Founded the Canadian software company Constellation Software in 1995 and was its president until October 2025.
The Constellation President's Letters are a primary source on serial acquisition, decentralisation and hurdle-rate discipline that a generation of software investors builds on.
19 letters · 3 articles
| Constellation Software Inc. 2021 President's Letter | Mark Leonard explains why Constellation Software may lower its hurdle rates and stop paying dividends to reinvest all its cash, as a director has long urged. | 2021 | ||
| Constellation Software Inc. 2017 President's Letter | Mark Leonard says he will write to Constellation Software shareholders only when he has something new and important to say, pointing to his letter archive. | 2017 | ||
| Constellation Software Inc. 2016 President's Letter | Mark Leonard continues his study of high-performance conglomerates, which earned extraordinary returns early in asset-light businesses before returns faded. | 2016 | ||
| Constellation Software Inc. 2015 President's Letter | Mark Leonard explains Constellation Software's study of high-performance conglomerates with at least a decade of superior shareholder returns. | 2015 | ||
| Constellation Software Inc. 2014 President's Letter | Mark Leonard updates Constellation Software's non-IFRS metrics and discusses its 2014 results. | 2014 | ||
| Constellation Software Inc. 2013 President's Letter | Mark Leonard updates Constellation Software's metrics with 2013 results over ten years, as CSI has grown much larger. | 2013 | ||
| Constellation Software Inc. 2012 President's Letter | Mark Leonard updates Constellation Software's metrics, including ROIC and maintenance revenue, with 2012 results. | 2012 | ||
| Constellation Software Inc. 2011 President's Letter | Mark Leonard writes about Constellation Software's business and what he has learned about managing its stock. | 2011 | ||
| Constellation Software Inc. 2010 President's Letter | Mark Leonard explains Constellation Software's 2010 review of strategic alternatives, which he says signals the company may be sold. | 2010 | ||
| Constellation Software Inc. 2009 President's Letter | Mark Leonard explains the non-GAAP measures Constellation Software provides, including adjusted net income, ROIC and organic growth. | 2009 | ||
| Constellation Software Inc. Q1 2009 President's Letter | Constellation Software's Q1 2009 revenue rose 32% year on year, but sequential figures show a less rosy picture. | 1 2009 | ||
| Constellation Software Inc. Q4 2008 President's Letter | Mark Leonard uses a reverse shaggy dog story to present Constellation Software's Q4 2008 results. | 4 2008 | ||
| Constellation Software Inc. Q3 2008 President's Letter | Mark Leonard commends the performance of all Constellation Software's operating groups in Q3 2008. | 3 2008 | ||
| Constellation Software Inc. Q2 2008 President's Letter | Constellation Software reports record adjusted EBITDA of $14 million and adjusted net income of $12 million in Q2 2008. | 2 2008 | ||
| Constellation Software Inc. Q1 2008 President's Letter | Constellation Software's Q1 2008 revenue rose 32% and adjusted net income 62% against a weak Q1 2007. | 1 2008 | ||
| Constellation Software Inc. Q4 2007 President's Letter | Constellation Software's Q4 2007 net revenue grew 24%, with organic growth up to 3%. | 4 2007 | ||
| Constellation Software Inc. Q3 2007 President's Letter | Constellation Software's Q3 2007 net revenue grew 14%, short of its 20% goal for 2006 to 2010. | 3 2007 | ||
| Constellation Software Inc. Q2 2007 President's Letter | Constellation Software's organic revenue recovered to 0.5% growth in Q2 2007 while homebuilding-related businesses weakened. | 2 2007 | ||
| Constellation Software Inc. Q1 2007 President's Letter | Constellation Software's revenue growth slowed to 9% in Q1 2007 as organic revenue contracted 1%. | 1 2007 |
| Letter to Shareholders, February 15, 2021 | Constellation Software Inc. | 2021 |
| President's Letter 2017 (the final annual letter) | Constellation Software Inc. | 2018 |
| President's Letter 2016 | Constellation Software Inc. | 2017 |
| Constellation Software’s elusive CEO Paywall | The Globe and Mail | 2014 |