Our approach
Our approach
A smart partnership to become the
next leader in Software & AI
Largest Benelux based Evergreen Private Equity fund for Software & AI entrepreneurs
We combine hands-on support with strategic insights and deep sector expertise to support B2B software and IT services companies in their ambition to become market leaders or strengthen their leadership position. We believe that companies applying data-driven business models and AI can create superior value for their customers.
Our sweet spot
Growth & Buy Out Capital at the intersection of sector expertise, B2B software & IT solutions, boosted by Data & AI technologies
Data & AI technologies
Prioritizing companies where data and AI are or can be core value drivers
B2B Software & IT services
Supporting transformative B2B Software and software-enabled services
Key areas of focus
Core verticals of interest include Healthcare, Industry 5.0, and Financial & Business Services
True Partnerships Work
Building on the success of our first fund, Smile Invest, we uphold the same values and adopt a shared approach to our investments and value creation.
What we stand for
We uphold mutual respect and integrity, deliver best-in-class professionalism, and build genuine lasting partnerships.
Ensuring full alignment
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.
Creating value that endures
As an evergreen fund, we are not constrained by time pressure. We focus on creating sustainable value with flexible exit strategies.
Investment metrics
We typically invest between €5 and €50 million in equity. Moreover, we can invest substantially larger amounts through co-investments with our sister fund, Smile Invest, as well as with our Tier-1 entrepreneurial LPs.
(*) Our revenue and EBITDA ranges vary depending on the business model and growth stage, with flexibility for high-growth opportunities.
Equity investment
Revenue
EBITDA
Investment types and Deal structures
As an evergreen fund, we offer maximum flexibility in transaction types, deal structures, and holding periods. Whether growth financing, replacement capital, or minority and majority stakes, we ensure full alignment with entrepreneurs, co-owners, and management teams, fostering a respectful and impactful partnership.
Growth buy-outs
Acquisition of significant or controlling stakes in profitable, growing businesses, often using a mix of equity and debt.
Growth capital
Combination of primary and/or secondary capital invested in fast-growing companies to accelerate growth.
Majority ownership
Controlling stakes enabling active involvement in strategic and operational decision-making.
Minority ownership
Minority stakes with the goal of being a non-controlling strategic partner to the existing leadership and founders.
Our value add
We combine strategic insights with hands-on support, helping founders and leadership teams scale through smart growth strategies, operational excellence, and active partnerships, all grounded in an impactful and respectful way of working that strengthens trust and empowers teams.
Accelerate your business plan
Our team has extensive hands-on experience in creating and accelerating your business plan. Both in your existing markets as well as geographical expansion and adding new solutions to your offering.
Operational impact
Growth can only be sustained by structured and effective operations. We support our companies in building fundamentally sound businesses from the core.
Add-on acquisitions
We help our portfolio companies to set the acquisition strategy, identify potential acquisition targets, and support throughout the process. Post acquisition we support on the execution of the value creation plan.