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Dennis Woodside Insider Profile
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Dennis Woodside, COO at Dropbox, holds 2.29M shares in Freshworks (Ticker: FRSH), holds 8.33K shares in ServiceNow (Ticker: NOW), holds 765.14K shares in Dropbox (Ticker: DBX).
Profitable Transactions
1 out of 2 Profitable Transactions
Average Return
-13.40%
Average return per transaction
Time Frame
Compare to
Insider Holdings
Insider Roles
Roles that Dennis Woodside holds in companies
Most Profitable Insider Trade
The most profitable trade made by Dennis Woodside
Dennis Woodside's Trading History
Dropbox
Sep 06, 2018
COO
Uninformative Sell
4.96M
$21.75M
ServiceNow
Jun 13, 2022
Director
Uninformative Buy
―
$1.28M
Freshworks
Dec 02, 2025
CEO & President, Director
Uninformative Sell
1.16M
$28.85M
List of latest transactions for each holding click on a transaction to see Dennis Woodside's performance on stock
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Dennis Woodside insider profile FAQ
What is the percentage of profitable transactions made by Dennis Woodside?
The percentage of profitable transactions made by Dennis Woodside is 50%.
What is the average return per transaction made by Dennis Woodside?
The average return per transaction made by Dennis Woodside is -13.40%.
What stocks does Dennis Woodside hold?
Dennis Woodside holds: DBX, NOW, FRSH stocks.
What was Dennis Woodside’s latest transaction?
Dennis Woodside latest transaction was an Uninformative Sell of $1.16M.
What was Dennis Woodside's most profitable transaction?
Dennis Woodside’s most profitable transaction was an Informative Buy of FRSH stock on November 12, 2025. The return on the trade was 12.90%.
What is Dennis Woodside's role in Dropbox?
Dennis Woodside's role in Dropbox is COO.
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