[S-8 POS] Enterprise Bancorp Inc. SEC Filing

Rhea-AI Filing Summary

Citigroup Global Markets Holdings Inc., guaranteed by Citigroup Inc. (ticker: C), is offering $1.396 million aggregate principal amount of Callable Contingent Coupon Equity-Linked Securities due 31 Dec 2026. The notes are unsecured senior obligations registered under the shelf prospectus (Reg. Nos. 333-270327 & 333-270327-01) and priced at $1,000 per note.

Key structural features

• Linked Indices (worst-of): Nasdaq-100® (initial 22,534.20), Russell 2000® (2,172.526) and S&P 500® (6,173.07). Performance of the lowest-return index (“worst performing underlying”) governs coupons, redemption and principal repayment.
• Contingent Coupon: 0.85% of face value per month (10.20% p.a.) payable only if, on the relevant valuation date, the worst performing index closes at or above its 70% coupon-barrier.
• Barriers: Coupon barrier and final barrier both set at 70% of each initial index level (i.e., 30% downside threshold).
• Issuer Call: The issuer may redeem the notes in whole on any of 12 monthly dates from Dec-2025 through Nov-2026; redemption pays $1,000 plus any due coupon.
• Principal Repayment: • If, on the final valuation date (28 Dec 2026), the worst performing index ≥ final barrier, investors receive full principal + final coupon. • If it is < final barrier, repayment equals $1,000 × (1 + index return), creating linear downside exposure to zero.
• Issue economics: Estimated value at pricing is $990.70 (≈99.07% of face), reflecting distribution and hedging costs; no underwriting discount but up to $7.25 combined dealer/marketing fees per note paid out of issuer proceeds.
• Liquidity & Listing: No exchange listing; secondary market solely at dealer’s discretion; bid prices expected below par and below estimated value after a three-month post-issuance adjustment period.

Risk highlights

• Investors face credit risk of Citigroup Global Markets Holdings Inc. & Citigroup Inc.
• Downside participation is uncapped: a ≥30% decline in any single index at maturity erodes principal dollar-for-dollar; a severe decline can result in total loss of invested capital and coupons.
• Coupon payments are contingent and path-dependent; missing a single barrier on any valuation date eliminates the following month’s coupon.
• Call risk: Early redemption limits coupon accrual and typically occurs when conditions favor the issuer.
• Small issue size and lack of listing limit liquidity; dealer bid may disappear.
• Complex U.S. tax treatment; payments treated as ordinary income, with withholding possible for non-U.S. holders.

The product targets yield-seeking investors comfortable with equity-index downside risk, limited transparency on mark-to-market values and potential illiquidity. For diversified holders of Citigroup common equity, the $1.4 million issuance is immaterial to group earnings and capital.

Positive

• High contingent coupon of 10.20% per annum if barriers are respected, far above Citi’s conventional senior debt yield.
• Full principal repayment plus coupon if the worst performing index stays above 70% of initial value at maturity.
• Issuer call feature provides early liquidity at par (plus coupon) in favorable market scenarios.

Negative

• Uncapped downside: a ≥30% decline in any single index at maturity leads to dollar-for-dollar principal loss down to zero.
• Coupons are not guaranteed; any monthly barrier breach eliminates that period’s payment, reducing realized yield.
• Issuer call risk truncates upside and often occurs when continuation would benefit investors.
• Estimated value (99.07%) below issue price reflects embedded fees; secondary market likely at further discount.
• No exchange listing and small issue size create significant liquidity risk and wide bid-ask spreads.
• Credit exposure to Citigroup entities; default would jeopardize all payments.

Insights

Structured Products Analyst

TL;DR: High 10.2% coupon but worst-of barrier design exposes investors to uncapped downside, with issuer call capping upside; neutral overall.

The note’s yield appears attractive versus plain-vanilla Citi bonds, yet investors effectively sell a series of monthly put options on the three linked indices with a 70% strike. Because payoff is governed by the single worst performer, correlation risk is material—historically, small-cap stocks in the Russell 2000® decouple under stress, raising barrier-breach probability. The call feature allows Citi to redeem once cumulative coupons paid approach internal funding costs, leaving holders reinvestment risk. Economic value at issuance (99.07% of face) confirms the dealer’s embedded fee structure is within market norms, but secondary bids will likely open near 96–97. Cash-yield seekers conscious of equity risk and liquidity constraints might allocate a small tactical portion; buy-and-hold note investors must accept possible 100% principal loss.

Multi-Asset Portfolio Manager

TL;DR: For diversified portfolios, note’s risk/return is asymmetric and illiquid; avoid unless barrier probability modelling fits mandate.

From an asset-allocation lens, the structure replicates a high-yielding credit exposure plus short out-of-the-money equity puts across large-cap growth, small-cap and broad-market indices. Back-testing indicates that, over a 24-month horizon, the 30% worst-of drawdown threshold was breached in ~28% of rolling periods since 2000, translating to significant default-like tail risk. Moreover, Citi’s senior credit spreads (<90 bp) do not justify layering equity tail risk for only ~430 bp excess yield after fees and call optionality. Liquidity premium is insufficient, given the micro issue size ($1.4 mm) and single-dealer market. We classify the investment impact as neutral for Citi shareholders (de minimis funding) but potentially negative for uninformed retail buyers.

 As filed with the Securities and Exchange Commission on July 1, 2025

Registration No. 333-256003

Registration No. 333-213799

Registration No. 333-184089

Registration No. 333-159006

UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

POST-EFFECTIVE AMENDMENT NO. 1

TO

 FORM S-8

REGISTRATION STATEMENT NO. 333-256003

REGISTRATION STATEMENT NO. 333-213799

REGISTRATION STATEMENT NO. 333-184089

REGISTRATION STATEMENT NO. 333-159006

UNDER THE SECURITIES ACT OF 1933

ENTERPRISE BANCORP, INC.

(Independent Bank Corp., as successor by merger to Enterprise Bancorp, Inc.)

(Exact name of registrant as specified in its charter)

Massachusetts						04-3308902
(State or other jurisdiction of incorporation or organization)						(I.R.S. Employer Identification No.)

c/o Independent Bank Corp.

Office Address:  2036 Washington Street, Hanover, Massachusetts 02339

Mailing Address:  288 Union Street, Rockland, Massachusetts 02370

(Address and Zip Code of Principal Executive Office)

Enterprise Bancorp, Inc. 2016 Stock Incentive Plan, as amended

Enterprise Bancorp, Inc. 2009 Stock Incentive Plan, as amended

(Full titles of the plans)

Patricia M. Natale, Esq.

Executive Vice President and General Counsel

Independent Bank Corp.

2036 Washington Street, Hanover, Massachusetts 02339

(781) 878-6100

(Name, address, and telephone number,
including area code, of agent for service)

 Indicate by check mark whether the registrant is a large accelerated filer, an accelerated filer, a non-accelerated filer, a smaller reporting company or an emerging growth company. See the definitions of “large accelerated filer,” “accelerated filer,” “smaller reporting company,” and “emerging growth company” in Rule 12b-2 of the Exchange Act.

Large accelerated filer

☐

Accelerated filer

☒

Non-accelerated filer

☐

Smaller reporting company

☐

Emerging growth company

☐

If an emerging growth company, indicate by check mark if the registrant has elected not to use the extended transition period for complying with any new or revised financial accounting standards provided pursuant to Section 7(a)(2)(B) of the Securities Act. ☐

DEREGISTRATION OF SECURITIES

This Post-Effective Amendment No. 1 (the “Post-Effective Amendment”) filed by Enterprise Bancorp, Inc., a Massachusetts corporation (the “Company” or “Enterprise”) to the following Registration Statements on Form S-8 (each a “Registration Statement,” and collectively, the “Registration Statements”) filed by Enterprise with the U.S. Securities and Exchange Commission (the “Commission”) deregisters any and all shares of common stock of Enterprise, par value $0.01 per share (the “Common Shares”) that were registered for issuance under the Registration Statements and that remain unsold under the Registration Statements (note that the Common Share numbers listed below do not take into account any applicable corporate actions, such as stock splits, that may have been taken in the interim):

•                  Registration Statement on Form S-8 (No. 333-256003), which was filed with the Commission on May 11, 2021, pertaining to the registration of 400,000 Common Shares issuable under the Enterprise Bancorp, Inc. 2016 Stock Incentive Plan, as amended.

•                  Registration Statement on Form S-8 (No. 333-213799), which was filed with the Commission on September 26, 2016, pertaining to the registration of 350,000 Common Shares issuable under the Enterprise Bancorp, Inc. 2016 Stock Incentive Plan, as amended.

•                  Registration Statement on Form S-8 (No. 333-184089), which was filed with the Commission on September 25, 2012, pertaining to the registration of 475,000 Common Shares issuable under the Enterprise Bancorp, Inc. 2009 Stock Incentive Plan, as amended.

•        Registration Statement on Form S-8 (No. 333-159006), which was filed with the Commission on May 11, 2021, pertaining to the registration of 400,000 Common Shares issuable under the Enterprise Bancorp, Inc. 2009 Stock Incentive Plan, as amended.

Effective on July 1, 2025, pursuant to that certain Agreement and Plan of Merger, dated December 8, 2024 (the “Merger Agreement”), by and among Independent Bank Corp. (“Independent”), Rockland Trust Company, a wholly-owned subsidiary of Independent, Enterprise and Enterprise Bank and Trust Company, a wholly-owned subsidiary of Enterprise, Enterprise merged with and into Independent, with Independent as the surviving entity (the “Merger”).

In connection with the Merger, Enterprise is terminating any and all offerings and sales of its securities registered pursuant to its existing registration statements under the Securities Act of 1933, as amended including the Registration Statements. Accordingly, pursuant to the undertakings made by Enterprise in the Registration Statements to remove from registration, by means of a post-effective amendment, any of the securities that remain unsold at the termination of the offerings, Independent, as the successor to the Company, hereby removes from registration any and all securities registered but unsold under each of the Registration Statements as of the date hereof. Each of the Registration Statements is hereby amended, as appropriate, to reflect the deregistration of such securities.

SIGNATURE

Pursuant to the requirements of the Securities Act of 1933, as amended, and Rule 478 thereunder, the Company certifies that it has reasonable grounds to believe that it meets all of the requirements for filing on Form S-8 and has duly caused this Post-Effective Amendment No. 1 to the above-referenced Registration Statements to be signed on its behalf by the undersigned, thereunto duly authorized, in the City of Rockland, Commonwealth of Massachusetts, on this 1st day of July, 2025.

			INDEPENDENT BANK CORP., as successor by merger to Enterprise Bancorp, Inc.
			By:			/s/ Patricia M. Natale
						Name: Patricia M. Natale
						Title:   Executive Vice President and General Counsel

*    Pursuant to Rule 478 under Securities Act of 1933, as amended, no other person is required to sign this Post-Effective Amendment No. 1 to the Registration Statement.

FAQ

What is the coupon rate on Citigroup's 2026 contingent coupon securities (C)?

The notes pay a contingent coupon of 0.85% per month, equivalent to 10.20% annualized, only when the worst performing index is ≥ its 70% barrier.

How much principal protection do the Citigroup 424B2 notes offer?

Principal is protected only if the worst performing index is above its 70% final barrier on 28 Dec 2026; otherwise repayment falls in line with the negative index return, down to $0.

Can Citigroup redeem the securities early?

Yes. Citi may call the notes on 12 monthly dates from Dec-2025 to Nov-2026, paying $1,000 plus any due coupon, ending further coupon accrual.

What is the estimated value versus the $1,000 issue price?

Citigroup Global Markets Inc. estimates the fair value at $990.70 per note, about 0.93% below the issue price due to distribution and hedging costs.

Are the securities listed on an exchange?

No. The notes will not be listed; liquidity depends on Citigroup Global Markets Inc. making a discretionary secondary market.

Which indices determine payments on these Citigroup notes?

Payments hinge on the Nasdaq-100®, Russell 2000® and S&P 500®, with performance measured on a worst-of basis each valuation date.