Constellation Software Inc.

TO OUR SHAREHOLDERS

Last year I used our study of high-performance conglomerates (“HPC’s”) as a framework for this letter.
One of the findings from studying the HPC’s was that they followed a multi-decade pattern, with
extraordinary returns in asset-light businesses in their early days, followed by a period of attractively
priced acquisitions to which they applied their increasingly refined operating practices. Eventually, they
drifted towards paying higher multiples for larger acquisitions as the HPC’s became very large. The high
acquisition prices led to declining pre-tax, pre-interest returns on Total Capital. While the average return
on Total Capital for the HPC’s still exceeds that of the S&P 500, it is much closer to that benchmark now
than it was fifteen years ago.

In the last couple of years, a number of journalists and analysts have hinted that the Constellation
Software Inc. (“CSI”) historical performance is too good to be true. They frequently conclude, in the best
case, that our performance will revert to the mean. Reversion towards the mean is consistent with what
we found for all the HPC’s, so I don’t disagree with their observation. Our goal, however, is to have our
return on Total Capital revert to the mean as slowly as possible, while still deploying most of the Free
Cash Flow (“FCF”) that we generate.
Table 1
Adjusted Net Average Organic Net ROIC + Organic
Income Invested Revenue Growth Net Revenue
(a) Capital ROIC (YoY) Growth

2007 33 154 22% 1% 23%

2008 54 195 28% 5% 33%
2009 62 256 24% -3% 21%
2010 84 325 26% -2% 24%
2011 140 394 36% 7% 43%
2012 172 491 35% 2% 37%
2013 207 585 35% 4% 39%
2014 274 739 37% 3% 40%
2015 371 965 38% -3% 35%
2016 395 1261 31% 1% 32%
(a) Historical figures restated to comply with revised definition.

In our non-GAAP results for 2016 (Table 1), you can see evidence of reversion to the mean. Adjusted
Net Income grew only 6% in 2016, as compared to our ten-year compound average growth rate
(“CAGR”) of 31%. Our Average Invested Capital grew 31% as compared to our ten year CAGR of 26%.
On the face of it, the increasingly rapid accumulation of Invested Capital is attractive, but only if we can
invest that capital at high rates of return. ROIC was 31% in 2016, in line with our 10-year average, but
lower than we've achieved in each of the last five years. ROIC was depressed because we were unable to
invest all of our FCF during 2016 and so were carrying excess cash by year-end, and because we made a
number of larger acquisitions with lower returns over the last couple of years. Organic Net Revenue
Growth for the year was 1%, an improvement vs. 2015, but below our 10-year average.

We have just completed the Maintenance Revenue analysis (Table 2) for 2016. The same cautions apply
to this year's analysis as to those in prior years, i.e. while the totals are materially the same as our
Maintenance Revenue for financial reporting purposes, the individual components reflected in the table

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are generated by examining and categorising tens of thousands of records, and the estimated FX
adjustment was calculated by translating the Maintenance amounts in major foreign currencies into U.S.
dollars at the average FX rates for each year. We believe that the data presented is a fair illustration of the
trends in our Maintenance base.

Total organic growth in Maintenance Revenue declined to 5% for 2016. In my letter last year, I explained
that we sometimes buy shrinking businesses, and despite the shrinkage, we still expect to generate good
returns on those investments. Growing businesses are more attractive to us, but we can't always acquire
enough growing businesses at reasonable prices to invest all of our FCF. Our "next best" use of capital is
acquiring shrinking VMS businesses which still meet or exceed our hurdle rate. Mixing growing and
contracting businesses in one company creates a number of interesting cultural and management
challenges. This might be a lively discussion topic for shareholders to raise with our management team
during the Annual General Meeting (AGM). During the last few years we purchased several healthcare
software businesses and a real estate software business that were all contracting, but generating strong
current results. Those acquisitions improved our short-term profitability but depressed our organic growth
rate in Maintenance Revenue by over 1% in 2016.
Table 2
(US$MM) 2007 2008 2009 2010 2011 2012 2013 2014 2015 2016
Maintenance Revenue 142 193 252 337 417 510 725 1015 1170 1400
Growth from:
Acquisitions 11% 25% 27% 25% 15% 15% 34% 32% 15% 16%

Organic Sources
a) New Maintenance 9% 9% 8% 8% 8% 8% 10% 10% 8% 9%
b) Price Increases & Other 9% 9% 4% 6% 5% 5% 6% 7% 5% 5%
c) Attrition- lost modules -2% -3% -3% -3% -2% -2% -2% -4% -2% -4%
d)Attrition- lost customers -4% -4% -4% -4% -3% -4% -5% -5% -5% -5%
Total organic growth* 12% 10% 4% 7% 7% 8% 8% 8% 7% 5%

Estimated effect of FX 0% 0% -1% 1% 2% -1% -1% -1% -6% -2%

Total maintenance
growth* 23% 35% 31% 34% 24% 22% 42% 40% 15% 20%
* Certain totals may not reconcile due to rounding

Our overall organic growth in revenue has averaged 2% during the last 10 years. The organic growth in
Maintenance Revenue has averaged close to 8%. The discrepancy between the two figures has been
possible because Maintenance Revenue as a portion of total revenue has increased. While some of the
change in revenue mix is due to the elimination of low-margin, non-Maintenance activities, a portion is
because we have knowingly traded off one-time licenses for increased recurring revenues. To some
extent, particularly where we've adopted a SaaS model, we may have also traded off professional service
revenues for increased recurring revenue. These trade-offs create revenue streams that are more stable
and make managing our businesses easier. As Maintenance Revenue becomes a larger portion of total
revenues, the discrepancy between the organic growth in total revenue and Maintenance Revenue is likely
to be smaller.

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This will be the last year that we present the Maintenance analysis in this format. Our business units
("BU's") monitor customer health in many ways and tend to do so on a much shorter cycle than annually.
When we ask them to produce the information in Table 2, there is a large, unautomated process of
classifying data and making it consistent between BU's. The benefit of providing this information for
shareholders feels like it is outweighed by the effort of compiling it, if we can do it another way. For
reporting purposes, Jamal began (last quarter) an alternative process of measuring organic growth by
revenue stream, including maintenance, on a quarterly basis. This is a top-down analysis, and can be
done quickly without a lot of ad hoc effort. Jamal will describe the calculation in managements’
discussion of the Q1 results, but a significant difference is that instead of using only the prior year’s
Maintenance Revenue as the denominator for the growth calculations, he adds a run-rate assumption for
acquired Maintenance Revenue to the denominator for such calculations. We will be reporting that data
quarterly, and will provide quarterly historical comparisons going back to Q1 2016. While the
information presented will not be as detailed as in Table 2, the increased frequency of reporting should be
valuable for our shareholders.

Because some of our shareholders prefer IFRS-sanctioned data, we regularly present a couple of IFRS
metrics that we find informative (Table 3). Total revenue per share increased 16% in 2016, up from 10%
the prior year but down from the 26% CAGR that we achieved during the last decade. I consider 16%
growth in Revenue per Share to be superb performance. The S&P 500's Revenue per Share grew less
than 3% in 2016 and its growth has averaged 2% for the last decade.

Our Cash Flow from Operating Activities per Share grew 24% in 2016, down from the 33% CAGR that
we achieved during the last decade. The S&P 500 seems to have grown its Cash Flow from Operating
Activities per share in the mid to high single digit percentage range during the last decade, depending
upon which source you believe, and whether financial companies are included in the calculation or not.
CSI has done an outstanding job of growing cash flow per share, but that surfeit of cash contributes to our
reinvestment challenges.
Table 3
Total Revenue Cash Flow from Operating YoY
per Share YoY  Activities per Share 
2007 11.47 15% 1.62 19%
2008 15.60 36% 2.96 83%
2009 20.67 32% 3.85 30%
2010 29.92 45% 5.06 32%
2011 36.49 22% 6.49 28%
2012 42.05 15% 6.83 5%
2013 57.13 36% 10.40 52%
2014 78.77 38% 16.11 55%
2015 86.75 10% 18.68 16%
2016 100.28 16% 23.16 24%
CAGR 26% 33%

CSI is still an exceptional company by most standards, but we are clearly not performing as well as we
have in the past. Part of that slippage is due to external factors. Part of it is due to internal execution
issues.

Externally, competition to buy vertical market software (“VMS”) businesses is intense. Vista Equity
Partners and Thoma Bravo are two of the most prominent private equity (“PE”) firms that concentrate on

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software acquisitions. Roper Industries is a large publicly traded industrial conglomerate that we included
in our HPC study and that also actively competes for VMS acquisitions. Vista currently manages
approximately $28 billion of capital and Thoma Bravo is managing approximately $16 billion. Both have
raised multi-billion dollar funds in the last couple of years. CSI is currently managing only $1.4 billion of
capital. In the last 9 years, Roper Industries has invested five times as much capital in the VMS sector as
CSI has since its inception, 22 years ago.

In addition to these three daunting competitors, there are a dozen or so PE firms who each manage in
excess of a billion dollars and who have well-established software track records. At the lowest end of the
market, every quarter we seem to profile for our Operating Group Managers at least one new competitor
that proposes to create a CSI look-alike. A number of these new competitors are trolling our employee
base for talent. This much capital targeting the VMS sector has driven and will continue to drive up
purchase price multiples.

The internal execution issues upon which we currently focus are: Maintaining investment discipline,
avoiding overhead creep, and increasing our investment in growth, both organic and acquired. Even if we
execute superbly on the first two, it is difficult to foresee consistent multiyear growth in intrinsic value
per share (assuming that dividends are reinvested) that exceeds 10% to 12%.

Maintaining Investment Discipline:

I recently worked on a large transaction. With every day that passed, I could feel my commitment to the
process growing… not because the news was getting better, just because I was spending more time on the
prospect. The investment didn’t quite meet our hurdle rate. We were not able to negotiate a structure that
got us an extra couple of points of IRR, and the big one got away. The difference between investing and
not, was tiny.

Currently, we have 26 Operating Group and Portfolio Managers who spend >50% of their time on M&A,
and another 60 full-time M&A professionals spread across CSI. We are trying to ramp up our M&A
capacity from the 40 acquisitions that we did last year, to 100 per annum. It was useful for me to once
again experience the temptations that these people face every day. It also reaffirmed for me that when we
pursue a very large acquisition, the diligence, structuring, negotiating and integration needs to be led by a
single person who is one of our highly-experienced acquirers, and who will shoulder responsibility for the
process and the outcome.

Bernie tries to be the last line of defense when our Operating Groups and BU’s propose borderline
investments. Some of our Operating Groups have developed or are developing senior M&A people to
help Bernie filter out over-optimistic acquisition proposals, but Bernie is still the primary provider of this
acquisition control function for some of the Operating Groups.

If a small investment with a borderline hurdle rate is proposed, we sometimes allow it to proceed. Our
rationale is that if the investment goes sideways, then it becomes a “lesson” for the Operating Group or
BU personnel that proposed it. If the investment goes well, it becomes a “lesson” for Bernie and me.

An investment only becomes a lesson if we diligently track its post-acquisition performance and take the
time to analyse the outcome while the investment is still fresh in everyone’s mind. We have a process for
this that we call a post-acquisition review, or “PAR”. We try to schedule the PAR’s about a year after the
initial investment. The PAR’s originated as a head office led process approximately four years ago. Just
over a year ago, we started delegating them down to the Operating Groups.

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One of the useful things that head office can do, is pilot new processes and champion new ideas. If the
ideas add enough value to the BU’s and Operating Groups, and they choose to maintain them, then I’m
delighted. Nevertheless, I think all processes should be periodically re-examined for their cost and
benefit. An ad-hoc analysis done to understand a problem or opportunity is more likely to translate into
action than a quarterly report that gets generated because “we’ve always done it that way”. The former
requires curiosity and intelligence, the latter bureaucracy and compliance. If the Operating Groups can
learn from their acquisitions by some less burdensome method than PAR’s, I’m all for it.

As we teach more people at CSI how to deploy capital, we lean on the accumulated data from our
historical acquisitions to help maintain investment discipline. We have base rates for a variety of key
operating metrics. Whether it is a neophyte investment champion arguing that a particular acquisition is
“special”, or a senior executive being tempted by a large acquisition, we have enough data to make the
discussion rational, not emotional. We all know whether the key assumptions are being pushed to the 55th
or 95th percentiles of our historical distributions.

My only significant concern regarding investment discipline, is that we’ll be tempted to drop our hurdle
rates as our cash balances climb.

Avoiding Overhead Creep:

Overhead creep is a short-term concern of mine and the BU Managers.

It is human nature to build empires. The slippery slope looks something like this:
I add value to the CSI Operating Groups and BU’s, and CSI is doing well, hence the expenditures that
I make at head office are justified.
Our Operating Group Managers add value to their BU’s, and their Operating Groups are doing well,
hence their expenditures are justified (although they find the expenditures at head office questionable).
The Portfolio Managers who work for the Operating Group Managers add value to their BU’s hence
their expenditures are justified, etc., etc.
There’s no real feedback in the process, until the costs of head office, the Operating Groups, the Portfolio
Managers and their staff, and the Player/Coaches who work for the Portfolio Managers, all get allocated
down to the BU’s. We do this allocation, but the BU Managers often don’t feel that they can control
allocated overheads.

The only way we’ve been able to consistently stifle overhead growth at head office is to arbitrarily limit
headcount additions. That has allowed us to reduce the head office burden from 3.0% of Net Revenue in
2004, to 0.5% last year. We hope it will be lower in 2017.

I have struggled to find a less arbitrary means of appropriately sizing overheads. A couple of years ago,
our head office tax folks seemed to have an insatiable appetite for increased headcount. I couldn’t argue
with their justification, but I asked them to start billing the Operating Groups for the incremental services,
separate from our normal overhead allocation. There were two short-term results… our head office tax
people hated billing the Operating Groups and justifying their bills, and one of the Operating Groups went
off and hired their own tax person. The long-term result also pleased me: the head office tax people have
stopped asking about hiring additional staff. Now, if I could just figure out how to stop them spending all
that money with outside tax consultants…

Each of the Operating Groups is the equivalent of what CSI was ten years ago (plus or minus three years).
If every Operating Group manages to develop six or seven Portfolio Managers to whom they can
download the monitoring, coaching and acquisition control functions, and seeks to operate their

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remaining overheads with cost parameters similar to those that CSI’s head office exhibited at the
comparable time/size of portfolio, then overhead creep should be controllable.

Increasing Investment in Growth, both Organic and Acquired

This is a big topic. The Operating Group Managers and I are concerned that our BU’s are not investing
enough in the pursuit of profitable Organic growth. Equally important, we would like to see the company
investing all of its FCF (and perhaps more) in acquisitions.

I believe that optimising organic growth investment is the single toughest management task in software.
It requires a long-term orientation and an intimate understanding of customers and capabilities from our
BU Managers. Historically, organic growth has not been a struggle for our best BU Managers. When
most of our current Operating Group Managers ran single BU’s, they had strong organic growth
businesses. As those managers gave up their original BU management position to oversee a larger Group
of BU’s (i.e. became Portfolio Managers), the organic growth of their original BU’s decreased and the
profitability of those BU’s increased. Perhaps those trade-offs were rational and inevitable, and it was
just a function of maturing verticals and higher market share. Nevertheless, once you’ve experienced
higher organic growth with all of its ancillary benefits for employees and for the depth and radius of your
business moat, the move towards higher profit and lower growth is much less satisfying. Across the
board, our Operating Group Managers have organic growth as the primary objective for their BU
Managers.

When we study organic growth, there are no easy answers from CSI’s data. We are just as likely to have
good organic growth in our small BU’s as in our large ones. We are just as likely to have good
profitability in our small BU’s as in our large ones. If you believe that small implies agile and responsive,
then the former observation is counter-intuitive. If you believe that economies of scale are the primary
drivers of profitability in the software business, then the latter observation is counter-intuitive.

One of my research acquaintances says that most people keep torturing the data until it confesses. In this
instance, we can do that… we can make a case for “small is beautiful”. Our businesses with fewer than
100 employees are a tiny bit more profitable and have a bit more organic growth. Unfortunately, we can
flip that finding by excluding only a couple of outlier data points. Despite the lack of compelling data, I
believe that small BU’s are more manageable and do a better job of serving clients in the VMS industry.
Sometimes belief and gut feel are all you have, and you must act upon them until there’s more evidence to
influence your thinking.

CSI’s BU demographics (as of December 2016) appear below. There are some BU’s that are independent
but are run by the same BU manager, that get aggregated as single BU’s into this tally, i.e. the total
number of BU’s is slightly higher and the average size is slightly lower than indicated in Table 4.

Table 4
# of BU's BU Size (Employees)
6 >200
29 100-200
158 <100

CSI's strategy is to be a good owner of hundreds (and perhaps someday thousands) of growing
autonomous small businesses that generate high returns on capital. Our strategy is unusual. Most CEO's
of public companies would rather run a single big business - perhaps two or three big businesses, but
rarely 200 businesses. They expect (or hope) to get above average returns on capital by pursuing

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economies of scale and by crushing or acquiring their smaller competition. "We are #1 in this large and
growing market" is their normal aspirational paradigm. It's also a formula with which shareholders,
analysts and boards are comfortable. We recognise that economies of scale, centralised management and
world class talent competing in large and growing markets can be a great business-building formula. But,
it isn't what we do.

We seek out vertical market software businesses where motivated small teams composed of good people,
can produce superior results in tiny markets. These markets are usually characterised by a gradually
consolidating customer base, so partnering with the right clients, and helping them survive and prosper is
an important part of our job. What we offer our BU Managers is autonomy, an environment that supports
them in mastering vertical market software management skills, and the chance to build an enduring and
competent team in a “human-scale” business.

While we have developed some techniques and best practices for fostering organic growth, I think our
most powerful tool is using human-scale BU’s. When a VMS business is small, its manager usually has
five or six functional managers to work with: Marketing & Sales, Research & Development ("R&D"),
Professional Services, Maintenance & Support and General & Administration. Each of those functional
managers starts off heading a single working group. If the business leader is smart, energetic and has
integrity, these tend to be halcyon days. All the employees know each other, and if a team member isn't
trusted and pulling his weight, he tends to get weeded-out. If employees are talented, they can be quirky,
as long as they are working for the greater good of the business. Priorities are clear, systems haven't had
time to metastasise, rules are few, trust and communication are high, and the focus tends to be on how to
increase the size of the pie, not how it gets divided. That's how I remember my favourite venture
investments when I was a venture capitalist, and it's how I remember many of the early CSI acquisitions.

That structure usually suffices until there are perhaps 30 to 40 people in the business. At that stage, some
of the teams - perhaps R&D if the product is rapidly evolving or has high needs for interfaces or
compliance changes - must grow beyond the five to nine optimal team size. If the head of R&D in this
example is brilliant and is willing to work hours that are unsustainable for most of us, he may be able to
parse out tasks for each of the team members despite the increased team size. He may be able to judge
the capabilities and cater to the development needs of each of his direct reports. He may be able to recruit
excellent new employees, and he may be able to manage the demands and trade-offs required to co-
ordinate with the other functional managers. The more likely outcome, is that the R&D manager isn't a
brilliant workaholic and cannot cope as the team size exceeds double digits. Instead, he'll break his team
up into multiple teams. A new level of middle managers will be born, with all the potential for overhead
creation, politics, and bureaucracy that comes with another tier of middle managers.

The larger a business gets, the more difficult it becomes to manage and the more policies, procedures,
systems, rules and regulations are generated to handle the growing complexity. Talented people get
frustrated, innovation suffers, and the focus shifts from customers and markets to internal communication,
cost control, and rule enforcement. The quirky but talented rarely survive in this environment. A huge
body of academic research confirms that complexity and co-ordination effort increase at a much faster
rate than headcount in a growing organisation.

If the BU is small enough, and has a competent BU manager who has several years experience in the
vertical, and good functional managers, then he/she will be able to cope with complexity for a while,
making the right calls to optimise organic growth as the business grows. The challenge of running a BU
of this size is human-scaled. As a BU becomes larger (by our standards, that’s greater than 100
employees), I worry that even an extraordinarily brilliant and energetic manager, who has been in the
vertical and the BU for a very long time, and is surrounded by a strong team that he/she has selected and

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trained and winnowed over many years, is going to struggle to steer the business to above industry-
average organic growth.

No one wants to admit that they’ve hit their limit. Some BU Managers lack the humility, some lack the
courage, and most lack the time for reflection, to notice that their task is getting too large, and the
sacrifices are getting too great. This is the point at which our Operating Group Managers or Portfolio
Managers can provide coaching. If a large BU is not generating the organic growth that we think it
should, the BU manager needs to be asked why employees and customers wouldn't be better served by
splitting the BU into smaller units. Our favourite outcome in this sort of situation is that the original BU
Manager runs a large piece of the original BU and spins off a new BU run by one of his/her proteges.
Ideally, he/she has been grooming a promising functional manager who’ll be enthusiastic about running
and growing a tightly focused, customer-centric BU.

This dividing of larger BU’s into smaller units is rare, but not unknown, in other large companies. One of
the HPC’s that we studied was Illinois Tool Works Inc. (“ITW”). It has hundreds of BU’s. We began
following the company from afar in 2005. The most relevant period in ITW’s history for CSI was the
tenure of John Nichols. Nichols began consulting to ITW in 1979, and appears to have been the primary
author of its decentralisation strategy. He was CEO as the company went from $369 million in revenues
in 1981 to $4.2 billion in 1995 ($6.7 billion in today’s dollars). Prior to Nichols's tenure, ITW had
acquired only 3 businesses. During his tenure, ITW aggressively acquired and often split the larger
acquisitions into smaller BU’s. ITW had 365 separate operating units by 1996 when Nichols retired. I’m
sorry I didn’t reach out to some of the ITW employees and ex-employees until 2015. When I did talk
with one of the senior managers, he said (I’m paraphrasing) “Something wonderful happens when you
spin off a new business unit.” … “With a clean sheet of paper, the leader only takes those he needs. They
set up in an open office with good communication and no overheads. They cover for each other. They
leave all the bureaucracy and the crap behind”. I did record a couple of verbatim quotes from that
conversation: "Don't share sales, R&D, HR, etc. because the accountants never get the allocations right
and the business units always treat the allocated costs as outside their control", and "When you get big
you lose entrepreneurship".

I don’t want to give you the impression that the "human-scale" BU idea is a universally accepted doctrine
in our ranks. For that, I suspect we’d need more compelling data. However, we have been successfully
experimenting with the concept for a long time. Volaris and TSS regularly divide their larger BU's into
smaller BU's that focus on sub-segments of their markets. Volaris feels strongly that splitting larger BU’s
into smaller ones allows more targeted products and services that differentiate their offerings from their
more horizontal competitors. Harris has very successfully acquired multiple BU's in the same industry
and run them independently rather than combining them into one BU. Both tactics forego obvious and
easily obtainable benefits from economies of scale. We think we get something valuable when we
constrain BU headcount, but it isn’t a panacea for all of our organic growth challenges.

The other way we grow is via acquisitions. The vast majority of our acquisitions fall into the sub-100
employee category and were owner-managed prior to our acquisition. In 2016 we made 40 acquisitions,
of which 35 had fewer than 100 employees. 30 of those acquisitions were from owner-managers.

I believe that CSI can be a great home for an owner-managed business. If the business has more than a
handful of employees, we nearly always run it as a stand-alone BU. We respect the vertical-specific
knowledge of the employees and give them the chance to learn from employees running similar
departments and functions in our other BU’s. We don’t sunset products and we believe that customers
and BU Managers, not head office CTO’s or product strategists, should choose which products get
continued investment. If the owner-manager wants to transition out quickly, the probability is very high
that the successor that he/she designates will end up running the business for CSI. If the owner-manager

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wishes to stay for several years, perhaps spending less time on day to day management and more on
acquisitions, then we are just as happy with that outcome. If you are an owner-manager of a VMS
company and fall into either camp, we can arrange for you to meet with former owners like yourself who
have sold to CSI.

We have best practices for acquisitions, just as we have best practices for fostering organic growth.
When our BU managers encounter natural limits we coach them on how to get the most leverage from
their skills and team. We apply a similar model when our Portfolio Managers encounter the limits to their
monitoring, coaching, and acquisition related activities. I was CSI’s first Portfolio Manager. Somewhere
between mid-2005 and mid-2006, I ran out of capacity. CSI had $200 million in revenue, seven
Operating Groups and about thirty BU’s at that time. I could do the short-term BU monitoring portion of
the job, but I couldn’t stay abreast of the important longer-term factors for the BU’s: details about
competitors, market share, major customers, product strategy, initiatives, management competencies, etc.
Without those details, my ability to provide context-sensitive coaching for BU Managers and Portfolio
Managers rapidly deteriorated. I had been involved in all the large acquisitions that CSI had done up until
2005 and I had chased down a second significant acquisition for several of those verticals. By 2006 I
could no longer be the primary driver of our acquisition activities. I began to ask our Operating Group
Managers to shoulder the entire responsibility for monitoring and coaching their BU’s and to also assume
responsibility for deploying the majority of our FCF.

I didn’t have complete confidence in a couple of the Operating Group Managers so the delegation process
dragged on for a while. We eventually terminated two managers. It cost us some severance pay and time
but we were able to find capable and trusted replacements from within CSI. There was a bit of a hiccup
in our growth in 2006 and 2007 but the current Operating Group Managers - Barry, Dexter, Jeff, John,
Mark, and Robin - have driven most of our capital deployment since 2006. They’ve developed their
teams, put their own unique stamp on their groups and done a magnificent job of growing CSI’s revenue
and FCF per share by more than tenfold. Each is now running a group of BU’s that is similar in size to
CSI when I ran out of capacity. All of the Operating Group Managers have started the process of
delegating their monitoring, coaching, and acquisition activities down to their Portfolio Managers, so the
cycle begins anew.

When I look at the current generation of Portfolio Managers, I see some that have the potential to be
exceptional managers and capital deployers. While that bodes well for continued growth, there aren’t
enough of them to get us the ten-fold growth that we’ve had in the last eleven years. To generate that sort
of growth, we need more Portfolio Managers and they need to be as competent as our current Operating
Group Managers. That’s a tall order. It will require an intense training and coaching effort with our
existing Portfolio Managers, possibly some outside hires into Portfolio Manager roles, and the
acceleration of some existing BU Managers into Player/Coach and Portfolio Manager roles. Until these
Portfolio Management roles are filled with people that have the complete confidence of their Operating
Group Managers, delegating the majority of capital allocation won’t happen, and the sustainable 20% plus
growth rates of the past are impossible.

In December, we asked our Operating Groups to identify new “Potential Portfolio Managers”. The good
news was that there were 45 BU Managers on the list and 84% of them had been internal promotions to
BU manager, or had arrived as part of an acquisition. The bad news is that newly identified high-
potential BU Managers must first demonstrate that they can run a BU well, build a team, and generate
optimal organic growth. Then they need to learn some non-trivial M&A skills. They’ll have lots of
support in this process, but it doesn’t happen overnight. If we manage to get even a dozen of these 45 BU
managers to the point where they are running 500-1000 employee portfolios in ten years’ time, that will
be a huge achievement.

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I have a bias towards developing our Portfolio Managers internally or having them join us via an
acquisition. Our best managers have risen through the ranks and developed a following. When they
make it to BU Manager, they act like they “own” their BU and they stick with it. They have career-
spanning relationships with their employees and their clients. They feel responsibility heavily. If the
industry they serve is suffering, they find a way to grow the business organically, or they roll up their
vertical via acquisition. They progress to running one BU and coaching others. If they’re ambitious for
themselves and their team, they evolve into deeply experienced Portfolio Managers with a tried and
trusted cadre of employees that can help them do acquisitions and they continue to build out their
Portfolio. It starts small. It’s incremental. It’s slow, but over the course of a long career their mastery,
satisfaction, wealth and the number of their followers, all compound.

This sort of career path obviously worked for our current Operating Group Managers, who all either came
up through the ranks or joined us via an acquisition. I believe that attracting, developing, and keeping
that sort of talent, is the internal execution issue that poses the greatest threat to our continued success.

I don’t know if the analysts and journalists who predict reversion to average performance for CSI will be
proved correct in the next few years. Our plan is to maintain investment discipline, keep overheads low
and hire and coach a new generation of ambitious, hard-working BU Managers who can be taught how to
be competent long-term “owners”. Hopefully we’ll still be having this reversion debate ten years from
now.

Some businesses get their unique advantage from government-granted monopolies, some from natural
resources, some from large patent portfolios, and some from enormous fixed assets. CSI doesn’t have
these advantages. Our employees, and the customer relationships that those employees have built and
fostered over many years, provide our competitive advantage. I hope all of our shareholders will join me
in thanking our thirteen thousand employees for the company’s continued prosperity.

We will be hosting the AGM on Friday, April 28th. Many of our Directors and Officers and a number of
our employee shareholders will be in attendance. We look forward to talking about our business and
answering your questions. We hope to see you there.

Mark Leonard,

President

Constellation Software Inc.

April 25th, 2017

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Glossary

For 2009 and prior periods, the financial information for CSI was derived from the consolidated financial
statements which were prepared in accordance with Canadian generally accepted accounting principles
(“GAAP”). 2010 and subsequent year financial information for the Company was derived from the
consolidated financial statements which were prepared in accordance with International Financial
Reporting Standards (“IFRS”). Certain totals, subtotals and percentages may not reconcile due to
rounding.

‘‘Adjusted net income’’ effective Q1 2008, means adjusting GAAP or IFRS net income for non-cash
expenses (income) such as amortization of intangible assets, deferred income taxes, the TSS membership
liability revaluation charge, and certain other expenses (income), and excludes the portion of the adjusted
net income of Total Specific Solutions (TSS) B.V. (“TSS”) attributable to the minority owners of TSS.
Prior to Q1 2008, Adjusted net income was derived by adjusting GAAP net income for the non-cash
amortization of intangibles and charges related to appreciation in common shares eligible for redemption.
The calculation was changed to include future income taxes since the majority of future income taxes
relate to the amortization of intangible assets, and thus are added back to more closely match the non-cash
future tax recovery with the amortization of intangibles. All previously reported Adjusted net income
figures have been restated in the table above to reflect the new calculation method. The Company
believes that Adjusted net income is useful supplemental information as it provides an indication of the
results generated by the Company’s main business activities prior to taking into consideration
amortization of intangible assets, deferred income taxes, the TSS membership liability revaluation charge,
and certain other non-cash expenses (income) incurred or recognized by the Company from time to time,
and adjusts for the portion of TSS’ Adjusted net income not attributable to shareholders of CSI.

“Average Invested Capital” represents the average equity capital of the Company, and is based on the
Company’s estimate of the amount of money that its common shareholders had invested in CSI.
Subsequent to that estimate, each period the Company has kept a running tally, adding Adjusted net
income, subtracting any dividends, adding any amounts related to share issuances and making some
minor adjustments, including adjustments relating to our use of certain incentive programs and the
amortization of impaired intangibles. The Company believes that Average Invested Capital is a useful
measure as it approximates the retained earnings of the Company prior to taking into consideration
amortization of intangible assets, deferred income taxes, and certain other non-cash expenses (income)
incurred or recognized by the Company from time to time. ROIC” means Return on Invested Capital and
represents a ratio of Adjusted net income to Average Invested Capital. The Company believes this is a
useful profitability measure as it excludes non-cash expenses (income) from both the numerator and
denominator.

“Net Revenue”. Net Revenue is gross revenue for GAAP or IFRS purposes less any third party and flow-
through expenses. The Company believes Net Revenue is a useful measure since it captures 100% of the
license, Maintenance and services revenues associated with CSI’s own products, and only the margin on
the lower value-added revenues such as commodity hardware or third party software.

“Total Capital” is the sum of Net debt plus Invested Capital

“Net Debt” is debt less cash.

“Maintenance Revenue” primarily consists of fees charged for customer support on our software
products post-delivery and also includes, to a lesser extent, recurring fees derived from software

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as a service, subscriptions, combined software/support contracts, transaction-related revenues,
and hosted products.

“Free Cash Flow” in this letter, unlike under IFRS is cash flow from operating activities less interest paid
and property and equipment purchased. I figure if you have to pay interest and buy new computers, the
cash used for those purposes is no longer available, and shouldn’t be included in FCF.

“EBITA” is earnings before interest, taxes and the amortisation of intangible assets.

“HPCs”: Ametek, Berkshire Hathaway, Danaher, Dover, Illinois Tool Works, Roper, Jack Henry &
Associates, Transdigm, and United Technologies.

Forward Looking Statements

Certain statements in this letter may contain “forward looking” statements that involve risks, uncertainties
and other factors that may cause the actual results, performance or achievements of the Company or
industry to be materially different from any future results, performance or achievements expressed or
implied by such forward-looking statements. Words such as “may”, “will”, “expect”, “believe”, “plan”,
“intend”, “should”, “anticipate” and other similar terminology are intended to identify forward looking
statements. These statements reflect current assumptions and expectations regarding future events and
operating performance as of the date of this letter. Forward looking statements involve significant risks
and uncertainties, should not be read as guarantees of future performance or results, and will not
necessarily be accurate indications of whether or not such results will be achieved. A number of factors
could cause actual results to vary significantly from the results discussed in the forward looking
statements. Although the forward looking statements contained in this letter are based upon what
management of the Company believes are reasonable assumptions, the Company cannot assure investors
that actual results will be consistent with these forward looking statements. These forward looking
statements are made as of the date of this letter and the Company assumes no obligation, except as
required by law, to update any forward looking statements to reflect new events or circumstances. This
report should be viewed in conjunction with the Company’s other publicly available filings, copies of
which can be obtained electronically on SEDAR at www.sedar.com.

Non-GAAP/IFRS Measures

Adjusted net income and Organic Net Revenue Growth are not recognized measures under GAAP or
IFRS and, accordingly, shareholders are cautioned that Adjusted net income and Organic Net Revenue
Growth should not be construed as alternatives to net income determined in accordance with GAAP or
IFRS as an indicator of the financial performance of the Company or as a measure of the Company’s
liquidity and cash flows. The Company’s method of calculating Adjusted net income and Organic Net
Revenue Growth may differ from other issuers and, accordingly, may not be comparable to similar
measures presented by other issuers. Please refer to CSI’s most recently filed Management’s Discussion
and Analysis for reconciliation, where applicable, between the IFRS, GAAP and non-GAAP/IFRS
measures referred to above.

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