LendingTree CHRO exercises 9,999 RSUs, tax shares withheld

LendingTree, Inc. Chief Human Resources Officer Jill Olmstead reported compensation-related equity activity.

Rhea-AI Filing Summary

LendingTree, Inc. Chief Human Resources Officer Jill Olmstead reported compensation-related equity activity. She exercised restricted stock units into 9,999 shares of common stock at $0.00 per share, and after this exercise held 20,001 restricted stock units directly. Following related common stock entries, she directly owned 40,274 shares of common stock. A separate entry shows 3,689 shares of common stock were withheld at $42.65 per share to satisfy tax obligations. The filing notes that restricted stock units convert into common stock on a one-for-one basis and vest in three substantially equal annual installments beginning on March 10, 2026 in line with the original award terms.

Insider Trade Summary

9,999 shares exercised/converted

Exercise 3 txns

Insider Olmstead Jill

Role Chief Human Resources Officer

Type	Security	Shares	Price	Value
Exercise	Restricted Stock Units	9,999	$0.00	$0.00
Exercise	Common Stock	9,999	$0.00	$0.00
Exercise Price or Tax Liability	Common Stock	3,689	$42.65	$157K

Holdings After Transaction: Restricted Stock Units — 20,001 contracts (Direct); Common Stock — 40,274 shares (Direct)

Footnotes (2)

1. F1. Restricted stock units convert into common stock on a one-for-one basis.
2. F2. These restricted stock units vest in three substantially equal annual installments beginning on March 10, 2026 in accordance with the terms of the original award agreement.

FAQ

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

What insider transactions did LendingTree (TREE) report for Jill Olmstead?

Jill Olmstead exercised restricted stock units into 9,999 shares of LendingTree common stock and had 3,689 shares withheld for taxes. After these transactions, she directly owned 40,274 common shares and 20,001 restricted stock units.

How many LendingTree (TREE) shares does Jill Olmstead hold after this Form 4?

After the reported transactions, Jill Olmstead directly holds 40,274 shares of LendingTree common stock. She also directly holds 20,001 restricted stock units, which are separate equity awards that can convert into common shares according to their vesting schedule.

What was the size of Jill Olmstead’s equity award exercise at LendingTree (TREE)?

Jill Olmstead exercised restricted stock units covering 9,999 underlying shares of LendingTree common stock at $0.00 per share. This reflects the conversion of previously granted equity awards rather than an open-market purchase of shares.

Why were 3,689 LendingTree (TREE) shares disposed of in Jill Olmstead’s Form 4?

The 3,689 LendingTree shares were withheld at $42.65 per share to cover tax obligations tied to the equity vesting or exercise. This is a tax-withholding disposition, not an open-market sale initiated for portfolio or valuation reasons.

How do Jill Olmstead’s restricted stock units in LendingTree (TREE) vest?

Her restricted stock units vest in three substantially equal annual installments beginning on March 10, 2026. As they vest, each restricted stock unit converts into one share of LendingTree common stock on a one-for-one basis under the award terms.

What is the overall signal from Jill Olmstead’s recent LendingTree (TREE) Form 4?

The Form 4 primarily reflects routine compensation activity: exercising 9,999 restricted stock units and related tax withholding of 3,689 shares. There were no open-market purchases or sales reported, making this a standard equity award and tax-settlement event.

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 03/12/2026 - 04:03 PM 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^*

Olmstead Jill

(Last) (First) (Middle)

1415 VANTAGE PARK DRIVE

SUITE 700

(Street)

CHARLOTTE NC 28203

(City) (State) (Zip)

2. Issuer Name and Ticker or Trading Symbol
LendingTree, Inc. [ TREE ]

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

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

3. Date of Earliest Transaction (Month/Day/Year)
03/10/2026

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

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

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

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	03/10/2026		M		9,999	A	(1)	43,963	D
Common Stock	03/10/2026		F		3,689	D	$42.65	40,274	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)
				Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares
Restricted Stock Units	(1)	03/10/2026		M			9,999	(2)	(2)	Common Stock	9,999	$0	20,001	D

Explanation of Responses:

1. Restricted stock units convert into common stock on a one-for-one basis.

2. These restricted stock units vest in three substantially equal annual installments beginning on March 10, 2026 in accordance with the terms of the original award agreement.

	/s/ Heather Enlow-Novitsky, as Attorney-in-Fact for Jill Olmstead	03/12/2026
	** 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.