UPWK SEC Filing News — Upwork Inc.

Latest SEC filings for Upwork Inc. (UPWK) explained in plain English. Covers insider buying and selling (Form 4), proposed insider sales (Form 144), material company events (8-K), and quarterly & annual reports (10-Q / 10-K). StrongBuyAnalytics provides navigation and brief excerpts or summaries; original filings remain at the SEC/source links and were authored by their filers, not StrongBuyAnalytics. Filing dates shown are source dates. Coverage and detection can be delayed or incomplete because of SEC availability, amendments, parsing, caching, or outages. Latest source filing date shown: 2026-09-22.

Upwork Inc., together with its subsidiaries, provides platforms and workforce solutions that connect businesses with freelance, agency, fractional, and payrolled talent in the United States, the Philippines, India, Pakistan, and internationally. The company offers Upwork Marketplace, a human and AI-powered work marketplace that connects businesses with on-demand access to independent talent across a range of categories, including AI-related projects, administrative support, sales and marketing, …
Sector: Communication Services Industry: Internet Content & Information Market Cap: $1.1B CIK: 1627475
20
Total Filings
0
Bullish Classifications
11
Bearish Classifications
11
Insider Transactions
2
Material Events (8-K)
1
Periodic Reports
Rule-based classifications for UPWK currently lean bearish. Of the 20 filing records displayed, 11 carry bearish classifications (such as insider sales or negative 8-K disclosures) versus 0 bullish. This does not necessarily signal fundamental deterioration — insiders sell for many reasons — but it is worth monitoring alongside the company's core financial metrics.
UPWK Filing Activity Snapshot 2026-06-23 — 2026-09-22
Insider Transactions (Form 4)
0 buys vs 11 sells
Net insider selling in this period — insiders sell for many reasons beyond conviction.
Largest Form 144 Filing
$617.2K
Brown Hayden (Director, President & CEO) · 2026-08-20
73,241 shares · Form 4
Form 144 Notices
6
Proposed insider sales filed — Form 144 is a notice of intent, not a confirmed transaction. Actual sales are confirmed via Form 4.
Insider Transactions 11 · Forms 3, 4 and 5

A Form 4 is filed within two business days of a company insider — an officer, a director, or a holder of more than ten percent of the stock — changing their position in the shares. All 11 filings in this group are Form 4s for Upwork Inc.

The difficulty with reading these filings as a group is that a single form type covers transactions that mean entirely different things. An executive spending their own money to buy stock and an executive having shares withheld to pay tax on a vesting grant both appear as a Form 4. Every filing below is therefore tagged with the nature of the underlying transaction, taken from the transaction code reported on the form itself.

Across the 11 insider filings shown, the breakdown is 11 open-market sale. 11 of them involved a discretionary open-market trade; the rest are compensation and administrative mechanics.

What each transaction type means

Open-market sale ×11
The insider sold shares on the open market. Sales may be discretionary or executed automatically under a pre-arranged Rule 10b5-1 trading plan, and a Form 4 does not always make clear which applies.
Form 4 Open-market sale Insider Selling 2026-09-22

UPWK insider Mekhalfa Sabrina (Chief Accounting Officer) sold 1,299 shares (~$11.0K)

Mekhalfa Sabrina, listed as Chief Accounting Officer at UPWORK, INC, reported an open-market sale of 1,299 UPWK shares in a Form 4 filing. This is a confirmed insider sale, not just a proposed sale notice.

The insider sold shares on the open market. Sales may be discretionary or executed automatically under a pre-arranged Rule 10b5-1 trading plan, and a Form 4 does not always make clear which applies.

Transactions reported on this filing
Code Nature Shares Price Value
M Option exercise 3,578 — —
S Open-market sale 1,299 $8.45 $11.0K
M Option exercise derivative · Restricted Stock Units 3,578 — —
Filing: Form 4 (Insider Transaction) Insider: Mekhalfa Sabrina (Chief Accounting Officer) Shares: 1,299 Est. Value: $11.0K
View on SEC EDGAR → Open Filing Document →
Form 4 Open-market sale Insider Selling 2026-09-22

UPWK insider Kappus Anthony Ray (GM & Chief Operating Officer) sold 45,732 shares (~$386.5K)

Kappus Anthony Ray, listed as GM & Chief Operating Officer at UPWORK, INC, reported an open-market sale of 45,732 UPWK shares in a Form 4 filing. This is a confirmed insider sale, not just a proposed sale notice.

The insider sold shares on the open market. Sales may be discretionary or executed automatically under a pre-arranged Rule 10b5-1 trading plan, and a Form 4 does not always make clear which applies.

Transactions reported on this filing
Code Nature Shares Price Value
M Option exercise 114,860 — —
S Open-market sale 45,732 $8.45 $386.5K
M Option exercise derivative · Restricted Stock Units 114,860 — —
Filing: Form 4 (Insider Transaction) Insider: Kappus Anthony Ray (GM & Chief Operating Officer) Shares: 45,732 Est. Value: $386.5K
View on SEC EDGAR → Open Filing Document →
Form 4 Open-market sale Insider Selling 2026-09-22

UPWK insider Gessert Erica (Chief Financial Officer) sold 9,336 shares (~$78.9K)

Gessert Erica, listed as Chief Financial Officer at UPWORK, INC, reported an open-market sale of 9,336 UPWK shares in a Form 4 filing. This is a confirmed insider sale, not just a proposed sale notice.

The insider sold shares on the open market. Sales may be discretionary or executed automatically under a pre-arranged Rule 10b5-1 trading plan, and a Form 4 does not always make clear which applies.

Transactions reported on this filing
Code Nature Shares Price Value
M Option exercise 8,433 — —
M Option exercise 9,700 — —
S Open-market sale 9,336 $8.45 $78.9K
M Option exercise derivative · Restricted Stock Units 8,433 — —
M Option exercise derivative · Restricted Stock Units 9,700 — —
Filing: Form 4 (Insider Transaction) Insider: Gessert Erica (Chief Financial Officer) Shares: 9,336 Est. Value: $78.9K
View on SEC EDGAR → Open Filing Document →
Form 4 Open-market sale Insider Selling 2026-09-22

UPWK insider Brown Hayden (Director, President & CEO) sold 23,893 shares (~$201.9K)

Brown Hayden, listed as Director, President & CEO at UPWORK, INC, reported an open-market sale of 23,893 UPWK shares in a Form 4 filing. This is a confirmed insider sale, not just a proposed sale notice.

The insider sold shares on the open market. Sales may be discretionary or executed automatically under a pre-arranged Rule 10b5-1 trading plan, and a Form 4 does not always make clear which applies.

Transactions reported on this filing
Code Nature Shares Price Value
M Option exercise 17,733 — —
M Option exercise 28,677 — —
S Open-market sale 23,893 $8.45 $201.9K
M Option exercise derivative · Restricted Stock Units 17,733 — —
M Option exercise derivative · Restricted Stock Units 28,677 — —
Filing: Form 4 (Insider Transaction) Insider: Brown Hayden (Director, President & CEO) Shares: 23,893 Est. Value: $201.9K
View on SEC EDGAR → Open Filing Document →
Form 4 Open-market sale Insider Selling 2026-08-20

UPWK insider Brown Hayden (Director, President & CEO) sold 73,241 shares (~$617.2K)

Brown Hayden, listed as Director, President & CEO at UPWORK, INC, reported an open-market sale of 73,241 UPWK shares in a Form 4 filing. This is a confirmed insider sale, not just a proposed sale notice.

The insider sold shares on the open market. Sales may be discretionary or executed automatically under a pre-arranged Rule 10b5-1 trading plan, and a Form 4 does not always make clear which applies.

Transactions reported on this filing
Code Nature Shares Price Value
M Option exercise 14,850 — —
M Option exercise 18,333 — —
M Option exercise 13,639 — —
S Open-market sale 23,241 $8.43 $195.8K
S Open-market sale 50,000 $8.43 $421.4K
M Option exercise derivative · Restricted Stock Units 14,850 — —
M Option exercise derivative · Restricted Stock Units 18,333 — —
M Option exercise derivative · Restricted Stock Units 13,639 — —
Filing: Form 4 (Insider Transaction) Insider: Brown Hayden (Director, President & CEO) Shares: 73,241 Est. Value: $617.2K
View on SEC EDGAR → Open Filing Document →
Form 4 Open-market sale Insider Selling 2026-08-20

UPWK insider Gessert Erica (Chief Financial Officer) sold 22,844 shares (~$192.5K)

Gessert Erica, listed as Chief Financial Officer at UPWORK, INC, reported an open-market sale of 22,844 UPWK shares in a Form 4 filing. This is a confirmed insider sale, not just a proposed sale notice.

The insider sold shares on the open market. Sales may be discretionary or executed automatically under a pre-arranged Rule 10b5-1 trading plan, and a Form 4 does not always make clear which applies.

Transactions reported on this filing
Code Nature Shares Price Value
M Option exercise 37,500 — —
M Option exercise 8,524 — —
S Open-market sale 22,844 $8.43 $192.5K
M Option exercise derivative · Restricted Stock Units 37,500 — —
M Option exercise derivative · Restricted Stock Units 8,524 — —
Filing: Form 4 (Insider Transaction) Insider: Gessert Erica (Chief Financial Officer) Shares: 22,844 Est. Value: $192.5K
View on SEC EDGAR → Open Filing Document →
Form 4 Open-market sale Insider Selling 2026-08-20

UPWK insider Kappus Anthony Ray (GM & Chief Operating Officer) sold 1,964 shares (~$16.5K)

Kappus Anthony Ray, listed as GM & Chief Operating Officer at UPWORK, INC, reported an open-market sale of 1,964 UPWK shares in a Form 4 filing. This is a confirmed insider sale, not just a proposed sale notice.

The insider sold shares on the open market. Sales may be discretionary or executed automatically under a pre-arranged Rule 10b5-1 trading plan, and a Form 4 does not always make clear which applies.

Transactions reported on this filing
Code Nature Shares Price Value
M Option exercise 5,115 — —
S Open-market sale 1,964 $8.43 $16.5K
M Option exercise derivative · Restricted Stock Units 5,115 — —
Filing: Form 4 (Insider Transaction) Insider: Kappus Anthony Ray (GM & Chief Operating Officer) Shares: 1,964 Est. Value: $16.5K
View on SEC EDGAR → Open Filing Document →
Form 4 Open-market sale Insider Selling 2026-07-21

UPWK insider Kappus Anthony Ray (GM & Chief Operating Officer) sold 558 shares (~$5.1K)

Kappus Anthony Ray, listed as GM & Chief Operating Officer at UPWORK, INC, reported an open-market sale of 558 UPWK shares in a Form 4 filing. This is a confirmed insider sale, not just a proposed sale notice.

The insider sold shares on the open market. Sales may be discretionary or executed automatically under a pre-arranged Rule 10b5-1 trading plan, and a Form 4 does not always make clear which applies.

Transactions reported on this filing
Code Nature Shares Price Value
M Option exercise 1,412 — —
S Open-market sale 558 $9.06 $5.1K
M Option exercise derivative · Restricted Stock Units 1,412 — —
Filing: Form 4 (Insider Transaction) Insider: Kappus Anthony Ray (GM & Chief Operating Officer) Shares: 558 Est. Value: $5.1K
View on SEC EDGAR → Open Filing Document →
Form 4 Open-market sale Insider Selling 2026-06-23

UPWK insider Gessert Erica (Chief Financial Officer) sold 9,169 shares (~$74.7K)

Gessert Erica, listed as Chief Financial Officer at UPWORK, INC, reported an open-market sale of 9,169 UPWK shares in a Form 4 filing. This is a confirmed insider sale, not just a proposed sale notice.

The insider sold shares on the open market. Sales may be discretionary or executed automatically under a pre-arranged Rule 10b5-1 trading plan, and a Form 4 does not always make clear which applies.

Transactions reported on this filing
Code Nature Shares Price Value
M Option exercise 8,432 — —
M Option exercise 9,700 — —
S Open-market sale 9,169 $8.15 $74.7K
M Option exercise derivative · Restricted Stock Units 8,432 — —
M Option exercise derivative · Restricted Stock Units 9,700 — —
Filing: Form 4 (Insider Transaction) Insider: Gessert Erica (Chief Financial Officer) Shares: 9,169 Est. Value: $74.7K
View on SEC EDGAR → Open Filing Document →
Form 4 Open-market sale Insider Selling 2026-06-23

UPWK insider Mekhalfa Sabrina (Chief Accounting Officer) sold 1,276 shares (~$10.4K)

Mekhalfa Sabrina, listed as Chief Accounting Officer at UPWORK, INC, reported an open-market sale of 1,276 UPWK shares in a Form 4 filing. This is a confirmed insider sale, not just a proposed sale notice.

The insider sold shares on the open market. Sales may be discretionary or executed automatically under a pre-arranged Rule 10b5-1 trading plan, and a Form 4 does not always make clear which applies.

Transactions reported on this filing
Code Nature Shares Price Value
M Option exercise 3,577 — —
S Open-market sale 1,276 $8.15 $10.4K
M Option exercise derivative · Restricted Stock Units 3,577 — —
Filing: Form 4 (Insider Transaction) Insider: Mekhalfa Sabrina (Chief Accounting Officer) Shares: 1,276 Est. Value: $10.4K
View on SEC EDGAR → Open Filing Document →
Form 4 Open-market sale Insider Selling 2026-06-23

UPWK insider Brown Hayden (Director, President & CEO) sold 23,468 shares (~$191.3K)

Brown Hayden, listed as Director, President & CEO at UPWORK, INC, reported an open-market sale of 23,468 UPWK shares in a Form 4 filing. This is a confirmed insider sale, not just a proposed sale notice.

The insider sold shares on the open market. Sales may be discretionary or executed automatically under a pre-arranged Rule 10b5-1 trading plan, and a Form 4 does not always make clear which applies.

Transactions reported on this filing
Code Nature Shares Price Value
M Option exercise 17,733 — —
M Option exercise 28,678 — —
S Open-market sale 23,468 $8.15 $191.3K
M Option exercise derivative · Restricted Stock Units 17,733 — —
M Option exercise derivative · Restricted Stock Units 28,678 — —
Filing: Form 4 (Insider Transaction) Insider: Brown Hayden (Director, President & CEO) Shares: 23,468 Est. Value: $191.3K
View on SEC EDGAR → Open Filing Document →
Proposed Insider Sales 6 · Form 144

A Form 144 is a notice of intent to sell restricted or control securities. It is not a record that anything was sold. Upwork Inc. has 6 such notices in this period.

The distinction matters because a Form 144 is frequently reported as though it were a completed insider sale. The filer may sell all of the shares covered, some of them, or none at all, and there is no obligation to update the notice either way. A sale that is actually executed by an officer or director shows up separately on a Form 4, which is the filing to check before treating a proposed sale as a real one.

Form 144 Proposed Insider Sale 2026-09-18

UPWK Form 144 filed for proposed insider sale by ERICA GESSERT (9,336 shares) ~$78.9K

ERICA GESSERT filed a Form 144 with the SEC indicating intent to sell UPWK (UPWORK, INC) shares. Form 144 reflects a proposed sale, not a completed transaction. The actual execution, if any, would typically appear later in a Form 4.

Filing: Form 144 (Proposed Sale Notice) Insider: ERICA GESSERT Shares: 9,336 Est. Value: $78.9K
View on SEC EDGAR → Open Filing Document →
Form 144 Proposed Insider Sale 2026-09-18

UPWK Form 144 filed for proposed insider sale by HAYDEN BROWN (23,893 shares) ~$201.9K

HAYDEN BROWN filed a Form 144 with the SEC indicating intent to sell UPWK (UPWORK, INC) shares. Form 144 reflects a proposed sale, not a completed transaction. The actual execution, if any, would typically appear later in a Form 4.

Filing: Form 144 (Proposed Sale Notice) Insider: HAYDEN BROWN Shares: 23,893 Est. Value: $201.9K
View on SEC EDGAR → Open Filing Document →
Form 144 Proposed Insider Sale 2026-09-18

UPWK Form 144 filed for proposed insider sale by ANTHONY KAPPUS (45,732 shares) ~$386.5K

ANTHONY KAPPUS filed a Form 144 with the SEC indicating intent to sell UPWK (UPWORK, INC) shares. Form 144 reflects a proposed sale, not a completed transaction. The actual execution, if any, would typically appear later in a Form 4.

Filing: Form 144 (Proposed Sale Notice) Insider: ANTHONY KAPPUS Shares: 45,732 Est. Value: $386.5K
View on SEC EDGAR → Open Filing Document →
Form 144 Proposed Insider Sale 2026-08-18

UPWK Form 144 filed for proposed insider sale by HAYDEN BROWN (23,241 shares) ~$195.8K

HAYDEN BROWN filed a Form 144 with the SEC indicating intent to sell UPWK (UPWORK, INC) shares. Form 144 reflects a proposed sale, not a completed transaction. The actual execution, if any, would typically appear later in a Form 4.

Filing: Form 144 (Proposed Sale Notice) Insider: HAYDEN BROWN Shares: 23,241 Est. Value: $195.8K
View on SEC EDGAR → Open Filing Document →
Form 144 Proposed Insider Sale 2026-08-18

UPWK Form 144 filed for proposed insider sale by ERICA GESSERT (22,844 shares) ~$192.5K

ERICA GESSERT filed a Form 144 with the SEC indicating intent to sell UPWK (UPWORK, INC) shares. Form 144 reflects a proposed sale, not a completed transaction. The actual execution, if any, would typically appear later in a Form 4.

Filing: Form 144 (Proposed Sale Notice) Insider: ERICA GESSERT Shares: 22,844 Est. Value: $192.5K
View on SEC EDGAR → Open Filing Document →
Form 144 Proposed Insider Sale 2026-08-18

UPWK Form 144 filed for proposed insider sale by HAYDEN BROWN (50,000 shares) ~$409.5K

HAYDEN BROWN filed a Form 144 with the SEC indicating intent to sell UPWK (UPWORK, INC) shares. Form 144 reflects a proposed sale, not a completed transaction. The actual execution, if any, would typically appear later in a Form 4.

Filing: Form 144 (Proposed Sale Notice) Insider: HAYDEN BROWN Shares: 50,000 Est. Value: $409.5K
View on SEC EDGAR → Open Filing Document →
Material Events 2 · Form 8-K

An 8-K reports a material event in the window between scheduled reports. There are 2 in this period for Upwork Inc. Each 8-K names the item number it is filed under, and that number is the fastest way to tell a routine disclosure from a consequential one.

Item 2.02 is an earnings release, Item 5.02 is a change of directors or officers, and Item 1.01 or 2.01 covers a material agreement or a completed acquisition. Item 7.01 and Item 8.01 are the general-purpose disclosure items and carry no fixed meaning on their own.

Form 8-K Material Company Update 2026-08-10

UPWK filed 8-K — material company event

UPWORK, INC filed an 8-K with the SEC reporting a material event. Summary unavailable — view the original SEC filing for the full text.

Filing: 8-K (Material Event)
View on SEC EDGAR → Open Filing Document →
Form 8-K Material Company Update 2026-07-16

UPWK filed 8-K — material company event

UPWORK, INC filed an 8-K with the SEC reporting a material event. Summary unavailable — view the original SEC filing for the full text.

Filing: 8-K (Material Event)
View on SEC EDGAR → Open Filing Document →
Periodic Reports 1 · Forms 10-K and 10-Q

The periodic reports are where the audited and reviewed financial statements live. This period contains 1 quarterly report (10-Q) for Upwork Inc.

The two are not equivalent in weight. A 10-K is audited by an external firm and includes the full risk factor disclosure, business description and management discussion; a 10-Q is unaudited, reviewed rather than examined, and much shorter. When a figure in a quarterly report is later revised, the annual report is usually where the correction appears.

An amended report — 10-K/A or 10-Q/A — restates or corrects something in the original filing, and is worth reading against the version it replaces.

Form 10-Q Quarterly Report 2026-08-10

UPWK filed Quarterly Report (10-Q)

UPWORK, INC filed its quarterly report with the SEC. This report includes unaudited financial statements and management discussion for the quarter.

Filing: 10-Q (Quarterly Report)
View on SEC EDGAR → Open Filing Document →

How we classify Upwork Inc.'s filings

Straight from EDGAR

Each displayed record links to an original source document. StrongBuyAnalytics provides navigation and brief excerpts or summaries, not the filing itself. Parsing may omit context or contain errors, so read the original document in full.

Transaction codes, not guesswork

The nature shown on each insider filing comes from the transaction code the filer entered on the form itself — P for an open-market purchase, A for a compensation award, F for shares withheld to pay tax, M for an option exercise. Where one filing contains several codes, the transaction table lists them line by line.

Why the distinction matters

Insider activity is routinely summarised as buying or selling, which flattens together decisions that mean very different things. Shares withheld for tax on a vesting grant are an automatic administrative step; shares bought on the open market are someone committing their own money at the current price.

What this page does not tell you

A filing records what happened, not why. Form 4 does not always disclose whether a sale was executed under a pre-arranged Rule 10b5-1 plan, and no single filing is a basis for a decision on UPWK. Read these alongside the fundamentals rather than in isolation.

Frequently Asked Questions — UPWK SEC Filings

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Publisher, sources & limitations — September 15, 2026. StrongBuyAnalytics provides navigation and brief excerpts or summaries for educational use. Original filings remain at SEC EDGAR or other displayed source links; StrongBuyAnalytics does not author them. Filing dates are source dates, not publication dates for this page. Coverage can be delayed, incomplete, amended, or unavailable because of SEC/source availability, parsing, caching, or outages. Verify every material statement in the original filing.
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