Enterprise Financial CEO increases holdings through ESPP purchase

Rhea-AI Filing Summary

Enterprise Financial Services Corp. (EFSC) – Form 4 insider activity

Chief Executive Officer and Director James Brian Lally reported a purchase of 450 common shares on 30 June 2025 through the Company’s 2018 Employee Stock Purchase Plan (ESPP). The shares were acquired at $46.84, reflecting the plan’s 15 % discount to the closing price, and the transaction is coded “J,” indicating an exempt ESPP acquisition under Rule 16b-3.

Following this trade, Lally’s direct holdings rise to 101,335 shares. He also reports 18,535 shares held indirectly via the 401(k) unitized stock fund and 4,107 jointly-held shares with his spouse. In addition, the filing details sizeable derivative positions, including 105,205 non-qualified stock options with strike prices ranging from $39.50 to $57.17 and expiration dates between 2031-2035, plus 31,395 restricted stock units scheduled to vest between 2026-2028.

The purchase increases Lally’s direct ownership by roughly 0.4 % and, while modest in size, reinforces ongoing insider participation in corporate equity programs.

Positive

• Insider purchase: CEO James Brian Lally acquired 450 EFSC shares on 06/30/2025.
• Increased direct ownership: Direct holdings rose to 101,335 shares, indicating continued alignment with shareholders.
• No insider sales reported: The filing contains only acquisitions and routine option/RSU positions.

Negative

• Small transaction size: The 450-share purchase adds only ~0.4 % to the CEO’s existing direct stake, limiting market relevance.

Insights

Securities Analyst

TL;DR: CEO buys 450 EFSC shares via ESPP, upping direct stake to 101k; signal positive but quantitatively small.

The voluntary ESPP purchase shows continued alignment between CEO James Brian Lally and shareholders. Buying at a discounted $46.84 demonstrates confidence and participation in broad-based employee ownership programs. However, the incremental 450 shares represent only about 0.4 % of his existing direct holdings, so the transaction is immaterial to the overall insider ownership profile and unlikely to affect market sentiment materially. No sales were reported, and option/RSU disclosures are routine roll-forwards without new grants. Overall impact: neutral-to-slightly positive.

Corporate Governance Expert

TL;DR: Routine ESPP trade; governance positive, market impact minimal.

From a governance standpoint, insider participation in the ESPP under transparent Rule 16b-3 exemption supports best-practice alignment. Lally’s cumulative equity—over 101k shares plus sizeable options/RSUs—shows meaningful skin-in-the-game. The absence of dispositions limits any negative signaling. Nonetheless, the small share count and automatic plan mechanics mean investors should not over-interpret the purchase. I view the filing as procedurally sound and moderately reassuring, but not materially influential.

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^*

LALLY JAMES BRIAN

(Last) (First) (Middle)

150 N. MERAMEC

(Street)

CLAYTON MO 63105

(City) (State) (Zip)

2. Issuer Name and Ticker or Trading Symbol
ENTERPRISE FINANCIAL SERVICES CORP [ EFSC ]

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

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

3. Date of Earliest Transaction (Month/Day/Year)
06/30/2025

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	06/30/2025		J(1)	V	450	A	$46.84(2)	101,335	D
Common Stock								18,535	I	401 (K) Plan(3)
Common Stock								4,107	D(4)

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
Non Qualified Stock Option (Right to Buy)	$43.81							02/06/2024	02/25/2031	Common Stock	17,637		17,637	D
Non Qualified Stock Option (Right to Buy)	$48.34							(5)	02/24/2032	Common Stock	20,325		20,325	D
Non Qualified Stock Option (Right to Buy)	$54.46							(6)	02/28/2033	Common Stock	20,438		20,438	D
Non Qualified Stock Option (Right to Buy)	$39.5							(7)	02/28/2034	Common Stock	30,661		30,661	D
Non Qualified Stock Option (Right to Buy)	$57.17							(8)	03/04/2035	Common Stock	16,144		16,144	D
Restricted Share Units	(9)							(10)	(10)	Common Stock	4,176		4,176	D
Restricted Share Units	(9)							(11)	(11)	Common Stock	5,857		5,857	D
Restricted Share Units	(9)							(12)	(12)	Common Stock	5,398		5,398	D
Restricted Share Units	(9)							(13)	(13)	Common Stock	15,964		15,964	D

Explanation of Responses:

1. The reporting person is voluntarily reporting the acquisition of shares of the Issuer's common stock pursuant to the Issuer's 2018 Employee Stock Purchase Plan ("ESPP") for the ESPP purchase period of January 1, 2025, through June 30, 2025. This transaction is exempt under Section 16b-3(c).

2. In accordance with the terms of the ESPP, the reported shares were acquired based on 85% of the closing price of the Issuer's common stock on June 30, 2025.

3. These securities are represented by units held in a unitized stock fund through the Company's 401(k) Plan. The unitized stock fund consists of cash and common stock in amounts that vary from time to time.

4. These shares are held jointly with spouse.

5. This option becomes exercisable in the first quarter of 2025, subject to continued employment by the reporting person.

6. This option becomes exercisable in the first quarter of 2026, subject to continued employment by the reporting person.

7. This option becomes exercisable in the first quarter of 2027, subject to continued employment by the reporting person.

8. The option becomes exercisable in the first quarter of 2028, subject to continued employment by the reporting person.

9. The RSU's were granted pursuant to the Company's 2018 Stock Incentive Plan. Each RSU represents the right to receive one share of Common Stock, subject to adjustment as provided in the Grant Agreement.

10. The RSU vest 100% in the first quarter of 2026, subject to continued employment by the reporting person.

11. The RSU's vest 100% in the first quarter of 2027, subject to continued employment by the reporting person.

12. The RSU's vest 100% in the first quarter of 2028, subject to continued employment by the reporting person.

13. The RSUs vest over six years in one-third installments on each of February 24, 2024, February 24, 2026, and February 24, 2028. Vesting is subject to continued employment of the reporting person. On each vesting date, for each RSU vesting on such date, the reporting person will receive one share of Common Stock.

	/s/James Brian Lally	07/09/2025
	** 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.
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FAQ

What did EFSC CEO James Brian Lally purchase on 30 Jun 2025?

He bought 450 shares of EFSC common stock through the 2018 ESPP.

At what price were the EFSC shares acquired?

The shares were acquired at $46.84, reflecting 85 % of the closing price on the purchase date.

How many EFSC shares does Lally now directly own?

After the transaction, he directly owns 101,335 shares.

Under which plan was the transaction executed?

The purchase was made under the Enterprise Financial Services Corp. 2018 Employee Stock Purchase Plan.

What does transaction code "J" signify in the EFSC Form 4?

Code "J" indicates an exempt acquisition under Rule 16b-3, here for the ESPP purchase.

How many derivative securities does Lally hold after this filing?

He holds 105,205 non-qualified stock options and 31,395 restricted stock units with various vesting schedules.