IS NOW THE TIME TO BUY?

Can a model built on the acquisition of thousands of small, niche software businesses survive an era where AI promises to commoditize code and the leader has recently changed?
The legendary Mark Leonard has stepped down, and the market is nervous. But if you look closer, Constellation Software (TSX: CSU) isn’t just a person, it’s an institutionalized capital allocation machine. With new President Mark Miller at the helm (a 30-year veteran who helped build the model from day one), the company’s decentralized engine is primed to continue its «business as usual» trajectory of high-volume, niche acquisitions.
While skeptics fear AI will commoditize code, they miss the nature of Vertical Market Software (VMS). These systems aren’t just tools, they are the mission-critical backbones of hospitals, utilities, and transit networks where switching costs are astronomical and data gravity is absolute. By adopting a disciplined «fast follower» approach, Constellation is integrating AI tools like «Smart Edit» to enhance customer value, proving that domain expertise remains the ultimate moat in the LLM era.

The financial engine remains a masterclass in efficiency. Over the past decade, revenue has compounded at a 22% CAGR, fueled by an acquisition flywheel that targets thousands of fragmented niche providers globally. Because CSU utilizes a negative cash conversion cycle, effectively collecting maintenance fees in advance, it funds its billion-dollar M&A pipeline without diluting shareholders or relying on excessive leverage.

We are currently seeing a rare valuation reset. Trading at approximately C$2,357, the stock has retreated 55% from its 2025 highs, pushing its free cash flow yield to levels not seen in nearly a decade. For a company generating C$2.6 billion in LTM FCF with a fortress balance sheet (0.8x Net Debt/EBITDA), this sentiment driven drawdown could offer a compelling entry point for long-term compounders.

A price target of C$3,650 represents a potential 55% upside, anchored in a reality where software durability beats temporary hype, so far. As the company heads toward its March 10th conference call, the focus remains on execution over narrative. In 2026, the «Architecture of Permanence» is not just intact, it could be significantly undervalued.
For more details, read our Analysis on Constellation Software in the following link:
Constellation Software (TSX: CSU) Initiation Coverage Report
Disclaimer:
We wrote this article ourselves, and it reflects our own opinions. We did not receive compensation for it. We have no business relationship with any company whose stock is mentioned in this article.
The views contained in this document are for informational and educational purposes only, and should not be construed as a recommendation to buy or sell any of the securities mentioned, or as a solicitation of transactions or clients. Past performance is not indicative of future results. Investments in equities carry risks, including loss of principal. The analysis is based on data available as of December 5, 2025. The information contained herein is believed to be appropriate; however, under no circumstances should any person act solely based on the information provided. We do not recommend that anyone act on any investment information without first consulting an investment advisor regarding the suitability of such investments for their specific situation.
Irrational Investors and/or its affiliates may hold a position in the securities mentioned in this report and may make purchases or sales of such securities from time to time in the open market or otherwise. The analyst primarily responsible for this report may also hold a personal position in the subject securities.
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