Kappus Anthony Ray
SEC insider (Form 3/4/5 filer). CIK 0001860481. GM & Chief Operating Officer at UPWORK, INC (UPWK) and 1 other issuer. 39 reported Form 4/5 transactions since Sep 2024; latest on Oct 19, 2026. Located in PALO ALTO, CA.
Companies Kappus Anthony Ray has filed insider reports for
- UPWORK, INC (UPWK): Officer, GM & Chief Operating Officer
- Redfin Corp (RDFN): Officer, Chief Legal Officer
Kappus Anthony Ray
CIK: 0001860481
Transaction Breakdown
Open Market Buys (P)0 (0.0%)
High conviction signal
Open Market Sales (S)7 (17.9%)
Position reduction
Option Exercises (M)17 (43.6%)
Derivative conversions
Awards (A)2 (5.1%)
Compensation grants
Other (G, F, J, C, D, …)13 (33.3%)
Gifts, tax withholding, conversions, dispositions to the issuer and other codes
Discretionary Trading P&L
Holdings
Transaction History (39 total)
- Oct 19, 2026UPWK
UPWORK, INC
SaleDirect559 shares at avg. $8.43$5K - Oct 18, 2026UPWK
UPWORK, INC
ExerciseDirect1.4K shares- - Sep 18, 2026UPWK
UPWORK, INC
SaleDirect45.7K shares at avg. $8.45$386K - Sep 18, 2026UPWK
UPWORK, INC
ExerciseDirect114.9K shares- - Aug 18, 2026UPWK
UPWORK, INC
SaleDirect2K shares at avg. $8.43$17K - Aug 18, 2026UPWK
UPWORK, INC
ExerciseDirect5.1K shares- - Jul 18, 2026UPWK
UPWORK, INC
SaleDirect558 shares at avg. $9.06$5K - Jul 18, 2026UPWK
UPWORK, INC
ExerciseDirect1.4K shares- - May 18, 2026UPWK
UPWORK, INC
ExerciseDirect5.1K shares- - May 18, 2026UPWK
UPWORK, INC
SaleDirect1.9K shares at avg. $8.66$17K
| Type | Shares | Price | Ownership | |||
|---|---|---|---|---|---|---|
| Oct 19, 2026 |  UPWK UPWORK, INC | Sale | 559 | $8.43 | $4,712 | Direct |
| Oct 18, 2026 | UPWK UPWORK, INC | Exercise | 1,413 | - | $0 | Direct |
| Sep 18, 2026 | UPWK UPWORK, INC | Sale | 45,732 | $8.45 | $386,472 | Direct |
| Sep 18, 2026 | UPWK UPWORK, INC | Exercise | 114,860 | - | $0 | Direct |
| Aug 18, 2026 | UPWK UPWORK, INC | Sale | 1,964 | $8.43 | $16,548 | Direct |
| Aug 18, 2026 | UPWK UPWORK, INC | Exercise | 5,115 | - | $0 | Direct |
| Jul 18, 2026 | UPWK UPWORK, INC | Sale | 558 | $9.06 | $5,053 | Direct |
| Jul 18, 2026 | UPWK UPWORK, INC | Exercise | 1,412 | - | $0 | Direct |
| May 18, 2026 | UPWK UPWORK, INC | Exercise | 5,114 | - | $0 | Direct |
| May 18, 2026 | UPWK UPWORK, INC | Sale | 1,905 | $8.66 | $16,504 | Direct |
1-10 of 39 transactions