Upstart CLO sells 727 shares for RSU tax withholding

Upstart Holdings Chief Legal Officer Scott Darling reported small stock transactions mainly tied to equity compensation.

Rhea-AI Filing Summary

Upstart Holdings Chief Legal Officer Scott Darling reported small stock transactions mainly tied to equity compensation. On May 15, 2026, he sold a total of 727 shares of common stock in open-market transactions at weighted average prices around the high-$20s to low-$30s per share to cover tax withholding obligations from restricted stock unit vesting. After these sales, he still holds 102,609 shares directly, and an additional 32,451 shares indirectly through the Darling Family Trust.

Insights

Equity compensation and insider-trading analyst

Routine, small-scale tax-related sales with substantial holdings remaining.

The filing shows Scott Darling, Chief Legal Officer of Upstart Holdings, sold 727 shares of common stock on May 15, 2026. Footnotes state these shares were sold to cover tax withholding obligations tied to vesting restricted stock units, a common administrative step for equity compensation.

The transactions occurred in two weighted-average price ranges between about $28.44 and $30.54 per share, indicating standard open-market executions. Following the sales, Darling still owns 102,609 shares directly and 32,451 shares indirectly through the Darling Family Trust, so the reported activity represents a very small portion of his visible position.

Because the sales are described as tax-withholding related rather than discretionary portfolio moves, and given the modest number of shares versus his remaining holdings, the informational value for investors is limited. There are no derivative exercises reported, and derivative positions are not shown as remaining in this filing, reinforcing that this is primarily a housekeeping update on compensation-driven stock deliveries and associated tax payments.

Insider Trade Summary

Net Seller: 727 shares

Net Sell 3 txns

Insider Darling Scott

Role Chief Legal Officer

Sold 727 shs ($21K)

Type	Security	Shares	Price	Value
Sale	Common Stock	286	$28.8396	$8K
Sale	Common Stock	441	$29.9949	$13K
holding	Common Stock	--	--	--

Holdings After Transaction: Common Stock — 102,609 shares (Direct); Common Stock — 32,451 shares (Indirect, See Footnote)

Footnotes (6)

1. F1. These shares were sold to cover tax withholding obligations in connection with the vesting of restricted stock units (RSUs).
2. F2. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $28.44 to $29.27. 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.
3. F3. Certain of these securities are RSUs. Each RSU represents a contingent right to receive one share of Common Stock, subject to the applicable vesting schedule and conditions of each RSU.
4. F4. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $29.58 to $30.54. 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.
5. F5. The shares are held by the Darling Family Trust.
6. F6. The number of shares held reflects the deposit of 814 shares of Common Stock from the Reporting Person to the Darling Family Trust.

Key Figures

Total shares sold: 727 shares First sale size: 441 shares Second sale size: 286 shares +4 more

7 metrics

Total shares sold 727 shares Open-market sales on May 15, 2026

First sale size 441 shares Common stock sale at $29.9949 weighted average

Second sale size 286 shares Common stock sale at $28.8396 weighted average

Direct holdings after transactions 102,609 shares Common stock held directly after May 15, 2026

Indirect holdings after transactions 32,451 shares Common stock held by Darling Family Trust

Price range for 286-share sale $28.44–$29.27 Multiple transactions, weighted average reported

Price range for 441-share sale $29.58–$30.54 Multiple transactions, weighted average reported

Key Terms

restricted stock units (RSUs), weighted average price, Darling Family Trust, indirect ownership, +1 more

5 terms

restricted stock units (RSUs) financial

"These shares were sold to cover tax withholding obligations in connection with the vesting of restricted stock units (RSUs)."

Restricted stock units (RSUs) are a type of company promise to give employees shares of stock in the future, usually after certain conditions like working for a set time. They are like a gift promised today that you receive later, which can become valuable if the company's stock price goes up. RSUs matter because they are a way companies reward employees and can be a significant part of compensation.

weighted average price financial

"The price reported in Column 4 is a weighted average price."

Weighted average price is the average price of a security where each trade or component is counted according to its size, so bigger trades pull the average more than smaller ones. Think of it like calculating the average cost of a grocery haul where items you bought more of have greater influence on the final per-item cost. Investors use it to understand the true average price paid or received, judge execution quality, and compare trading performance against market movement.

Darling Family Trust financial

"The shares are held by the Darling Family Trust."

indirect ownership financial

"The shares are held by the Darling Family Trust."

tax withholding obligations financial

"These shares were sold to cover tax withholding obligations in connection with the vesting of restricted stock units (RSUs)."

FAQ

AI-generated questions and answers. How Rhea-AI works. Not financial advice.

What insider transactions did Upstart (UPST) report for Scott Darling on May 15, 2026?

Upstart reported that Chief Legal Officer Scott Darling sold 727 shares of common stock on May 15, 2026. These were open-market transactions executed in small blocks, with prices in the high-$20s to low-$30s per share, primarily to satisfy tax withholding obligations.

Why did Upstart’s Chief Legal Officer sell 727 UPST shares in this Form 4?

The 727 shares were sold to cover tax withholding obligations arising from the vesting of restricted stock units. This type of sale is a common, mechanical step when equity awards vest and does not necessarily reflect a discretionary change in the insider’s view of the stock.

What prices were received for the Upstart (UPST) shares sold by Scott Darling?

The filing reports weighted average prices for the sales. One sale of 286 shares had prices ranging from $28.44 to $29.27, and another sale of 441 shares had prices between $29.58 and $30.54, reflecting execution across multiple small trades within each range.

How many Upstart (UPST) shares does Scott Darling hold after these transactions?

After the reported sales, Scott Darling holds 102,609 shares of Upstart common stock directly. He also has an indirect interest in 32,451 additional shares held by the Darling Family Trust, as reflected in the holding entry and related footnotes in the Form 4.

What is the role of the Darling Family Trust in Scott Darling’s UPST holdings?

Some Upstart shares are held indirectly through the Darling Family Trust, which holds 32,451 shares after a deposit of 814 shares from Scott Darling. The filing classifies these as indirect ownership, indicating they are held in the trust rather than directly in his personal name.

Does this Upstart (UPST) Form 4 show any new option exercises or derivative transactions?

No, the Form 4 does not report any option exercises or other derivative transactions. The derivative summary is empty, and all reported activity involves common stock, with the key events being small open-market sales connected to restricted stock unit vesting and tax withholding.

AI-generated analysis. How Rhea-AI works. Not financial advice.

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Accepted by SEC EDGAR 05/18/2026 - 05:07 PM EDT Learn about SEC filing dates

SEC Form 4

FORM 4

UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940

OMB APPROVAL

OMB Number:			3235-0287
Estimated average burden
hours per response:			0.5

Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.

1. Name and Address of Reporting Person^*

Darling Scott

(Last) (First) (Middle)

C/O UPSTART HOLDINGS, INC.

2950 S. DELAWARE STREET, SUITE 410

(Street)

SAN MATEO CALIFORNIA 94403

(City) (State) (Zip)

UNITED STATES

(Country)

2. Issuer Name and Ticker or Trading Symbol
Upstart Holdings, Inc. [ UPST ]

5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

	Director		10% Owner
X	Officer (give title below)		Other (specify below)
	Chief Legal Officer

2a. Foreign Trading Symbol

3. Date of Earliest Transaction (Month/Day/Year)
05/15/2026

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

4. If Amendment, Date of Original Filed (Month/Day/Year)

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	3. Transaction Code (Instr. 8)		4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5)			5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4)	6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
			Code	V	Amount	(A) or (D)	Price
Common Stock	05/15/2026		S(1)		286	D	$28.8396(2)	103,864(3)	D
Common Stock	05/15/2026		S(1)		441	D	$29.9949(4)	102,609(3)	D
Common Stock								32,451	I	See Footnote(5)(6)

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned (e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	4. Transaction Code (Instr. 8)		5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5)		6. Date Exercisable and Expiration Date (Month/Day/Year)		7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4)		8. Price of Derivative Security (Instr. 5)	9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4)	10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
				Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares

Explanation of Responses:

1. These shares were sold to cover tax withholding obligations in connection with the vesting of restricted stock units (RSUs).

2. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $28.44 to $29.27. 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.

3. Certain of these securities are RSUs. Each RSU represents a contingent right to receive one share of Common Stock, subject to the applicable vesting schedule and conditions of each RSU.

4. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $29.58 to $30.54. 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.

5. The shares are held by the Darling Family Trust.

6. The number of shares held reflects the deposit of 814 shares of Common Stock from the Reporting Person to the Darling Family Trust.

Remarks:

	/s/ Steven Madrid, by power of attorney	05/18/2026
	** Signature of Reporting Person	Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.
* Form 4: SEC 1474 (03-26)