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 8 filings in this group are Form 4s for Upland Software, 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 8 insider filings shown, the breakdown is 4 open-market sale, 3 tax withholding and 1 compensation award. 4 of them involved a discretionary open-market trade; the rest are compensation and administrative mechanics.
Form 4
Tax withholding
Tax / Compensation Filing
2026-09-21
UPLD insider Form 4 filed for equity award, exercise, or tax withholding
Doman Dan (Chief Operating & Product Ofcr) 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 withheld by the company to settle tax due when equity vested. This is an automatic administrative step and not a decision to sell.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
F |
Tax withholding on vested shares
|
2,952 |
$3.94 |
$11.6K |
Filing: Form 4 (Insider Transaction)
Insider: Doman Dan (Chief Operating & Product Ofcr)
Shares: 2,952
Form 4
Tax withholding
Tax / Compensation Filing
2026-09-21
UPLD insider Form 4 filed for equity award, exercise, or tax withholding
Nathaniel Sean (CEO and President) 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 withheld by the company to settle tax due when equity vested. This is an automatic administrative step and not a decision to sell.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
F |
Tax withholding on vested shares
|
1,640 |
$3.94 |
$6.5K |
Filing: Form 4 (Insider Transaction)
Insider: Nathaniel Sean (CEO and President)
Shares: 1,640
Form 4
Tax withholding
Tax / Compensation Filing
2026-09-21
UPLD insider Form 4 filed for equity award, exercise, or tax withholding
Simon Jennifer L. (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.
Shares were withheld by the company to settle tax due when equity vested. This is an automatic administrative step and not a decision to sell.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
F |
Tax withholding on vested shares
|
1,117 |
$3.94 |
$4.4K |
Filing: Form 4 (Insider Transaction)
Insider: Simon Jennifer L. (Chief Financial Officer)
Shares: 1,117
Form 4
Compensation award
Tax / Compensation Filing
2026-08-18
UPLD insider Form 4 filed for equity award, exercise, or tax withholding
Simon Jennifer L. (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.
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
|
30,000 |
— |
— |
A |
Compensation award
derivative · Performance Share Unit
|
6,666 |
— |
— |
Filing: Form 4 (Insider Transaction)
Insider: Simon Jennifer L. (Chief Financial Officer)
Shares: 30,000
Form 4
Open-market sale
Insider Selling
2026-08-11
UPLD insider Mattox Timothy (Director) sold 847 shares (~$3.6K)
Mattox Timothy, listed as Director at Upland Software, Inc., reported an open-market sale of 847 UPLD shares in a Form 4 filing. This is a confirmed insider sale, not just a proposed sale notice.
The insider sold shares on the open market. Sales may be discretionary or executed automatically under a pre-arranged Rule 10b5-1 trading plan, and a Form 4 does not always make clear which applies.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
S |
Open-market sale
|
847 |
$4.28 |
$3.6K |
Filing: Form 4 (Insider Transaction)
Insider: Mattox Timothy (Director)
Shares: 847
Est. Value: $3.6K
Form 4
Open-market sale
Insider Selling
2026-08-10
UPLD insider Mattox Timothy (Director) sold 1,000 shares (~$4.3K)
Mattox Timothy, listed as Director at Upland Software, Inc., reported an open-market sale of 1,000 UPLD shares in a Form 4 filing. This is a confirmed insider sale, not just a proposed sale notice.
The insider sold shares on the open market. Sales may be discretionary or executed automatically under a pre-arranged Rule 10b5-1 trading plan, and a Form 4 does not always make clear which applies.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
S |
Open-market sale
|
1,000 |
$4.27 |
$4.3K |
Filing: Form 4 (Insider Transaction)
Insider: Mattox Timothy (Director)
Shares: 1,000
Est. Value: $4.3K
Form 4
Open-market sale
Insider Selling
2026-08-06
UPLD insider Mattox Timothy (Director) sold 2,000 shares (~$8.9K)
Mattox Timothy, listed as Director at Upland Software, Inc., reported an open-market sale of 2,000 UPLD shares in a Form 4 filing. This is a confirmed insider sale, not just a proposed sale notice.
The insider sold shares on the open market. Sales may be discretionary or executed automatically under a pre-arranged Rule 10b5-1 trading plan, and a Form 4 does not always make clear which applies.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
S |
Open-market sale
|
1,000 |
$4.33 |
$4.3K |
S |
Open-market sale
|
1,000 |
$4.53 |
$4.5K |
Filing: Form 4 (Insider Transaction)
Insider: Mattox Timothy (Director)
Shares: 2,000
Est. Value: $8.9K
Form 4
Open-market sale
Insider Selling
2026-08-04
UPLD insider Mattox Timothy (Director) sold 2,000 shares (~$8.9K)
Mattox Timothy, listed as Director at Upland Software, Inc., reported an open-market sale of 2,000 UPLD shares in a Form 4 filing. This is a confirmed insider sale, not just a proposed sale notice.
The insider sold shares on the open market. Sales may be discretionary or executed automatically under a pre-arranged Rule 10b5-1 trading plan, and a Form 4 does not always make clear which applies.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
S |
Open-market sale
|
1,000 |
$4.48 |
$4.5K |
S |
Open-market sale
|
1,000 |
$4.45 |
$4.5K |
Filing: Form 4 (Insider Transaction)
Insider: Mattox Timothy (Director)
Shares: 2,000
Est. Value: $8.9K