Smile Sail

Smile Sail is a €260+ million Evergreen Private Equity fund that supports ambitious entrepreneurs and management teams in growing into Software & AI Leaders ('Sail').

Some key highlights: Pure focus on Software and AI entrepreneurs: We leverage deep industry expertise and operational excellence to support B2B Software and IT services companies in their ambition to become market leaders or expand their leadership position. We believe that companies that use data-driven business models and AI can create superior value for their customers. Local foundation with an international reach: Benelux based team with extensive experience in scaling software companies internationally further supported by sector experts that bring deep industry experience, networks and offer valuable insights within our key areas of focus (Healthcare, Financial & Business Services and Industry 5.0) 100% backed by entrepreneurs: Smile Sail is backed by 40+ Captains of Industry and Entrepreneurial families. With this entrepreneurial DNA at our core, we invest more than just capital – we bring knowledge, experience, and a powerful network to every partnership. Open-ended Evergreen PE structure: As an evergreen fund backed by entrepreneurial co-investors, we offer maximum flexibility in transaction types, ticket sizes, and holding periods. Whether it’s growth financing, replacement capital, minority or majority stakes, we adapt to your needs. Smile Sail aims to take a majority or minority position in European B2B Software and IT services businesses, and looks to invest €5 to €30 million of equity with the flexibility to go up to €50 million in select cases.