Posts  / UPWK  / #POST-237941
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My TOP 3 Premium Selling PICKS

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May 8, 2026 · 11:29

DAILY IV OPPORTUNITIES BRIEF — FRIDAY, MAY 8, 2026

**SECTION 1: MARKET CONTEXT**

Futures are green across the board this morning — SPY +0.51%, QQQ +0.73%, IWM +0.48%, DIA +0.33% — broad-based risk-on tone with tech leading. VIXY is down slightly (-0.22%), confirming complacency is creeping back in, which is exactly the environment where premium sellers want to be active. The tape is being driven by a combination of U.S.-Iran headlines, a key jobs report on deck, and a string of earnings catalysts still working through the system. Sector-wise, earnings IV is the dominant theme today — the screener is loaded with 95-100% earnings probability flags, meaning the market is actively pricing in binary risk across tech and growth names.

**SECTION 2: TOP 3 PICKS**

**UPWK — Upwork Inc. A**

Quick Stats:

Current Price: \~$10-12 range implied by chain | IV Rank: 97.65% | IV Pctl: 100%

IV is at a full-year high — earnings catalyst driving extreme premium inflation

Earnings: imminent (100% probability flag) — RED for directional, GREEN for premium sellers

Options Volume: +5.26% — building activity, not a blowout but healthy

Why It's Attractive:

UPWK is sitting at the top of the entire screener by IV Rank at 97.65% with a 100th percentile reading — this is peak premium territory. The options chain structure tells the story clearly: massive put OI at the 7.5 strike (12,481 contracts) and the 12.5 strike (4,962 puts) shows the market is hedging hard downside, inflating put premiums significantly. With a stock trading in the low-to-mid teens, the absolute dollar width on spreads stays manageable while the vol crush post-earnings should be sharp.

Trade Setup:

Structure: Short Strangle or Iron Condor (IC preferred for defined risk)

Target Expiration: May 15 (7 DTE — captures earnings vol crush)

Strike Guidance: Calls → look near the 12.5-15 area (\~0.09-0.23 delta range). Puts → the 7.5 strike carries a 0.22 delta and sits on the highest OI in the chain — this is your anchor level

Width: $2.50 wings appropriate given the price level

Management: Close at 50% max profit or exit the week of May 12 regardless

Size: 1-2 contracts — small-cap name, wide bid/ask likely, size down

Risk Factors:

UPWK is a low-price name in a challenged freelance labor market — a bad earnings print can cause a 20-30% gap that blows through a $2.50 wide spread without mercy. Defined risk structure is non-negotiable here.

Note: Pull up this ticker's live options chain in your broker before trading. Strike selection and premiums must come from real-time quotes.

**PENG — Penguin Solutions Inc. A-**

Quick Stats:

Current Price: \~$38-42 range implied by chain | IV Rank: 92.59% | IV Pctl: 100%

IV at full-year highs, earnings catalyst fully baked in

Earnings: imminent (100% probability flag) — RED for directional, GREEN for premium sellers

Options Volume: flat (-0.03%) — modest activity, but OI is well-distributed

Why It's Attractive:

PENG hits the sweet spot — IV Rank above 90, 100th percentile, and the options chain shows a clear skew worth noting. Call-side OI is heavily concentrated at the 45 strike (5,963 contracts) and the 40 strike (2,523), while put-side OI is thin and spread across the 25-35 range with deltas in the -0.02 to -0.19 territory. That tells you the market is positioned for upside but not aggressively hedging downside — put premium may be relatively cheap, but the call wing is where the real interest sits. The 35-strike calls carry a 0.92 delta, confirming stock is trading in the high 30s to low 40s.

Trade Setup:

Structure: Iron Condor

Target Expiration: May 15 (7 DTE)

Strike Guidance: Put side → look at the 30-35 area (0.05-0.19 delta). Call side → look at the 45-50 area (0.09-0.19 delta). The 45 call is the most liquid strike on the chain by a wide margin

Width: $5 wings given the $40 stock price

Management: Close at 50% max profit, or no later than May 13

Size: 1-2 contracts — liquidity is decent at the key strikes but drops off fast at the wings

Risk Factors:

Options volume is essentially flat today — lower liquidity means wider bid/ask on the wings, which cuts into net credit. Confirm you can collect meaningful premium before entering; if the IC doesn't pencil, a naked short put spread on the 30/25 level alone may be cleaner.

Note: Pull up this ticker's live options chain in your broker before trading. Strike selection and premiums must come from real-time quotes.

**HUBS — HubSpot Inc. B+**

Quick Stats:

Current Price: \~$240-260 implied by chain concentration | IV Rank: 91.53% | IV Pctl: 97.02%

IV near annual highs, earnings-driven inflation

Earnings: imminent (99% probability flag) — RED for directional, GREEN for premium sellers

Options Volume: +3.64% — rising into earnings, solid confirmation

Why It's Attractive:

HUBS is the large-cap name on the list today — higher stock price means wider absolute spread widths and more premium per contract to work with. IV Rank at 91.53% and 97th percentile is strong. The chain shows good OI distribution: call interest stacked from 230 through 300, with the 300 strike carrying 949 contracts at a 0.15 delta — that's your upper boundary. Put-side OI clusters around 200-220, with the 180 put showing a -0.23 delta as the clearest data point on the downside.

Trade Setup:

Structure: Iron Condor

Target Expiration: May 15 (7 DTE)

Strike Guidance: Calls → 280-300 range (0.15-0.23 delta). Puts → 200-220 range (delta data sparse — use 180 at -0.23 as your reference floor and go tighter from there)

Width: $10-20 wide wings appropriate for a $250 stock

Management: Close at 50% max profit or exit by May 13 ahead of any weekend risk

Size: 1 contract — this is a $250 stock; full notional exposure is significant, keep position sizing honest

Risk Factors:

HUBS can move 10-15% on earnings — a $250 stock moving 12% puts you at $280 or $220 in a hurry, which is right where the OI walls are. The B+ grade reflects that the wings need to be set wide enough to survive a real move, which compresses the credit. Price the chain carefully before committing.

Note: Pull up this ticker's live options chain in your broker before trading. Strike selection and premiums must come from real-time quotes.

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