This isn’t the first time we’ve released our annual Year in Review late, and it probably won’t be the last.

But it’s a good problem to have.

Business has been busy. In the rush of the past few months, our usual end of year reflection has had to take a back seat.

So we hope you’ll excuse us putting out a year-end piece in February.

But man, what a hell of a year it was.

At the beginning of every new year, we thought we knew what to expect.

But by the end, every single time, we’re blown away.

2018 was a phenomenal year for Rootstrap.

We moved into a state-of-the-art, 20K square foot new office.

If it doesn’t have a foosball and ping pong table, is it really a new office?



We revamped our internal corporate framework and built a new high-performance sales organization.

And we launched a new iteration of our flagship service offering.

We broke ground with projects in new sectors and industries, and we landed whale clients like Google & MasterClass – things we could barely have dreamed of when we first started this company.

But perhaps most important, we clarified our focus in 2018.

And looking back, we couldn’t be more pleased with the results.

Let’s take a look at what we accomplished this past year.


Where We’ve Been


Goodbye Yellow Brick Roadmapping

Roadmapping started as a service offering of Neon Roots, the first iteration of our agency business. In essence, Roadmapping was a pre-development product workshop that sought to hone the concept of a digital product, validate the idea in the marketplace, and create a clear roadmap towards a full development engagement.

It was so successful that we had to partner with a Uruguayan development shop called TopTier Labs to handle our client flow. Eventually, the success of Roadmapping led us to merge both agencies under a new banner: Rootstrap.

Roadmapping helped us grow. But it also came to define our company ethos.

Instead of just building pretty products, our mission has always been to offer development services grounded in strategy that advance our clients’ real business goals instead of just building pretty products. Roadmapping iconified that ethos.

But alas, all things must come to an end. And after 7 years of Roadmapping, we’ve come to see the flaws in the model.

The problem with our original Roadmapping workshop was that it spent too much time on minutiae, too early in the process. While pre-development discovery work is important, it’s a double-edged sword – and too often, clients would get caught in a holding pattern of endless analysis.

So now, we’re saying goodbye to Roadmapping and transitioning into a new format for our pre-development work: Discovery.

Discovery is Roadmapping 2.0: it’s leaner, faster, more strategic, and designed to generate better ROI for clients.

Discovery still allows us to answer the important questions before putting down development money, but it doesn’t trap us in pre-dev analysis paralysis or create unnecessary design waste.

It’s a lighter, better approach to our pre-development service offering. And we’re pleased to report that our clients are already seeing the results.


Open Source

Another key strategic change for us this year was a pivot away from building internal products.

Rootstrap has had its fair share of forays into developing internal products. Many have done well – Arbor and Pocket Buddy both went #1 on ProductHunt, and Goth Unicorns received tens of thousands of downloads on the App Store.

But on the whole, internal products were not a successful venture for us. All told, we invested over $500K into developing internal products, and while we learned a lot, we didn’t come close to a positive ROI.

That’s why in 2018, we moved away from developing our own products and focused on something new: our open source profile.

Instead of trying to build our own branded games and digital products, we’ve reprioritized giving back to the developer community.

We’ve steadily built a collection of open source code that’s available for anyone to use, both as a way to give back to the community and to amplify our brand. We’ve already had a few gems go trending on Github – check out our Rails API base and our Active Admin Chat plugin in particular – and we’re excited to keep it rolling in 2019.


Client Work

Besides building out our open source footprint, we redoubled our efforts in client work this year.

And the results were fantastic.We took on more projects than ever in 2018, expanding our horizons into new industries and new technologies. We also added some exciting marquee names to our client roster: Google, MasterClass, and Globalization Partners, to name a few.

What excites us most, however, is how diverse our client roster is getting. Here are a few of the industries we tackled with clients in 2018.


Enterprise: Google

Because of the unique value of our Roadmapping and Discovery workshops, we tend to work with a lot of startups. We’re proud of that: we’ve helped over 1,000 founders get funded and scale their business. But moving more into enterprise development has been a priority of ours for a while now, and this year, we made it happen.

While we had plenty of enterprise projects in the air this year, the most exciting for us had to be our work with Google.

For this project, we worked with the Google Opus team: a multifunctional team within Google that sought to create a new, centralized software product suite that would streamline and improve productivity in Google data centers. Essentially, Google wanted to design a new, one-stop-shop product suite for its data center teams and build it from the ground up.

They reached out to us for help, and our very own Design Director, Napoleon Martinez, organized and facilitated the sprint.

The result was a fast-paced, large scale design sprint involving 12 people over 2 days. The team dove deep into sprint goals, user requirements, challenges, and solutions to clarify a plan for the Opus team to move forward. Essentially, it was a Discovery workshop on steroids.


The Google Opus design sprint team hard at work.


While intense, the process was a resounding success, and the Google Opus team told us that they’d basically defined their next year of work in just 2 days. We’re pretty excited to have participated in this project and we’re looking forward to doing more innovative solution design work with Google – and of course, we’re all feeling pretty proud of Nap right now.


Ecommerce: Linhaus

At this point it’s practically a cliche to say ecommerce is the future of shopping, but that’s exactly why I’m so happy we’re keeping such a strong presence there. We worked on a ton of ecommerce projects last year, our favorite was probably Linhaus.

Linhaus is an ecommerce platform that’s going to revolutionize not just the wedding ring industry, but the greater jewelry industry at large. Because Linhaus doesn’t just let couples conveniently shop for engagement rings: it lets them design their own rings through a custom software interface.

And it leverages new technology to make custom-made wedding rings affordable to almost anyone.

We worked with the founder of Linhaus to help define the core value offering of the product, identify the most important feature requirements, and ideate the visual language and layout of the end product.

Linhaus offers a more sustainable, more cost-effective, and more personalized approach to engagement rings and jewelry, and we loved being able to help shape it.


E-Learning: MasterClass

At Rootstrap, we’ve dipped our hands into e-learning many times, releasing a number of e-courses including our Mastering Project Roadmaps course with Brennan Dunn and our fundraising course with Karl House.

But this past year, we got our hands dirty in ecommerce development with a really exciting client: MasterClass.

When they came to us, MasterClass was already an impressive company with a renowned reputation, boasting superstar names like Gordon Ramsay, Malcolm Gladwell, and now Elon Musk as teachers. But they had bigger ambitions: their goal was to disrupt traditional education with their unique model and grow to over $100 million in annual revenue. To do that, they needed tools to scale and a development team that could grow with them. That’s where we came in.

We outfitted them with a development strike force to tackle priorities as they arose. At first, this was just a handful of developers, but eventually we grew to more than 15 Rootstrap engineers working on MasterClass’s core platform.

MasterClass loved our development approach and process so much that when the time came, they demanded that we help them vet in-house dev hires – and we, of course, obliged. In the end, we helped empower MasterClass to aggressively scale their product and achieve their initial goal, growing from $50 million to $100 million ARR in just a few years.


Working On the Business

On the business side, one of the big themes of 2018 was setting the stage for rapid growth.

Rootstrap is at an inflection point right now. With 95+ employees, we’re no longer a small dev shop. We’ve figured out what works and what doesn’t. We’re good at what we do, and we know the value we’re bringing to the table.

Now we’re ready to hit the turbo on our growth.

At the beginning of the year, we moved into a gorgeous new UY headquarters in Montevideo, right next to the Office of the President. The new office gives our Montevideo team room to grow to more than 150 employees.

To achieve that growth, we’ve been working hard this year to get our internal ducks in a row. We’ve appointed David Jarrett as our new CEO, further systematized our service offerings and internal structures, and in particular, we’ve been working double-time on our sales operation.


New Marketing & Sales Departments

In 2017, we discovered the power of building my personal brand and leveraging it to get us clients

But in 2018, I saw that personal brand can also be limiting. It can’t be the whole picture.

That’s why we built a full marketing & sales team in 2018.

Up to now, I’ve always had to do both: as CRO, I was in charge of both leading marketing and closing sales. While I certainly know how to do it, that was inherently limiting.

Now we have a real marketing department and a high-performance sales organization.

We built a new framework for our sales operation that synthesizes all the tactics and techniques we’ve found effective: social selling, growth hacking, hyper-automation, and old-fashioned tactics like conferences and email marketing.

Then, we compiled it all into a comprehensive internal Sales Bible: a 40-page document that holds all our secrets and allows any new employee to hit the ground running.


New HR System

We’ve also completely revamped our HR.

In the past, we hired fast and furious. If it felt like a good fit and the candidate wanted to work for us, we’d usually give them a go. And while that helped us stay agile, it can’t work in a larger company.

This year saw us develop a real, honest-to-goodness HR system. We’ve brought on Valeria Viera, who used to head up HR for Mercado Libre (think South America’s Ebay), as our dedicated HR manager. And we’ve built a much more structured interview process, complete with technical tests, culture tests, and other improvements that have greatly improved the quality and fit of our new hires.

The goal for all of this has been to prepare for 2019.

So to finish up, let’s talk about where we’re going.


Where We’re Going

It’s hard to believe we’re already a month and a half into 2019, but it makes us even more excited for what lies ahead.

This year will be crucial for our business.

And as always, we have a lot of goals in our sights.

The biggest priority for us?


We’ve honed our business model, our service offerings, and our working process over many years and thousands of projects. Now we know exactly what we’re doing and why we do it.

In other words, we’re ready.

It’s time to expand.

Rootstrap is now 85 people across 3 countries.

But in 2019, we plan on growing to over 120.

And that doesn’t just mean Uruguay, either. We’re setting our sights to growing our geographic footprint as well.

I’ve got my eyes on opening new delivery locations in other parts of the world, with Argentina and Colombia as prime targets. I’m still not sure what it will look like, but we think it’s time for us to go more global.

That also means amping up our new sales organization and building our team.

We want to do at least one new sales hire per quarter to keep expanding our sales operation.

Furthermore, we want our UY team members to spend more time in US cities like San Francisco, LA, and New York to build the experience and abilities of our current workforce.

Increasing our sales efforts will help us target new markets and break into new countries, and we’re planning on attending more conferences, trying new sales tactics, and cranking up deal flow.  

And finally, we want to double down on helping large companies be more agile.

We already work with some of the largest corporate and enterprise brands in the world: Google, Epson, Spotify, and MasterClass are all clients. It’s fun work for us, and we bring a lot of value. By helping these larger corporations stay agile in their approach to digital products, we offer a more strategic development service.

But we know we could be doing a lot more.

And moving into 2019, that will be one of our biggest targets for growth.

We had a big year in 2018.

But we have even bigger things planned for 2019.

And while we have some difficult tasks ahead of us this year, we feel confident.

This company has been through a lot in the past 8 years, but time and again, we’ve proven that we’re up to the challenge.

Even more importantly, the past 8 years have shown me that the people who make Rootstrap what it is – the engineers, the designers, the product owners, and so many more – are the best I’ve ever had the pleasure of working with.

And if there’s one thing that makes me feel excited, confident, and ready for the coming year, it’s them.

2019 is going to be our best year yet.

And we hope you’ll join us along the way.


Happy New Year,


Ben Lee, and the Rootstrap Team


CEO and Co-founder of Rootstrap Ben Lee is the co-founder and CEO of Rootstrap, a digital development agency with a mission to destroy the development model and rebuild it from the ground up. After a brief correspondence with Fidel Castro at age nine, Ben decided to start doing things his own way, going from busboy to club manager at a world-class nightclub before he turned 18. Since then, Ben has founded or taken a leading role in 5 businesses in everything from software development to food and entertainment.