Liquidity Events and Cayman Sandwich Structures at SP Tech Week

KLA and Gunderson Dettmer discussed venture capital exit structures and taxation in a panel that was part of SP Tech Week 2026, featuring partners Laura Cossi, Francisco Alverne, and Adan Muller

KLA and the American firm Gunderson Dettmer brought together players from the venture capital ecosystem for a breakfast panel on liquidity events, part of the SP Tech Week 2026 programming. The discussion took as its starting point the Cayman sandwich structure, a recurring model among Brazilian startups that have gone through a corporate flip. From there, the conversation walked through four exit scenarios built on that structure: the sale of shares in the Cayman holding company, the merger, the direct sale of the Brazilian operating company, and the Brazilian FIP as an alternative vehicle for VC funds.

KLA Private Equity and Venture Capital partners Laura Cossi and Francisco Alverne, alongside Adan Muller, partner at Gunderson Dettmer, led the discussion from both a legal and a tax perspective on each alternative. Topics covered included the mechanics of stock option cash-out and acceleration, and the possibility of an unflip to enable a direct sale of the Brazilian operation.

On the tax side, the panel also featured KLA partner Henrique Lopes and attorney Denys Yamamoto, who addressed the tax treatment applicable to each seller profile (Brazilian founders, Cayman funds, FIPs, optionees, and American investors).

The panel further addressed the most recent points of attention in structuring these deals: the risk of the offshore sale being requalified as an indirect sale of a Brazilian asset, the role of the tax opinion as a defense and negotiation tool, and the calibration of escrow and indemnification provisions in transactions spanning multiple jurisdictions.

The discussion reinforced that the choice of exit structure depends less on a more favorable tax regime and more on the buyer’s profile and preferences.

SP Tech Week brings together, between September 13 and 18, hundreds of events independently organized by startups, funds, and law firms around São Paulo’s technology and innovation agenda.

The meeting between KLA and Gunderson Dettmer, held at KLA’s office in São Paulo, was part of that programming with a technical focus on the legal and tax structuring of venture capital exits, and reinforced the firm’s role in the most relevant discussions for founders and investors in the sector in Brazil.

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