How We Doubled a Software Company in the Final Two Years Before Exit
Many people have asked how to prepare a software company for an eventual exit, what the process looks like end-to-end, and what it takes to double a business over a two-year period while maintaining profitability. I’ve heard these questions from founders, operators, private equity professionals, and friends, so I thought I’d share the experience as it actually unfolded.
If there’s a useful insight here for someone building or scaling a software company, then writing this will have been worthwhile.
This isn’t a playbook or a formula. It’s simply what happened — a two-year journey from a strong foundation to doubling the company while staying profitable. Let’s begin.
A Quiet Question at the End of 2019
At the end of 2019, I was enjoying running the company. I wasn’t looking to step away, but I began thinking more seriously about optionality. A simple question surfaced:
Do I want to run this company indefinitely, or might I one day want to sell?
I wasn’t sure of the answer yet. But I did know one thing: if I were ever going to sell, I didn’t want to sell at a plateau. I wanted the company to be operating at its best.
At the time, we were an enterprise software company that had not taken on venture capital, private equity, or debt. This meant that by necessity we had to be extremely capital-efficient.
We served professional services firms — accounting, consulting, and especially large law firms. We had over a thousand enterprise deployments and a strong presence among large law firms globally. Top-line growth was in the 15–20% range, and EBITDA margins were in the mid-60% range. The company was healthy. Nothing was broken.
We were well regarded and trusted by our customers. Over the years, private equity firms and strategic buyers reached out periodically. I never returned those calls — I was focused on building the business.
But I told myself that if I ever did decide to explore a sale, I wanted the company to be in the best possible position.
That led to a private and ambitious goal: double the company’s topline revenue over two years while maintaining profitability.
To understand why this was challenging, it helps to look at the Rule of 40 — a common software benchmark where a company’s growth rate plus profit margin should equal 40. For example, 20% growth and 20% profitability would meet that standard.
At the time, we were already operating well above that threshold. The goal was to push much further — toward a profile that combined roughly 40% growth with mid-60% EBITDA margins.
It was an aggressive target, but one I felt was worth pursuing.
The Conference in December 2019
A few weeks later, I flew to a conference. Travel always gives me clarity — I step out of my routine, and the noise falls away. Travelling is actually one of my favorite ways to solve a strategy problem or any challenge for that matter. One afternoon, I took a notebook into a quiet conference room at the hotel and closed the door.
Over the course of a few hours, a clear strategy began to take shape.
Only later did I realize that what I had written closely resembled a private-equity style growth plan. I wasn’t trying to emulate one. The approach simply emerged from focusing on the most effective growth levers available, using only what the business already had and without taking on outside capital or debt. That constraint forced discipline, efficiency, and focus.
Below are the six steps that ultimately helped us double the company while staying profitable.
1. The Wave Platform — Our Keystone
Our user interface was solid and functional, and it had served us well. As the product suite matured, it became clear that a more cohesive and modern UI/UX would help modernize the look and feel of the software and tie the entire platform together. At the time, we had six products, all built on a single enterprise software foundation.
Around this period, Salesforce released Salesforce Lightning. We used Salesforce extensively for customer relationship management, sales operations, and customer care, so I paid close attention. Lightning introduced a new user experience. The most interesting part wasn’t the interface itself — it was the strategy behind it.
If you wanted access to Salesforce’s newer modules, you had to adopt Lightning across the board. Once you did, everything else followed.
That approach stood out to me.
Steve Jobs once said:
“Good artists copy; great artists steal.”
I don’t believe in stealing, but I do believe in borrowing strong ideas and adapting them thoughtfully. We decided to create our own version of that approach — a single, unifying initiative that could anchor the rest of the strategy and give the product suite a shared identity following the redesign.
I spent some time thinking about what to call it, until one name felt right:
Wave.
The Wave Platform.
It felt clean, energetic, and symbolic — like momentum moving through the organization and across the product line.
We hired UI/UX designers, re-skinned every module, and rebuilt the user experience from the ground up. The legacy interface became “Classic.” Everything new would live on Wave.
Wave became the user experience reset the company needed, and it provided a clear foundation for the initiatives that followed.
2. Build the Seventh Product (Resource Allocation)
We had six enterprise modules in our strategic people-management suite. As part of the broader growth plan, we decided to add a seventh. One of the advantages of vertical market software is that it’s often easier to introduce additional products within the same vertical than to take a new product across many different markets.
Before deciding what that product should be, I spent time speaking with customers about their most pressing operational challenges. The same theme came up repeatedly.
Resource allocation — staffing the right people on the right projects at the right time. For professional services firms, this is the core of the business: assembling teams to do billable work efficiently and predictably.
This was before the COVID pandemic.
Resource allocation emerged as a clear opportunity, and we chose to build the new product natively on the Wave platform. In retrospect, the timing proved to be significant.
Shortly after we launched internally, COVID hit. Large law firms with hundreds or thousands of professionals suddenly shifted to fully remote work. Staffing projects — already a complex task — became much more difficult.
The new product addressed a problem that had quickly become more acute, and customer interest increased accordingly.
3. Migrate Customers to the Cloud
Another pillar of the strategy was modernizing our delivery architecture.
We deepened our partnership with Microsoft and committed fully to Azure. Over time, we built a multi-location Azure deployment, introduced a cloud program with multi-year contracts, and transitioned customers — including legacy on-prem and subscription users — to the cloud.
This shift helped:
improve performance and security
simplify infrastructure
increase reliability
better align contracts with delivered value
support the product roadmap ahead
It also created a more scalable commercial model, with the Wave platform delivered through our Azure cloud environment.
4. Update the Price Book
With Wave in place, a new product built, and cloud migration underway, it was the right moment to rebuild our pricing model from the ground up.
We introduced:
new modular pricing
new product packages and bundles
cloud incentives
a full-suite adoption model
A clean, disciplined commercial reset.
5. Charge for Implementations
Historically, implementations were bundled into our annual SaaS (Software as a Service) subscription fee. This made sense early on, but with growth accelerating, it was time for a change.
We shifted to charging implementation fees as a percentage of annual subscription value. This improved:
margins
delivery scoping
customer outcomes
And it funded many of the new hires we needed for the growth plan.
6. Rebuild the Entire Go-To-Market Engine
To support the broader strategy, we strengthened every part of the go-to-market function:
hired a senior marketing leader
hired a demand generation manager
built an outbound SDR (Sales Development Representatives) team
upgraded sales talent
redesigned the sales compensation plan
implemented a modern GTM technology stack
rebuilt the sales methodology
Together, the above six steps supported the goal of doubling the company’s revenue over a two-year period.
With these pieces in place, the organization was aligned around the Wave platform, the new product, and the cloud program.
Internal Alignment: Launching Wave Inside the Company
Before sharing The Wave Platform more broadly, we introduced it internally.
We held an all-hands meeting to walk through the direction of the company and the changes ahead. The team understood where we were going and what we were building toward. It marked the beginning of a multi-quarter, multi-year effort that would require patience, focus, and discipline.
It reminded me of the well-known marshmallow test: the work happens now, and the reward comes later. This phase of the journey was about delayed gratification and committing to a longer-term goal.
February–July 2020: Preparing to Execute the Strategy
As mentioned earlier, our financial year ended on July 31. That timing provided a natural lead-in before formally starting the initiative to double the company. There was a clear ramp-up period.
One of the first steps was a webinar for customers and prospects in February 2020, shortly before COVID. It was an opportunity to introduce Wave, along with the new product structure and bundles. Attendance was strong, and the timing proved fortunate — a month later, when COVID disrupted everything, it would have been much harder to convene that audience.
From February through July 2020, we focused on preparation internally:
officially launching Wave with the new branding and transitioning prior products to “Classic”
presenting the strategy to customers and prospects
aligning engineering, sales, marketing, operations, and implementation
completing technical work on Wave
building the cloud program
updating pricing
strengthening the go-to-market engine
By the end of that period, the plan was in place, the organization was aligned, and we were ready to begin executing.
August 1, 2020 — Pedal to the Metal
Our financial year began on August 1, 2020, and this marked the point at which the two-year clock officially started.
The objective was clear: double the company’s revenue within two financial years, by July 31, 2022.
From that point forward, execution became the focus. Across the business, we saw steady progress in several areas:
adoption of the Wave platform
cloud migrations
demand for the resource allocation product
top-of-funnel pipeline
contract value
customer expansion
By July 31, 2021 — the end of the first year of the strategy — the core elements were in place and performing as expected. The company was growing, and momentum was beginning to build.
One lesson that became clear during this period was that growth of this kind is non-linear. There is inertia to overcome early on, followed by a phase where progress compounds more quickly.
The doubling trajectory was visible, but it required continued focus and consistent execution.
End of 2021 — To Sell or Not to Sell?
By the end of 2021, I was about a year and a half into the two-year strategy. The core elements were in place, and the plan was unfolding as intended.
To sell or not to sell — that was the question.
Toronto had reopened briefly for Christmas after an extended COVID lockdown. I remember returning to the gym during that short window. Shortly after New Year’s, the Omicron variant emerged and the city went into lockdown again.
I booked a one-way ticket to Miami. I needed warmth, running weather, and some distance to think clearly.
We were roughly three-quarters of the way through the doubling plan. The Wave platform was gaining traction, the new product was being adopted, customer retention remained strong, and sales performance was steady.
At the same time, software company valuations were particularly strong.
The timing felt aligned.
I returned the call to the investment bankers who had reached out over the years and said,
“Guys, it’s showtime.”
At that point, I decided to formally explore a sale of the company. We began working with the bankers on the preparation process, including historical performance, the product roadmap, and forward-looking plans. It was a rigorous exercise, and it offered a new perspective on the business I had been focused on building day to day.
The Final Six Months — Pressure and Precision
Once the sale-of-the-company process began, the pressure increased noticeably. Private equity firms and strategic acquirers were now reviewing performance closely. As mentioned earlier, doubling a business is rarely linear, and the final six months required sustained focus and execution to stay on track.
Performance was being monitored frequently, and there was little room for error. Customer retention and growth needed to remain steady throughout this period.
I found that pressure clarifying. It sharpened priorities across the organization and reinforced the importance of execution. The team responded well, and we continued to deliver quarter after quarter.
In the final two quarters of the year — ending April 30 and July 31 — the sales team met their targets very closely. I remember a meeting about two weeks before quarter-end where I used a Michael Jordan analogy. Jordan won his championships in Game 6 rather than pushing things to Game 7, viewing it as a way to reduce unnecessary risk.
We aimed to close the quarter early for the same reason, but that didn’t quite happen. Going into the final week, I remember saying, “We’re going to Game 7.” The team stayed focused, and the quarter came together in the end.
Hitting the Goal
By the end of the second year, on July 31, we had doubled the company’s revenue. The result was very close to the original target.
Top-line growth reached approximately 40%, while EBITDA margins remained in the mid-60% range. In practical terms, this put the business well above the Rule of 40 benchmark.
The outcome reflected the cumulative effect of a series of focused decisions over time. Progress compounded gradually, and the results aligned closely with the original goal.
The company was subsequently acquired by Roper Technologies, a long-term owner of mission-critical software businesses. Looking back, I’m comfortable with the decision and how the process unfolded.
A Team Effort
Although I’m the one writing this article, the outcome was very much a team effort. Across engineering, implementation, support, marketing, sales, product, and operations, people showed up consistently and did the work required to make the plan real.
What made the difference wasn’t individual heroics, but alignment around a shared goal.
Clarity Comes From Stillness
The entire two-year journey began in a quiet conference room with nothing but a notebook and a simple question:
Do I want to run this company indefinitely, or might I one day want to sell?
Looking back, the process of growth was as meaningful as the outcome itself. The work required patience, discipline, and sustained focus, and I found that journey deeply rewarding.
An added benefit was the clarity it brought. The path helped me think more clearly about what I wanted to do next, and the conversations that followed during the sale process naturally opened the door to the next chapter.
Sometimes the most important decisions begin in silence.
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