DDOG insider ownership: who sold, why, and what they still hold

Who	Shares	Price	% of total stake	Total stake after	Trade date	Filed
Alexis Le-Quoc Chief Technology Officer, Director	43,224	$252.17	n/a	n/a	Sep 23, 2026	Sep 25, 2026

Who	Shares	Price	% of total stake	Total stake after	Trade date	Filed
David Obstler Chief Financial Officer	16,000	$241.25	n/a	n/a	Sep 21, 2026	Sep 23, 2026

Who	Shares	Price	% of total stake	Total stake after	Trade date	Filed
David Obstler Chief Financial Officer	64,000	$227.47 avg	n/a	n/a	Sep 14, 2026	Sep 16, 2026 +1 more
Kerry Acocella General Counsel and Secretary	5,280	$228.85	3.1%	165K	Sep 14, 2026	Sep 16, 2026

Who	Shares	Price	% of total stake	Total stake after	Trade date	Filed
Yanbing Li Chief Product Officer	12,700	$221.26	4.8%	250K	Sep 11, 2026	Sep 15, 2026
Sean Walters Chief Revenue Officer	11,710	$221.04	2.9%	389K	Sep 11, 2026	Sep 15, 2026

What stands out

Seven insiders sold more than 25% of vested holdings: Michael Callahan (55% of holdings, $39.8M, all under a disclosed plan), Sean Walters (39% of holdings, $23.0M, 49% under a disclosed plan) and Adam Blitzer (38% of holdings, $22.0M, 87% under a disclosed plan), plus 4 more.Michael Callahan: largest sale, Jun 12, 2026 · Sean Walters: largest sale, Jun 2, 2026 · Adam Blitzer: largest sale, Mar 2, 2026

Two directors sold $69.3M with no disclosed plan: Matthew Jacobson ($35.0M) and Dev Ittycheria ($34.3M). The filings don't state a reason.Matthew Jacobson: largest such sale, Aug 13, 2026 · Dev Ittycheria: largest such sale, Jun 3, 2026

Shareholders represented on the board by Matthew Jacobson, not part of management, sold $87.1M of stock.Largest sale, Nov 10, 2025

Percentages cover 9 of 17 officers and directors. 8 are left out

Left out: Alexis Le-Quoc, David Obstler and Ami Vora (holdings couldn't be fully reconciled); Amit Agarwal (most holdings were last confirmed in 2022); Matthew Jacobson (most holdings were last confirmed in 2019); Dev Ittycheria (most holdings were last confirmed in 2020); Julie Richardson (most of their shares vested during the period, so a percentage would mislead); Dominic Phillips (held no vested shares at the start).

Disclosed company stock is not an insider's whole wealth.

Who sold, and how much of their stake

Officers and directors, past 12 months. Each bar is the insider's vested stake at the start of the period (Oct 8, 2025). The gold part is what they sold.

SoldRest of starting stakeAdded during the period

Olivier Pomel

Chief Executive Officer, Director

15% · $284M93% planned

Alexis Le-Quoc

Chief Technology Officer, Director

No bar: holdings couldn't be fully reconciled.

$209M94% planned

Amit Agarwal

Director

No bar: most holdings were last confirmed in 2022.

$76.1MDisclosed plan

David Obstler

Chief Financial Officer

No bar: holdings couldn't be fully reconciled.

$50.1M71% planned

Michael Callahan

Director

55% · $39.8MDisclosed plan

All 15 sellers

Selling by month

Officers and directors, Oct 2025 to Oct 2026. Each sale is counted once: under a disclosed plan, else to cover taxes, else no plan disclosed.

Disclosed planTo cover taxesNo plan disclosed

Outside holders, reported separately

Matthew Jacobson (for the outside shareholder represented on the board) sold $87.1M in the past 12 months. Large shareholders and the funds or companies that board members represent are not part of management, so they are left out of the figures above.

Details

Common questions

Is the Datadog, Inc. CEO selling stock?

Yes. Olivier Pomel sold 1.37M shares ($284M, 15% of starting holdings) in the past 12 months, 93% of it under a trading plan disclosed in the filings.

Why are Datadog, Inc. insiders selling?

Filings rarely give a reason, and we don't guess at one. What they show is how the sales were made: 81% of sales by value ran under 10b5-1 trading plans disclosed in the filings, 10% were to cover taxes and 9% had no disclosed plan. A trading plan schedules sales in advance.

Are any Datadog, Inc. insiders buying?

No. Officers and directors reported no purchases in the past 12 months.

How much of their stake did Datadog, Inc. insiders sell?

About 19% overall. As a group they ended with more shares than they started with. These figures leave out Matthew Jacobson, the largest holder (most holdings were last confirmed in 2019). That covers the 12 months to Oct 8, 2026 and counts vested shares reported on SEC Forms 3, 4 and 5, which is not an insider's whole wealth.

The evidence

Who sold15 officers and directors: amount, % of holdings, trading plan

Who sold	Amount	% of holdings	Trading plan
Olivier Pomel Chief Executive Officer, Director	$284M 1.37M shares	15%	93% under a disclosed plan
Alexis Le-Quoc Chief Technology Officer, Director	$209M 1.14M shares	i No percentage: holdings couldn't be fully reconciled.	94% under a disclosed plan
Amit Agarwal Director	$76.1M 400K shares	i No percentage: most holdings were last confirmed in 2022.	Disclosed plan
David Obstler Chief Financial Officer	$50.1M 240K shares	i No percentage: holdings couldn't be fully reconciled.	71% under a disclosed plan
Michael Callahan Director	$39.8M 171K shares	55%	Disclosed plan
Matthew Jacobson Director	$35.0M 151K shares	i No percentage: most holdings were last confirmed in 2019.	No plan disclosed
Dev Ittycheria Director	$34.3M 138K shares	i No percentage: most holdings were last confirmed in 2020.	No plan disclosed
Sean Walters Chief Revenue Officer	$23.0M 135K shares	39%	49% under a disclosed plan
Adam Blitzer Chief Operating Officer	$22.0M 134K shares	38%	87% under a disclosed plan
Yanbing Li Chief Product Officer	$15.7M 85K shares	41%	18% under a disclosed plan
Kerry Acocella General Counsel and Secretary	$11.4M 66K shares	46%	45% under a disclosed plan
Shardul Shah Director	$7.9M 55K shares	15%	Disclosed plan
David Galloreese Chief People Officer	$5.0M 28K shares	35%	23% under a disclosed plan
Julie Richardson Director	$3.3M 16K shares	i No percentage: most of their shares vested during the period, so a percentage would mislead.	Disclosed plan
Titilope Cole Director	$1.3M 5.1K shares	81%	No plan disclosed

Board members representing outside shareholders, reported separately: Matthew Jacobson (the shareholder sold $87.1M), Shardul Shah. Details

The full ownership picture14 of 17 insiders fully reconciled · 17 officers and directors

Vested shares across all share classes, held directly and through trusts, LLCs and family members, as reported on SEC Forms 3, 4 and 5. Unvested awards and options are never counted as owned shares.

Insider

Held Oct 8, 2025

Sold

Held Oct 8, 2026

Still held

Alexis Le-Quoc

Holdings couldn't be fully reconciled. A footnote describes a transfer or distribution between related entities, but the amounts could not be matched to the balance change. Largest: +43,224 shares on Dec 8, 2025 (Direct). See the filing Sales and other transactions for Alexis Le-Quoc are complete.

Chief Technology Officer, Director

n/a

−1.14M

n/a

Vesting, gifts, unvested awards and holding lines for Alexis Le-Quoc

0shares vested or exercised

−180Kgifted (net of own trusts)

none reportedunvested awards, start → end

Additional holdings last reported more than 3 years ago are shown separately and excluded from totals.

Holdings couldn't be fully reconciled. A footnote describes a transfer or distribution between related entities, but the amounts could not be matched to the balance change. Largest: +43,224 shares on Dec 8, 2025 (Direct). The balances below are as reported, not verified totals.

Held through	Share class	Oct 8, 2025	Oct 8, 2026
Direct	Class A Common Stock	438,885	488,033
Alexis Le-Quoc Revocable Trust	Class A Common Stock	169	169
Direct	Class B Common Stock	2,688,860	2,160,030
Alexis Le-Quoc Revocable Trust	Class B Common Stock	6,326,835	6,146,835

Additional holdings last reported Mar 2, 2023, not confirmed since: 5,518,492 shares. Not included in any total or percentage on this page.

Alexis Le-Quoc 2016 GRAT, Class A Common Stock: 111,300 shares, last reported Oct 6, 2021
Alexis Le-Quoc 2016 GRAT, Class B Common Stock: 3,505,569 shares, last reported Sep 23, 2019
Pomel Descendents' 2018 Trust, Class B Common Stock: 600,000 shares, last reported Sep 23, 2019
Artemis Le-Quoc 2018 Trust, Class B Common Stock: 550,000 shares, last reported Feb 3, 2020
Agathe Le-Quoc 2018 Trust, Class B Common Stock: 550,000 shares, last reported Feb 3, 2020
Direct, Common A Common Stock: 201,623 shares, last reported Mar 2, 2023

Stock options (not counted as shares):

Options held	Strike price	Expires	Intrinsic value (estimate)
131,250	$10.74	Jul 19, 2029	$32.2M

Estimate: options held × ($256.15 − strike price), using the most recent insider trade price on Form 4 (Sep 23, 2026), not a market close.

Olivier Pomel

Additional holdings last reported more than 3 years ago are shown separately and excluded from totals.

Chief Executive Officer, Director

8.99M

−1.37M

9.32M

+3.7%

Vesting, gifts, unvested awards and holding lines for Olivier Pomel

0shares vested or exercised

−348Kgifted (net of own trusts)

none reportedunvested awards, start → end

Additional holdings last reported more than 3 years ago are shown separately and excluded from totals.

Held through	Share class	Oct 8, 2025	Oct 8, 2026
Direct	Class A Common Stock	533,358	586,416
Direct	Class B Common Stock	8,453,738	8,730,525

Additional holdings last reported Sep 5, 2023, not confirmed since: 2,117,784 shares. Not included in any total or percentage on this page.

Pomel Descendents' 2018 Trust, Class B Common Stock: 600,000 shares, last reported Sep 23, 2019
Agathe Le-Quoc 2018 Trust, Class B Common Stock: 600,000 shares, last reported Sep 23, 2019
Artemis Le-Quoc 2018 Trust, Class B Common Stock: 600,000 shares, last reported Sep 23, 2019
Direct, Common A Common Stock: 317,784 shares, last reported Sep 5, 2023

Stock options (not counted as shares):

Options held	Strike price	Expires	Intrinsic value (estimate)
190,590	$0.91	Oct 25, 2027	$48.6M
631,163	$10.74	Jul 19, 2029	$155M

Estimate: options held × ($256.15 − strike price), using the most recent insider trade price on Form 4 (Sep 23, 2026), not a market close.

Amit Agarwal

Most of this insider's holdings were last confirmed in 2022. Confirmed in the last three years: 1,119,003 shares. Not confirmed since: 4,902,018 shares, left out of this row. "Still held" is not shown because it would cover only the smaller, confirmed part.

Director

1.54M

−400K

1.12M

see note

Vesting, gifts, unvested awards and holding lines for Amit Agarwal

0shares vested or exercised

−20Kgifted (net of own trusts)

none reportedunvested awards, start → end

Additional holdings last reported more than 3 years ago are shown separately and excluded from totals.

Held through	Share class	Oct 8, 2025	Oct 8, 2026
Direct	Class A Common Stock	27,999	29,071
Agarwal 2019 Family Trust	Class A Common Stock	6,541	6,541
Agarwal 2018 Family Trust	Class A Common Stock	1,640	1,640
Agarwal 2019 Family Trust	Class B Common Stock	603,464	593,464
Agarwal 2018 Family Trust	Class B Common Stock	590,059	190,059
Spouse	Class B Common Stock	53,063	42,976
Direct	Common A Common Stock	247,071	247,071
Agarwal 2019 Family Trust	Common A Common Stock	6,541	6,541
Agarwal 2018 Family Trust	Common A Common Stock	1,640	1,640

Additional holdings last reported Aug 5, 2022, not confirmed since: 4,902,018 shares. Not included in any total or percentage on this page.

Amit Agarwal 2019 GRAT, Class A Common Stock: 3,261 shares, last reported May 6, 2022
GRAT, Class B Common Stock: 3,745,491 shares, last reported May 1, 2020
Amit Agarwal 2018 GRAT, Class B Common Stock: 1,148,365 shares, last reported Sep 2, 2021
GRAT, Common A Common Stock: 4,901 shares, last reported Aug 5, 2022

David Obstler

Holdings couldn't be fully reconciled. A footnote describes a transfer or distribution between related entities, but the amounts could not be matched to the balance change. Largest: -46,198 shares on Sep 14, 2026 (Trust). See the filing Sales and other transactions for David Obstler are complete.

Chief Financial Officer

n/a

−240K

n/a

Vesting, gifts, unvested awards and holding lines for David Obstler

0shares vested or exercised

−7.5Kgifted (net of own trusts)

none reportedunvested awards, start → end

Additional holdings last reported more than 3 years ago are shown separately and excluded from totals.

Holdings couldn't be fully reconciled. A footnote describes a transfer or distribution between related entities, but the amounts could not be matched to the balance change. Largest: -46,198 shares on Sep 14, 2026 (Trust). The balances below are as reported, not verified totals.

Held through	Share class	Oct 8, 2025	Oct 8, 2026
Direct	Class A Common Stock	386,651	368,067
Trust	Class A Common Stock	0	0
Direct	Class B Common Stock	15,603	8,103
GRAT	Class B Common Stock	192,397	192,397
Trust	Class B Common Stock	92,397	31,199

Additional holdings last reported Jun 2, 2023, not confirmed since: 275,218 shares. Not included in any total or percentage on this page.

Direct, Common A Common Stock: 275,218 shares, last reported Jun 2, 2023

Matthew Jacobson

Most of this insider's holdings were last confirmed in 2019. Confirmed in the last three years: 524,708 shares. Not confirmed since: 30,145,965 shares, left out of this row. "Still held" is not shown because it would cover only the smaller, confirmed part.

Director

676K

−151K

525K

see note

Vesting, gifts, unvested awards and holding lines for Matthew Jacobson

0shares vested or exercised

0gifted (net of own trusts)

none reportedunvested awards, start → end

Additional holdings last reported more than 3 years ago are shown separately and excluded from totals.
Shares held through ICONIQ II, ICONIQ II Co-Invest, ICONIQ II-B and others belong to an outside shareholder this director represents; they are listed under "Board members representing outside shareholders", not here.

Held through	Share class	Oct 8, 2025	Oct 8, 2026
Direct	Class A Common Stock	675,558	524,708

Additional holdings last reported Sep 18, 2019, not confirmed since: 30,145,965 shares. Not included in any total or percentage on this page.

Direct, Common Stock: 5,163,993 shares, last reported Sep 18, 2019
Direct, Series A Preferred Stock: 119,496 shares, last reported Sep 18, 2019
Direct, Series B Preferred Stock: 127,800 shares, last reported Sep 18, 2019
Direct, Series D Preferred Stock: 23,809,212 shares, last reported Sep 18, 2019
Direct, Series Seed Preferred Stock: 925,464 shares, last reported Sep 18, 2019

Shardul Shah

Shares held through 1,891,229 shares of Class A Common Stock pro-rata to its partners, including its limited partners and its general partner, Index Venture Associates VI Limited, 2,072,501 shares of Class A Common Stock pro-rata to its partners, including its limited partners and its general partner, Index Venture Associates VI Limited, 2,279,173 shares of Class A Common Stock pro-rata to its partners, including its limited partners and its general partner, Index Venture Associates VI Limited and others belong to an outside shareholder this director represents; they are listed under "Board members representing outside shareholders", not here.

Director

374K

−55K

320K

85%

Vesting, gifts, unvested awards and holding lines for Shardul Shah

0shares vested or exercised

0gifted (net of own trusts)

none reportedunvested awards, start → end

Shares held through 1,891,229 shares of Class A Common Stock pro-rata to its partners, including its limited partners and its general partner, Index Venture Associates VI Limited, 2,072,501 shares of Class A Common Stock pro-rata to its partners, including its limited partners and its general partner, Index Venture Associates VI Limited, 2,279,173 shares of Class A Common Stock pro-rata to its partners, including its limited partners and its general partner, Index Venture Associates VI Limited and others belong to an outside shareholder this director represents; they are listed under "Board members representing outside shareholders", not here.

Held through	Share class	Oct 8, 2025	Oct 8, 2026
Direct	Class A Common Stock	2,106	3,178
Trust	Class A Common Stock	372,365	316,953

Adam Blitzer

Chief Operating Officer

356K

−134K

412K

+16%

Vesting, gifts, unvested awards and holding lines for Adam Blitzer

0shares vested or exercised

0gifted (net of own trusts)

none reportedunvested awards, start → end

Held through	Share class	Oct 8, 2025	Oct 8, 2026
Direct	Class A Common Stock	181,728	237,927
Direct	Common A Common Stock	174,237	174,237

Sean Walters

Minor difference of 160 shares. Difference is stated in footnotes (unreported vesting, exempt acquisition or transfer). Includes unvested RSUs, amount not disclosed.

Chief Revenue Officer

348K

−135K

390K

+12%

Vesting, gifts, unvested awards and holding lines for Sean Walters

0shares vested or exercised

0gifted (net of own trusts)

none reportedunvested awards, start → end

Includes unvested RSUs, amount not disclosed.

Held through	Share class	Oct 8, 2025	Oct 8, 2026
Direct includes unvested RSUs, amount not disclosed	Class A Common Stock	191,957	233,135
Son	Class A Common Stock	8	8
Direct	Common A Common Stock	156,445	156,445
son	Common A Common Stock	8	8

Reconciliation: minor difference of 160 shares. Difference is stated in footnotes (unreported vesting, exempt acquisition or transfer).

Michael Callahan

Includes unvested RSUs, amount not disclosed. Additional holdings last reported more than 3 years ago are shown separately and excluded from totals.

Director

308K

−171K

121K

39%

Vesting, gifts, unvested awards and holding lines for Michael Callahan

0shares vested or exercised

−18Kgifted (net of own trusts)

none reportedunvested awards, start → end

Includes unvested RSUs, amount not disclosed.
Additional holdings last reported more than 3 years ago are shown separately and excluded from totals.

Held through	Share class	Oct 8, 2025	Oct 8, 2026
Direct includes unvested RSUs, amount not disclosed	Class A Common Stock	19,612	20,684
Trust	Class A Common Stock	12,496	14,996
Trust	Class B Common Stock	276,375	85,542

Additional holdings last reported Nov 5, 2021, not confirmed since: 20,000 shares. Not included in any total or percentage on this page.

Michael Callahan Grantor Retained Annuity Trust, Class A Common Stock: 20,000 shares, last reported Nov 5, 2021

Yanbing Li

Minor difference of 213 shares. Difference is stated in footnotes (unreported vesting, exempt acquisition or transfer).

Chief Product Officer

206K

−85K

250K

+22%

Vesting, gifts, unvested awards and holding lines for Yanbing Li

0shares vested or exercised

0gifted (net of own trusts)

none reportedunvested awards, start → end

Held through	Share class	Oct 8, 2025	Oct 8, 2026
Direct	Class A Common Stock	206,035	250,446

Reconciliation: minor difference of 213 shares. Difference is stated in footnotes (unreported vesting, exempt acquisition or transfer).

Kerry Acocella

Includes unvested RSUs, amount not disclosed.

General Counsel and Secretary

143K

−66K

165K

+15%

Vesting, gifts, unvested awards and holding lines for Kerry Acocella

0shares vested or exercised

−2.6Kgifted (net of own trusts)

none reportedunvested awards, start → end

Includes unvested RSUs, amount not disclosed.

Held through	Share class	Oct 8, 2025	Oct 8, 2026
Direct includes unvested RSUs, amount not disclosed	Class A Common Stock	93,419	115,243
Direct	Common A Common Stock	49,533	49,533

Dev Ittycheria

Most of this insider's holdings were last confirmed in 2020. Confirmed in the last three years: 113,206 shares. Not confirmed since: 1,130,889 shares, left out of this row. "Still held" is not shown because it would cover only the smaller, confirmed part.

Director

130K

−138K

113K

see note

Vesting, gifts, unvested awards and holding lines for Dev Ittycheria

0shares vested or exercised

0gifted (net of own trusts)

none reportedunvested awards, start → end

An owner entity could not be identified from the footnotes.
Additional holdings last reported more than 3 years ago are shown separately and excluded from totals.

Held through	Share class	Oct 8, 2025	Oct 8, 2026
Direct	Class A Common Stock	39,235	40,307
LLC	Class A Common Stock	90,899	72,899
Direct	Class B Common Stock	0	0

Additional holdings last reported May 14, 2020, not confirmed since: 1,130,889 shares. Not included in any total or percentage on this page.

Ittycheria Family Trust, Class A Common Stock: 1,130,889 shares, last reported May 14, 2020

Stock options (not counted as shares):

Options held	Strike price	Expires	Intrinsic value (estimate)
120,000	$3.07	Dec 29, 2028	$30.4M

Estimate: options held × ($256.15 − strike price), using the most recent insider trade price on Form 4 (Sep 23, 2026), not a market close.

David Galloreese

Minor difference of 98 shares. Difference is stated in footnotes (unreported vesting, exempt acquisition or transfer).

Chief People Officer

80K

−28K

116K

+46%

Vesting, gifts, unvested awards and holding lines for David Galloreese

0shares vested or exercised

0gifted (net of own trusts)

none reportedunvested awards, start → end

Held through	Share class	Oct 8, 2025	Oct 8, 2026
Direct	Class A Common Stock	79,911	116,431

Reconciliation: minor difference of 98 shares. Difference is stated in footnotes (unreported vesting, exempt acquisition or transfer).

Titilope Cole

Director

6.3K

−5.1K

2.3K

36%

Vesting, gifts, unvested awards and holding lines for Titilope Cole

0shares vested or exercised

0gifted (net of own trusts)

none reportedunvested awards, start → end

Held through	Share class	Oct 8, 2025	Oct 8, 2026
Direct	Class A Common Stock	6,347	2,288

Julie Richardson

Minor difference of 2,301 shares. Difference is stated in footnotes (unreported vesting, exempt acquisition or transfer).

Director

4.7K

−16K

3.2K

not meaningful

Vesting, gifts, unvested awards and holding lines for Julie Richardson

0shares vested or exercised

0gifted (net of own trusts)

none reportedunvested awards, start → end

Held through	Share class	Oct 8, 2025	Oct 8, 2026
Direct	Class A Common Stock	4,670	3,178
Direct	Class B Common Stock	0	0

Stock options (not counted as shares):

Options held	Strike price	Expires	Intrinsic value (estimate)
16,878	$7.96	Jun 12, 2029	$4.2M

Estimate: options held × ($256.15 − strike price), using the most recent insider trade price on Form 4 (Sep 23, 2026), not a market close.

Reconciliation: minor difference of 2,301 shares. Difference is stated in footnotes (unreported vesting, exempt acquisition or transfer).

Ami Vora

Holdings couldn't be fully reconciled. Balance changed without a matching transaction, and the footnote does not state the amount: +9,325 shares on Jun 15, 2026 (Trust). See the filing Sales and other transactions for Ami Vora are complete.

Director

n/a

Vesting, gifts, unvested awards and holding lines for Ami Vora

0shares vested or exercised

0gifted (net of own trusts)

none reportedunvested awards, start → end

Holdings couldn't be fully reconciled. Balance changed without a matching transaction, and the footnote does not state the amount: +9,325 shares on Jun 15, 2026 (Trust). The balances below are as reported, not verified totals.

Held through	Share class	Oct 8, 2025	Oct 8, 2026
Direct	Class A Common Stock	4,311	5,383
Trust	Class A Common Stock	0	9,325

Dominic Phillips

Started reporting during the period; starting holdings are from the Form 3.

Director

6.4K

no sales

Vesting, gifts, unvested awards and holding lines for Dominic Phillips

0shares vested or exercised

0gifted (net of own trusts)

none reportedunvested awards, start → end

Started reporting during the period; starting holdings are from the Form 3.

Held through	Share class	Oct 8, 2025	Oct 8, 2026
Direct	Class A Common Stock	0	6,368

14 of 17 insiders fully reconciled: starting holdings plus reported transactions match ending holdings (10 exactly, 4 with a minor or footnoted difference). For 3 we show sales but not holdings; the ! icon on their rows explains why. Percentages cover 9 of 17 officers and directors. Left out: Alexis Le-Quoc, David Obstler and Ami Vora (holdings couldn't be fully reconciled); Amit Agarwal (most holdings were last confirmed in 2022); Matthew Jacobson (most holdings were last confirmed in 2019); Dev Ittycheria (most holdings were last confirmed in 2020); Julie Richardson (most of their shares vested during the period, so a percentage would mislead); Dominic Phillips (held no vested shares at the start). "Still held" compares ending with starting vested shares; a plus sign means the holding grew.

What explains the selling$818M of sales by plan status, purpose, seller and month

Officer and director open-market sales: $818M across 4,124,828 shares. Plan status and stated purpose are separate questions, and a sale can have both.

By plan status

Disclosed plan · $662M · 81%

19%

The lighter segment is sales with no plan disclosed in the filing ($155M), including tax-related sales outside a plan.

No plan disclosed · $74.5M

Sales with no 10b5-1 plan and no tax reference in the filing. $35.0M of it is Matthew Jacobson. No plan disclosed is a statement about the filing, not about why the sale happened. Largest such sale: Dev Ittycheria, Jun 3, 2026

Taxes

$97.7M of sales (12.0%) cite tax obligations in their footnotes, $16.8M of them also under a plan. Example: David Galloreese, Sep 2, 2026

Charitable gifts · 558K shares

Gifts the filings describe as charitable. Gifts are not sales and are not included in the sale totals.

Seller	Shares sold	Proceeds	Under a disclosed plan	Share of total	Sales dates
Olivier Pomel Chief Executive Officer, Director	1.37M	$284M	93%	35%	Oct 9, 2025 to Sep 8, 2026
Alexis Le-Quoc Chief Technology Officer, Director	1.14M	$209M	94%	26%	Nov 11, 2025 to Sep 23, 2026
Amit Agarwal Director	400K	$76.1M	100%	9%	Mar 9, 2026 to Aug 13, 2026
David Obstler Chief Financial Officer	240K	$50.1M	71%	6%	Dec 2, 2025 to Sep 21, 2026
Michael Callahan Director	171K	$39.8M	100%	5%	Oct 14, 2025 to Aug 4, 2026
Matthew Jacobson Director	151K	$35.0M	0%	4%	May 8, 2026 to Aug 14, 2026
Dev Ittycheria Director	138K	$34.3M	0%	4%	Jun 3, 2026 to Jun 3, 2026
Sean Walters Chief Revenue Officer	135K	$23.0M	49%	3%	Dec 2, 2025 to Sep 11, 2026
Adam Blitzer Chief Operating Officer	134K	$22.0M	87%	3%	Dec 2, 2025 to Sep 3, 2026
Yanbing Li Chief Product Officer	85K	$15.7M	18%	2%	Dec 2, 2025 to Sep 11, 2026
Kerry Acocella General Counsel and Secretary	66K	$11.4M	45%	1%	Dec 2, 2025 to Sep 14, 2026
Shardul Shah Director	55K	$7.9M	100%	1.0%	Oct 13, 2025 to Apr 15, 2026
David Galloreese Chief People Officer	28K	$5.0M	23%	0.6%	Dec 2, 2025 to Sep 2, 2026
Julie Richardson Director	16K	$3.3M	100%	0.4%	May 5, 2026 to Sep 4, 2026
Titilope Cole Director	5.1K	$1.3M	0%	0.2%	Jun 4, 2026 to Jun 4, 2026

Sales by month

Month	Sale proceeds	Disclosed plan	To cover taxes	No plan disclosed
Oct 2025	$14.9M	$14.9M	$0	$0
Nov 2025	$49.9M	$49.9M	$0	$0
Dec 2025	$44.1M	$36.0M	$8.1M	$0
Jan 2026	$11.3M	$11.3M	$0	$0
Feb 2026	$8.7M	$8.7M	$0	$0
Mar 2026	$62.1M	$34.9M	$27.2M	$0
Apr 2026	$27.5M	$27.5M	$0	$0
May 2026	$91.7M	$72.8M	$0	$18.9M
Jun 2026	$212M	$151M	$21.0M	$40.6M
Jul 2026	$99.2M	$99.2M	$0	$0
Aug 2026	$99.4M	$84.4M	$0	$15.0M
Sep 2026	$96.6M	$72.0M	$24.6M	$0
Oct 2026	$0	$0	$0	$0

Board members representing outside shareholders (2)Listed and sourced; not part of the management totals or the answer line

Directors whose reported holdings sit mostly in an investment fund or a corporate shareholder they represent, not in their own name, with beneficial ownership disclaimed except for their own financial interest. Listed and sourced here; not part of the management totals or the answer line. Shares a fund hands to its own investors are distributions, not sales.

Board member

Held Oct 8, 2025

Sold

Held Oct 8, 2026

Still held

Matthew Jacobson

Most of this insider's holdings were last confirmed in 2021. Confirmed in the last three years: 1,067,330 shares. Not confirmed since: 76,422,535 shares, left out of this row. "Still held" is not shown because it would cover only the smaller, confirmed part.

Director

1.50M

−436K

1.07M

see note

Vesting, gifts, unvested awards and holding lines for Matthew Jacobson

0shares vested or exercised

0gifted (net of own trusts)

none reportedunvested awards, start → end

Additional holdings last reported more than 3 years ago are shown separately and excluded from totals.

Held through	Share class	Oct 8, 2025	Oct 8, 2026
ICONIQ Strategic Partners IV-B, L.P	Class A Common Stock	1,067,330	1,067,330
ICONIQ Strategic Partners VI-B, L.P	Class A Common Stock	259,805	0
ICONIQ Strategic Partners VI, L.P	Class A Common Stock	176,311	0

Additional holdings last reported Sep 14, 2021, not confirmed since: 76,422,535 shares. Not included in any total or percentage on this page.

On May 13, 2020, ICONIQ Strategic Partners II, LP, Class A Common Stock: 2,564,608 shares, last reported Apr 21, 2020
On August 20, 2020, ICONIQ Strategic Partners II, LP, Class A Common Stock: 1,865,746 shares, last reported May 13, 2020
On February 18, 2020, ICONIQ Strategic Partners II, LP, Class A Common Stock: 1,431,099 shares, last reported Dec 10, 2019
On August 6, 2021, ICONIQ Strategic Partners II, LP, Class A Common Stock: 1,397,725 shares, last reported Dec 8, 2020
On December 4, 2020, ICONIQ Strategic Partners II, LP, Class A Common Stock: 1,166,884 shares, last reported Aug 20, 2020
ICONIQ IV-B, Class A Common Stock: 945,977 shares, last reported Sep 14, 2021
On May 13, 2020, ICONIQ Strategic Partners II Co-Invest, L.P., DD Series, Class A Common Stock: 927,826 shares, last reported Apr 21, 2020
On April 21, 2020, ICONIQ Strategic Partners II, LP, Class A Common Stock: 732,237 shares, last reported Feb 18, 2020
On September 14, 2021, ICONIQ Strategic Partners II Co-Invest, L.P., DD Series, Class A Common Stock: 719,867 shares, last reported Sep 14, 2021
On August 20, 2020, ICONIQ Strategic Partners II Co-Invest, L.P., DD Series, Class A Common Stock: 673,755 shares, last reported May 13, 2020
On September 14, 2021, ICONIQ Strategic Partners IV, L.P, Class A Common Stock: 573,984 shares, last reported Sep 14, 2021
On February 18, 2020, ICONIQ Strategic Partners II Co-Invest, L.P., DD Series, Class A Common Stock: 515,739 shares, last reported Dec 10, 2019
On August 6, 2021, ICONIQ Strategic Partners II Co-Invest, L.P., DD Series, Class A Common Stock: 508,142 shares, last reported Dec 8, 2020
ICONIQ Strategic Partners III-B, LP, Class A Common Stock: 436,857 shares, last reported Sep 14, 2021
On December 4, 2020, ICONIQ Strategic Partners II Co-Invest, L.P., DD Series, Class A Common Stock: 419,684 shares, last reported Aug 20, 2020
ICONIQ Strategic Partners III, LP, Class A Common Stock: 408,849 shares, last reported Sep 14, 2021
On April 21, 2020, ICONIQ Strategic Partners II Co-Invest, L.P., DD Series, Class A Common Stock: 261,668 shares, last reported Feb 18, 2020
ICONIQ II, Class A Common Stock: 118,591 shares, last reported Dec 4, 2020
On September 14, 2021, ICONIQ Strategic Partners II, L.P, Class A Common Stock: 116,478 shares, last reported Aug 6, 2021
ICONIQ II Co-Invest, Class A Common Stock: 40,016 shares, last reported Dec 4, 2020
On December 10, 2019, ICONIQ Strategic Partners II, LP, Class B Common Stock: 11,333,424 shares, last reported Sep 23, 2019
On February 18, 2020, ICONIQ Strategic Partners II, LP, Class B Common Stock: 9,902,325 shares, last reported Dec 10, 2019
ICONIQ II-B, Class B Common Stock: 8,871,768 shares, last reported Sep 23, 2019
On May 13, 2020, ICONIQ Strategic Partners II, LP, Class B Common Stock: 8,069,954 shares, last reported Apr 21, 2020
On August 6, 2021, ICONIQ Strategic Partners II, LP, Class B Common Stock: 6,790,820 shares, last reported Dec 8, 2020
On February 18, 2020, ICONIQ Strategic Partners II Co-Invest, L.P., DD Series, Class B Common Stock: 3,604,521 shares, last reported Dec 10, 2019
On May 13, 2020, ICONIQ Strategic Partners II Co-Invest, L.P., DD Series, Class B Common Stock: 2,938,363 shares, last reported Apr 21, 2020
On August 6, 2021, ICONIQ Strategic Partners II Co-Invest, L.P., DD Series, Class B Common Stock: 2,468,799 shares, last reported Dec 8, 2020
ICONIQ IV-B, Class B Common Stock: 2,463,904 shares, last reported Sep 14, 2021
On September 14, 2021, ICONIQ Strategic Partners II Co-Invest, L.P., DD Series, Class B Common Stock: 1,791,277 shares, last reported Sep 14, 2021
On September 14, 2021, ICONIQ Strategic Partners IV, L.P, Class B Common Stock: 1,515,942 shares, last reported Sep 14, 2021
ICONIQ Strategic Partners III-B, L.P, Class B Common Stock: 436,857 shares, last reported Sep 23, 2019
ICONIQ Strategic Partners III, L.P, Class B Common Stock: 408,849 shares, last reported Sep 23, 2019

Shardul Shah

Most of this insider's holdings were last confirmed in 2022. Confirmed in the last three years: 0 shares. Not confirmed since: 3,102,067 shares, left out of this row. "Still held" is not shown because it would cover only the smaller, confirmed part.

Director

see note

Vesting, gifts, unvested awards and holding lines for Shardul Shah

0shares vested or exercised

0gifted (net of own trusts)

none reportedunvested awards, start → end

Additional holdings last reported more than 3 years ago are shown separately and excluded from totals.

Additional holdings last reported Jun 15, 2022, not confirmed since: 3,102,067 shares. Not included in any total or percentage on this page.

Index VI, Class A Common Stock: 2,279,177 shares, last reported Jun 15, 2022
Index Growth III, Class A Common Stock: 767,041 shares, last reported Jun 15, 2022
Index VI Parallel, Class A Common Stock: 46,005 shares, last reported Jun 15, 2022
hout consideration, 908,774 shares of Class A Common Stock pro-rata to its limited partners and its general partner, Index Venture Growth Associates III Limited, Class A Common Stock: 2,908 shares, last reported Aug 9, 2021
hout consideration, 767,042 shares of Class A Common Stock pro-rata to its limited partners and its general partner, Index Venture Growth Associates III Limited, Class A Common Stock: 2,666 shares, last reported Feb 14, 2022
hout consideration, 697,487 shares of Class A Common Stock pro-rata to its limited partners and its general partner, Index Venture Growth Associates III Limited, Class A Common Stock: 2,232 shares, last reported Aug 20, 2021
hout consideration, 636,482 shares of Class A Common Stock pro-rata to its limited partners and its general partner, Index Venture Growth Associates III Limited, Class A Common Stock: 2,037 shares, last reported Nov 23, 2021
Index Ventures VI, Class A Common Stock: 1 shares, last reported Nov 19, 2020

Is this normal? Selling year by year5 earlier years to compare with

In line with the past 5 years. 15 insiders sold; the average is 12 a year.

12 months ending	Shares sold	Insiders who sold	Proceeds
Oct 8, 2026 Latest 12 months	4.12M	15	$818M
Oct 8, 2025 1 year earlier	4.48M	13	$586M
Oct 8, 2024 2 years earlier	3.81M	13	$457M
Oct 9, 2023 3 years earlier	3.33M	11	$291M
Oct 9, 2022 4 years earlier	4.13M	13	$674M
Oct 9, 2021 5 years earlier	12.77M	11	$1.34B

Open-market sales (Form 4 code S) by people who were officers or directors, in split-adjusted shares. Earlier years include people who have since left. A sale that an outside holder also reports (a family trust, a fund) is counted with outside holders in every year. Shares, not dollars, are compared, so a change in the stock price doesn't look like a change in selling. Years the filings don't fully cover are shown but left out of the average.

Known gaps and uncertainty3 insiders whose holdings couldn't be fully reconciled

Alexis Le-Quoc: holdings couldn't be fully reconciled (difference of 53,912 shares). A footnote describes a transfer or distribution between related entities, but the amounts could not be matched to the balance change. Largest: +43,224 shares on Dec 8, 2025 (Direct). Filing, Dec 8, 2025

Footnote: "Each share of Class B Common Stock is convertible at any time at the option of the Reporting Person into one share of Class A Common Stock and has no expiration date. Each share of Class B Common Stock will convert automatically into one share of Class A Common Stock upon the earliest of: (i) any transfer, whether or not for value, except for certain "Permitted Transfers" as defined in the Issuer's amended and restated certificate of incorporation, (ii) the death of the Reporting Person in the case of shares held directly or in a trustee capacity, and (iii) the tenth anniversary of the Issuer'"

David Obstler: holdings couldn't be fully reconciled (difference of -31,198 shares). A footnote describes a transfer or distribution between related entities, but the amounts could not be matched to the balance change. Largest: -46,198 shares on Sep 14, 2026 (Trust). Filing, Sep 14, 2026

Footnote: "Each share of Class B Common Stock is convertible at any time at the option of the Reporting Person into one share of Class A Common Stock and has no expiration date. Each share of Class B Common Stock will convert automatically into one share of Class A Common Stock upon the earliest of: (i) any transfer, whether or not for value, except for certain "Permitted Transfers" as defined in the Issuer's amended and restated certificate of incorporation, (ii) the death of the Reporting Person in the case of shares held directly or in a trustee capacity, and (iii) the tenth anniversary of the Issuer'"

Ami Vora: holdings couldn't be fully reconciled (difference of 9,325 shares). Balance changed without a matching transaction, and the footnote does not state the amount: +9,325 shares on Jun 15, 2026 (Trust). Filing, Jun 15, 2026

Footnote: "Reporting Person serves as trustee."

Sean Walters: minor difference of 160 shares. Difference is stated in footnotes (unreported vesting, exempt acquisition or transfer).

Yanbing Li: minor difference of 213 shares. Difference is stated in footnotes (unreported vesting, exempt acquisition or transfer).

David Galloreese: minor difference of 98 shares. Difference is stated in footnotes (unreported vesting, exempt acquisition or transfer).

Julie Richardson: minor difference of 2,301 shares. Difference is stated in footnotes (unreported vesting, exempt acquisition or transfer).

Inferred rename: "Olivier Pomel 2018 GRAT" is treated as the same holder as "GRAT", because the old name was never reported again and the new one opened with the same balance (4,500,000 shares). Old name, new name

Inferred rename: "David Obstler 2019 GRAT" is treated as the same holder as "GRAT", because the old name was never reported again and the new one opened with the same balance (618,750 shares). Old name, new name

Inferred rename: "Index Ventures Growth III" is treated as the same holder as "Index Growth III", because the old name was never reported again and the new one opened with the same balance (13,096,854 shares). Old name, new name

Inferred rename: "ICONIQ Strategic Partners II, LP" is treated as the same holder as "On December 10, 2019, ICONIQ Strategic Partners II, LP", because the old name was never reported again and the new one opened with the same balance (11,333,424 shares). Old name, new name

Inferred rename: "ICONIQ Strategic Partners II-B, LP" is treated as the same holder as "ICONIQ II-B", because the old name was never reported again and the new one opened with the same balance (8,871,768 shares). Old name, new name

Inferred rename: "On December 10, 2019, ICONIQ Strategic Partners II, LP" is treated as the same holder as "On February 18, 2020, ICONIQ Strategic Partners II, LP", because the old name was never reported again and the new one opened with the same balance (1,431,099 shares). Old name, new name

Inferred rename: "On December 10, 2019, ICONIQ Strategic Partners II Co-Invest, L.P., DD Series" is treated as the same holder as "On February 18, 2020, ICONIQ Strategic Partners II Co-Invest, L.P., DD Series", because the old name was never reported again and the new one opened with the same balance (515,739 shares). Old name, new name

Inferred rename: "On February 18, 2020, ICONIQ Strategic Partners II, LP" is treated as the same holder as "On April 21, 2020, ICONIQ Strategic Partners II, LP", because the old name was never reported again and the new one opened with the same balance (732,237 shares). Old name, new name

Inferred rename: "On February 18, 2020, ICONIQ Strategic Partners II Co-Invest, L.P., DD Series" is treated as the same holder as "On April 21, 2020, ICONIQ Strategic Partners II Co-Invest, L.P., DD Series", because the old name was never reported again and the new one opened with the same balance (261,668 shares). Old name, new name

Inferred rename: "On April 21, 2020, ICONIQ Strategic Partners II, LP" is treated as the same holder as "On May 13, 2020, ICONIQ Strategic Partners II, LP", because the old name was never reported again and the new one opened with the same balance (2,564,608 shares). Old name, new name

Inferred rename: "On April 21, 2020, ICONIQ Strategic Partners II Co-Invest, L.P., DD Series" is treated as the same holder as "On May 13, 2020, ICONIQ Strategic Partners II Co-Invest, L.P., DD Series", because the old name was never reported again and the new one opened with the same balance (927,826 shares). Old name, new name

Inferred rename: "On April 21, 2020, ICONIQ Strategic Partners III, LP" is treated as the same holder as "ICONIQ Strategic Partners III, LP", because the old name was never reported again and the new one opened with the same balance (408,849 shares). Old name, new name

Inferred rename: "ICONIQ III-B" is treated as the same holder as "ICONIQ Strategic Partners III-B, LP", because the old name was never reported again and the new one opened with the same balance (436,857 shares). Old name, new name

Inferred rename: "ICONIQ Strategic Partners IV, LP" is treated as the same holder as "ICONIQ Strategic Partners IV, L.P", because the old name was never reported again and the new one opened with the same balance (199,500 shares). Old name, new name

Inferred rename: "ICONIQ Strategic Partners IV-B, LP" is treated as the same holder as "ICONIQ Strategic Partners IV-B, L.P", because the old name was never reported again and the new one opened with the same balance (325,500 shares). Old name, new name

Inferred rename: "On May 13, 2020, ICONIQ Strategic Partners II, LP" is treated as the same holder as "On August 20, 2020, ICONIQ Strategic Partners II, LP", because the old name was never reported again and the new one opened with the same balance (1,865,746 shares). Old name, new name

Inferred rename: "On May 13, 2020, ICONIQ Strategic Partners II Co-Invest, L.P., DD Series" is treated as the same holder as "On August 20, 2020, ICONIQ Strategic Partners II Co-Invest, L.P., DD Series", because the old name was never reported again and the new one opened with the same balance (673,755 shares). Old name, new name

Inferred rename: "On August 20, 2020, ICONIQ Strategic Partners II, LP" is treated as the same holder as "On December 4, 2020, ICONIQ Strategic Partners II, LP", because the old name was never reported again and the new one opened with the same balance (1,166,884 shares). Old name, new name

Inferred rename: "On August 20, 2020, ICONIQ Strategic Partners II Co-Invest, L.P., DD Series" is treated as the same holder as "On December 4, 2020, ICONIQ Strategic Partners II Co-Invest, L.P., DD Series", because the old name was never reported again and the new one opened with the same balance (419,684 shares). Old name, new name

Inferred rename: "On December 4, 2020, ICONIQ Strategic Partners II, LP" is treated as the same holder as "ICONIQ II", because the old name was never reported again and the new one opened with the same balance (118,591 shares). Old name, new name

Inferred rename: "On December 4, 2020, ICONIQ Strategic Partners II Co-Invest, L.P., DD Series" is treated as the same holder as "ICONIQ II Co-Invest", because the old name was never reported again and the new one opened with the same balance (40,016 shares). Old name, new name

Inferred rename: "ICONIQ II" is treated as the same holder as "On August 6, 2021, ICONIQ Strategic Partners II, LP", because the old name was never reported again and the new one opened with the same balance (1,397,725 shares). Old name, new name

Inferred rename: "ICONIQ II Co-Invest" is treated as the same holder as "On August 6, 2021, ICONIQ Strategic Partners II Co-Invest, L.P., DD Series", because the old name was never reported again and the new one opened with the same balance (508,142 shares). Old name, new name

Inferred rename: "On August 6, 2021, ICONIQ Strategic Partners II, LP" is treated as the same holder as "On September 14, 2021, ICONIQ Strategic Partners II, L.P", because the old name was never reported again and the new one opened with the same balance (116,478 shares). Old name, new name

Inferred rename: "On August 6, 2021, ICONIQ Strategic Partners II Co-Invest, L.P., DD Series" is treated as the same holder as "On September 14, 2021, ICONIQ Strategic Partners II Co-Invest, L.P., DD Series", because the old name was never reported again and the new one opened with the same balance (42,345 shares). Old name, new name

Inferred rename: "On September 14, 2021, ICONIQ Strategic Partners II, L.P" is treated as the same holder as "ICONIQ Strategic Partners II, L.P", because the old name was never reported again and the new one opened with the same balance (4,927,187 shares). Old name, new name

Inferred rename: "ICONIQ II-B" is treated as the same holder as "ICONIQ Strategic Partners II-B, L.P", because the old name was never reported again and the new one opened with the same balance (3,856,988 shares). Old name, new name

External context: we only cite outside events when a documented connection exists. None is shown for this period.

Sources and methodology1,030 filings from SEC EDGAR, and how we read them

All 1,030 Forms 3, 4 and 5 filed for Datadog, Inc. (SEC CIK 1561550) from Sep 18, 2019 to Oct 2, 2026, retrieved from SEC EDGAR on Oct 8, 2026. Prices are the ones reported in each filing, often weighted averages.

Holdings. Each holding line (a share class plus an owner, such as a trust or LLC) carries its last reported balance forward. Entities first reported during the period start at zero, so transfers between an insider's own trusts don't count as selling. Lines not reported for three years or more are listed separately and left out of totals.

Sales. A sale counts as under a 10b5-1 plan if its footnote cites one or the filing's Rule 10b5-1 box is checked, and as tax-related if its footnote cites tax obligations or sell-to-cover. Shares withheld by the company for taxes are listed separately. Sales with neither attribute are labeled "no plan disclosed".

Full methodology

Former or inactive filers (7)No filing in 18 months; last reported balances, not in any total

Name	Last filed	Last reported balance
Armelle De Madre	Jul 1, 2024	180,745 shares, last reported balance as of Jun 27, 2024
Laszlo Kopits	Jan 6, 2022	174,456 shares, last reported balance as of Jan 4, 2022
ICONIQ STRATEGIC PARTNERS II, L.P.	Aug 10, 2021	14,836,479 shares, last reported balance as of Aug 6, 2021
Dan Fougere	Jun 4, 2021	327,010 shares, last reported balance as of Jun 2, 2021
Index Ventures VI (Jersey) LP	May 19, 2021	243,542 shares, last reported balance as of May 17, 2021
OpenView Management, LLC	Mar 11, 2020	4,513 shares, last reported balance as of Mar 9, 2020
CONTOUR VENTURE PARTNERS LP	Mar 10, 2020	273,001 shares, last reported balance as of Mar 9, 2020

Datadog, Inc. insiders sold $818M in the past 12 months. How much of their stake is that?

What stands out

Who sold, and how much of their stake

Selling by month

Outside holders, reported separately

Common questions

Is the Datadog, Inc. CEO selling stock?

Why are Datadog, Inc. insiders selling?

Are any Datadog, Inc. insiders buying?

How much of their stake did Datadog, Inc. insiders sell?

The evidence

No plan disclosed · $74.5M

Taxes

Charitable gifts · 558K shares

Sales by month