[144] Clover Health Investments, Corp SEC Filing

Rhea-AI Filing Summary

Form 144 filed for Datadog, Inc. (DDOG) discloses a planned sale of insider shares under Rule 144.

• Seller & volume: David Obstler intends to sell 15,000 Class A common shares, representing roughly 0.005 % of the 319,498,060 shares outstanding.
• Estimated proceeds: At an aggregate market value of $2.03 million, the transaction is scheduled for 07 July 2025 through broker Morgan Stanley Smith Barney LLC on the NASDAQ.
• Acquisition details: The shares derive from a 07 July 2025 stock-option exercise paid in cash.
• 10b5-1 activity: The filing lists six prior sales in the last three months under a 10b5-1 plan, totaling 105,016 shares and approximately $12.6 million in gross proceeds.

The filing contains the standard certification that the seller possesses no undisclosed material adverse information. There is no indication of new corporate developments, earnings data, or changes to capital structure; the document strictly concerns insider share dispositions.

Positive

• None.

Negative

• Continued insider selling—over 105 k shares sold in the last three months plus 15 k now planned—can be interpreted as weak insider confidence, albeit small relative to float.

Insights

Financial Analyst

TL;DR – Routine insider sale; small versus float, modest negative sentiment.

This Form 144 signals continued insider selling by David Obstler, who has already liquidated over 105 k shares in the prior quarter. The new 15 k-share notice is immaterial relative to the 319 M float, but cumulative sales near $14 M may raise eyebrows among momentum or governance-sensitive investors. The use of a 10b5-1 plan tempers concerns by framing transactions as pre-scheduled, and market impact should be negligible. Overall, the filing is not fundamentally impactful yet contributes to a slightly negative narrative on insider sentiment.

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	19789	51253.51	416541578	07/03/2025	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	06/30/2025	Performance Stock Units	Issuer			19789	06/30/2025	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 JAMIE REYNOSO 30 MONTGOMERY STREET JERSEY CITY NJ 07302	Common	06/17/2025	20450	58525.86

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

How many Datadog (DDOG) shares are being sold under this Form 144?

15,000 Class A common shares are slated for sale.

What is the estimated value of the planned DDOG share sale?

The aggregate market value is $2,025,150 based on the filing.

When is the approximate sale date for the DDOG insider transaction?

The shares are expected to be sold on or about 07/03/2025.

How many Datadog shares has the insider sold in the past three months?

The filing lists 105,016 shares previously sold between 02 June 2025 and 30 June 2025.

What percentage of Datadog’s outstanding shares does the new sale represent?

Roughly 0.005 % of the 319,498,060 shares outstanding.

Which broker will handle the DDOG insider sale?

Morgan Stanley Smith Barney LLC, Executive Financial Services, New York, NY.