A Form 4 is filed within two business days of a company insider — an officer, a director, or a holder of more than ten percent of the stock — changing their position in the shares. All 9 filings in this group are Form 4s for Tiptree Inc.
The difficulty with reading these filings as a group is that a single form type covers transactions that mean entirely different things. An executive spending their own money to buy stock and an executive having shares withheld to pay tax on a vesting grant both appear as a Form 4. Every filing below is therefore tagged with the nature of the underlying transaction, taken from the transaction code reported on the form itself.
Across the 9 insider filings shown, the breakdown is 6 compensation award, 2 open-market purchase and 1 option exercise. 2 of them involved a discretionary open-market trade; the rest are compensation and administrative mechanics.
Form 4
Compensation award
Tax / Compensation Filing
2026-10-07
TIPT insider Form 4 filed for equity award, exercise, or tax withholding
Smith Bradley E. (Director) filed a Form 4 covering compensation-related activity such as stock awards, option exercises, conversions, or tax withholding. These filings are usually neutral.
Shares were granted as compensation rather than purchased. No cash changed hands, so the filing reflects a pay decision by the company, not a judgement about the price.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
A |
Compensation award
|
1,807 |
— |
— |
Filing: Form 4 (Insider Transaction)
Insider: Smith Bradley E. (Director)
Shares: 1,807
Form 4
Compensation award
Tax / Compensation Filing
2026-10-07
TIPT insider Form 4 filed for equity award, exercise, or tax withholding
Goldwasser Lesley (Director) filed a Form 4 covering compensation-related activity such as stock awards, option exercises, conversions, or tax withholding. These filings are usually neutral.
Shares were granted as compensation rather than purchased. No cash changed hands, so the filing reflects a pay decision by the company, not a judgement about the price.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
A |
Compensation award
|
1,084 |
— |
— |
Filing: Form 4 (Insider Transaction)
Insider: Goldwasser Lesley (Director)
Shares: 1,084
Form 4
Compensation award
Tax / Compensation Filing
2026-07-06
TIPT insider Form 4 filed for equity award, exercise, or tax withholding
Smith Bradley E. (Director) filed a Form 4 covering compensation-related activity such as stock awards, option exercises, conversions, or tax withholding. These filings are usually neutral.
Shares were granted as compensation rather than purchased. No cash changed hands, so the filing reflects a pay decision by the company, not a judgement about the price.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
A |
Compensation award
|
1,768 |
— |
— |
Filing: Form 4 (Insider Transaction)
Insider: Smith Bradley E. (Director)
Shares: 1,768
Form 4
Compensation award
Tax / Compensation Filing
2026-07-06
TIPT insider Form 4 filed for equity award, exercise, or tax withholding
Goldwasser Lesley (Director) filed a Form 4 covering compensation-related activity such as stock awards, option exercises, conversions, or tax withholding. These filings are usually neutral.
Shares were granted as compensation rather than purchased. No cash changed hands, so the filing reflects a pay decision by the company, not a judgement about the price.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
A |
Compensation award
|
1,061 |
— |
— |
Filing: Form 4 (Insider Transaction)
Insider: Goldwasser Lesley (Director)
Shares: 1,061
Form 4
Open-market purchase
Insider Buying
2026-05-28
TIPT insider Ilany Jonathan (Director) bought 990 shares (~$17.3K)
Ilany Jonathan, listed as Director at TIPTREE INC., reported an open-market purchase of 990 TIPT shares in a Form 4 filing. Insider buying is often treated as a bullish signal because company insiders are committing their own capital.
The insider bought shares on the open market with their own money. This is the only Form 4 category that requires a discretionary cash outlay at the prevailing price.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
P |
Open-market purchase
|
990 |
$17.45 |
$17.3K |
Filing: Form 4 (Insider Transaction)
Insider: Ilany Jonathan (Director)
Shares: 990
Est. Value: $17.3K
Form 4
Compensation award
Tax / Compensation Filing
2026-04-06
TIPT insider Form 4 filed for equity award, exercise, or tax withholding
Smith Bradley E. (Director) filed a Form 4 covering compensation-related activity such as stock awards, option exercises, conversions, or tax withholding. These filings are usually neutral.
Shares were granted as compensation rather than purchased. No cash changed hands, so the filing reflects a pay decision by the company, not a judgement about the price.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
A |
Compensation award
|
1,907 |
— |
— |
Filing: Form 4 (Insider Transaction)
Insider: Smith Bradley E. (Director)
Shares: 1,907
Form 4
Compensation award
Tax / Compensation Filing
2026-04-06
TIPT insider Form 4 filed for equity award, exercise, or tax withholding
Goldwasser Lesley (Director) filed a Form 4 covering compensation-related activity such as stock awards, option exercises, conversions, or tax withholding. These filings are usually neutral.
Shares were granted as compensation rather than purchased. No cash changed hands, so the filing reflects a pay decision by the company, not a judgement about the price.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
A |
Compensation award
|
1,144 |
— |
— |
Filing: Form 4 (Insider Transaction)
Insider: Goldwasser Lesley (Director)
Shares: 1,144
Form 4
Open-market purchase
Insider Buying
2026-03-13
TIPT insider McKinney Scott T. (Chief Financial Officer) bought 3,832 shares (~$61.7K)
McKinney Scott T., listed as Chief Financial Officer at TIPTREE INC., reported an open-market purchase of 3,832 TIPT shares in a Form 4 filing. Insider buying is often treated as a bullish signal because company insiders are committing their own capital.
The insider bought shares on the open market with their own money. This is the only Form 4 category that requires a discretionary cash outlay at the prevailing price.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
P |
Open-market purchase
|
2,600 |
$16.15 |
$42.0K |
P |
Open-market purchase
|
1,232 |
$15.98 |
$19.7K |
Filing: Form 4 (Insider Transaction)
Insider: McKinney Scott T. (Chief Financial Officer)
Shares: 3,832
Est. Value: $61.7K
Form 4
Option exercise
Tax / Compensation Filing
2026-02-23
TIPT insider Form 4 filed for equity award, exercise, or tax withholding
McKinney Scott T. (Chief Financial Officer) filed a Form 4 covering compensation-related activity such as stock awards, option exercises, conversions, or tax withholding. These filings are usually neutral.
The insider converted options into shares. The exercise price was fixed when the options were granted, so the timing usually tracks an expiry schedule.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
M |
Option exercise
|
15,110 |
— |
— |
F |
Tax withholding on vested shares
|
5,143 |
$17.06 |
$87.7K |
M |
Option exercise
derivative · Restricted Stock Units
|
15,110 |
— |
— |
Filing: Form 4 (Insider Transaction)
Insider: McKinney Scott T. (Chief Financial Officer)
Shares: 20,253