TIPT

SEC source: 0001393726-25-000017 · wk-form4_1740604472.xml · nonDerivative · entry 2

Rifkind Neil Charles · CIK 0001580685 · General Counsel and Secretary

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 32,301

F2 · kind: Represents the number of shares withheld to satisfy the Reporting Person's withholding tax liability upon vesting of the RSUs.

F3 · price: Represents the closing stock price as of the transaction date.

SEC source: 0001393726-25-000017 · wk-form4_1740604472.xml · nonDerivative · entry 1

Rifkind Neil Charles · CIK 0001580685 · General Counsel and Secretary

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 43,391

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 acquisition of the common stock resulted from the cliff vesting of matching restricted stock units ("RSUs") granted to the Reporting Person on February 17, 2022.

F1 · price: The acquisition of the common stock resulted from the cliff vesting of matching restricted stock units ("RSUs") granted to the Reporting Person on February 17, 2022.

SEC source: 0001393726-25-000004 · wk-form4_1736799095.xml · nonDerivative · entry 1

Goldwasser Lesley · CIK 0001465575 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 107,413

F1 · shares: Represents the stock component of the director's annual retainer fee, which is paid quarterly in arrears.

SEC source: 0001393726-25-000003 · wk-form4_1736799030.xml · nonDerivative · entry 1

Friedman Paul M · CIK 0001648181 · Director

10b5-1 filing: No plan indicated

Ownership: Indirect · By Living Trust

Disclosed balance after: 115,401

F1 · shares: Represents the stock component of the director's annual retainer fee, which is paid quarterly in arrears.

F2 · ownership.nature: At the director's request, all director fees issued in shares are to be deposited into The Paul M. Friedman Living Trust dated 3/5/2019 (the "Living Trust"), of which the Reporting Person and his spouse are trustees.

SEC source: 0001393726-24-000103 · wk-form4_1733931501.xml · nonDerivative · entry 2

Friedman Paul M · CIK 0001648181 · Director

10b5-1 filing: No plan indicated

Ownership: Indirect · By Living Trust

Disclosed balance after: 113,887

F2 · shares: Reflects the shares gifted to the Living Trust previously held directly by the Reporting Person, in which the Reporting Person and his spouse are trustees.

SEC source: 0001393726-24-000103 · wk-form4_1733931501.xml · nonDerivative · entry 1

Friedman Paul M · CIK 0001648181 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

F1 · shares: Reflects the gift of directly held shares to the Paul M. Friedman Living Trust dated 3/5/2019 (the "Living Trust"), of which the Reporting Person and his spouse are trustees.

SEC source: 0001393726-24-000101 · wk-form4_1731685259.xml · nonDerivative · entry 2

Friedman Paul M · CIK 0001648181 · Director

10b5-1 filing: No plan indicated

Ownership: Indirect · By Living Trust

Disclosed balance after: 93,887

F2 · shares: Reflects the shares gifted to the Living Trust previously held directly by the Reporting Person, in which the Reporting Person and his spouse are trustees.

SEC source: 0001393726-24-000101 · wk-form4_1731685259.xml · nonDerivative · entry 1

Friedman Paul M · CIK 0001648181 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 20,000

F1 · shares: Reflects the gift of directly held shares to the Paul M. Friedman Living Trust dated 3/5/2019 (the "Living Trust"), of which the Reporting Person and his spouse are trustees.

SEC source: 0001393726-24-000099 · wk-form4_1730491366.xml · derivative · entry 2

Barnes Michael Gene · CIK 0001498811 · Director · Executive Chairman · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,200,000

Underlying: Common Stock · 200,000 shares

Expires not disclosed

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

F2 · derivative.exercise_price: These PRSUs were granted to the Reporting Person on August 4, 2021. Each PRSU will vest upon Tiptree achieving each of three Tiptree share price target milestones, based on the average of the thirty (30) trading day closing stock price, ranging from $30 to $60 (adjusted for dividends paid) prior to the tenth anniversary of the date of grant, subject to the Reporting Person's continued employment with Tiptree. Each PRSU represents a contingent right to receive one share of Tiptree common stock. Any unvested PRSUs shall expire on August 4, 2031.

F2 · derivative.exercise_date: These PRSUs were granted to the Reporting Person on August 4, 2021. Each PRSU will vest upon Tiptree achieving each of three Tiptree share price target milestones, based on the average of the thirty (30) trading day closing stock price, ranging from $30 to $60 (adjusted for dividends paid) prior to the tenth anniversary of the date of grant, subject to the Reporting Person's continued employment with Tiptree. Each PRSU represents a contingent right to receive one share of Tiptree common stock. Any unvested PRSUs shall expire on August 4, 2031.

F2 · derivative.expiration_date: These PRSUs were granted to the Reporting Person on August 4, 2021. Each PRSU will vest upon Tiptree achieving each of three Tiptree share price target milestones, based on the average of the thirty (30) trading day closing stock price, ranging from $30 to $60 (adjusted for dividends paid) prior to the tenth anniversary of the date of grant, subject to the Reporting Person's continued employment with Tiptree. Each PRSU represents a contingent right to receive one share of Tiptree common stock. Any unvested PRSUs shall expire on August 4, 2031.

SEC source: 0001393726-24-000099 · wk-form4_1730491366.xml · nonDerivative · entry 1

Barnes Michael Gene · CIK 0001498811 · Director · Executive Chairman · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 9,902,095

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 · price: The acquisition of the common stock resulted from the vesting of an equal number of performance restricted stock units ("PRSUs") upon achieving the $20 Tiptree Inc. ("Tiptree") share price target milestone (adjusted for dividends paid).

SEC source: 0001393726-24-000092 · wk-form4_1729541051.xml · derivative · entry 4

McKinney Scott T. · CIK 0001959663 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 300,000

Underlying: Common Stock · 50,000 shares

Expires not disclosed

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

F3 · derivative.exercise_price: These PRSUs were granted to the Reporting Person on October 14, 2022. The PRSUs will vest upon Tiptree achieving each of three Tiptree share price target milestones, based on the average of the thirty (30) trading day closing stock price, ranging from $30 to $60 (adjusted for dividends paid) prior to August 4, 2031, subject to the Reporting Person's continued employment with Tiptree. Each PRSU represents a contingent right to receive one share of Tiptree common stock. Any unvested PRSUs shall expire on August 4, 2031.

F3 · derivative.exercise_date: These PRSUs were granted to the Reporting Person on October 14, 2022. The PRSUs will vest upon Tiptree achieving each of three Tiptree share price target milestones, based on the average of the thirty (30) trading day closing stock price, ranging from $30 to $60 (adjusted for dividends paid) prior to August 4, 2031, subject to the Reporting Person's continued employment with Tiptree. Each PRSU represents a contingent right to receive one share of Tiptree common stock. Any unvested PRSUs shall expire on August 4, 2031.

F3 · derivative.expiration_date: These PRSUs were granted to the Reporting Person on October 14, 2022. The PRSUs will vest upon Tiptree achieving each of three Tiptree share price target milestones, based on the average of the thirty (30) trading day closing stock price, ranging from $30 to $60 (adjusted for dividends paid) prior to August 4, 2031, subject to the Reporting Person's continued employment with Tiptree. Each PRSU represents a contingent right to receive one share of Tiptree common stock. Any unvested PRSUs shall expire on August 4, 2031.

SEC source: 0001393726-24-000092 · wk-form4_1729541051.xml · nonDerivative · entry 2

McKinney Scott T. · CIK 0001959663 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 82,186

F2 · shares: Shares withheld to satisfy the Reporting Person's withholding tax liability upon vesting of the 2021 PRSUs.

SEC source: 0001393726-24-000092 · wk-form4_1729541051.xml · nonDerivative · entry 1

McKinney Scott T. · CIK 0001959663 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 105,194

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 · price: The acquisition of the common stock resulted from the vesting of an equal number of performance restricted stock units ("PRSUs") upon achieving the $20 Tiptree Inc. ("Tiptree") share price target milestone (adjusted for dividends paid).

SEC source: 0001393726-24-000090 · wk-form4_1729281885.xml · derivative · entry 4

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,200,000

Underlying: Common Stock · 200,000 shares

Expires not disclosed

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

F3 · derivative.exercise_price: These PRSUs were granted to the Reporting Person on August 4, 2021. The PRSUs will vest upon Tiptree achieving each of three Tiptree share price target milestones, based on the average of the thirty (30) trading day closing stock price, ranging from $30 to $60 (adjusted for dividends paid) prior to the tenth anniversary of the date of grant, subject to the Reporting Person's continued employment with Tiptree. Each PRSU represents a contingent right to receive one share of Tiptree common stock. Any unvested PRSUs shall expire on August 4, 2031.

F3 · derivative.exercise_date: These PRSUs were granted to the Reporting Person on August 4, 2021. The PRSUs will vest upon Tiptree achieving each of three Tiptree share price target milestones, based on the average of the thirty (30) trading day closing stock price, ranging from $30 to $60 (adjusted for dividends paid) prior to the tenth anniversary of the date of grant, subject to the Reporting Person's continued employment with Tiptree. Each PRSU represents a contingent right to receive one share of Tiptree common stock. Any unvested PRSUs shall expire on August 4, 2031.

F3 · derivative.expiration_date: These PRSUs were granted to the Reporting Person on August 4, 2021. The PRSUs will vest upon Tiptree achieving each of three Tiptree share price target milestones, based on the average of the thirty (30) trading day closing stock price, ranging from $30 to $60 (adjusted for dividends paid) prior to the tenth anniversary of the date of grant, subject to the Reporting Person's continued employment with Tiptree. Each PRSU represents a contingent right to receive one share of Tiptree common stock. Any unvested PRSUs shall expire on August 4, 2031.

SEC source: 0001393726-24-000090 · wk-form4_1729281885.xml · nonDerivative · entry 2

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

F2 · kind: The reporting person gifted the vested portion of the PRSUs on October 17, 2024 to a family trust of which the reporting person has no control or beneficial interest.

SEC source: 0001393726-24-000090 · wk-form4_1729281885.xml · nonDerivative · entry 1

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 200,000

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 · price: The acquisition of the common stock resulted from the vesting of an equal number of performance restricted stock units ("PRSUs") upon achieving the $20 Tiptree Inc. ("Tiptree") share price target milestone (adjusted for dividends paid).

SEC source: 0001393726-24-000088 · wk-form4_1728677006.xml · derivative · entry 3

Maultsby Randy · CIK 0001855788 · Director · President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 400,000

Underlying: Common Stock · 66,667 shares

Expires not disclosed

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

F3 · derivative.exercise_price: These PRSUs were granted to the Reporting Person on August 4, 2021. The PRSUs will vest upon Tiptree achieving each of three Tiptree share price target milestones, based on the average of the thirty (30) trading day closing stock price, ranging from $30 to $60 (adjusted for dividends paid) prior to the tenth anniversary of the date of grant, subject to the Reporting Person's continued employment with Tiptree. Each PRSU represents a contingent right to receive one share of Tiptree common stock. Any unvested PRSUs shall expire on August 4, 2031.

F3 · derivative.exercise_date: These PRSUs were granted to the Reporting Person on August 4, 2021. The PRSUs will vest upon Tiptree achieving each of three Tiptree share price target milestones, based on the average of the thirty (30) trading day closing stock price, ranging from $30 to $60 (adjusted for dividends paid) prior to the tenth anniversary of the date of grant, subject to the Reporting Person's continued employment with Tiptree. Each PRSU represents a contingent right to receive one share of Tiptree common stock. Any unvested PRSUs shall expire on August 4, 2031.

F3 · derivative.expiration_date: These PRSUs were granted to the Reporting Person on August 4, 2021. The PRSUs will vest upon Tiptree achieving each of three Tiptree share price target milestones, based on the average of the thirty (30) trading day closing stock price, ranging from $30 to $60 (adjusted for dividends paid) prior to the tenth anniversary of the date of grant, subject to the Reporting Person's continued employment with Tiptree. Each PRSU represents a contingent right to receive one share of Tiptree common stock. Any unvested PRSUs shall expire on August 4, 2031.

SEC source: 0001393726-24-000088 · wk-form4_1728677006.xml · nonDerivative · entry 2

Maultsby Randy · CIK 0001855788 · Director · President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 47,244

F2 · shares: Shares withheld to satisfy the Reporting Person's withholding tax liability upon vesting of the 2021 PRSUs.

SEC source: 0001393726-24-000088 · wk-form4_1728677006.xml · nonDerivative · entry 1

Maultsby Randy · CIK 0001855788 · Director · President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 78,137

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 · price: The acquisition of the common stock resulted from the vesting of an equal number of performance restricted stock units ("PRSUs") upon achieving the $20 Tiptree Inc. ("Tiptree") share price target milestone (adjusted for dividends paid).

SEC source: 0001393726-24-000084 · wk-form4_1728399801.xml · nonDerivative · entry 1

Goldwasser Lesley · CIK 0001465575 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 105,596

F1 · shares: Represents the stock component of the director's annual retainer fee, which is paid quarterly in arrears.

SEC source: 0001393726-24-000086 · wk-form4_1728399922.xml · nonDerivative · entry 1

Friedman Paul M · CIK 0001648181 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 109,887

F1 · shares: Represents the stock component of the director's annual retainer fee, which is paid quarterly in arrears.

SEC source: 0001393726-24-000073 · wk-form4_1720559213.xml · nonDerivative · entry 1

Goldwasser Lesley · CIK 0001465575 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 103,686

F1 · shares: Represents the stock component of the director's annual retainer fee, which is paid quarterly in arrears.

SEC source: 0001393726-24-000075 · wk-form4_1720559354.xml · nonDerivative · entry 1

Friedman Paul M · CIK 0001648181 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 108,296

F1 · shares: Represents the stock component of the director's annual retainer fee, which is paid quarterly in arrears.

SEC source: 0001393726-24-000065 · wk-form4_1716926883.xml · nonDerivative · entry 1

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Indirect · By 401K

Disclosed balance after: 192,021

SEC source: 0001393726-24-000048 · wk-form4_1712329715.xml · nonDerivative · entry 1

Goldwasser Lesley · CIK 0001465575 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 101,359

F1 · shares: Represents the stock component of the director's annual retainer fee, which is paid quarterly in arrears.

SEC source: 0001393726-24-000050 · wk-form4_1712329837.xml · nonDerivative · entry 1

Friedman Paul M · CIK 0001648181 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 106,357

F1 · shares: Represents the stock component of the director's annual retainer fee, which is paid quarterly in arrears.

SEC source: 0001393726-24-000037 · wk-form4_1709752986.xml · nonDerivative · entry 1

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Indirect · By 401K

Disclosed balance after: 190,471

SEC source: 0001393726-24-000034 · wk-form4_1709242843.xml · derivative · entry 3

Rifkind Neil Charles · CIK 0001580685 · General Counsel and Secretary

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 73,206

Underlying: Common Stock · 23,792 shares

Expires not disclosed

F1 · derivative.exercise_price: The Reporting Person was granted 11,896 matching restricted stock units on February 27, 2024, which represent the right to receive 2 shares of the Issuer's Common Stock for each restricted stock unit, pursuant to the Issuer's Equity Plan. As such the total in boxes 5 and 7 reflects the grant of 23,792 shares of the Issuer's Common Stock upon cliff vesting on February 20, 2027 subject to continuous employment from the grant date until such date and subject to certain terms contained in the Reporting Person's award agreement.

F1 · derivative.exercise_date: The Reporting Person was granted 11,896 matching restricted stock units on February 27, 2024, which represent the right to receive 2 shares of the Issuer's Common Stock for each restricted stock unit, pursuant to the Issuer's Equity Plan. As such the total in boxes 5 and 7 reflects the grant of 23,792 shares of the Issuer's Common Stock upon cliff vesting on February 20, 2027 subject to continuous employment from the grant date until such date and subject to certain terms contained in the Reporting Person's award agreement.

F1 · derivative.expiration_date: The Reporting Person was granted 11,896 matching restricted stock units on February 27, 2024, which represent the right to receive 2 shares of the Issuer's Common Stock for each restricted stock unit, pursuant to the Issuer's Equity Plan. As such the total in boxes 5 and 7 reflects the grant of 23,792 shares of the Issuer's Common Stock upon cliff vesting on February 20, 2027 subject to continuous employment from the grant date until such date and subject to certain terms contained in the Reporting Person's award agreement.

SEC source: 0001393726-24-000018 · wk-form4_1704903757.xml · nonDerivative · entry 1

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 0

F1 · kind: Shares were a charitable donation to a donor advised fund.

SEC source: 0001393726-24-000016 · wk-form4_1704825735.xml · nonDerivative · entry 1

Rifkind Neil Charles · CIK 0001580685 · General Counsel and Secretary

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 16,641

F1 · price: This sale was executed in multiple sales at prices ranging from $19.50 to $19.58, inclusive. The price reported above reflects the weighted average price. The reporting person undertakes to provide to the issuer, any security holding of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares and prices at which the transaction was effected.

SEC source: 0001393726-24-000012 · wk-form4_1704487328.xml · nonDerivative · entry 1

Goldwasser Lesley · CIK 0001465575 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 99,164

F1 · shares: Represents the stock component of the director's annual retainer fee, which is paid quarterly in arrears.

SEC source: 0001393726-24-000014 · wk-form4_1704487456.xml · nonDerivative · entry 1

Friedman Paul M · CIK 0001648181 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 104,528

F1 · shares: Represents the stock component of the director's annual retainer fee, which is paid quarterly in arrears.

SEC source: 0001393726-24-000010 · wk-form4_1704487212.xml · nonDerivative · entry 1

Mielle Dominique · CIK 0001759191 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 65,212

F1 · shares: Represents the stock component of the director's annual retainer fee, which is paid quarterly in arrears.

SEC source: 0001393726-24-000008 · wk-form4_1704229882.xml · derivative · entry 3

McKinney Scott T. · CIK 0001959663 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 137,500

Underlying: Common Stock · 137,500 shares

Expires not disclosed

F1 · derivative.exercise_price: Each performance restricted stock unit (PRSU) represents a contingent right to receive one share of Tiptree Inc. ("Tiptree") common stock. The PRSUs will vest upon Tiptree achieving a share price target milestone based on the average of the thirty (30) trading day closing stock price of $70 (adjusted for dividends paid) prior to the 10th anniversary of the grant date, subject to the Reporting Person's continued employment with Tiptree. Any unvested PRSUs shall expire on January 1, 2034.

F1 · derivative.exercise_date: Each performance restricted stock unit (PRSU) represents a contingent right to receive one share of Tiptree Inc. ("Tiptree") common stock. The PRSUs will vest upon Tiptree achieving a share price target milestone based on the average of the thirty (30) trading day closing stock price of $70 (adjusted for dividends paid) prior to the 10th anniversary of the grant date, subject to the Reporting Person's continued employment with Tiptree. Any unvested PRSUs shall expire on January 1, 2034.

F1 · derivative.expiration_date: Each performance restricted stock unit (PRSU) represents a contingent right to receive one share of Tiptree Inc. ("Tiptree") common stock. The PRSUs will vest upon Tiptree achieving a share price target milestone based on the average of the thirty (30) trading day closing stock price of $70 (adjusted for dividends paid) prior to the 10th anniversary of the grant date, subject to the Reporting Person's continued employment with Tiptree. Any unvested PRSUs shall expire on January 1, 2034.

SEC source: 0001393726-24-000006 · wk-form4_1704229746.xml · derivative · entry 2

Maultsby Randy · CIK 0001855788 · Director · President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 183,333

Underlying: Common Stock · 183,333 shares

Expires not disclosed

F1 · derivative.exercise_price: Each performance restricted stock unit (PRSU) represents a contingent right to receive one share of Tiptree Inc. ("Tiptree") common stock. The PRSUs will vest upon Tiptree achieving a share price target milestone based on the average of the thirty (30) trading day closing stock price of $70 (adjusted for dividends paid) prior to the 10th anniversary of the grant date, subject to the Reporting Person's continued employment with Tiptree. Any unvested PRSUs shall expire on January 1, 2034.

F1 · derivative.exercise_date: Each performance restricted stock unit (PRSU) represents a contingent right to receive one share of Tiptree Inc. ("Tiptree") common stock. The PRSUs will vest upon Tiptree achieving a share price target milestone based on the average of the thirty (30) trading day closing stock price of $70 (adjusted for dividends paid) prior to the 10th anniversary of the grant date, subject to the Reporting Person's continued employment with Tiptree. Any unvested PRSUs shall expire on January 1, 2034.

F1 · derivative.expiration_date: Each performance restricted stock unit (PRSU) represents a contingent right to receive one share of Tiptree Inc. ("Tiptree") common stock. The PRSUs will vest upon Tiptree achieving a share price target milestone based on the average of the thirty (30) trading day closing stock price of $70 (adjusted for dividends paid) prior to the 10th anniversary of the grant date, subject to the Reporting Person's continued employment with Tiptree. Any unvested PRSUs shall expire on January 1, 2034.

SEC source: 0001393726-24-000004 · wk-form4_1704229594.xml · derivative · entry 3

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 550,000

Underlying: Common Stock · 550,000 shares

Expires not disclosed

F1 · derivative.exercise_price: Each performance restricted stock unit (PRSU) represents a contingent right to receive one share of Tiptree Inc. ("Tiptree") common stock. The PRSUs will vest upon Tiptree achieving a share price target milestone based on the average of the thirty (30) trading day closing stock price of $70 (adjusted for dividends paid) prior to the 10th anniversary of the grant date, subject to the Reporting Person's continued employment with Tiptree. Any unvested PRSUs shall expire on January 1, 2034.

F1 · derivative.exercise_date: Each performance restricted stock unit (PRSU) represents a contingent right to receive one share of Tiptree Inc. ("Tiptree") common stock. The PRSUs will vest upon Tiptree achieving a share price target milestone based on the average of the thirty (30) trading day closing stock price of $70 (adjusted for dividends paid) prior to the 10th anniversary of the grant date, subject to the Reporting Person's continued employment with Tiptree. Any unvested PRSUs shall expire on January 1, 2034.

F1 · derivative.expiration_date: Each performance restricted stock unit (PRSU) represents a contingent right to receive one share of Tiptree Inc. ("Tiptree") common stock. The PRSUs will vest upon Tiptree achieving a share price target milestone based on the average of the thirty (30) trading day closing stock price of $70 (adjusted for dividends paid) prior to the 10th anniversary of the grant date, subject to the Reporting Person's continued employment with Tiptree. Any unvested PRSUs shall expire on January 1, 2034.

SEC source: 0001393726-24-000002 · wk-form4_1704229431.xml · derivative · entry 2

Barnes Michael Gene · CIK 0001498811 · Director · Executive Chairman · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 550,000

Underlying: Common Stock · 550,000 shares

Expires not disclosed

F1 · derivative.exercise_price: Each performance restricted stock unit (PRSU) represents a contingent right to receive one share of Tiptree Inc. ("Tiptree") common stock. The PRSUs will vest upon Tiptree achieving a share price target milestone based on the average of the thirty (30) trading day closing stock price of $70 (adjusted for dividends paid) prior to the 10th anniversary of the grant date, subject to the Reporting Person's continued employment with Tiptree. Any unvested PRSUs shall expire on January 1, 2034.

F1 · derivative.exercise_date: Each performance restricted stock unit (PRSU) represents a contingent right to receive one share of Tiptree Inc. ("Tiptree") common stock. The PRSUs will vest upon Tiptree achieving a share price target milestone based on the average of the thirty (30) trading day closing stock price of $70 (adjusted for dividends paid) prior to the 10th anniversary of the grant date, subject to the Reporting Person's continued employment with Tiptree. Any unvested PRSUs shall expire on January 1, 2034.

F1 · derivative.expiration_date: Each performance restricted stock unit (PRSU) represents a contingent right to receive one share of Tiptree Inc. ("Tiptree") common stock. The PRSUs will vest upon Tiptree achieving a share price target milestone based on the average of the thirty (30) trading day closing stock price of $70 (adjusted for dividends paid) prior to the 10th anniversary of the grant date, subject to the Reporting Person's continued employment with Tiptree. Any unvested PRSUs shall expire on January 1, 2034.

SEC source: 0001393726-23-000098 · wk-form4_1702933543.xml · nonDerivative · entry 1

Rifkind Neil Charles · CIK 0001580685 · General Counsel and Secretary

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 34,825

F1 · price: This sale was executed in multiple sales at prices ranging from $19.50 to $19.52, inclusive. The price reported above reflects the weighted average price. The reporting person undertakes to provide to the issuer, any security holding of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares and prices at which the transaction was effected.

SEC source: 0001393726-23-000073 · wk-form4_1696618539.xml · nonDerivative · entry 1

Goldwasser Lesley · CIK 0001465575 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 97,491

F1 · shares: Represents the stock component of the director's annual retainer fee, which is paid quarterly in arrears.

SEC source: 0001393726-23-000079 · wk-form4_1696618886.xml · nonDerivative · entry 1

Smith Bradley E. · CIK 0001579089 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 103,588

F1 · shares: Represents the stock component of the director's annual retainer fee, which is paid quarterly in arrears.

SEC source: 0001393726-23-000077 · wk-form4_1696618768.xml · nonDerivative · entry 1

Friedman Paul M · CIK 0001648181 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 102,855

F1 · shares: Represents the stock component of the director's annual retainer fee, which is paid quarterly in arrears.

SEC source: 0001393726-23-000075 · wk-form4_1696618658.xml · nonDerivative · entry 1

Mielle Dominique · CIK 0001759191 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 63,539

F1 · shares: Represents the stock component of the director's annual retainer fee, which is paid quarterly in arrears.

SEC source: 0001393726-23-000062 · wk-form4_1688741951.xml · nonDerivative · entry 1

Goldwasser Lesley · CIK 0001465575 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 95,603

F1 · shares: Represents the stock component of the director's annual retainer fee, which is paid quarterly in arrears.

SEC source: 0001393726-23-000065 · wk-form4_1688742134.xml · nonDerivative · entry 1

Smith Bradley E. · CIK 0001579089 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 102,833

F1 · shares: Represents the stock component of the director's annual retainer fee, which is paid quarterly in arrears.

SEC source: 0001393726-23-000064 · wk-form4_1688742076.xml · nonDerivative · entry 1

Friedman Paul M · CIK 0001648181 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 100,967

F1 · shares: Represents the stock component of the director's annual retainer fee, which is paid quarterly in arrears.

SEC source: 0001393726-23-000063 · wk-form4_1688742014.xml · nonDerivative · entry 1

Mielle Dominique · CIK 0001759191 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 61,651

F1 · shares: Represents the stock component of the director's annual retainer fee, which is paid quarterly in arrears.

SEC source: 0001393726-23-000057 · wk-form4_1686161392.xml · nonDerivative · entry 1

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Indirect · By 401K

Disclosed balance after: 187,571

SEC source: 0001393726-23-000040 · wf-form4_168081483059025.xml · nonDerivative · entry 1

Goldwasser Lesley · CIK 0001465575 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 93,405

F1 · shares: Represents the stock component of the director's annual retainer fee, which is paid quarterly in arrears.

SEC source: 0001393726-23-000042 · wf-form4_168081491841652.xml · nonDerivative · entry 1

Smith Bradley E. · CIK 0001579089 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 101,954

F1 · shares: Represents the stock component of the director's annual retainer fee, which is paid quarterly in arrears.

SEC source: 0001393726-23-000038 · wf-form4_168081474103155.xml · nonDerivative · entry 1

Friedman Paul M · CIK 0001648181 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 98,769

F1 · shares: Represents the stock component of the director's annual retainer fee, which is paid quarterly in arrears.