Roadmunk wins a spot on Deloitte’s 2019 Technology Fast 50™

Latif Nanji
Nov 7, 2019 · 5 min read
Deloitte’s Fast 50 recognizes technology companies with the highest revenue-growth percentage over the past four years.

Today is a special day in Roadmunk history — so strap yourself in, because it’s humblebrag time.

I’m proud to announce that our company made Deloitte’s Technology Fast 50. It’s Deloitte’s way of honouring the 50 Canadian technology companies with the highest revenue-growth percentage over the past four years. We scooped up the 12th spot on the list.

But the celebrations don’t end there. Roadmunk also ranked № 96 in Deloitte’s Technology Fast 500, its annual ranking of the 500 fastest-growing technology companies in North America.

These two awards from Deloitte mean a lot to the Roadmunk team. It gives us a chance to celebrate our growing global customer base, as well as our Canadian roots in Toronto and the Kitchener-Waterloo area, where we continue to grow our team and innovate our product.

It’s a big win for us and we’re extremely proud of this achievement.

Last year, we published this medium post going over Roadmunk’s biggest challenges, surprising delights + hard-knock lessons since 2013 (the first year of Roadmunk’s existence). So we thought we’d update it with the years 2018–2019 as part of our celebrations.


Being away from the business to meet and vet investment firms had one unfortunate side effect: it took the leadership’s attention away from the work being done by their teams.

We came back to a lower eNPS (Employee Net Promoter Score), which was late in the year when teams are sprinting to ship, sell and operationalize before heading off for the holidays. Thankfully, the team here has the grit and perseverance of salmon swimming upstream, and we came out stronger on the other side.

This did result in more work for leaders in the long term because we had to fix those issues that were born out of our absence. During this recovery process, we realized that we were in a stronger business position, so we walked away from that potential fundraising partner (they, ultimately, weren’t a good match for us).

We were able to successfully bootstrap the business ourselves without outside capital.

The most delightful: We were cashflow positive.

The average SaaS company — at a similar stage to Roadmunk — has likely raised more than $20 million dollars. And we’ve raised a tenth of that. This is thanks to our heavy investment in a flywheel business model that is driven by product-led growth and an excellent customer success team that provides world class service.

This all led to the addition of over 1,000 new customers in 2018 and put us in a cashflow positive position — something that I’m incredibly proud of the team for.

The biggest lesson: Find a leadership team that builds deep trust with one another.

I was recently listening to Ben Horowitz on a podcast and he said that “If most founders knew what they were getting into, they would never start a company.”

It’s hard not to empathize with that statement. but it sparks an interesting question: why do founders continue? For me, I wake up excited because I get to work with an ambitious, talented and energetic team every single day. We are solving hard and challenging problems. It can be very stressful.

But we learned that the amount of work and stress needs to be distributed among a strong leadership team or all that burden will lead to paralysis and a team won’t be able to scale.

Extract the time to find those people and invest in them. Spend the resources you need to find those people and the business moves faster.


Giving feedback is, without a doubt, one of the hardest things to do — even if you’re a skilled manager or leader.

A growing company = new layer of middle management and that = more 1:1s. And people are eager for feedback so that they can improve.

As leaders, we’re constant getting “I want more feedback!” as feedback. But it’s difficult to position and deliver critical feedback so that it lands (yeah, you probably need to deliver it multiple times) and it’s even more difficult to keep the recipient of said feedback accountable to it.

We completed management training this year (and it helped) but I do believe this is something that will continue to be a challenge as we scale.

The most delightful: Sending the team to work from beautiful Medellin, Colombia (which we wrote about here).

On top of that, another highlight this year has been watching the team solidify and grow to 110 people, which has allowed us to invest more time in deepening our relationships with our customers (read: a lot more plane rides for on-site visits) and getting to know them better.

This has allowed us to get a stronger understanding of common user pain points — and now we’re building a new feature set that addresses those headaches (spoiler alert: we’re introducing feedback and idea management into Roadmunk next year — our biggest release to date).

The biggest lesson: Our go-to-market plan had to change once we tapped into new data.

We saw that having a salesperson talk to a prospect before they become a customer is important. That’s because spending money requires having the right information, understanding how secure the application is, how Roadmunk will scale with that organization, and other questions that aren’t so obvious when you sign up for a software product like Roadmunk.

We had to balance being a demand gen, flywheel, customer-first/product-led growth organization with this new knowledge that sales has to play a bigger part in the user onboarding equation.

Looking ahead

I’m excited to see what the next year (and beyond) will bring!


For product people, by product people.