OpenAI vs Checkout.com: employee equity compared
Secondary market prices, valuation trajectory, equity structure, and liquidity outlook for employees choosing between OpenAI and Checkout.com.
OpenAI
Maker of ChatGPT, GPT-5, Sora and the OpenAI API.
IPO highly anticipated, likely 2026–2027 given massive scale. One of the most closely watched pre-IPO names in tech.
High-growth AI play; PPU (no exercise decision needed); fast-moving valuations reward timing
Checkout.com
Global payment infrastructure provider processing card, local, and alternative payment methods for enterprises at scale — customers include Revolut, Spotify, Pizza Hut, and Farfetch.
IPO possible 2026–2028 as scale builds. Secondary trades at a discount vs last round — exercise timing requires caution. No confirmed timeline; tender offers may provide interim liquidity.
Recurring revenue model; RSU (no exercise cost); secondary discount vs primary — price discovery ongoing; IPO likely once profitability demonstrated
Key differences for employees
Equity structure
OpenAI grants PPU — a profit participation unit unique to OpenAI. No strike price, no AMT risk. You receive cash or shares at distribution events. Checkout.com grants RSU — no exercise cost.
Secondary market premium
The secondary market is pricing OpenAI at a +0% premium over its last primary round ($852B → $853B). Checkout.com trades at +-71% over its last round ($40B → $11.8B). A higher secondary premium signals stronger investor demand and potentially better near-term liquidity for employees looking to sell.
Revenue and growth
OpenAI runs at $24B ARR, growing +60% YoY (fast). Checkout.com runs at $0.5B ARR, growing +20% YoY (solid). Revenue growth rate matters for equity because it drives the peer-multiple valuation — the method most correlated with exit multiples.
Liquidity timeline
OpenAI: IPO highly anticipated, likely 2026–2027 given massive scale. One of the most closely watched pre-IPO names in tech.
Checkout.com: IPO possible 2026–2028 as scale builds. Secondary trades at a discount vs last round — exercise timing requires caution. No confirmed timeline; tender offers may provide interim liquidity.
Calculate your specific grant
Enter your actual shares, equity type, and strike price. PrivatePulse calculates your personal equity value at both companies using 4 independent methods.