10% owner · May be part of a 13(d) group

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: Not disclosed

Ownership: Indirect · By TCV Member Fund, L.P.

Disclosed balance after: 45,945

F3 · ownership.nature: These securities are directly held by TCV Member Fund, L.P. ("TCV MF"). The TCM VII Directors are Class A Directors of Management VII, which is a general partner of TCV MF, and limited partners of TCV MF. The TCM VII Directors and Management VII may be deemed to beneficially own the securities held by TCV MF, but the TCM VII Directors and Management VII each disclaim beneficial ownership of such securities except to the extent of their pecuniary interest therein.

SEC source: 0001082906-17-000014 · edgar.xml · nonDerivative · entry 2

HOAG JAY C · CIK 0001082906 · 10% owner · May be part of a 13(d) group

KIMBALL RICK · CIK 0001197937 · 10% owner · May be part of a 13(d) group

DREW JOHN · CIK 0001188456 · 10% owner · May be part of a 13(d) group

REYNOLDS JON Q JR · CIK 0001188444 · 10% owner · May be part of a 13(d) group

Yuan David · CIK 0001406509 · 10% owner · May be part of a 13(d) group

Trudeau Robert · CIK 0001343722 · 10% owner · May be part of a 13(d) group

Marshall Christopher P · CIK 0001440008 · 10% owner · May be part of a 13(d) group

Rosenberg John C. · CIK 0001406576 · May be part of a 13(d) group

TCV VII LP · CIK 0001420295 · 10% owner · May be part of a 13(d) group

TCV VII(A) L P · CIK 0001419272 · 10% owner · May be part of a 13(d) group

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: Not disclosed

Ownership: Indirect · By TCV VII (A), L.P.

Disclosed balance after: 2,731,799

F2 · ownership.nature: These securities are directly held by TCV VII (A), L.P. The TCM VII Directors are Class A Directors of Management VII and limited partners of TCM VII. Management VII is the general partner of TCM VII, which is the general partner of TCV VII (A), L.P. The TCM VII Directors, Management VII and TCM VII may be deemed to beneficially own the securities held by TCV VII (A), L.P., but each of the TCM VII Directors, Management VII and TCM VII disclaim beneficial ownership of such securities except to the extent of their pecuniary interest therein.

SEC source: 0001082906-17-000014 · edgar.xml · nonDerivative · entry 1

HOAG JAY C · CIK 0001082906 · 10% owner · May be part of a 13(d) group

KIMBALL RICK · CIK 0001197937 · 10% owner · May be part of a 13(d) group

DREW JOHN · CIK 0001188456 · 10% owner · May be part of a 13(d) group

REYNOLDS JON Q JR · CIK 0001188444 · 10% owner · May be part of a 13(d) group

Yuan David · CIK 0001406509 · 10% owner · May be part of a 13(d) group

Trudeau Robert · CIK 0001343722 · 10% owner · May be part of a 13(d) group

Marshall Christopher P · CIK 0001440008 · 10% owner · May be part of a 13(d) group

Rosenberg John C. · CIK 0001406576 · May be part of a 13(d) group

TCV VII LP · CIK 0001420295 · 10% owner · May be part of a 13(d) group

TCV VII(A) L P · CIK 0001419272 · 10% owner · May be part of a 13(d) group

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: Not disclosed

Ownership: Indirect · By TCV VII, L.P.

Disclosed balance after: 5,260,299

F1 · ownership.nature: These securities are directly held by TCV VII, L.P. Timothy P. McAdam, Jay C. Hoag, Christopher P. Marshall, Jon Q. Reynolds, Jr., Richard H. Kimball, John L. Drew, Robert W. Trudeau, John C. Rosenberg and David L. Yuan (collectively, the "TCM VII Directors") are Class A Directors of Technology Crossover Management VII, Ltd. ("Management VII") and limited partners of Technology Crossover Management VII, L.P. ("TCM VII"). Management VII is the general partner of TCM VII, which is the general partner of TCV VII, L.P. The TCM VII Directors, Management VII and TCM VII may be deemed to beneficially own the securities held by TCV VII, L.P., but each of the TCM VII Directors, Management VII and TCM VII disclaim beneficial ownership of such securities except to the extent of their pecuniary interest therein.

SEC source: 0001498115-17-000004 · edgar.xml · nonDerivative · entry 3

McAdam Timothy P · CIK 0001498115 · Director · 10% owner · May be part of a 13(d) group

TCV Member Fund, L.P. · CIK 0001361345 · 10% owner · May be part of a 13(d) group

Technology Crossover Management VII, L.P. · CIK 0001467001 · 10% owner · May be part of a 13(d) group

Technology Crossover Management VII, Ltd. · CIK 0001466999 · 10% owner · May be part of a 13(d) group

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: Not disclosed

Ownership: Indirect · By TCV Member Fund, L.P.

Disclosed balance after: 45,945

F3 · ownership.nature: These securities are directly held by TCV Member Fund, L.P. ("TCV MF"). The TCM VII Directors are Class A Directors of Management VII, which is a general partner of TCV MF, and limited partners of TCV MF. The TCM VII Directors and Management VII may be deemed to beneficially own the securities held by TCV MF, but the TCM VII Directors and Management VII each disclaim beneficial ownership of such securities except to the extent of their pecuniary interest therein.

SEC source: 0001498115-17-000004 · edgar.xml · nonDerivative · entry 2

McAdam Timothy P · CIK 0001498115 · Director · 10% owner · May be part of a 13(d) group

TCV Member Fund, L.P. · CIK 0001361345 · 10% owner · May be part of a 13(d) group

Technology Crossover Management VII, L.P. · CIK 0001467001 · 10% owner · May be part of a 13(d) group

Technology Crossover Management VII, Ltd. · CIK 0001466999 · 10% owner · May be part of a 13(d) group

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: Not disclosed

Ownership: Indirect · By TCV VII (A), L.P.

Disclosed balance after: 2,731,799

F2 · ownership.nature: These securities are directly held by TCV VII (A), L.P. The TCM VII Directors are Class A Directors of Management VII and limited partners of TCM VII. Management VII is the general partner of TCM VII, which is the general partner of TCV VII (A), L.P. The TCM VII Directors, Management VII and TCM VII may be deemed to beneficially own the securities held by TCV VII (A), L.P., but each of the TCM VII Directors, Management VII and TCM VII disclaim beneficial ownership of such securities except to the extent of their pecuniary interest therein.

SEC source: 0001498115-17-000004 · edgar.xml · nonDerivative · entry 1

McAdam Timothy P · CIK 0001498115 · Director · 10% owner · May be part of a 13(d) group

TCV Member Fund, L.P. · CIK 0001361345 · 10% owner · May be part of a 13(d) group

Technology Crossover Management VII, L.P. · CIK 0001467001 · 10% owner · May be part of a 13(d) group

Technology Crossover Management VII, Ltd. · CIK 0001466999 · 10% owner · May be part of a 13(d) group

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: Not disclosed

Ownership: Indirect · By TCV VII, L.P.

Disclosed balance after: 5,260,299

F1 · ownership.nature: These securities are directly held by TCV VII, L.P. Timothy P. McAdam, Jay C. Hoag, Christopher P. Marshall, Jon Q. Reynolds, Jr., Richard H. Kimball, John L. Drew, Robert W. Trudeau, John C. Rosenberg and David L. Yuan (collectively, the "TCM VII Directors") are Class A Directors of Technology Crossover Management VII, Ltd. ("Management VII") and limited partners of Technology Crossover Management VII, L.P. ("TCM VII"). Management VII is the general partner of TCM VII, which is the general partner of TCV VII, L.P. The TCM VII Directors, Management VII and TCM VII may be deemed to beneficially own the securities held by TCV VII, L.P., but each of the TCM VII Directors, Management VII and TCM VII disclaim beneficial ownership of such securities except to the extent of their pecuniary interest therein.

SEC source: 0000899243-17-015647 · doc4.xml · nonDerivative · entry 1

Nye Benjamin · CIK 0001427438 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Indirect · See Footnotes

Disclosed balance after: 7,581,230

F1 · ownership.nature: Represents shares of Common Stock held directly by Bain Capital Venture Fund 2007, L.P., BCIP Venture Associates and BCIP Venture Associates-B (collectively, the "Bain Capital Entities").

F2 · ownership.nature: The governance, investment strategy and decision making process with respect to investments held by the Bain Capital Entities is directed by the Executive Committee of Bain Capital Ventures Investors, LLC ("BCVI"). Mr. Nye is a Managing Director of BCVI. By virtue of the relationships described in these footnotes, Mr. Nye may be deemed to share voting and dispositive power with respect to all of the shares of Common Stock held by the Bain Capital Entities. Mr. Nye disclaims beneficial ownership of such securities except to the extent of his pecuniary interest therein.

SEC source: 0000899243-17-015648 · doc4.xml · nonDerivative · entry 1

BAIN CAPITAL VENTURE INVESTORS, LLC · CIK 0001309469 · 10% owner

Bain Capital Venture Partners 2007, L.P. · CIK 0001408678 · 10% owner

Bain Capital Venture Fund 2007, L.P. · CIK 0001408677 · 10% owner

BCIP Venture Associates · CIK 0001408649 · 10% owner

BCIP VENTURE ASSOCIATES-B · CIK 0001408676 · 10% owner

KRUPKA MICHAEL A · CIK 0001212150 · 10% owner

Agarwal Ajay · CIK 0001708763 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: Not disclosed

Ownership: Indirect · See Footnotes

Disclosed balance after: 7,581,230

F1 · ownership.nature: Bain Capital Venture Investors, LLC ("BCVI") is the general partner of Bain Capital Venture Partners 2007, L.P. ("Partners 2007"), which is the general partner of Bain Capital Venture Fund 2007, L.P. ("Fund 2007"). As a result, Partners 2007 may be deemed to share voting and dispositive power with respect to shares of Common Stock held by Fund 2007. Partners 2007 disclaims beneficial ownership of such securities except to the extent of its pecuniary interest therein. On June 6, 2017, Fund 2007 sold 1,223,772 shares of Common Stock. Following such sale Fund 2007 held 6,626,923 shares of Common Stock.

F2 · ownership.nature: On June 6, 2017, BCIP Venture Associates ("BCIP VA"), whose managing partner is Boylston Coinvestors, LLC ("Boylston"), sold 174,053 shares of Common Stock. Following such sale BCIP VA held 942,527 shares of Common Stock.

F3 · ownership.nature: On June 6, 2017, BCIP Venture Associates-B ("BCIP VA-B" and together with Fund 2007 and BCIP VA, the "Bain Capital Entities"), whose managing partner is Boylston, sold 2,175 shares of Common Stock. Following such sale BCIP VA-B held 11,780 shares of Common Stock.

F4 · ownership.nature: The governance, investment strategy and decision-making process with respect to the investments held by the Bain Capital Entities is directed by the Executive Committee of BCVI, which consists of Michael A. Krupka and Ajay Agarwal. As a result, BCVI and Messrs. Krupka and Agarwal may be deemed to share voting and dispositive power with respect to all of the shares of Common Stock held by the Bain Capital Entities. BCVI and Messrs. Krupka and Agarwal each disclaim beneficial ownership of such securities except to the extent of its or his pecuniary interest therein.

SEC source: 0000899243-17-013501 · doc4.xml · nonDerivative · entry 1

Burton Andrew F. · CIK 0001532808 · Chief Operating Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 200,315

F1 · shares: Represents shares withheld by the Issuer to satisfy Mr. Burton's tax withholding obligation upon the vesting of restricted stock units previously granted to Mr. Burton on October 3, 2016 and January 31, 2017.

SEC source: 0000899243-17-013500 · doc4.xml · nonDerivative · entry 1

Weiner Lee David · CIK 0001647617 · Chief Product Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 57,428

F1 · shares: Represents shares withheld by the Issuer to satisfy Mr. Weiner's tax withholding obligation upon the vesting of restricted stock units previously granted to Mr. Weiner on February 2, 2016 and January 31, 2017.

SEC source: 0000899243-17-013499 · doc4.xml · nonDerivative · entry 1

Thomas Corey E. · CIK 0001647486 · Director · President and CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 232,350

F1 · shares: Represents shares withheld by the Issuer to satisfy Mr. Thomas' tax withholding obligation upon the vesting of restricted stock units previously granted to Mr. Thomas on February 2, 2016 and January 31, 2017.

SEC source: 0000899243-17-010345 · doc4.xml · nonDerivative · entry 1

Burton Andrew F. · CIK 0001532808 · Chief Operating Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 201,429

F1 · shares: Represents shares withheld by the Issuer to satisfy Mr. Burton's tax withholding obligation upon the vesting of restricted stock awards previously granted to Mr. Burton under the Rapid7, Inc. 2015 Equity Incentive Plan, as amended, in connection with the acquisition of Logentries by the Issuer in October 2015.

SEC source: 0000899243-17-005239 · doc4.xml · derivative · entry 3

Weiner Lee David · CIK 0001647617 · Chief Product Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 41,125

Underlying: Common Stock · 15,000 shares

Expires 2023-03-12

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 · kind: The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on June 3, 2016.

F3 · derivative.exercise_date: One-fourth of the shares underlying the option vested on March 12, 2014, and the remaining shares vest and become exercisable in 36 equal monthly installments thereafter, subject to the reporting person's continuous service through each vesting date.

SEC source: 0000899243-17-005239 · doc4.xml · nonDerivative · entry 2

Weiner Lee David · CIK 0001647617 · Chief Product Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 58,644

F1 · kind: The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on June 3, 2016.

F2 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $15.40 to $15.74, inclusive. The reporting person undertakes to provide to the Issuer, any security holder of the Issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0000899243-17-005239 · doc4.xml · nonDerivative · entry 1

Weiner Lee David · CIK 0001647617 · Chief Product Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 73,644

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 · kind: The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on June 3, 2016.

SEC source: 0000899243-17-004506 · doc4.xml · nonDerivative · entry 1

Burton Andrew F. · CIK 0001532808 · Chief Operating Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 205,988

F1 · shares: Represents shares withheld by the Issuer to satisfy Mr. Burton's tax withholding obligation upon the vesting of restricted stock units previously granted to Mr. Burton on October 3, 2016.

SEC source: 0000899243-17-004511 · doc4.xml · nonDerivative · entry 1

Weiner Lee David · CIK 0001647617 · Chief Product Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 58,644

F1 · shares: Represents shares withheld by the Issuer to satisfy Mr. Weiner's tax withholding obligation upon the vesting of restricted stock units previously granted to Mr. Weiner on February 2, 2016.

SEC source: 0000899243-17-004505 · doc4.xml · nonDerivative · entry 1

Thomas Corey E. · CIK 0001647486 · Director · President and CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 235,594

F1 · shares: Represents shares withheld by the Issuer to satisfy Mr. Thomas' tax withholding obligation upon the vesting of restricted stock units previously granted to Mr. Thomas on February 2, 2016.

SEC source: 0000899243-17-004045 · doc4.xml · derivative · entry 3

Weiner Lee David · CIK 0001647617 · Chief Product Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 56,125

Underlying: Common Stock · 15,000 shares

Expires 2023-03-12

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 · kind: The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on June 3, 2016.

F2 · derivative.exercise_date: One-fourth of the shares underlying the option vested on March 12, 2014, and the remaining shares vest and become exercisable in 36 equal monthly installments thereafter, subject to the reporting person's continuous service through each vesting date.

SEC source: 0000899243-17-004045 · doc4.xml · nonDerivative · entry 2

Weiner Lee David · CIK 0001647617 · Chief Product Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 59,235

F1 · kind: The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on June 3, 2016.

SEC source: 0000899243-17-004045 · doc4.xml · nonDerivative · entry 1

Weiner Lee David · CIK 0001647617 · Chief Product Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 74,235

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 · kind: The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on June 3, 2016.

SEC source: 0000899243-17-004035 · doc4.xml · nonDerivative · entry 1

Thomas Corey E. · CIK 0001647486 · Director · President and CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 237,831

F1 · kind: The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on June 2, 2016.

SEC source: 0000899243-17-002592 · doc4.xml · derivative · entry 3

Thomas Corey E. · CIK 0001647486 · Director · President and CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 134,000

Underlying: Common Stock · 134,000 shares

Expires 2027-01-31

F4 · derivative.exercise_date: This option vests and becomes exercisable in sixteen equal quarterly installments, with the first installment vesting on May 15, 2017, subject to the Reporting Person's continued service with the Issuer.

SEC source: 0000899243-17-002592 · doc4.xml · nonDerivative · entry 1

Thomas Corey E. · CIK 0001647486 · Director · President and CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 247,831

F1 · security: This security represents restricted stock units. Each restricted stock unit represents a contingent right to receive one share of common stock of the Issuer.

F2 · shares: This restricted stock unit grant vests in sixteen equal quarterly installments, with the first installment vesting on May 15, 2017, subject to the Reporting Person's continued service with the Issuer.

SEC source: 0000899243-17-002591 · doc4.xml · derivative · entry 2

Burton Andrew F. · CIK 0001532808 · Chief Operating Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 20,000

Underlying: Common Stock · 20,000 shares

Expires 2027-01-31

F3 · derivative.exercise_date: This option vests and becomes exercisable in sixteen equal quarterly installments, with the first installment vesting on May 15, 2017, subject to the Reporting Person's continued service with the Issuer.

SEC source: 0000899243-17-002591 · doc4.xml · nonDerivative · entry 1

Burton Andrew F. · CIK 0001532808 · Chief Operating Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 206,900

F1 · security: This security represents restricted stock units. Each restricted stock unit represents a contingent right to receive one share of common stock of the Issuer.

F2 · shares: This restricted stock unit grant vests in sixteen equal quarterly installments, with the first installment vesting on May 15, 2017, subject to the Reporting Person's continued service with the Issuer.

SEC source: 0000899243-17-002590 · doc4.xml · derivative · entry 2

Weiner Lee David · CIK 0001647617 · Chief Product Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 60,000

Underlying: Common Stock · 60,000 shares

Expires 2027-01-31

F3 · derivative.exercise_date: This option vests and becomes exercisable in sixteen equal quarterly installments, with the first installment vesting on May 15, 2017, subject to the Reporting Person's continued service with the Issuer.

SEC source: 0000899243-17-002590 · doc4.xml · nonDerivative · entry 1

Weiner Lee David · CIK 0001647617 · Chief Product Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 59,235

F1 · security: This security represents restricted stock units. Each restricted stock unit represents a contingent right to receive one share of common stock of the Issuer.

F2 · shares: This restricted stock unit grant vests in sixteen equal quarterly installments, with the first installment vesting on May 15, 2017, subject to the Reporting Person's continued service with the Issuer.

SEC source: 0001209191-18-005993 · doc4.xml · nonDerivative · entry 1

Matthews Alan · CIK 0001647460 · Director · Chairman of the Board

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 2,892,177

F1 · kind: The shares were sold in a public offering by the Issuer, pursuant to a Form S-3 Registration Statement which was declared effective on June 2, 2017. The reported sale price reflects the price at which the shares were sold to the underwriters.

SEC source: 0000899243-17-001442 · doc4.xml · nonDerivative · entry 1

Burton Andrew F. · CIK 0001532808 · Chief Operating Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 196,900

F1 · shares: Represents shares withheld by the Issuer to satisfy Mr. Burton's tax withholding obligation upon the vesting of restricted stock awards previously granted to Mr. Burton under the Rapid7, Inc. 2015 Equity Incentive Plan, as amended, in connection with the acquisition of Logentries by the Issuer in October 2015.

SEC source: 0000899243-17-001102 · doc4.xml · derivative · entry 2

Kalowski Jeffrey · CIK 0001608600 · Chief Financial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 369,366

Underlying: Common Stock · 369,366 shares

Expires 2027-01-09

F3 · security: This option was granted under the Issuer's 2015 Equity Incentive Plan, as amended, to the Reporting Person in connection with his appointment as Chief Financial Officer of the Issuer.

F4 · derivative.exercise_date: This option shall vest and become exercisable over four years with 25% of the shares underlying this option vesting on January 15, 2018, and 6.25% of the shares underlying this option vesting on the 15th day of each calendar quarter thereafter, subject to the Reporting Person's continued service with the Issuer.

SEC source: 0000899243-17-001102 · doc4.xml · nonDerivative · entry 1

Kalowski Jeffrey · CIK 0001608600 · Chief Financial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 179,140

F1 · security: This security represents restricted stock units granted under the Issuer's 2015 Equity Incentive Plan, as amended, to the Reporting Person in connection with his appointment as Chief Financial Officer of the Issuer. Each restricted stock unit represents a contingent right to receive one share of common stock of the Issuer.

F2 · shares: The restricted stock unit grant vests over four years with 25% of the shares underlying the restricted stock unit grant vesting on January 15, 2018, and 6.25% of the shares underlying the restricted stock unit grant vesting on the 15th day of each calendar quarter thereafter, subject to the Reporting Person's continued service with the Issuer.

SEC source: 0000899243-16-036242 · doc4.xml · derivative · entry 5

Weiner Lee David · CIK 0001647617 · Chief Product Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 71,125

Underlying: Common Stock · 5,933 shares

Expires 2023-03-12

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 · kind: The transactions reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on June 3, 2016.

F3 · derivative.exercise_date: Immediately exercisable.

SEC source: 0000899243-16-036242 · doc4.xml · derivative · entry 4

Weiner Lee David · CIK 0001647617 · Chief Product Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 21,000

Underlying: Common Stock · 9,067 shares

Expires 2022-08-15

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 · kind: The transactions reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on June 3, 2016.

F3 · derivative.exercise_date: Immediately exercisable.

SEC source: 0000899243-16-036242 · doc4.xml · nonDerivative · entry 3

Weiner Lee David · CIK 0001647617 · Chief Product Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 29,235

F1 · kind: The transactions reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on June 3, 2016.

F2 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $12.26 to $12.76, inclusive. The reporting person undertakes to provide to the Issuer, any security holder of the Issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0000899243-16-036242 · doc4.xml · nonDerivative · entry 2

Weiner Lee David · CIK 0001647617 · Chief Product Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 44,235

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 · kind: The transactions reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on June 3, 2016.

SEC source: 0000899243-16-036242 · doc4.xml · nonDerivative · entry 1

Weiner Lee David · CIK 0001647617 · Chief Product Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 38,302

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 · kind: The transactions reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on June 3, 2016.

SEC source: 0000899243-16-034011 · doc4.xml · derivative · entry 3

Weiner Lee David · CIK 0001647617 · Chief Product Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 30,067

Underlying: Common Stock · 15,000 shares

Expires 2022-08-15

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

F2 · derivative.exercise_date: Immediately exercisable.