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TWLOTwilio · Insider ownership research

Twilio insiders sold $620M in the past 12 months. How much of their stake is that?

About 89% overall. As a group they still hold 16% of their starting shares.

Updated Oct 8, 2026 from SEC filings · covers Oct 9, 2025 to Oct 8, 2026
How this comparesMore of their stake sold than at 311 of the 311 other companies we can measure (#1 of 312)See ranking
0
buyers among officers and directors, past 12 months
5.6%
of sales were under disclosed trading plans, past 12 months
4 of 11
officers and directors sold shares, past 12 months
Recent activity · past 30 days, Sep 9, 2026 to Oct 8, 2026
Oct 5, 2026Khozema Shipchandler sold 14K shares ($4.2M) under a disclosed trading plan. That is 7.5% of the total stake held that day.
WhoSharesPrice% of total stakeTotal stake afterTrade dateFiled
Khozema Shipchandler
Chief Executive Officer, Director
14,442$291.037.5%179KOct 5, 2026Oct 7, 2026

"% of total stake" is the shares in this event against all the vested shares the person held that day, across every share class and holding entity, after that day's vesting. "n/a" means the person's holdings don't reconcile, or the row is a purchase. "Holdings record incomplete" means more shares were sold than the filings show the person held that day, so a percentage would be wrong.

Sep 30, 20262 executives sold 23K shares ($6.8M) to cover taxes on vesting stock. That is between 6.7% and 8.4% of each person's total stake held that day.
WhoSharesPrice% of total stakeTotal stake afterTrade dateFiled
Khozema Shipchandler
Chief Executive Officer, Director
13,898$294.086.7%193KSep 30, 2026Oct 2, 2026
Aidan Viggiano
Chief Financial Officer
9,084$294.658.4%99KSep 30, 2026Oct 2, 2026

"% of total stake" is the shares in this event against all the vested shares the person held that day, across every share class and holding entity, after that day's vesting. "n/a" means the person's holdings don't reconcile, or the row is a purchase. "Holdings record incomplete" means more shares were sold than the filings show the person held that day, so a percentage would be wrong.

Sep 15, 20262 directors gave away 681 shares as a gift. That is between 1.2% and 1.5% of each person's total stake held that day. 681 shares came in from vesting or option exercises the same day, so their combined holdings rose by 681 net.
WhoSharesPrice% of total stakeTotal stake afterTrade dateFiled
Erika Rottenberg
Director
344n/a1.2%28KSep 15, 2026Sep 17, 2026
Donna Dubinsky
Director
337n/a1.5%23KSep 15, 2026Sep 17, 2026

"% of total stake" is the shares in this event against all the vested shares the person held that day, across every share class and holding entity, after that day's vesting. "n/a" means the person's holdings don't reconcile, or the row is a purchase. "Holdings record incomplete" means more shares were sold than the filings show the person held that day, so a percentage would be wrong.

Is this normal? More than usual: about 10x the 5-year average. 4 insiders sold; the average is 6 a year. Year by year
Latest filing: Filed Oct 7 for a sale on Oct 5. Khozema Shipchandler sold 14K shares ($4.2M) under a disclosed plan. Filing
72 SEC ownership filings in the period · See the evidence

What stands out

Four insiders sold more than 25% of vested holdings: Andrew Stafman (96% of holdings, $567M, none under a disclosed plan), Khozema Shipchandler (85% of holdings, $37.9M, 73% under a disclosed plan) and Aidan Viggiano (55% of holdings, $13.0M, 42% under a disclosed plan), plus 1 more.Andrew Stafman: largest sale, May 27, 2026 · Khozema Shipchandler: largest sale, Jun 4, 2026 · Aidan Viggiano: largest sale, Jul 2, 2026

Percentages cover 10 of 11 officers and directors. Left out: Douglas Robinson (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
Andrew Stafman
Director
96% · $567MNo plan disclosed
Khozema Shipchandler
Chief Executive Officer, Director
85% · $37.9M73% planned
Aidan Viggiano
Chief Financial Officer
55% · $13.0M42% planned
Erika Rottenberg
Director
25% · $1.8MDisclosed plan
Amounts, filings and trading plans for each seller

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
Oct 2025: $924K under a disclosed planOctNov 2025: $66K under a disclosed planNov 2025: $187K to cover taxesNovDec 2025: $3.1M to cover taxesDec 2025: $129M no plan disclosedDecJan 2026: $2.8M under a disclosed planJanFeb 2026: $113K to cover taxesFebMar 2026: $101K under a disclosed planMar 2026: $2.6M to cover taxesMarApr 2026: $3.6M under a disclosed planAprMay 2026: $6.6M under a disclosed planMay 2026: $272K to cover taxesMay 2026: $315M no plan disclosed$322MMayJun 2026: $10.8M under a disclosed planJun 2026: $4.6M to cover taxesJunJul 2026: $4.8M under a disclosed planJulAug 2026: $881K under a disclosed planAug 2026: $327K to cover taxesAug 2026: $124M no plan disclosedAugSep 2026: $6.8M to cover taxesSepOct 2026: $4.2M under a disclosed planOct

Common questions

Is the Twilio CEO selling stock?

Yes. Khozema Shipchandler sold 188K shares ($37.9M, 85% of starting holdings) in the past 12 months, 73% of it under a trading plan disclosed in the filings.

Why are Twilio insiders selling?

Filings rarely give a reason, and we don't guess at one. What they show is how the sales were made: 6% of sales by value ran under 10b5-1 trading plans disclosed in the filings, 3% were to cover taxes and 92% had no disclosed plan. A trading plan schedules sales in advance.

Are any Twilio insiders buying?

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

How much of their stake did Twilio insiders sell?

About 89% overall. As a group they still hold 16% of their starting shares. 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 sold4 officers and directors: amount, % of holdings, trading plan
Who soldAmount% of holdingsTrading plan
Andrew Stafman
Director
$567M
3.17M shares
96%No plan disclosed
Khozema Shipchandler
Chief Executive Officer, Director
$37.9M
188K shares
85%73% under a disclosed plan
Aidan Viggiano
Chief Financial Officer
$13.0M
76K shares
55%42% under a disclosed plan
Erika Rottenberg
Director
$1.8M
8.8K shares
25%Disclosed plan
The full ownership picture11 of 11 insiders fully reconciled · 11 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.

InsiderHeld Oct 8, 2025SoldHeld Oct 8, 2026Still held
Andrew Stafman
i
Unvested RSUs stated in footnotes are excluded from owned shares. Held through Sachem Head LP; the director disclaims ownership beyond their own interest.
Director
3.31M−3.17M130K4%
Vesting, gifts, unvested awards and holding lines for Andrew Stafman
0shares vested or exercised
0gifted (net of own trusts)
none reportedunvested awards, start → end
  • Unvested RSUs stated in footnotes are excluded from owned shares.
  • Held through Sachem Head LP; the director disclaims ownership beyond their own interest.
Held throughShare classOct 8, 2025Oct 8, 2026
DirectClass A Common Stock10,04510,045
Sachem Head LPClass A Common Stock3,295,000120,000
Khozema Shipchandler
Chief Executive Officer, Director
220K−188K179K81%
Vesting, gifts, unvested awards and holding lines for Khozema Shipchandler
+76Kshares vested or exercised
0gifted (net of own trusts)
none reportedunvested awards, start → end
Held throughShare classOct 8, 2025Oct 8, 2026
DirectClass A Common Stock220,383178,863

Stock options (not counted as shares):

Options heldStrike priceExpiresIntrinsic value (estimate)
3,260$76.63Oct 31, 2028$710K

Estimate: options held × ($294.53 − strike price), using the most recent insider trade price on Form 4 (Oct 5, 2026), not a market close.

Aidan Viggiano
i
Minor difference of 208 shares. Difference is stated in footnotes (unreported vesting, exempt acquisition or transfer).
Chief Financial Officer
138K−76K99K72%
Vesting, gifts, unvested awards and holding lines for Aidan Viggiano
0shares vested or exercised
0gifted (net of own trusts)
none reportedunvested awards, start → end
Held throughShare classOct 8, 2025Oct 8, 2026
DirectClass A Common Stock137,65399,246

Reconciliation: minor difference of 208 shares. Difference is stated in footnotes (unreported vesting, exempt acquisition or transfer).

Jeff Epstein
i
Includes unvested RSUs, amount not disclosed.
Director
64K067Kno sales
Vesting, gifts, unvested awards and holding lines for Jeff Epstein
0shares vested or exercised
0gifted (net of own trusts)
none reportedunvested awards, start → end
  • Includes unvested RSUs, amount not disclosed.
Held throughShare classOct 8, 2025Oct 8, 2026
Direct
includes unvested RSUs, amount not disclosed
Class A Common Stock37,52640,367
Epstein Family Revocable TrustClass A Common Stock26,48426,484
Erika Rottenberg
i
Includes unvested RSUs, amount not disclosed.
Director
35K−8.8K28K81%
Vesting, gifts, unvested awards and holding lines for Erika Rottenberg
0shares vested or exercised
0gifted (net of own trusts)
none reportedunvested awards, start → end
  • Includes unvested RSUs, amount not disclosed.
Held throughShare classOct 8, 2025Oct 8, 2026
Direct
includes unvested RSUs, amount not disclosed
Class A Common Stock00
Trust
includes unvested RSUs, amount not disclosed
Class A Common Stock34,97028,237
Jeffrey Immelt
Director
33K035Kno sales
Vesting, gifts, unvested awards and holding lines for Jeffrey Immelt
0shares vested or exercised
0gifted (net of own trusts)
none reportedunvested awards, start → end
Held throughShare classOct 8, 2025Oct 8, 2026
DirectClass A Common Stock32,7561,463
TrustClass A Common Stock033,411
Donna Dubinsky
i
Includes unvested RSUs, amount not disclosed.
Director
25K023Kno sales
Vesting, gifts, unvested awards and holding lines for Donna Dubinsky
0shares vested or exercised
−4.1Kgifted (net of own trusts)
none reportedunvested awards, start → end
  • Includes unvested RSUs, amount not disclosed.
Held throughShare classOct 8, 2025Oct 8, 2026
Direct
includes unvested RSUs, amount not disclosed
Class A Common Stock00
Shustek-Dubinsky Family Trust
includes unvested RSUs, amount not disclosed
Class A Common Stock24,73322,698
Deval Patrick
i
Includes unvested RSUs, amount not disclosed.
Director
17K019Kno sales
Vesting, gifts, unvested awards and holding lines for Deval Patrick
0shares vested or exercised
0gifted (net of own trusts)
none reportedunvested awards, start → end
  • Includes unvested RSUs, amount not disclosed.
Held throughShare classOct 8, 2025Oct 8, 2026
Direct
includes unvested RSUs, amount not disclosed
Class A Common Stock17,02719,055
Charles Bell
i
Includes unvested RSUs, amount not disclosed.
Director
16K019Kno sales
Vesting, gifts, unvested awards and holding lines for Charles Bell
0shares vested or exercised
0gifted (net of own trusts)
none reportedunvested awards, start → end
  • Includes unvested RSUs, amount not disclosed.
Held throughShare classOct 8, 2025Oct 8, 2026
Direct
includes unvested RSUs, amount not disclosed
Class A Common Stock16,49218,565
Miyuki Suzuki
i
Includes unvested RSUs, amount not disclosed.
Director
16K018Kno sales
Vesting, gifts, unvested awards and holding lines for Miyuki Suzuki
0shares vested or exercised
0gifted (net of own trusts)
none reportedunvested awards, start → end
  • Includes unvested RSUs, amount not disclosed.
Held throughShare classOct 8, 2025Oct 8, 2026
Direct
includes unvested RSUs, amount not disclosed
Class A Common Stock16,11618,170
Douglas Robinson
i
Includes unvested RSUs, amount not disclosed.
Director
004.2Kno sales
Vesting, gifts, unvested awards and holding lines for Douglas Robinson
0shares vested or exercised
0gifted (net of own trusts)
none reportedunvested awards, start → end
  • Includes unvested RSUs, amount not disclosed.
Held throughShare classOct 8, 2025Oct 8, 2026
Direct
includes unvested RSUs, amount not disclosed
Class A Common Stock04,228

11 of 11 insiders fully reconciled: starting holdings plus reported transactions match ending holdings (10 exactly, 1 with a minor or footnoted difference). Percentages cover 10 of 11 officers and directors. Left out: Douglas Robinson (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$620M of sales by plan status, purpose, seller and month

Officer and director open-market sales: $620M across 3,447,905 shares. Plan status and stated purpose are separate questions, and a sale can have both.

By plan status

The lighter segment is sales with no plan disclosed in the filing ($585M), including tax-related sales outside a plan.

No plan disclosed · $567M

Sales with no 10b5-1 plan and no tax reference in the filing. $567M of it is Andrew Stafman. No plan disclosed is a statement about the filing, not about why the sale happened. Largest such sale: Andrew Stafman, May 27, 2026

Taxes

$17.9M of sales (2.9%) cite tax obligations in their footnotes. Example: Aidan Viggiano, Sep 30, 2026

Charitable gifts · 4.1K shares

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

SellerShares soldProceedsUnder a disclosed planShare of totalSales dates
Andrew Stafman
Director
3.17M$567M0%92%Dec 2, 2025 to Aug 12, 2026
Khozema Shipchandler
Chief Executive Officer, Director
188K$37.9M73%6%Dec 31, 2025 to Oct 5, 2026
Aidan Viggiano
Chief Financial Officer
76K$13.0M42%2%Oct 9, 2025 to Sep 30, 2026
Erika Rottenberg
Director
8.8K$1.8M100%0.3%Apr 21, 2026 to Aug 10, 2026

Sales by month

MonthSale proceedsDisclosed planTo cover taxesNo plan disclosed
Oct 2025$924K$924K$0$0
Nov 2025$253K$66K$187K$0
Dec 2025$132M$0$3.1M$129M
Jan 2026$2.8M$2.8M$0$0
Feb 2026$113K$0$113K$0
Mar 2026$2.7M$101K$2.6M$0
Apr 2026$3.6M$3.6M$0$0
May 2026$322M$6.6M$272K$315M
Jun 2026$15.4M$10.8M$4.6M$0
Jul 2026$4.8M$4.8M$0$0
Aug 2026$125M$881K$327K$124M
Sep 2026$6.8M$0$6.8M$0
Oct 2026$4.2M$4.2M$0$0
Is this normal? Selling year by year5 earlier years to compare with

More than usual: about 10x the 5-year average. 4 insiders sold; the average is 6 a year.

12 months endingShares soldInsiders who soldProceeds
Oct 8, 2026
Latest 12 months
3.45M4$620M
Oct 8, 2025
1 year earlier
206K4$22.0M
Oct 8, 2024
2 years earlier
223K4$13.7M
Oct 9, 2023
3 years earlier
221K5$13.5M
Oct 9, 2022
4 years earlier
187K9$44.1M
Oct 9, 2021
5 years earlier
875K9$309M

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 uncertaintyEvery officer and director reconciles

Every officer and director reconciles for this period.

Aidan Viggiano: minor difference of 208 shares. Difference is stated in footnotes (unreported vesting, exempt acquisition or transfer).

Inferred rename: "Trust" is treated as the same holder as "James and Linda McGeever Revocable Trust", because the old name was never reported again and the new one opened with the same balance (251,074 shares). Old name, new name

Inferred rename: "Trust" is treated as the same holder as "Karyn Smith Revocable Trust", because the old name was never reported again and the new one opened with the same balance (24,675 shares). Old name, new name

Inferred rename: "BVP VII, 1,976,134 Class B Common shares" is treated as the same holder as "BVP VII, 1,552,677 Class B Common shares", because the old name was never reported again and the new one opened with the same balance (14,395,041 shares). Old name, new name

Inferred rename: "BVP VII, 1,552,677 Class B Common shares" is treated as the same holder as "BVP VII, 1,270,372 shares of Class B Common Stock", because the old name was never reported again and the new one opened with the same balance (11,310,389 shares). Old name, new name

Inferred rename: "BVP VII, 1,270,372 shares of Class B Common Stock" is treated as the same holder as "BVP VII, 846,915 Class B Common shares", because the old name was never reported again and the new one opened with the same balance (9,253,955 shares). Old name, new name

Inferred rename: "BVP VII, 846,915 Class B Common shares" is treated as the same holder as "Bessemer Venture Partners VII L.P", because the old name was never reported again and the new one opened with the same balance (6,169,303 shares). Old name, new name

Inferred rename: "Bessemer Venture Partners VII L.P" is treated as the same holder as "BVP VII, 635,186 shares of Class B Common Stock", because the old name was never reported again and the new one opened with the same balance (6,169,303 shares). Old name, new name

Inferred rename: "BVP VII, 635,186 shares of Class B Common Stock" is treated as the same holder as "BVP VII, 423,457 shares of Class B Common Stock", because the old name was never reported again and the new one opened with the same balance (4,626,977 shares). Old name, new name

Inferred rename: "BVP VII, 423,457 shares of Class B Common Stock" is treated as the same holder as "BVP VII, 211,729 shares of Class B Common Stock", because the old name was never reported again and the new one opened with the same balance (3,084,651 shares). Old name, new name

Inferred rename: "BVP VII, 211,729 shares of Class B Common Stock" is treated as the same holder as "BVP VII, 105,864 shares of Class B Common Stock", because the old name was never reported again and the new one opened with the same balance (1,542,325 shares). Old name, new name

Inferred rename: "BVP VII, 105,864 shares of Class B Common Stock" is treated as the same holder as "BVP VII Funds", because the old name was never reported again and the new one opened with the same balance (771,162 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 methodology892 filings from SEC EDGAR, and how we read them

All 892 Forms 3, 4 and 5 filed for Twilio (SEC CIK 1447669) from Jun 22, 2016 to Oct 7, 2026, retrieved from SEC EDGAR on Oct 8, 2026. Prices are the ones reported in each filing, often weighted averages. 2 filings were left out because Twilio filed them as an owner of another company's stock.

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 (19)No filing in 18 months; last reported balances, not in any total
NameLast filedLast reported balance
Dana WagnerJan 3, 202532,590 shares, last reported balance as of Dec 31, 2024
Byron DeeterJun 7, 20241,799,088 shares, last reported balance as of Jun 5, 2024
Byron DeeterJun 7, 20243,079,413 shares, last reported balance as of Feb 1, 2019
Elena DonioNov 22, 2023404,832 shares, last reported balance as of Nov 20, 2023
Jeff LawsonJun 30, 20237,063,070 shares, last reported balance as of Jun 28, 2023
Richard DalzellJun 14, 202319,557 shares, last reported balance as of Jun 12, 2023
Eyal ManorFeb 24, 2023179,742 shares, last reported balance as of Feb 23, 2023
Marc BoroditskyMar 23, 202282,091 shares, last reported balance as of Mar 21, 2022
Karyn SmithDec 7, 202132,199 shares, last reported balance as of Dec 3, 2021
George HuNov 15, 202198,870 shares, last reported balance as of Nov 11, 2021
Chee ChewMay 19, 2021109,480 shares, last reported balance as of May 17, 2021
Bessemer Venture Partners VII L.P.Nov 29, 201975,573,963 shares, last reported balance as of May 3, 2019
Bessemer Venture Partners VIII L.P.Nov 29, 20193,696 shares, last reported balance as of Nov 26, 2019
Lee KirkpatrickFeb 14, 2019176,620 shares, last reported balance as of Oct 15, 2018
James McGeeverJun 14, 2017428,888 shares, last reported balance as of Jun 12, 2017
Scott RaneyFeb 13, 2017No balance on record
Scott RaneyFeb 13, 20172,028,411 shares, last reported balance as of Feb 9, 2017
UNION SQUARE VENTURES 2008 LPDec 22, 2016750,000 shares, last reported balance as of Dec 20, 2016
Roy NgJun 30, 201643,141 shares, last reported balance as of Jun 28, 2016