Upwork Inc
Upwork Inc (UPWK) Wheel Strategy
UPWK wheel strategy scan found 7 cash-secured put setups on the previous trading day. Probability of expiring worthless is above 50%. Annualized returns reach up to 46.1%.
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Running a UPWK wheel strategy lets you generate consistent premium income on Upwork Inc while setting your own entry and exit prices on the underlying. Upwork Inc's wheel combines cash-secured puts and covered calls into a repeatable cycle: sell puts at strikes where you'd be happy to own UPWK, and if assigned, sell calls at strikes where you'd be happy to sell. Use our scanner to find the best UPWK wheel strategy setups in real time.
The wheel works best on liquid, high-quality names with stable fundamentals and active options markets — exactly the profile many large-cap leaders fit. The mechanics are simple: sell a cash-secured put on UPWK, collect premium, and either keep the premium if it expires worthless or take assignment at a discount to current price. Once assigned, sell covered calls against the shares to keep collecting premium until they're called away. Choosing the right strikes, expirations, and IV environment is what separates a profitable UPWK wheel from a losing one.
Upwork Inc., together with its subsidiaries, operates a work marketplace that connects businesses with various independent professionals and agencies in the United States, India, the Philippines, and internationally. The company's work marketplace provides access to talent with various skills across a range of categories, including sales and marketing, customer service, data science and analytics, design and creative, web, mobile, and software development. Its work marketplace also enables clients to streamline workflows, such as talent sourcing, outreach, and contracting. The company's work marketplace offers access to various functionalities for remote engagements with talent, including communication and collaboration, ability to receive talent invoices through their work marketplace, and payment protection.
Its marketplace offerings include Upwork Basic, Upwork Plus, Upwork Enterprise, and Upwork Payroll, as well as managed and internet escrow agency services. The company was formerly known as Elance-oDesk, Inc. and changed its name to Upwork Inc. in May 2015. Upwork Inc. was incorporated in 2013 and is headquartered in San Francisco, California.
The difference between a wheel that compounds and one that bleeds comes down to strike selection, IV timing, and discipline on assignment. Our scanner handles the heavy lifting: it ranks every leg of the UPWK wheel strategy by delta, premium yield, IV rank, and days to expiration, so you can deploy capital where the math works. Build your UPWK wheel strategy on data, not gut feel — and let the options wheel do what it does best: pay you to wait.
| Nov 20, 2026 | 7.50 | $0.50 | $0.55 | -0.32 | 58 | 6% | 64.7% | 46.1% | 2 |
| Jan 15, 2027 | 7.50 | $0.65 | $0.75 | -0.32 | 114 | 6% | 58.8% | 32.0% | 4,665 |
| Oct 16, 2026 | 7.50 | $0.10 | $0.13 | -0.21 | 23 | 6% | 74.7% | 26.4% | 1,186 |
| Apr 16, 2027 | 7.50 | $0.90 | $1.10 | -0.32 | 205 | 6% | 54.4% | 26.1% | 19 |
| Jan 21, 2028 | 5.00 | $0.50 | $0.75 | -0.14 | 485 | 6% | 75.1% | 11.3% | 339 |
| Jan 15, 2027 | 5.00 | $0.05 | $0.18 | -0.09 | 114 | 6% | 95.5% | 11.2% | 315 |
| Apr 16, 2027 | 5.00 | $0.10 | $0.28 | -0.11 | 205 | 6% | 88.7% | 9.8% | 0 |
As of September 25, 2026
Run the Wheel on UPWK With Confidence
Find the best UPWK wheel strategy setups across strikes and expirations, plan ahead with at-strike values, and keep your covered calls and puts on track.
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