[144] FIVE9, INC. SEC Filing

Rhea-AI Filing Summary

Five9, Inc. (FIVN) Form 144 disclosure: An insider intends to sell 17,899 common shares through Morgan Stanley Smith Barney LLC on or about 09/04/2025, with an aggregate market value of $471,459.66. The shares were acquired as RSUs on 09/03/2025 and paid for on that date.

The filing also lists prior sales by the same person, Michael Burkland, of 5,475 shares on 06/04/2025 (gross proceeds $154,833) and 12,594 shares on 06/03/2025 (gross proceeds $342,194.28). Total outstanding shares reported: 77,262,690. The filer certifies no undisclosed material adverse information.

Positive

• Timely disclosure of proposed sale and full transaction details through Form 144, supporting transparency
• Use of major broker (Morgan Stanley Smith Barney LLC) for the transaction indicates standard execution channels

Negative

• Insider sold shares recently (June sales totaling 18,069 shares), which some investors may interpret as ongoing insider monetization

Insights

Securities Analyst

TL;DR: Routine insider sale of recently vested RSUs; size is small relative to outstanding shares and unlikely to be materially market-moving.

The filing shows a proposed sale of 17,899 shares valued at $471,459.66 executed through a major broker. The shares were RSUs acquired and settled the day before the proposed sale date, suggesting this is a liquidity event following vesting rather than a company-specific concern. Prior sales by the same insider in June total 18,069 shares for roughly $496,~k in proceeds, indicating ongoing monetization. Given the issuer's reported outstanding share count of 77.26 million, the proposed sale represents about 0.023% of shares outstanding, which is immaterial from a capitalization standpoint.

Corporate Governance Expert

TL;DR: Disclosure complies with Rule 144 mechanics; signer affirms no undisclosed material information, consistent with governance norms.

The Form 144 provides required broker, quantity, acquisition and payment details and includes the insider's attestation regarding material information. The use of an established broker and explicit dates for acquisition and payment align with standard compliance practices. Repeated sales by the same insider are disclosed, which is important for governance transparency, but the filing contains no statements indicating any change in company operations or governance events.

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	17899	471459.66	77262690	09/04/2025	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	09/03/2025	RSU	Issuer			17899	09/03/2025	Not Applicable

* 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
Michael Burkland 3001 Bishop Drive Suite 350 San Ramon CA 94583	Common	06/04/2025	5475	154833
Michael Burkland 3001 Bishop Drive Suite 350 San Ramon CA 94583	Common	06/03/2025	12594	342194.28

144: Remarks and Signature

Remarks

Date of Notice

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 transaction does the FIVN Form 144 report?

The filing reports a proposed sale of 17,899 common shares through Morgan Stanley Smith Barney LLC with an aggregate market value of $471,459.66, approximate sale date 09/04/2025.

Who is the seller named in the filing?

The seller is listed as Michael Burkland, with prior sales on 06/03/2025 (12,594 shares, $342,194.28) and 06/04/2025 (5,475 shares, $154,833).

How were the shares being sold acquired?

The 17,899 shares were acquired as RSUs on 09/03/2025 and paid for on that same date.

What proportion of outstanding shares does this proposed sale represent for FIVN?

Based on the filing's outstanding share count of 77,262,690, the proposed 17,899-share sale represents approximately 0.023% of outstanding shares.

Does the filing indicate any undisclosed material information about Five9?

The signer attests they do not know any material adverse information about the issuer that has not been publicly disclosed.