Upstart executive sells shares to cover RSU taxes

Q: Was the Upstart (UPST) insider sale related to options or RSUs?

Footnotes explain that the sale was tied to vesting restricted stock units (RSUs). Each RSU represents a contingent right to receive one share of common stock, and a portion of the resulting shares was sold to pay required tax withholding at vesting.

Upstart Holdings, Inc. insider Sanjay Datta, President, Capital & Enterprise, reported an open-market sale of 7,985 shares of common stock on May 20, 2026 at a weighted average price of $28.77 per share.

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Rhea-AI Filing Summary

Upstart Holdings, Inc. insider Sanjay Datta, President, Capital & Enterprise, reported an open-market sale of 7,985 shares of common stock on May 20, 2026 at a weighted average price of $28.77 per share. According to the footnotes, these shares were sold solely to cover tax withholding obligations tied to vesting restricted stock units. After this transaction, Datta directly holds 328,556 shares of Upstart common stock.

Insider Trade Summary

Net Seller: 7,985 shares

Net Sell 1 txn

Insider Datta Sanjay

Role President, Capital& Enterprise

Sold 7,985 shs ($230K)

Type	Security	Shares	Price	Value
Sale	Common Stock	7,985	$28.7714	$230K

Holdings After Transaction: Common Stock — 328,556 shares (Direct)

Footnotes (3)

F1. These shares were sold to cover tax withholding obligations in connection with the vesting of restricted stock units (RSUs).
F2. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $28.26 to $29.045. 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.
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.

Key Figures

Shares sold: 7,985 shares Weighted average sale price: $28.7714 per share Post-transaction holdings: 328,556 shares +1 more

4 metrics

Shares sold 7,985 shares Open-market sale on May 20, 2026

Weighted average sale price $28.7714 per share Common stock sale on May 20, 2026

Post-transaction holdings 328,556 shares Direct ownership after May 20, 2026 sale

Price range of trades $28.26 to $29.045 Multiple sale transactions on May 20, 2026

Key Terms

weighted average price, restricted stock units (RSUs), tax withholding obligations, contingent right

4 terms

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.

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.

tax withholding obligations financial

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

contingent right financial

"Each RSU represents a contingent right to receive one share of Common Stock, subject to the applicable vesting schedule and conditions of each RSU."

FAQ

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

What insider transaction did Upstart (UPST) report for Sanjay Datta?

Upstart reported that executive Sanjay Datta sold 7,985 shares of common stock on May 20, 2026. The shares were sold in the open market at a weighted average price of $28.77 per share, primarily to cover tax withholding obligations from vesting RSUs.

Why did Upstart (UPST) executive Sanjay Datta sell 7,985 shares?

The sale of 7,985 Upstart shares by Sanjay Datta was to cover tax withholding obligations related to vesting restricted stock units. This type of transaction is typically a mechanical step in equity compensation, rather than a discretionary decision to reduce economic exposure.

What price did the Upstart (UPST) insider shares sell for on May 20, 2026?

The reported weighted average sale price was $28.77 per Upstart share. Footnotes state the 7,985 shares were sold in multiple trades at prices ranging from $28.26 to $29.045, with full trade details available on request from the company or regulators.

How many Upstart (UPST) shares does Sanjay Datta hold after this transaction?

Following the May 20, 2026 sale, Sanjay Datta directly holds 328,556 shares of Upstart common stock. This post-transaction balance shows he retains a substantial equity position even after selling shares to satisfy tax withholding obligations from RSU vesting.

Is the Upstart (UPST) insider sale a routine tax withholding event?

Yes. The filing notes the 7,985 shares sold by Sanjay Datta were specifically to cover tax withholding obligations from RSU vesting. Such tax-related sales are generally considered routine administrative events rather than discretionary market-timing trades.

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

Form 4 Insider Transactions: What Each Field Means →

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Accepted by SEC EDGAR 05/22/2026 - 04:33 PM EDT

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^*

Datta Sanjay

(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)
	President, Capital& Enterprise

2a. Foreign Trading Symbol

3. Date of Earliest Transaction (Month/Day/Year)
05/20/2026

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)
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	Code	V	Amount	(A) or (D)	Price		6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
Common Stock	05/20/2026		S⁽¹⁾		7,985	D	$28.7714⁽²⁾	328,556⁽³⁾	D

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)
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)	Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares	8. Price of Derivative Security (Instr. 5)		10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)

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 $28.26 to $29.045. 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.

Remarks:

	/s/ Steven Madrid, by power of attorney	05/21/2026
	** 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)

Source: View Original Filing on SEC EDGAR