From one ship to one fleet — a three year journey

 • By
From one ship to one fleet

It has been going so well.

Silicon Straits started with a small team. As we grew, we built our company around a flat structure which suited us the most back then. Teams were not permanent and were tactically formed to deal with specific requirements of each product. Such a system created a fluid environment for our team members to learn and adapt quickly while moving from products to products and even working on a few products at the same time.

This nonhierarchical and dynamic working environment provided the best conditions to nurture young talents. The variety of products and technologies demanded kept them on the edge, adapting new knowledge and skills constantly. Not being closely supervised by middle managers, they quickly learned how to become more independent, speak their minds, and get involved in decision-making process. This fitted very well with our specialty at the time: building minimum-viable-products (or MVPs) for startups.

Everything seemed to go well, and we reached the 2-year anniversary mark. It was then that we decided the time had come to change.

Calvin and Hobbes talking about changes
Calvin and Hobbes talking about changes – Comic strips by the great Bill Watterson.


At that time, the desire to change seemed to be driven more by internal forces. When we reached 40 people, we expanded our office. More projects were flowing in. Then we reached 50 people and looked forward to getting more extraordinary people to join our journey. On one hand, it was great that we survived and kept growing. On the other hand, it became increasingly difficult for us to maintain the flat organization and a lot of smaller things started breaking. There must be a better model.
However, was it the whole reason? Looking back, we realized there were much more than that.

Some pieces were missing. We looked out there and found that we wanted more.

The projects, while still interesting, were not as deeply satisfying. Our thirst did not stop at acquiring and adapting new technologies and techniques. Technical challenges were great, but we felt it was time to get more people in SS to tackle bigger challenges. We wanted to be more involved in the making of new products and delivering real-life impacts. After so many MVPs, there was a built-up desire to tackle products of larger scale and longer duration.

To sum it up, the three main reasons were:

  • Flat structure not suitable to manage a bigger team
  • The desire and readiness to work on bigger products
  • The needs to nurture the product mindset

Entered the squads

From the designs of the office to changes in the company structure, Silicon Straits has always been very transparent and opened for discussions within our team. We opened a Slack channel, and many joined to discuss how we could best move forward, adapting to the necessary changes while staying true to our values and culture. We moved the discussion offline, when we started to debate if we should stay with a flat structure or possibly move to the then popular holacracy style of management. Then we came across the squad structure pioneered by the Spotify team. We paused a bit and realized with some adjustment, this was what we had been looking for.

Basically, we structure the company both horizontally and vertically. Horizontally, we have squads, which are product-based. People in the same squad work together to deliver common outputs. The main change from our previous model is that squad members are permanent, so it would be easier to manage within and across squads. The main difference from traditional companies is that squads are not departmentalized. Each squad is full-stack with 8–12 squad members of a variety of roles and expertise, fully capable of building a full product by themselves.

Still, it’s not desirable that everyone sticks to their squads only. Vertically, chapters were introduced to bring people across squads together. Chapters are expertise-based, such as front end, back end, and quality assurance. The main function for chapters would be to share specific areas of knowledge, experience, and skills across different squads.

While chapters continued our commitment to nurturing the growth mindset, the squad structure was strategic for us to encourage the development of product mindset. From the very start, we have determined that each squad could be considered a mini startup, not just building but also being fully responsible for what they build. Our teams should not stop at being just product builders, over time, they had to grow into product owners.

Without great people you have nothing
The changes must guarantee to meet the desire and the potential to grow of our people.

The first hurdle

Dividing our then 50+ team members into squads was challenging, yet it was but the first step. The first critical challenge to our new model was about two months after the implementation. When we divided the squads, we aimed for each squad to be full-stack. Therefore, we also divided our design team so each squad had their own UI and UX designers. It worked for technical roles, so it should have worked well for designers.

We could not have been more wrong.

The first problem was that unlike technical roles, designers played the most important roles in the early phase of a product, after that the workload were lessened and focused on minor adjustments. It was very unlikely for a product to go through a full design overhaul later in the project phase. The second problem was that not all products were demanding in term of designs. The workloads for designers were uneven among squads both in terms of quantity and difficulty, which led to the third problem: designers worked better together, when they could interact and share easily.

It took us some time to realize it, and it was actually all thanks to our designers who first identified and raised the issue. Our solution: putting the designers together again as a hybrid of both chapters and squads. They are like other chapters, which are expertise-based. They also worked independently, providing their own service to other squads. All design tasks are centralized to the design squad, before assigning to each of the designers.

Beyond the expectations

Slowly revealed to us after the change was a sense of separation: we were no longer one big flat team working together like one family. It did not make it any easier since the change into squads was driven, and later happened, at the same time as the expansion of our company. As there were more people, many activities that were part of our culture were no longer possible. At one meeting, one member spurted out, “I can’t remember the last time our whole company went out for dinner.” Everyone knew that it was an unreasonable complaint with the current size of the team, still anyone was touched by nostalgia.

Then came the emergence of individual squads’ culture, which we welcomed with a bit of hesitation. Would they conflict with SS culture as a whole? People started to state that they were from this or that squad, instead of just everyone from SS. “This is just like Pink Squad.” “This is so Minion Squad”. Before that, each was a unique individual, then an SS member. Now there was a layer of separation in between the company as a whole and the individual.


However, over time, we realized that the squad cultures are now part of our culture. Each squad develops a unique set of characteristics that set them apart from each other, yet aligned with our core values. Before the change, there were healthy competitions among individuals. After the change, a much interesting phenomenon emerged: competitions among squads.

Thinking like this: competitions among individuals were mostly about individual technical skills. Among squads, they included technical skills, product management skills, teamwork, and more. No individual would claim themselves the best, but as squads, there was a healthy commitment to prove that their squad was the most capable.

Most significantly to us, one thing that had been amiss for a long time came back. As we grew bigger, it became more difficult to experiment. Even though being venturous was part of our values, the big team made it very challenging to adequately allocate resources while mitigating potential risks. The squads, however, were at just the right size of 7 to 10 people. It’s not too small that there would be not enough resources to explore. It’s not too big that it’s too risky to go beyond our comfort zone. We found that our people now had more opportunities and resources to try new things, and it showed very quickly.

Together, the healthy competitions among squads and the higher level of risk tolerance brought us another surprise: we now had a much-expanded range of sharing topics as well as a stronger desire to share them. This was no less allowed thanks to further encouragement by the management teams, since sharing was the best method for cross-squad bonding as well as for keeping the competition going strong.

We then realized our transformation was successful thanks to a key factor: the culture we had persistently built over two years. It was strong but flexible, hence it wasn’t replaced with the implementation of the new structure. Instead, it evolved and became much richer with more diversities and potentials. Now, on their own, each squad is a small unique family, together, we are one big unique tribe.

Looking back one year on…

It has been almost a year since the change. Change-makers sometimes are the ones who are most afraid of the consequences, for they are the ones putting themselves on the line. However, we knew that what had made us successful in the first place would not be enough to guarantee a healthy company for the long-term. We had to keep moving, adapting to the new structure, adjusting where we saw fit, and mitigating unavoidable circumstances.

It was a challenging transformation for us. It was critical because it was driven by the needs to grow bigger while maintaining our culture and commitment to deliver great products. We welcomed the emerging cultures from each squad with a bit of hesitation at the start, and are now delighted to realize that they have become the fabric of our culture as a whole. Chapters had very mixed results so we are brainstorming a different structure to nurture the growth mindset. We are still in the early days of building the product mindset to the level we want, but we are convinced that we are going in the right direction toward building it.

Ultimately, we strongly believe in the new structure for one good reason: It was not just a change driven by needs. It was a change driven by a desire to become better and stronger.

Does it mean we have stopped changing? No, for every day there are challenges to be faced and battles to be fought. Things break, things change, things improve and we keep on pushing ourselves. All of that is part of our life and this is what makes it more fun to be a pirate than to join the navy — whether as a small group of outcasts on a boat or as part of an agile and powerful bigger fleet!

Calvin and Hobbes talking about fate
Three years ago, we started a journey that no one could have predicted where it would take us. Now we realize it was not scary that we did not know the future. It’s actually exciting. The scary thought would be there were no land untouched and no horizon unexplored. Luckily we are not and hopefully would never be quite there yet — Another wise comic strip from the great Bill Watterson.