Guillermo Pérez of Octobot: “Not trying to do everything alone”

The first is not trying to do everything alone. It’s essential, as an entrepreneur, to learn the importance of creating teams that can lead initiatives and make things happen. You’ll achieve results faster and better by relying on a team than only yourself! Entrepreneurs have to overcome many challenges when they get started, but this […]

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The first is not trying to do everything alone. It’s essential, as an entrepreneur, to learn the importance of creating teams that can lead initiatives and make things happen. You’ll achieve results faster and better by relying on a team than only yourself! Entrepreneurs have to overcome many challenges when they get started, but this changes when your organization starts to grow.


As a part of our series called ‘Five Things I Wish Someone Told Me Before I Became A CEO’ we had the pleasure of interviewing Guillermo Pérez.

Guillermo has a mixed background in business and technology and has in the past nine years helped companies transform problems and opportunities into successful digital solutions across different industries. He co-founded Octobot, and as CEO, he has focused on creating a customer-focused organization by fostering customer acquisition, high-quality service, retention, and growth practices, as well as empowering the intersection between technology and design to develop transformative solutions.


Thank you so much for joining us in this interview series! Before we dig in, our readers would like to get to know you a bit more. Can you tell us about your backstory? What led you to this particular career path?

Since I was a kid, I always fancied technology. I remember being 12 years old, and my friend Juan, who would become my business partner several years later, came and showed me the website he built. It blew my mind away! Soon, I started to research and learn how to create websites and program software. When I was 16, I already worked as a freelance developer, and thanks to the projects I took, I could pay for my university degree. Some years later, all of these experiences led me to start a new business with two friends and colleagues, Juan Saavedra and Luciano Ferrari.

In addition to my tech background, I also learned a lot about interacting with clients as a freelancer: how to discuss ideas, how to set goals and deadlines, how to have difficult conversations, how to actively listen to the client’s needs, and create a useful proposition, etc. Naturally, when we got the business started, I chose the sales role because I had experience in this area.

Can you share the most interesting story that happened to you since you began leading your company?

At the very beginning of Octobot, we had a turning point that, in my opinion, was decisive for the company’s next steps. We got started in 2012, a software development company working from Uruguay, but our goal was always to thrive in the U.S. market. Around a year after the business launch, we felt we were able to create a positive foundation and set values that were being lived inside our teams. However, we noticed we were still far away from creating a brand in the United States. We needed to make sure our solution was heard and seen by the businesses we wanted to partner with. Therefore, we made some bold decisions such as traveling to the United States, 100% marketing focused on this market, and investing in actions that could help us position Octobot abroad. It was a real before-and-after situation, and we could grow and establish ourselves there thanks to that. Today, the vast majority of our clients are American, and we intend to keep growing and helping the underserved market of U.S. companies that need to transform their business with technology.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

One of our mistakes at the beginning of Octobot was doing everything by ourselves. As founders and entrepreneurs, we were excited about building and polishing every aspect of our business. However, sometimes, we took things too far. Once we needed to reform the floor of our first office, my partner and I dedicated a whole afternoon to replace the floor tiles without any specialized help. It was madness; we ended that day with terrible back pain! Over time we understood we didn’t need to do everything ourselves; it was necessary (and intelligent) to ask for help. If you don’t delegate, you won’t grow.

None of us can achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I can’t think of one unique person, but I believe that I learned something that I apply in my life today from every inspiring colleague I met or had in the past. Ex-coworkers, partners, clients, you name it. For instance, I remember once I worked with a Product Owner that had stellar communication skills. He explained his thoughts and decisions in such a clear and refined way; it was inspiring. And I like to think I incorporated some of his abilities. I can also think of a former colleague that was a source of knowledge in managing conflict and challenging situations, and I absorbed a lot of the things he used to do. Before Octobot, I had another startup. I participated in an entrepreneurship training that connected us with mentors. I remember having conversations with those mentors who were businessmen with many years of experience. I learned the importance of thinking in the long run from them: where is the business heading? How will your decisions today affect the company in the future? And things like that, which are still motivating me today.

My college degree was also significant for my professional development because I studied a technical career with a strong background in software development and business. Therefore, I learned a great deal of concepts related to sales and management, which were key for developing my company.

Last but not least, I’m very grateful for my business partners. It’s an amazing experience to grow a company side by side with people I trust. I feel very much accompanied and supported by them, and we are constantly learning from each other.

As you know, the United States is currently facing an important self-reckoning about race, diversity, equality, and inclusion. This may be obvious to you, but it will be helpful to spell this out. Can you articulate to our readers a few reasons why a business or organization needs to have a diverse executive team?

One of the diversity challenges we face in the software development industry is gender equality. I’m proud to say that Octobot has almost 100% gender parity since our team comprises diverse male and female colleagues in every area. For me, fostering a diverse culture is the only way to escape the status quo and make a change. If we are all the same, we’ll think of the same ideas and come up with the same solutions. There’s no room for creativity or whatsoever. Therefore, in Octobot, we strive to see beyond gender and focus only on people’s capacities and passions. We want to give opportunities to everyone who has something to contribute and wants to grow with us. That way, we’ll create innovative products that change people’s lives. Also, we’ll develop diverse code, more affluent code that makes more impactful products for those who will use them.

As a business leader, can you please share a few steps we must take to truly create an inclusive, representative, and equitable society? Kindly share a story or example for each.

In general, we strive to develop processes and communicate internally and externally in the most inclusive, diverse way. We also want to foster diversity in the next generations of developers. In the last few years, we have organized an annual event to show the IT sector’s opportunities for girls and teenagers who are thinking about what they’d like to study. It’s a national initiative organized by Uruguay’s IT Chamber. We’re happy to be part of it because we believe the only way to overcome the gender gap is by abolishing gender stereotypes and fostering more female participation in the industry from a very early age.

Ok, thank you for that! Now, let’s jump to the primary focus of our interview. Most of our readers — in fact, most people — think they have a pretty good idea of what a CEO or executive does. But in just a few words, can you explain what an executive does that is different from the responsibilities of other leaders?

My role as CEO isn’t typical, I think. One of the reasons for that is that I divide a lot of the CEO’s workload with my business partners. If I had to tell you what my day-to-day looks like, I’d say I dedicate a big part of my time to the business development area, as I am the responsible for Octobot’s sales and marketing results. But I also separate a section of my day to be aware of what’s going on in the projects and how our activities relate to the company’s primary purpose. I like to be that guy who is always saying, “this is where we want to go, this is what we want to do!” to ensure we don’t forget our core. For that, I like to track metrics and be on top of the company’s results. I’m a very analytical person, so checking out data and coming up with conclusions and insights is one of my passions.

I’m also fond of following up with other companies, competitors, or even businesses from different industries to see what they’re doing and the results they’re getting — with the goal of comparing them to us and brainstorming new ideas. All of that helps me visualize opportunities and make decisions regarding where we’re taking the business to. When it’s time to make a decision that will impact the organization as a whole, on a more macro level, I always discuss the options with my partners and together we select the path we want to go. For us, it’s been positive to have clear responsibilities — I’m the sales responsible, Juan is the CTO, and Luciano the COO, so we have the autonomy to focus on what we like the most. Still, we rely on each other to make the big decisions as a team.

What are the “myths” that you would like to dispel about being a CEO or executive, and can you explain what you mean?

There’s this belief that CEOs are always in meetings, and that’s not true. You have to sit down and do things as well. Another wrong perception of CEOs is that they are heroes that know everything and never need help. I don’t agree with that. I want Octobot to become a more and more independent organization. We’ll grow faster if people feel they have our trust to make their calls. I prefer to see my teammates doing things, trying out, making mistakes, and thereby learning from them, rather than them waiting for me to validate everything before they move forward. My goal is to generate an organization that provides people with the right tools to do what they think is best. Over the years, we’ve surrounded ourselves with amazing people interested in what they do, so it makes no sense if we decide to don’t listen to their ideas. If your organization depends on the CEO’s approval for everything, it will never scale. I believe in the opposite, in creating an environment where people feel welcomed to develop themselves and grow along with the company.

What is the most striking difference between your actual role and how you thought the job would be?

I had no expectations of the role, actually. I believe my role has evolved and shifted over time, which is something positive. As I had no expectations, I was able to adapt and open myself up to different activities and ways of doing things. It’s been fun and dynamic. Also, it’s a privilege to be part of an organization that grew from three to 80 people. Truly mind-blowing! Over the nine years of Octobot’s existence, I’ve had many responsibilities. I was a programmer, product owner, tester, recruiter, and much more. My partners and I experimented with all the roles! And I guess I got something from each experience, and each one of them shaped the role I perform today, which will continue to evolve in the future also, I hope.

Do you think everyone is cut out to be an executive? In your opinion, which specific traits increase the likelihood that a person will be a successful executive, and what type of person should avoid aspiring to be an executive? Can you explain what you mean?

Anyone can be a CEO, but some people may have conditions to do it better than others. Recently, I read “Built to Last,” a book that analyzes how huge companies have grown over time. There’s a part where the author talks about misconceptions regarding CEOs, and one of them is the idea that a leader needs to be outgoing and super nice, someone that stands out in the crowd, but that’s not true. You don’t need to have these characteristics to be a CEO, not necessarily. In fact, if you are like that, but you can’t delegate and let your team do things independently, you will probably fail. The key to being a CEO is creating organizations that transcend the people who are part of them. I want Octobot to last more than the period Juan, Luciano, and myself are part of it. That’s why we prefer focusing on other aspects, such as generating a company’s purpose and values and fostering them within our team to generate a culture of growth and achievement.

What advice would you give to other business leaders to help create a fantastic work culture? Can you share a story or an example?

Another concept I loved from “Built to Last” was this: you shouldn’t be a time-teller but rather a clock-maker. My interpretation is that instead of telling people what to do, you should support them in their growth process to learn and make the best decisions they can. I’d also recommend business leaders to put a lot of effort into setting up the organization’s purpose and values; it’s the core that shapes everything. In Octobot, our purpose and values work as a lighthouse that we turn to every time we decide and prioritize our actions. They also represent the company’s foundation for generating a collaborative, healthy, and positive work environment.

How have you used your success to make the world a better place?

Octobot’s primary purpose is to transform people’s digital experiences. With that, we intend to make people’s lives easier by providing them with great digital tools. In my opinion, this is how we impact the world and is our small contribution towards a better planet. For example, when we help one of our clients, a medical provider, to make it easier for patients to get their medicines with a web app, we’re achieving this purpose, which motivates us to keep going.

I also feel we generate a positive work environment where people work and develop themselves as professionals and individuals. It’s important to us that our people feel welcomed and happy with what they’re doing. Sometimes, team members of Octobot outgrow the company and start their own startups, and it’s rewarding to see people who were once part of our organization generating their own! More entrepreneurs mean more jobs and solutions to this world, so I love to think I’m contributing to this as well.

Fantastic. Here is the principal question of our interview. What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each).

The first is not trying to do everything alone. It’s essential, as an entrepreneur, to learn the importance of creating teams that can lead initiatives and make things happen. You’ll achieve results faster and better by relying on a team than only yourself! Entrepreneurs have to overcome many challenges when they get started, but this changes when your organization starts to grow. The second is about the importance of having a clear focus at all times. There’s no such thing as multiple focuses — if you’re dedicating your attention to two things at the same time, you are not focused. When we got the business together, we focused on many things and realized quickly that we weren’t going to grow either if we were not able to dedicate all of our energy to one big, audacious project. And that’s what we did.

As my business grew, there were two main insights that I had and that I would like to share with you. First, in the beginning, there’s very little to support a decision-making process. There’s not much data or information, simply because the business is young. At that moment, I believe it’s important to trust your instincts. Even if you can justify an idea at 100%, go with it if your gut tells you something. It’s important to move forward and start growing. Sooner or later, your company will begin to gather data and experiences, which will provide you with a lot of insights. Here, my advice is: don’t overthink. When there’s too much information, it’s easy to get stuck analyzing all the possibilities and forget to act. Choose one option and go for it. Sometimes you may get it wrong, but at least you’ll learn from it and get it better next time.

And finally, work on the organization’s culture as soon as possible. In our case, it took us several years to prioritize this, but now we understand its importance, and it is without a doubt the core of our growth. If I could go back in time, I’d begun working on our cultural aspects much earlier than we actually did.

You are a person of great influence. If you could inspire a movement that would bring the most good for the greatest number of people, what would that be? You never know what your idea can trigger.

I’d love to see more people joining the software industry. Our sector needs more talent, and we lack professionals, so it’s going to be essential to have more developers, designers, and product experts joining us. But, besides sectorial benefits, it’s also a fantastic place to grow and evolve. I truly think it changes people’s lives as it works as a platform where professionals can develop themselves and where the sky’s the limit.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

There’s a sentence I always think about which is transforming challenges into opportunities. This quote really gets me going; it gives me direction. Every time I faced something difficult in my life, I always tried to change perspectives and work to convert the problem into an opportunity. And it always pays off!

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world or the U.S. with whom you would love to have a private breakfast or lunch, and why?

I’d like to have coffee with Jeff Bezos so he can tell what it was like going into space!

Thank you for these fantastic insights. We greatly appreciate your time spent on this.

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