Checkout.com vs Cursor (Anysphere): employee equity compared
Secondary market prices, valuation trajectory, equity structure, and liquidity outlook for employees choosing between Checkout.com and Cursor (Anysphere).
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
Cursor (Anysphere)
AI-native IDE built on a fork of VS Code.
IPO plausible 2027–2029 if growth trajectory holds. Liquidity may come via tender offer or strategic acquisition before listing.
High-growth AI play; ISO/NSO options; fast-moving valuations reward timing
Key differences for employees
Equity structure
Checkout.com grants RSU — no exercise cost. Your equity vests and converts to cash or shares automatically at a liquidity event. Cursor (Anysphere) grants ISO/NSO with strike prices from $150–$190.
Secondary market premium
The secondary market is pricing Checkout.com at a +-71% premium over its last primary round ($40B → $11.8B). Cursor (Anysphere) trades at +0% over its last round ($29.3B → $29.3B). A higher secondary premium signals stronger investor demand and potentially better near-term liquidity for employees looking to sell.
Revenue and growth
Checkout.com runs at $0.5B ARR, growing +20% YoY (solid). Cursor (Anysphere) runs at $2B ARR, growing +500% YoY (hypergrowth). Revenue growth rate matters for equity because it drives the peer-multiple valuation — the method most correlated with exit multiples.
Liquidity timeline
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.
Cursor (Anysphere): IPO plausible 2027–2029 if growth trajectory holds. Liquidity may come via tender offer or strategic acquisition before listing.
Calculate your specific grant
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