Smile Sail

About Us

Smile Sail is an evergreen private equity fund designed to partner with B2B software companies through strategic investments.

Backed by entrepreneurial families and managed by a seasoned investment team, we leverage deep industry expertise and operational excellence to support software companies in their ambition to become market leaders or expand their leadership position. We believe that software companies that use data-driven business models and AI can create superior value for their customers.

Our entrepreneurial culture is embedded in every aspect of our operations—our investors, advisory board, investment committee, and operational team, all share this passion and drive.

Why Partner with Smile Sail?

Deep Operational Expertise: With decades of experience in building software companies, AI, and succesfull business models, we create value through deep partnerships. What you may expect from us, is in-depth business knowledge and the shared passion and drive to create strategic, long-term value.
Growth & Flexible Capital: Investments ranging from €5M to €35M, ensuring the financial backing you need to scale.
Creative Deal Structuring: 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.
Strategic Partnerships: We don’t just invest, we become your true partner. Our field-proven experience translates into strategic and operational guidance, creating value together.
Global Network: Gain access to Smile Sail’s extensive network of industry experts, business leaders, and co-investors.

What We Offer

We invest in innovative B2B software companies where we see clear opportunities to accelerate growth through the application of AI technologies.

Key Areas of Focus

Healthcare: Drug development technologies, diagnostics, preventive care, and treatment solutions.
Industry 5.0: Automation and AI-enhanced productivity in manufacturing & robotics.
Financial & Business Services: compliance, operational efficiency, and enhanced customer experiences.

Operational Support

With Smile Sail, you gain strategic insights on growth, internationalisation, buy-and-build strategies, and business model innovation to maximize long-term value. In addition to strategy support we also support initiatives on operational excellence. Top performing companies combine a compelling vision, with a winning strategy and disciplined execution.

Influential Partner

Whether as a majority or minority investor, we bring industrial – and operational expertise, network access, and are present in whatever capacity the company and its financing require. Beyond board representation, we actively engage as a partner in the field, providing hands-on support when needed to drive growth and success. All of this is done with the utmost respect for the entrepreneur's vision and leadership. This comes naturally to us, as entrepreneurship is in our DNA—being entrepreneurs ourselves, we deeply understand both the challenges and opportunities.

True partnering works

Building on the success of our first fund, Smile Invest, we uphold the same values and adopt a shared approach to investment and value creation.

Our Values: Mutual respect and integrity, best-in-class professionalism, and genuine partnerships.
Tailored Investments: Every business is unique. Smile Sail tailors its investments to meet the specific needs of each company, ensuring alignment with its vision and growth trajectory.
Sustainable Value Creation: As an evergreen fund, we are not constrained by time pressure. We focus on creating sustainable value with flexible exit strategies, tailored to each company’s market conditions and long-term potential.

Let’s Grow Together

Partner with a team that understands the power of AI-driven software solutions and is committed to helping you scale. Let’s innovate and shape the future of Europe’s economy and society through transformational B2B software solutions.