[Form 4] Enterprise Bancorp Inc. Insider Trading Activity

Rhea-AI Filing Summary

Jefferies Financial Group Inc. is offering Medium-Term Notes, Series A, structured as Market Linked Securities tied to the worst performing of the S&P 500® and NASDAQ-100® indices. The notes price on 31 Jul 2025, settle on 5 Aug 2025 and mature on 4 Feb 2027 (approx. 18 months).

• Face amount: $1,000 per note; denominations of $1,000.
• Upside: 100 % participation in any positive index move, capped at a maximum return of ≥14.20 % ($1,142 per note).
• Contingent absolute return: if the worst index finishes 0 – 15 % below the start level, investors receive a positive return equal to the absolute decline (max 15 %).
• Buffer: 15 % fixed buffer. If the worst index falls >15 %, investors lose principal 1-for-1 beyond the buffer and may forfeit up to 85 % of face value.
• No coupons, no dividends, no early call, no listing.
• Estimated value: $972.60 (≈97.26 % of face), reflecting issuance, structuring and hedging costs; agent discount up to $23.25 (2.325 %).
• Credit risk: senior unsecured obligation of Jefferies Financial Group Inc. (NYSE: JEF); payments depend on issuer solvency.

In essence, the note combines limited upside, contingent buffered downside and correlation risk (performance determined solely by the lowest index). It may suit investors comfortable with Jefferies’ credit, willing to trade potentially higher equity returns for partial downside protection and a defined cap over a short horizon, and prepared to hold to maturity given the anticipated thin secondary market.

Positive

• 15 % downside buffer combined with absolute return feature offers limited protection in shallow market pullbacks.
• Short 18-month tenor may appeal to investors seeking tactical exposure with defined risk parameters.

Negative

• Upside capped at ≥14.2 %, materially below historical index returns in strong rallies.
• ‘Worst-of’ methodology exposes holders to the full decline of the weaker index, increasing probability of loss.
• Estimated fair value (≈97 %) is below issue price, embedding dealer fees and hedging costs from day one.
• No secondary market listing; liquidity and exit pricing depend solely on dealer willingness.
• Credit risk of Jefferies; note holders rank as senior unsecured creditors without FDIC insurance.

Insights

Structured Products Analyst

TL;DR 14.2 % capped upside, 15 % buffer, worst-of two indices; note delivers asymmetric profile but significant tail and credit risk.

The structure offers three payout zones: (1) full 100 % upside participation up to a hard cap (≥14.2 %), which may lag a direct ETF allocation if indices rally strongly; (2) a contingent absolute return for moderate declines, providing up to a 15 % positive payout; and (3) unbuffered losses beyond –15 %, creating exposure to 85 % principal loss. Because payoff is based on the worst index, correlation risk is pronounced; a sharp drawdown in only one benchmark negates gains in the other. At issuance, investors pay ~2.74 % over the dealer’s estimated value and accept Jefferies’ unsecured credit. Liquidity will be dealer-driven and priced at a discount, particularly after the 3-month post-issue window when hedging cost amortisation ends. Overall risk-adjusted return looks modest unless an investor has a defined view that either index remains range-bound (–15 % to +14 %) over the next 18 months.

Multi-Asset Portfolio Manager

TL;DR From a portfolio view, structure behaves like short out-of-the-money put plus short call spread on worst-of basket—limited alpha, meaningful downside.

Allocators should model this security as: long bond component (~18-month Jefferies credit) plus options replicating 100 % long exposure capped at 14.2 %, short a 15-% OTM put on the worst index, and long a 15-% digital absolute return. Implied volatility & correlation make the worst-of put expensive for investors; dealers capture that premium, explaining the sub-par estimated value. The capped upside constrains equity beta (~0.35 ex-ante), so risk-adjusted return relative to an equity index ETF is inferior unless markets trade sideways. Given Jefferies’ BBB/Baa rating, credit spread adds incremental tail risk versus Treasuries. Impact on JEF capital structure is negligible, therefore market impact is neutral.

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

X

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^*

DUNCAN GEORGE L

(Last) (First) (Middle)

C/O ENTERPRISE BANCORP

222 MERRIMACK STREET

(Street)

LOWELL MA 01852

(City) (State) (Zip)

2. Issuer Name and Ticker or Trading Symbol
ENTERPRISE BANCORP INC /MA/ [ EBTC ]

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

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

3. Date of Earliest Transaction (Month/Day/Year)
07/01/2025

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	07/01/2025		F		3,437	D	$39.64	360,206(1)	D
Common Stock	07/01/2025		D		360,206	D	(2)	0(1)	D
Common Stock	07/01/2025		D		18,445	D	(2)	0	I	By Estate
Common Stock	07/01/2025		D		49,164.399	D	(2)	0	I	By Trust

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
Option (Right to Buy)	$21.86	07/01/2025		D			3,095	(3)	03/14/2026	Common Stock	3,095	(3)	0	D
Option (Right to Buy)	$30.46	07/01/2025		D			2,157	(3)	03/20/2027	Common Stock	2,157	(3)	0	D
Option (Right to Buy)	$34.33	07/01/2025		D			2,040	(3)	03/20/2028	Common Stock	2,040	(3)	0	D
Option (Right to Buy)	$29.84	07/01/2025		D			2,810	(3)	03/19/2029	Common Stock	2,810	(3)	0	D
Option (Right to Buy)	$28.22	07/01/2025		D			2,909	(3)	03/17/2030	Common Stock	2,909	(3)	0	D
Stock Option (Right to Buy)	$32.73	07/01/2025		D			2,046	(3)	03/15/2031	Common Stock	2,046	(3)	0	D
Stock Option (Right to Buy)	$38.58	07/01/2025		D			1,698	(3)	03/14/2032	Common Stock	1,698	(3)	0	D

Explanation of Responses:

1. In accordance with the Merger Agreement, all unvested shares of restricted stock automatically vested in full at the Effective Time (as defined in the Merger Agreement) to the extent not previously forfeited, and was considered outstanding shares of Enterprise common entitled to receive the Merger Consideration (as defined in the Merger Agreement).

2. Pursuant to the Agreement and Plan of Merger, dated as of December 8, 2024 (the "Merger Agreement"), by and among Enterprise Bancorp, Inc. ("Enterprise"), Enterprise Bank and Trust Company, Independent Bank Corp. ("Independent") and Rockland Trust Company, each issued and outstanding share of Enterprise common stock was converted into the right to receive (i) $2.00 in cash and (ii) 0.60 shares of Independent common stock (subject to the payment of cash in lieu of fractional shares).

3. In accordance with the Merger Agreement, each option to purchase Issuer common stock, whether vested or unvested, automatically converted to the right to receive a cash payment equal to (i) the number of shares of Enterprise common stock provided for in such option and (ii) the excess, if any, of the Per Share Cash Equivalent Consideration (as defined in the Merger Agreement) over the exercise price per share of Enterprise common stock provided for in such option, which cash payment was made without interest and was net of all applicable withholding taxes.

	/s/ Joseph R. Lussier as attorney-in-fact for George L. Duncan	07/01/2025
	** Signature of Reporting Person	Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
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FAQ

What is the maximum potential return on the JEF Market Linked Securities?

The maximum return is at least 14.20 %, capping the maturity payment at a minimum of $1,142 per $1,000 note.

How much principal can investors lose on these Jefferies notes?

If the lowest performing index falls more than 15 %, investors lose principal 1-for-1 beyond the 15 % buffer, up to an 85 % loss.

Do the securities pay any interest or dividends before maturity?

No. The notes are zero-coupon; investors receive only the maturity payment, which may be above or below face value.

What credit exposure do holders assume?

Payments rely on Jefferies Financial Group Inc. as a senior unsecured issuer; default would jeopardize repayment.

Can I sell the notes before February 4, 2027?

The notes are not exchange-listed. Dealers may offer to buy them, but secondary market liquidity and pricing are uncertain.