Ep. 225 – Jobsity COO, Santiago Castro

Our guest today is Jobsity’s COO, Santiago Castro.

With over 16 years of experience in the technology and software industry and 12 of those years at Jobsity, Santiago has performed a variety of roles including UX/UI web designer, senior front-end developer, technical project manager, and account manager.

Wearing all of these hats has provided him with a wide range of expertise and the ability to manage teams, create solutions, and understand industry needs. Santiago is also an Endeavor mentor to companies that are just starting and others that are scaling rapidly.

At present, Santiago runs the Operations Department at Jobsity, creating a high-level strategy for the company’s success and leading a team of more than 400 professionals in their work on major projects for current and past clients like Zebra Technologies, Intuit, USA Today, Freshbooks, and McGraw Hill Education.

In This Conversation, We Discuss:

  • How COVID affected their business and the transition to a remote workplace
  • How Santiago made the transition from coding to business management
  • Lessons learned in management growing a team from 20 to over 200 employees
  • How shifting your mindset to the different needs of the business helps to scale
  • The difference between managing your staff vs managing your leaders


Connect with Santiago Castro: LinkedIn

Jobsity – https://jobsity.com

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We have Jobsity’s COO, Santiago Castro. With over 16 years of experience in the technology and software industry and 12 of those years at Jobsity, Santiago has performed a variety of roles including UX/UI, web designer, senior, front-end developer, technical project manager, and account manager, wearing all of these hats that provided him with a wide range of expertise in the ability to manage teams, create solutions, and understand industry needs.

Santiago is also an endeavor mentor to companies that are starting and to others that are scaling rapidly. Santiago runs the Operations Department at Jobsity, creating a high-level strategy for the company’s success, and leading a team of more than 400 professionals in their work on major projects for current and past clients like Zebra Technologies, Intuit, USA Today, FreshBooks, and McGraw-Hill Education. Santiago is from Ecuador. Santiago, welcome to the show.

Thanks for having me here.

How did you guys connect with FreshBooks

We have different channels with our sales team. With some of like our biggest clients, we reached them, basically by referral. We approach tons of leads every week, but most of the bigger clients are referrals from other biggest clients. That’s interesting.

The reason that I even asked specifically about FreshBooks, I know that probably came right at a left field, was I met the Founder of FreshBooks, who’s Canadian as well at an event hosted by the Entrepreneur’s Organization. I’m curious whether you and your CEO are members of the Entrepreneur’s Organization.

My partner and CEO are part of the organization. It’s interesting because yet he hasn’t met FreshBooks’ CEO. Maybe they will meet someday soon.

Maybe it was one degree of separation or something connected. Why don’t you start off by telling us a little bit about what Jobsity is in case any of the readers aren’t clear on it? I then want to go back into what got you into the COO role. In technology, there are not a lot of people that started on the coding and IT side and got into the COO role. It’s a very different path. Tell us a little bit about Jobsity to start. 

Jobsity is a nearshore IT staff augmentation firm. We provide developers, programmers, or any role related to IT to companies in the US in a staff augmentation model. That means we place these developers or engineers with our clients in the States. They work directly with the clients, and we take charge of everything else like payroll, training, and equipment. It’s a staff augmentation business.

Are you staffing all out of Ecuador or around the world? Where does your talent come from?

We have staff from South America, Central America, Mexico, and the Caribbean. We are in all the Americas. It’s important to focus on the time zone. That’s one of our strengths. The talent pooling in America is huge. That’s one of the keys to the business.

Time zones make a lot of sense. It’s tough to do business from Europe to Latin America, but very easy for you to sell into the US market. That makes a lot of sense. For American companies, then it’s also easier to have all these developers in their time zones for the meetings with their normal team versus dealing with technology groups that are in India, the Philippines, or somewhere else.

The time zone is important. That separates us from other talent pools or other markets like India and Eastern Europe. The other thing that is important and a key to our business is the culture. Countries and people from Latin America, we are on the same site as the US. When we are young, we consume a lot of the American culture. We see American movies and hear American music. The second language in all countries in South America is English. All of our workers adapt easily to the culture of the state. That’s also a plus, besides the time zone.

SIC 225 | Jobsity

Jobsity: One thing that is important and a key to any business is its culture.


You’ve been with the company for a long time. Prior to dealing with COVID, were you a location-based business other than your coders? Were they remote or location-based?

It was a mix. My business partner and CEO started working in New York City. The company was founded there, and I was working in Quito, Ecuador. We started with people here in Ecuador, but one year after that, we start hiring in other places like Colombia, Peru, and Argentina. At that time, we had a hybrid work environment where we have like offices in Ecuador and Colombia.

Also, people working from home in other countries. In some cities, we had co-working spaces. Even in the states, in New York, Houston, and Denver, we had a mix of home offices. After COVID, we got rid of the offices because of precaution and everything, and it turned out well. It was a good solution. We adapt easily to work 100% distributed.

Will you go back to having offices or are you going to stay as a distributed workforce now? 

We are going to stay as a distributed workforce now. We are thinking of opening maybe 2 or 3 little spaces where mostly management can get together because, for me, most of our talent is a profile of engineers. They enjoy working from their homes. Now, that’s a must. With the management team, it’s different. We also like to work from home, but we need these spaces to share and discuss ideas. For me, it’s different and needed for tasks that are involved with strategy or creative thinking. That’s the plan, but now we are 100% distributed.

Go way back to the beginning then. How did you get involved with a partner and CEO who’s in New York and you’re based in Ecuador? Were you going to school or working in New York? How did you guys connect? 

The story is simple. You mentioned this thing about the COOs and the tech industry. It’s hard to transition to being a COO in a tech company. I have a degree in Graphic Design. I don’t have any background in business or technology. I learned everything by myself. When I was young, it was my 2nd or 3rd job, I applied to a company at a super-smallest startup here in Quito. I started working there. One of the partners of that company was my CEO, Andres.

We started working together. I was a super young junior guy that wanted to learn everything and he has a partner. We started working like that. We get to know each other. When the time was right, my CEO and I decided to expand and scale the company. We were small at that time. He put all his trust in me. He invited me to join this amazing journey. That is the story. It’s simple. We met at work.

Meeting up that way and starting off as a designer starts to make a little bit of sense because you tend to have a little bit more exposure to the sales and marketing and some of the ops side of things. How did you make the transition from the tech side into managing? Were you doing coding yourself on the UX/UI side and then you started managing people? Walk us through some of that and how you grew from there. 

It started organically. I call it by request because when I first started, I was hired to do simple coding work. I remember at the university, I had 1 or 2 courses in Basic Programming. I started to code basic stuff and keep learning. We created a team. The team that I was working with started to grow. The company at that time needed someone to manage the other people. It came naturally to me. I started managing the other people.

At first, it was 1 person, then 2, 3, 4, and so on. I remember that it grew fast that I ended up handling the client that I was working with. I started graphic design. I am a people person. Most of the engineers have this other profile that they are not that people-oriented. They are like engineers. I was the one that could take the opportunity and handle the team. That’s how I started to manage clients. At that time when we talked with my CEO, he needed someone to help with other clients and to run the company. I took a step forward and did it. It wasn’t easy at all because I needed to learn many things. That’s part of the challenge, and I am proud of it. In summing up, it was organically. I learned by the need.

That’s what I was going to ask you about, “Was it all easy?” I was sure that you were going to say, “No, it wasn’t.” What part of the trajectory for you moving into the COO role was hard? What part did you have to work at? 

I remember, one of the hardest parts is the money part. I’m good with money, but I wasn’t good with money in a professional sense and professional way. I had to learn a lot of the rules, information, and theory about finance and accounting because at first, you do everything. Money handling and finance would be one of the challenges that I faced. This came after when we started scaling, people management. I am a people-oriented person, but that’s different from managing large groups and also to manage managers. That was a challenge as well. Those two are top of mind.

My first question related to that was you’re at 400-ish employees now. How many years back would that have been that you were maybe only 20 or 30? 

Around 4 or 5 years.

A few years ago, you were at 20 or 30 employees, and then all of a sudden, you hit this inflection point. What allowed you to start to scale from there? 

To be honest, just mentality. We got into this network that is called Endeavor. It is this huge organization worldwide that empowers and helps companies with their network, training, and mentoring. It pushes companies to scale exponentially. There are huge companies that are part of the network. Here in Latin America, for example, there is a globe that is one of the tech giants, in the region and in the world like Rappi and there are a few more.

SIC 225 | Jobsity

Jobsity: Endeavor is a huge organization worldwide that empowers and helps companies with their network, training, and mentoring.


Rappi is a delivery service like Uber.

It is like Uber and DoorDash of South America, but it’s huge. It’s massive. When we got accepted into Endeavor, our mentality changed. Before that happened, we were thinking like, “We need to be the best and the largest tech company in Ecuador.” After that, I was like, “We need to be the best in the region in South America.” A lot of mentorships and learning how to scale in companies and how to handle all the growth. The mentality was the trigger.

I’m super curious about the mental side of things. Was part of that mentality growth that you no longer felt like imposters that you realized that you were not as big or as good as the others, but you were like, “They’re figuring this out as they go. They might be bigger, but they’re people like us still figuring it out every day?” Was there a little bit of the imposter syndrome that broke away, or was it that because you’re surrounding yourself with these other people, you started to raise your game and your thinking in every way?

It was like the network and the people that we were surrounded by at that time. It’s a funny story because here in Ecuador, Colombia, or Peru, I remember that when we have business meetings with other business people, they always told us like, “You are growing fast. Your numbers are incredible. You are the best.” We were like, “Cool. Thank you.”

When we did the same in the States, everyone was like, “That’s cute. You have 500 employees and you are doing good, but we have 10,000 employees. Our revenue is that high.” We are not comfortable being the best in Ecuador, in the small region. We need to think like these other people. The people that we were surrounded like we started to feel like, “We can grow way more. They already did.”

They say, “Your income is the average of the five people you spend the most time with. Your physical fitness is the average of the five people you spend the most time with in your business.” Your business grows similarly. Your mindset changes. Give me one specific thing then that changed the mindset or that you did differently in the business because of that. 

This is not part of my area, but it was important for the company how the sales department was managing things. There was a huge change there in terms of, first of all, diversifying the channels of sales and sophisticating all the tools and processes that we handled on sales. That was a thing that changed from one day to another after this experience and I get surrounded by these people.

From the operation side, before this, I was focused on doing things greatly, handling myself all things, being aware of all the results, meeting the goals, and everything but by myself. After this, I learned and switched to a structure or scaling mode. I started thinking more about how this will work in the future when we are 100 or 200 employees. I started to think in terms of a structure on scaling. What will happen if we have 200 leads per week or 200 employees in the next months? I turned my mind into scaling mode.

When you do start thinking about that scaling mode, you start hiring bigger people, spending on structure, coaching the team differently, and setting bigger goals. Did you make any mistakes when you started to think bigger? Did you take any that were too big? 

Not that big, but that’s part of the business and scaling. A few years ago, we were at this point where we were hiring a mix of junior people to mentor them and make them grow like more senior people. Wrong hirings using the old mentality, “We need to save money. We need junior people. We train them and they will do the work.” Wrong, because that worked when we were on another level and we weren’t big. Hiring the wrong people, but based on when to hire senior people was a thing that I learned. It was hard for me because, believe it or not, it’s super hard for me to let people go.

I like people, but sometimes the wrong people are costing you way more money than they’re making you. I was speaking with one of our COO Alliance members. He is the COO of a company that’s about $30 million in revenue. We were talking about his team. He’s talking about, “Finally, all 70 of our employees are truly A-players.”

I went, “There’s no way that they’re all A-players. There’s no way that it’s God forbid they ever quit people. Let’s say they’re solid B-plus people. That I’ll agree to. What if you paid them all 20% more? If you could afford to go out and rehire for those roles and pay 20% more, would they be A’s?” He’s like, “You’re blowing my mind. They’d probably all be C-people.” You can always raise that bar. How do you decide when paying more for more talent is worthwhile or whether it’s loyalty to the people you’ve got is worthwhile? What’s the measure there?

For me, the mix is always needed. Loyal people that started from scratch with the company feel engaged because they grew in the company. Sometimes they get to an interesting point and sometimes not. For me, it’s needed. This makes between these people. The more experienced people that come from outside the company, usually, more senior people, that come with 15 or 20 years of experience are not that engaged. They don’t understand the initial dream. They are professional and do their work. Maybe some years later, they become engaged as the first group.

To be honest, I haven’t figured out that. I don’t have the formula to know when to start hiring more senior people. It’s like, “Close your door.” That happened to us. When we hired the first super senior people outside the company, we realized, “Now, we are that at this point. We need people that can manage themselves without handholding and people that come up with ideas and strategies. When you realize that, you start thinking, “I need these people.” That’s where the thing gets interesting. It’s important for me.

SIC 225 | Jobsity

Jobsity: We need people who can manage themselves without handholding and who have ideas and strategies.


It does come knocking on your door. All of a sudden, you realize, “We need them.” You just know. I agree with the mix. I’ve always said, “My A-players are racehorses. My B-players are the workhorses and the C players have to go to the glue factory.” You need a good solid mix of As. That’s a good one. You mentioned that it’s one thing to manage groups of people, and then it’s another thing to manage managers who are managing groups of people. When you go from 30 employees to 100, you are now managing managers. What are the key lessons you have there in terms of maybe for delegation, not having waste, leading, and getting results through people? Any key lessons you can share there?”

For me, it’s super clear. The difference between managing managers and managing people is the difference between being a leader and being a manager for me. When you manage people, you need a lot of skills. The most important thing in your work is to track progress and keep people motivated. When you manage managers, you need more work on the inspiration or mentoring side. I started to learn how to manage managers, and then I was struggling with how to do it.

You become a mentor. You stop focusing on checking results and tracking progress. You also do that, but now it’s not the most important thing and responsibility for you because that’s the manager’s responsibility. You need to mentor those managers on how to run their people and work on their own without asking a lot of things from their managers or their direct reports. You lead them to the managers’ path with a lot of mentoring. It was hard to describe, but it’s related to leadership.

What you’re saying is that the transition is when you’re managing people, it’s like project management and task management. You’re helping them get stuff done, but when you’re managing leaders, you’re growing their skills and confidence, mentoring them, inspiring them, and being there as a resource for them, but you’re not managing them as much as holding, helping, and growing them.

It also depends on your approach. I know successful companies that managers of managers micromanage managers, and they encourage their managers to micromanage their people and the companies are still successful. For us, many companies and mostly tech-related companies, the approach should be different to lead or motivate the manager and mentor him or her on how to manage their team like an independent entity. That’s key because if not, you will then track the progress of the manager, and that’s not the idea.

The next transition after that is you start hiring senior leaders who understand situational leadership, coaching, how to grow people, and how to run one-on-one meetings. They’re good at the soft skills of leadership. How do you lead those people? I would imagine typically when you go from 100 to 300 people is when you’re hiring your first true leadership team that has led teams before. What’s it like leading those people? 

It’s different. To hire leaders, not C-level but VP level, that’s strategic people. It’s similar to managing managers but different at the same time, for managing those leaders, it’s important to know how to communicate and get to understand your vision to those people. Communication is needed. How you translate that vision to this person is key. This person already came with all the knowledge without experience. They know how to handle things by themselves, but they need to understand the vision and then, they will execute the vision through strategy. That’s one. Put in a clear division.

You’re giving a real good crash course on how a leader has to emerge from being a manager to a leader to a leader of leaders, which is great. I’m curious about where you’ve gained some of these skills yourself as a leader. This is not this is like a Master’s degree in leadership out of the university. Where were you gaining the skills during the work? Was it through the Endeavor program?

I was a graphic designer that became a COO by learning everything. I learned all those things in two ways. First of all, my CEO is super important to me and has been my mentor. That’s one. My CEO and business partner have mentored me with all his knowledge and experience. Also, a lot of reading. We tried to read at least 2 or 3 books per month, business-related or topic related to leadership and management. Those are the two sources where I learn everything. I have a great list of books to recommend.

Do you have a favorite couple of business books? 

One of the most important books that I read is the bible of business. I guess you have read Good To Great. I read a book by Laszlo Bock called Work Rules!. It’s mind-blowing. It’s my favorite now. Before that, I read one. It’s about the Netflix approach that is No Rules Rules, but then I read Work Rules! and it blew my mind. That’s my favorite one.

SIC 225 | Jobsity

Work Rules!: Insights from Inside Google That Will Transform How You Live and Lead

I’m going to grab that one. I’ve been waiting for a new one to be listening to during my workout. That’ll be the one. I’m going to encourage you to read my first book, which was called Double Double. There are some key chapters in there that you might like as well. This is a strange question, but it came up at the beginning. When you’re a company that’s based in Latin America, what have your big lessons been in selling to the US market and selling into the US market as a foreign company or with foreign staffing? Any lessons there? 

I have several pieces of advice, and it can sound cliche, but it is knowing your market. If you don’t understand how people in the US run business, how they communicate, and the work culture there, you are going to fail. It’s important to understand all the values and cultures. In America, there are different working cultures in the States. You have Corporate America and the startup thing. If you don’t get it, you will fail. You need to understand that. If you can’t learn that from a book, you need to live in the States and work with someone or a company in the States. It takes time, but you need that scheme.

There had been a strong push against hiring offshore with India, and then, the trend became very strong to hire in Eastern Europe and the tech side. Has the US started to adopt the whole South American tech scene, or even though you’re a few years old, are you new to that emergence of that’s where a lot of the good tech talent is? 

For me, we are competing with other regions like Eastern Europe. That’s one of the best examples, but at the same time, it’s a different approach. For example, part of our clients has their nearshore teams in two time zones. They have Eastern Europe, India, and South America. They choose to do this because they know that they will use, for example, let’s say, Eastern Europe teams because engineers in Eastern Europe are good. They use it for specific things. Let’s say solving super complex engineering problems. They use South American teams to work on a daily basis to communicate, be part of their team, activities, and critical thinking because of the similarity in the culture.

It’s not a direct competition between Eastern Europe, India, and South America. It’s more the approach you want to follow. Every region has a good and a bad part, time zone. It’s a pain for us companies to work within India because of the time zone. Eastern Europe is still a pain. In South America, it’s super smooth. For me, it’s a complement.

You mentioned earlier that you have a hard time firing people. Have you gotten better at that or do you avoid that or it sucks, but it’s part of business?

I have improved. It’s needed. It doesn’t mean that I don’t do it. It’s necessary and sometimes time is of the essence that you need to do it. It’s more like I have improved on how I feel about it. It’s more personal. I remember many years ago, I needed to get prepared mentally and be strong. After the firing, I spent 1 or 2 days grieving, but I was young. You grow and learn. I still don’t like it, but I do it like this. It’s just experience. The people orientation is the thing that makes it a little bit harder.

I read something interesting in the book called The Hard Thing About Hard Things. Ben Horowitz was talking about how when a company fires someone, they’re often happy the person’s gone. He said the real work becomes when you sit down and say, “Why did we hire them in the first place? What did we miss in the interview process? What did we miss in the onboarding process? What did we miss in the leadership and development process that we had to then fire that person? When we hired them, we were excited about them. What changed? What did we miss? What did we screw up? That is quite interesting for sure.

After a firing, the first thing that you need to do is, “What went wrong?” It’s not just 1 or 2 things. Usually, it started with recruiting. I know this because our business is staff augmentation. We work with a lot of people, and we recruit tons of people. If a process is not well-calibrated or you are doing something wrong with recruiting, even when sourcing, you can get these firings later and sometimes you don’t realize the problem. It was at the start of the process. It’s important to think about it. It’s not like, “Didn’t this guy meet the expectations?” No. The work starts there. What happened?

It’s a good exercise for leaders to put themselves through as well as that introspective process of what our contribution was. I want to go back to the 21 or 22-year-old Santiago. He’s getting started in his career. What advice would you give yourself back then that you know to be true not but you wish you’d known when you were getting started? 

Invest in learning. That’s key. Now, I realize that you can learn different sources. I know going to college, reading books, or going to programs, but what you’re doing when you invest in learning, you’re buying time. Spending four years to learn something in a college, going to a super quick program, or hiring a consultant so he can teach you about something in 2 or 3 weeks. Time is valuable because time is the most important thing. You don’t want to lose it in personal time and time at work. Invest in learning. That’s one. Think about time. That would be another one.

The whole investing in learning is important that I even named the course that I launched Invest In Your Leaders. It’s all about growing those manager skills. I’m also going to send you my favorite poem later called Think Big. It’s about thinking bigger because you talked about how important it was to think bigger as a company, and you guys have done that. Congratulations on everything you’ve done with Jobsity. I appreciate the time you spending time with us on the show. Thank you.

Thank you.


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