[144] FIVE9, INC. SEC Filing

Rhea-AI Filing Summary

Bank of Montreal (BMO) is offering US$425,000 of Senior Medium-Term Notes, Series K – “Digital Return Buffer Notes” – maturing 3 August 2026. The notes are linked to the worst performer of three U.S. equity benchmarks: the S&P 500, NASDAQ-100 and Russell 2000 (each a “Reference Asset”).

Key economic terms:

• Digital Return: 10.40% payable at maturity if the closing level of the Least Performing Reference Asset on 29 July 2026 (the Valuation Date) is ≥ 85% of its 27 June 2025 Initial Level (“Digital Barrier”).
• Buffer: first 15% downside is absorbed. If the Least Performing Reference Asset drops >15%, principal is reduced point-for-point beyond the buffer, exposing investors to a maximum loss of 85%.
• No periodic coupons; single payment at maturity.
• Issue price: 100%; agent’s commission 0.375%; estimated initial value: $981.99 per $1,000, reflecting embedded fees and hedging costs.
• Credit exposure: unsecured, unsubordinated obligations of BMO; CUSIP 06376EMN9; not FDIC or CDIC insured; not exchange-listed.

Illustrative payouts: any Final Level ≥ 85% triggers a fixed $1,104 per $1,000 note (10.40% gain). A Final Level of 80% returns $950 (-5%); 60% returns $750 (-25%); 0% returns $150 (-85%). Upside is capped at 10.40% irrespective of index performance.

Risk considerations include potential loss of up to 85% of principal, limited upside versus direct index exposure, secondary-market illiquidity (no listing; dealer market making discretionary), BMO credit risk, tax uncertainty (treated as prepaid derivative contracts), and a price-to-public that exceeds the bank’s modeled value.

The product may appeal to investors with a moderately bullish to sideways view on large-, mega- and small-cap U.S. equities over the next ~13 months who are willing to trade upside beyond 10.40% for a 15% buffer and accept issuer credit and liquidity risk.

Positive

• 10.40% fixed upside if worst-performing index finishes ≥ 85%, providing an above-market yield in a flat or modestly rising environment.
• 15% downside buffer mitigates moderate equity declines, offering partial capital protection compared with direct index exposure.
• Short 13-month tenor limits long-term market and rate uncertainty.

Negative

• Upside capped at 10.40%, materially underperforming equities if indices rally >10.4%.
• Potential loss up to 85% of principal if the worst index falls more than 15%.
• Issuer credit risk: payments depend solely on Bank of Montreal’s ability to pay.
• Liquidity risk: no exchange listing; secondary market, if any, depends on BMOCM’s discretion at likely discounts.
• Initial value below issue price ($981.99 vs $1,000) reflects embedded fees and hedging costs, creating negative carry from day one.

Insights

Structured-Product Analyst

TL;DR Limited-term note offers 10.40% fixed upside with 15% buffer but significant tail-risk and BMO credit exposure.

The design is straightforward: a 13-month digital payoff contingent on the worst of three broad U.S. indices. Statistically, the 85% barrier provides moderate protection, yet historical drawdowns in small-caps (RTY) make breach plausible. Investors forfeit all upside beyond 10.40%, so risk-adjusted appeal depends on one’s view that a <15% decline is more likely than >10.4% appreciation. The 1.88-point markup (price – modeled value) plus 0.375% commission and potential 0.35% referral fee illustrate typical structured-note friction. An estimated breakeven occurs if the worst index ends between 84.999% and 90% of initial, where the buffer or digital feature marginally outperforms passive exposure. Net: product suits yield-seeking allocators comfortable with issuer risk; not compelling for growth-oriented investors.

Portfolio Manager

TL;DR Attractive headline return, but capped upside, liquidity constraints and small-cap drag temper enthusiasm.

From a portfolio construction angle, the note behaves like a credit-linked call spread: long digital on worst-of basket, short equity upside beyond 10.4%, long put struck at 85%. Correlation among SPX/NDX/RTY means RTY dominates risk; historical vol ≈ 22% vs 15% (SPX) makes buffer less reliable. Duration just over a year mitigates rate risk but heightens reinvestment uncertainty. Lack of listing complicates exit; dealer bids likely 2–4 points under theoretical value, especially after the three-month temporary premium expires. I would size conservatively (<2% of total AUM) and treat as a tactical expression if one has high conviction of sideways markets. Impact on BMO’s credit profile is immaterial given size.

Form 144 Filer Information	UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 144 NOTICE OF PROPOSED SALE OF SECURITIES PURSUANT TO RULE 144 UNDER THE SECURITIES ACT OF 1933
FORM 144

144: Filer Information

Filer CIK
Filer CCC
Is this a LIVE or TEST Filing?	LIVE TEST
Submission Contact Information
Name
Phone
E-Mail Address

144: Issuer Information

Name of Issuer

SEC File Number

Address of Issuer

Phone

Name of Person for Whose Account the Securities are To Be Sold

See the definition of "person" in paragraph (a) of Rule 144. Information is to be given not only as to the person for whose account the securities are to be sold but also as to all other persons included in that definition. In addition, information shall be given as to sales by all persons whose sales are required by paragraph (e) of Rule 144 to be aggregated with sales for the account of the person filing this notice.

Relationship to Issuer

144: Securities Information

Title of the Class of Securities To Be Sold	Name and Address of the Broker	Number of Shares or Other Units To Be Sold	Aggregate Market Value	Number of Shares or Other Units Outstanding	Approximate Date of Sale	Name the Securities Exchange
Common	Morgan Stanley Smith Barney LLC Executive Financial Services 1 New York Plaza 8th Floor New York NY 10004	1400	37072.00	76272014	07/01/2025	NASDAQ

Furnish the following information with respect to the acquisition of the securities to be sold and with respect to the payment of all or any part of the purchase price or other consideration therefor:

144: Securities To Be Sold

Title of the Class	Date you Acquired	Nature of Acquisition Transaction	Name of Person from Whom Acquired	Is this a Gift?	Date Donor Acquired	Amount of Securities Acquired	Date of Payment	Nature of Payment *
Common	06/03/2023	Restricted Stock Units	Issuer			1400	06/03/2023	N/A

* If the securities were purchased and full payment therefor was not made in cash at the time of purchase, explain in the table or in a note thereto the nature of the consideration given. If the consideration consisted of any note or other obligation, or if payment was made in installments describe the arrangement and state when the note or other obligation was discharged in full or the last installment paid.

Furnish the following information as to all securities of the issuer sold during the past 3 months by the person for whose account the securities are to be sold.

144: Securities Sold During The Past 3 Months

Name and Address of Seller	Title of Securities Sold	Date of Sale	Amount of Securities Sold	Gross Proceeds
10b5-1 Sales for ANDREW DIGNAN & JODI DIGNAN JT TEN 3001 Bishop Drive, Suite 350 San Ramon CA 94583	Common	06/05/2025	700	20461.00
10b5-1 Sales for ANDREW DIGNAN & JODI DIGNAN JT TEN 3001 Bishop Drive, Suite 350 San Ramon CA 94583	Common	06/04/2025	2667	74943.91
ANDREW DIGNAN 3001 Bishop Drive, Suite 350 San Ramon CA 94583	Common	06/04/2025	2178	61593.84
10b5-1 Sales for ANDREW DIGNAN & JODI DIGNAN JT TEN 3001 Bishop Drive, Suite 350 San Ramon CA 94583	Common	05/01/2025	700	17864.35

144: Remarks and Signature

Remarks

Date of Notice

Date of Plan Adoption or Giving of Instruction, If Relying on Rule 10b5-1

ATTENTION:

The person for whose account the securities to which this notice relates are to be sold hereby represents by signing this notice that he does not know any material adverse information in regard to the current and prospective operations of the Issuer of the securities to be sold which has not been publicly disclosed. If such person has adopted a written trading plan or given trading instructions to satisfy Rule 10b5-1 under the Exchange Act, by signing the form and indicating the date that the plan was adopted or the instruction given, that person makes such representation as of the plan adoption or instruction date.

Signature

ATTENTION: Intentional misstatements or omission of facts constitute Federal Criminal Violations (See 18 U.S.C. 1001)

FAQ

What return do the BMO Digital Return Buffer Notes provide at maturity?

Investors receive $1,104 per $1,000 note (a 10.40% gain) if the worst of the S&P 500, NASDAQ-100 or Russell 2000 ends at or above 85% of its initial level.

How much principal protection do the notes offer?

The notes include a 15% buffer; losses begin only if the worst index is more than 15% below its initial level, after which loss is 1-for-1 down to an 85% maximum loss.

When do the notes mature and what are the key dates?

Pricing Date: 27 Jun 2025; Settlement Date: 2 Jul 2025; Valuation Date: 29 Jul 2026; Maturity Date: 3 Aug 2026.

Are the notes listed or tradable on an exchange?

No. The notes will not be listed; any resale depends on dealer quotes from BMOCM, which may be limited and at a discount.

What is the estimated initial value versus the issue price?

BMO estimates the initial value at $981.99 per $1,000 note, below the $1,000 price, reflecting commissions and hedging costs.

What are the U.S. federal tax considerations?

BMO intends to treat the notes as pre-paid derivative contracts; however, the IRS could assert a different treatment. Investors should consult tax advisors.