
The Nearshore Cafe
Hear from Nearshoring veterans about what it's like living and doing business in LATAM. Join our hosts and numerous guests from LATAM & the U.S. with interesting real life experiences. This podcast is full of great stories and useful advice on how to navigate the world's most untapped talent market along with travel tips.
The Nearshore Cafe
Building a $6M Remote Sales Operation in Colombia 🎙 The Nearshore Cafe Podcast
In this episode of The Nearshore Cafe Podcast, host Brian Samson, founder of Plugg Technologies, chats with Amir Reiter, CEO of CloudTask, about how MedellĂn, Colombia has become a hidden gem for building high-performing global sales teams.
From building his first team in an Airbnb to scaling a $6M+ revenue operation with over 265 contractors, Amir shares how CloudTask evolved from a service agency into a full-blown B2B marketplace for GTM (go-to-market) talent and software.
They dive deep into:
- Why MedellĂn is ideal for remote-first teams
- How to scale with Latin American tech talent
- Contractor loyalty vs. W2 mindsets
- Navigating culture, compliance, and team-building in Colombia
- How AI is reshaping hiring and tech operations
- Lifestyle perks of living and working from MedellĂn
Whether you’re a startup founder, tech exec, or just exploring nearshore team strategies, this episode delivers real insights from someone who’s built it—on the ground.
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- Amir Reiter: linkedin.com/in/amirreiter
- CloudTask: cloudtask.com
- Brian Samson: linkedin.com/in/briansamson
- Plugg Technologies: plugg.tech
- The Nearshore Cafe Podcast: nearshorecafepodcast.com
📢 Don’t forget to LIKE, SUBSCRIBE, and TURN ON NOTIFICATIONS for more insights on Latin America’s growing tech scene! 🎧🔥
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âś… Host: Brian Samson | LinkedIn: https://www.linkedin.com/in/briansamson/
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Welcome everyone to another episode of the Nearshore Cafe podcast. I'm your host, brian Sampson. If you're interested in doing business in Colombia, running a software company out of Colombia, wow, this is going to be an episode for you. I've got Amir Ryder, ceo of CloudTask. Before we officially welcome Amir, let me thank our sponsor, plug Technologies pluggtech Great way to connect talent, especially technical talent, from Latin America, to growing US companies. Amir, so great to have you on the show. Likewise, dude, appreciate the invitation. Amir, where in Colombia are you calling from?
Speaker 2:Yeah, I'm in Medellin right now, but I spend a lot of my time in San Francisco where we have an office in the headquarters, and then I sneak back near shore for the good food and the good weather and the safety and security and just loving it here.
Speaker 1:I've actually been in a lot of places in Latin America. I have yet to make it to Medellin.
Speaker 2:Oh, you'd love Medellin.
Speaker 1:I've heard it's like perpetual spring, but for those like me who've never been there.
Speaker 2:They call it the internal spring.
Speaker 1:Yeah, yeah, Tell me more about Medellin like quality of life, what it's like living there. Yeah, yeah, Tell me. Tell me more about Medellin like quality life, what?
Speaker 2:it's like living there. Yeah, I wrote an article called the new American dream. It's on substack and I just you know, for me it's 65 to 82 degrees every day. There's no daylight savings, so like you're not up at nine o'clock with the light, like I sleep at 830. And I'm like just on an amazing schedule which is, like you know, really underrated, right, the food itself is 75% cheaper and healthier, and then you know everything. The cost of living is just much lower and healthcare like my healthcare in America is like 900 a month for me and my family, and here it's 190.
Speaker 2:And I just you know, for me it's an amazing place that I just truly love and there's just an awesome entrepreneurial network. There's, like the CEO of Beehive Shout out to Tyler Dank, who just moved here and just a lot of tech people and a huge community. I'm in like a paddle group of like 100 like CEOs of tech companies that live down here, which is great. And then, you know, I go to San Francisco all the time for just my clients and just you know, meeting the people that aren't as fortunate to be able to just move back and forth. Right, I guess I'm very lucky to be able to just have that liberty to be in two cities and split my time right.
Speaker 2:But yeah, it's for me it's just a magical place. You know, I know that you were in BA right, buenos Aires. So I kind of look at it like a ba of buenos aires, that's like a smaller city that's just closer to the americas right, like when you have buenos aires is like maybe, like I don't know, eight hour, ten hour flight to the states yeah and, like you know, colombia is like three hours from uh miami, but it's just.
Speaker 2:I went to argentina. I fell in love as well, right? So like, yeah, like it's a beautiful place.
Speaker 1:yeah, awesome, yeah, awesome. Yeah, we'd love to. We'd love to check it out. Tell us a story Like how, how did you end up there?
Speaker 2:Yeah. So I had a advisory board member, eric Agmon, who was the CEO of Answers on Demand. It was a POC, erp, medical software and he sold it for a great deal. And he was like, let me, let's go to Columbia. And he was my mentor and I was like sure, you know, like like I'm learning, you know, like my, my mentor, I'll, I'll come with you. I was like the 32 year old at the time that was like gifted with the gift of gab and socializing, and he was the you know, 60 year old, recently divorced, you know, getting back into the game, type person. Sorry, eric, if I you know, he'll be fine. So I went there. And then I also had a team in the Philippines at the time, which was great, they're awesome. But I came down here and the guy at the hotel who is now our VP of global talent his name is Danny Agudela and I was chatting with him and this guy spoke fluent English. I was like yo, what do you know? What do you make a month? And he's like 700, okay, and I decided that it would make sense to.
Speaker 2:At the time I wasn't running a B2B marketplace, I was an agency and we got to about 265 employees.
Speaker 2:I really I kind of brought down like B2B SaaS outsourcing from a sales and customer success perspective.
Speaker 2:I had amazing customers like RingCentral, expensify, apollo, all SaaS companies that would hire CS, cx and SDRs and AEs through us. So that brought me down, was like the talent I met and just the you know the adventure of something new where, like I already knew what, like Home Depot, and I kind of knew the whole America story like the back of my hand and like you can close your eyes and basically predict the next 15 years of your life where, like in Columbiaia, just this cool stuff, like just random, weird things, and you're just like this is strange but cool. So it's also very mentally engaging, um, and just different cultures are great, right and uh. So that brought me down here. Just a random trip with an advisory board member and then at the time I had a you know an agency like a call center type of thing, and I built a team here at that time and and well, you remember what year this was, that this 2016, 2016, okay, okay, well, how time is flying.
Speaker 1:Yeah, I'll be 42 in june don't fucking ask me how?
Speaker 2:but fortunately I got married, I have a daughter. So you know I'm I'm not peter pan anymore.
Speaker 1:Yeah yeah, funny enough, 2016 was the year that I first went to Argentina, so we were doing it like the same year, just in different countries. That's awesome.
Speaker 2:Yeah, our energies connected. Eight years later for the podcast.
Speaker 1:Yeah, I like it, I like it.
Speaker 2:Small world.
Speaker 1:Did you meet your spouse in Colombia?
Speaker 2:Yeah, I was buying computers for my team. She was working at the electronics store outside and I said guess what? I said? I said hi, how are you? What's your name? I'd love to take you on a date. Right, for anybody listening, that's pretty much all you need to say to get a date. Anything else is too much. Yeah, yeah, and we were like friends for eight years. She was going through law school and then, you know, we had a very mature conversation about building a family and she's actually our chief operating officer. Her name is Jessica and she's just great, you know, very fortunate to have a very traditional, non-traditional relationship where my wife gets to really focus on the family but also gets to, you know, be a part of every meeting in the company, and she's got equity in the company and she's smart, she deserves it, she earned it Right. So really lucky in that. I would bring the baby in, but too much time Show me a picture here.
Speaker 2:The picture.
Speaker 1:That's the wife and the baby. Yeah, I love it. Yeah, love the family. That's awesome.
Speaker 2:I'm a rebel so I was like we're going to have five kids.
Speaker 1:It's great, there you go. So was Medellin, the first city that you set up in.
Speaker 2:Yeah, and then I got an office in Bogota as well, but Bogota is a little bit cold and a little rainy and a little dangerous. Medellin is a sweet spot for me. I'm just really big into nature and hiking. On the weekends I go to a waterfall hike and I got a vishla, which is an awesome, very hyper dog. I got my dog in Argentina. We flew to Buenos Aires to pick him up. No kidding, yeah, yeah, the, the, the, you know from a champion breed and his little model. He like, he like, poses for pictures and stuff. It's in his blood. It's funny.
Speaker 1:Yeah, that's great. So talk us through that very first hire. Because there's people listening here they're like, wow, this is a really interesting thing. They're kind of hanging on every word of the VP of talent. You know the amazing arbitrage, like first hire. You know how did that all work out? Like, what did you do to make that happen?
Speaker 2:I, you know, I set up my job opening with my clear description of the job, my clear expectations and my salary range and I, you know, allowed people to apply to it and I reviewed the resumes and I interviewed people that matched that job opening and then I made an offer to the people that I felt were best fit and, unfortunately, the average the average everybody in my company now has been with me for eight years, which is awesome, and they're all contractors. So anybody who says they have to hire W2 for longevity is just not really thinking smart, because it really matters, you know, like your culture and your your, you know, payment structure versus the contract, right, Like the average two months. And you know I made friends with all the people I hired, 265 that were actively working and probably hire like 700. A lot of them have gone on to bigger and better things, the opening up agencies, and I just kept a good network of them and stay friendly with all of them.
Speaker 1:Yeah, and did you make that first hire? You were still living in San Francisco or you were already in Medellin by then.
Speaker 2:I was in Miami at that time.
Speaker 1:Yeah, I was in South.
Speaker 2:Beach. Yeah, and yeah, his name is Julian Moreno. He's now one of the VPs at Globalization Partners, which is a big company. He was one of my first hires out of Bogota and he brought someone else that he knew in his network and I flew to Columbia and got an Airbnb. We were all sharing it together and then I actually had this penthouse. That was huge, that I actually had Some of my founding employees lived with me. One, eddie Bejo, who was my co-founder, actually married Maria Sanchez, who was like the lady, who was like my CFO and did all the government's passports, and they ended up getting married and having a kid and it was interesting. It was like a work frat house, but a good time. I like to live life a little bit, you know.
Speaker 1:Yeah Now California, miami these are places where Spanish is already prevalent. Did you have to worry about like? Did you have to become bilingual to do it?
Speaker 2:No, I barely speak Spanish.
Speaker 2:I had handlers the whole time. So I've just been handled Like Maria was my initial handler, right? So just take me to all the banks, I'm signing things, I'm stamping things. So everybody I hired spoke English and I was like friends with them, kind of so like I constantly just had handlers and like now my wife is my handler, um, so she does all my visas, she's a lawyer, she takes me to the doctor's office, tells me to shut up and not be rude, you know things like that. She's happy I don't speak spanish because, you know, I got a little bit of a gift of gab and I just, you know, I I talk a lot, so she thinks it's good that I don't speak spanish.
Speaker 2:But in tienda son poquito, like, like I'm gonna, you know, I'm gonna continue learning, but I'm an anomaly, like for some of those who speak spanish. I met like the coolest people in medellin the business owners, the private families, like the founders, so like all my friends are just like top top performing people. So I guess that's like who I want to hang out with anyways. Yeah, but I'm also, you know, I'll admit that it's a little bit embarrassing that I don't speak spanish fluently, but nobody's perfect. You know I got areas of unity and uh, gotta work on it I think that gives a lot of people from the state's confidence.
Speaker 1:You know that you can not only you go around to miami, and they don't speak english yeah, yeah like miami.
Speaker 2:They're like how about it's just different? Because you're like you should speak english right here. You're not like you should speak english. You're like should I should speak spanish? Yeah, um, but like a second Google like translates language in real time. I don't know if anybody saw that update. Sorry, no excuses now. Yeah.
Speaker 1:Yeah, for sure, for sure. You know what you know. What's funny is, when I was in Argentina, absolutely, but I live in Hawaii. I really don't get a chance to practice it and, just like you, amir, everybody that I work with speaks advanced English. So, like you know, their English gets better, my Spanish gets worse. Yeah, yeah, yeah, yeah.
Speaker 2:And I was like, like I think having respect for the culture and the people on the land is equally as important as language. Right, like I don't come here and try to like, push my. I try to push my ambition and my speed and things that will help people get to the next level, but I embrace the culture, embrace the people and have a lot of respect for it, and it's a journey. Right like now that I have a daughter, I'm sure that she's going to be learning how to speak and I'm going to be learning how to speak spanish with her right yeah life's a marathon right, so maybe in like 10 years, me and you will be in medellin speaking spanish together love it, love it.
Speaker 1:Yeah, you never know right. So cloud task tell the audience a little more about, yeah, what it is, what does it do?
Speaker 2:yeah, we're a b2b marketplace that's focused on gtm services, full-time candidates and software. So we're kind of bringing together um, the account executives, the sdrs there's almost 120 positions that are just, you know, customer facing roles. Obviously, you know we partner with you guys on the development side, right, and then lots of software like Apollo, clay, wormley, all the technologies that people use for go to market functions and in GTM you got sales, marketing operations, customer success, customer support, right. And then with agencies, think about, like all the call centers, telemarketing centers, inbound centers, lead generation agencies, seo agents there's almost 50 types. So we basically help buyers know what they're buying and not have buyers remorse, because it's such there's like 40,000 call centers and 40,000 agencies, 1,000 GTM softwares right, thousand call centers and 40,000 agencies, thousand GTM softwares right. So we really make sure that people know what they're buying, like what the business challenge really is, so that they don't have buyer's remorse.
Speaker 2:And you know, think of it like a Upwork or you know an Airbnb or an Uber. But just for GTM functions, right, for sales support operations, cx, which is big right. So we're focused, but focused on a very big part of the market and that's what we do right. That's what we do. We help people find the right sellers and the right partners. We might even get you listed, because we have a business challenge called building teams and then website development, and that's where you're going to be in, because that's the business challenge you solve for right, that's right, that's where you're going to be in, because that's the business challenge you saw for.
Speaker 2:Right, that's right, that's right. We'll talk more about that, oh it's Don. Sorry, you're in.
Speaker 1:You opted in. Yeah, I appreciate that. Yeah, what I'm really interested in, amir, is the scale that you got your team to I mean phenomenal. And how did that maybe intersect with the original vision of CloudTask? Yeah, and where CloudTask evolved to, and scaling around that, yeah yeah. The energy of doing that.
Speaker 2:We scaled the 265 contractors, we were about $6 million in revenue, and in America you wouldn't be profitable with the math there, but because the cost of goods is 75% lower, we were very profitable and successful. And I really pivoted because I saw an opportunity to solve a big problem and to build a billion-dollar company. And, depending on how I stick the landing, I might be like, oh, that was a great idea, pat on the back, or I'd be like you're an idiot, right, because I took a very profitable business and ripped it apart. But it was, you know, for me. I just, you know, I saw myself kind of stuck with success, which is not a bad thing, right it just.
Speaker 2:I really saw the fact that buyers didn't know what they're buying and that the status quo like someone had to take a chance to like really help the industry because people just wanted to hear. If you came to me and you're like, hey, I want to hire some sales development reps, we need to generate meetings, and I told you, hey, it would take 90 days because there's no market validation and I can't promise you 15-minute meetings, the person would go to the competition who lied to them, and I felt like that wasn't the way people should buy right. So by being a marketplace, I got 5,000 options. I could really pay attention to your real business challenge and give you options and not sell you because I got it all. So it's kind of like if your car is a BMW but I got all the brands, I'll give you the right brand.
Speaker 2:Because I just didn't like the fact that status quo was telling people what they want to hear and that was the normal right and at the same time, like from a capitalistic like I wanted to fix a big problem and I wanted to do a good thing, but I also wanted to be rewarded for doing that right. I don't want to state that, like you know, I wanted to build a billion dollar company by doing that and also, at the same time, helping people getting out of the call centers, like you're doing right, which is a noble thing because you're helping young professionals that work very hard, just access jobs and opportunities they didn't have a chance to before, right. So that was why I did the pivot and, you know, hopefully partnerships like ours or you know make it worthwhile in the long run yeah, yeah just different business model.
Speaker 2:Right one birds cash, one makes money love it.
Speaker 1:Yeah, tell us more about, um, the actual scaling of your company, because I'm just like super impressed that.
Speaker 2:Yeah, yeah.
Speaker 1:So we scaled from zero to six million in like three years. Yeah.
Speaker 2:And a lot of it had to do with getting in a plane and meeting everybody face-to-face and driving Like some of our biggest clients I like land in New York City and then I drove to Boston seven hours and they're like, yeah, you won the business because you're the only ceo who got in the car and like drove seven hours and like looked me in the eye, yeah, so I built really strong relationships with people who you know it's required when they're trusting you to build and manage teams and, um, I treated the employees with more of a sense of entrepreneurship, where I was like teaching them like you know the world is and like they kind of saw me cold calling and like doing like whatever I asked them to do, I do myself, right.
Speaker 2:So I think in this culture there's more of like I'm the boss, you're the employee, and if they called me the boss, I'd be like I'm not your boss, I'm the chief, right, like I might be side with you, versus putting my feet up and bossing you around. And I think that was a big part of the reason why I scaled fast.
Speaker 2:It was because the culture was more like a San Francisco startup versus you know, like, like, yeah, like I was less like this is your job, more like you know this is your career type of thing, right, and and really, just, you know, I think that it was natural because I really felt that way and I think people can tell right that I was just ready to like get down and dirty with them, you know.
Speaker 1:Yeah, yeah, I like it. Can you you walk us through maybe even how you set up the org, Like did it mirror what? Like the type of titles and positions and departments? Did it mirror what you might see in San francisco?
Speaker 2:or yeah, yeah you know, like, had a coo. You know I had a uh, three account executives, maybe five account managers, a vp of operations. Very similar, no different. Everybody spoke english, everybody worked for american companies, most of people I hired already working for at&t and cricket. And you know the big organization, yeah, you know my co-founder, eddie bejo, was working for Fitbit customer support. So yeah, same title, same structure.
Speaker 2:The only difference was like, hey, there's 22 holidays on a Monday in Colombia. They're not for you, they're against you. So you could be lazy, you're going to work on this holiday. It's a different mentality of, like you know, I said I like drinking on a Monday because, like, think about it, right, they have 22 mondays off, okay, well, china's not taking off on monday, all right, and you're competing against the global stage. So I just kind of like showed them that like, hey, you're kind of being duped by your government into thinking that these holidays they didn't even know the holidays. They didn't even know the holidays. What is the holiday? They had no idea. No idea. Multiple saint days, right, but they don't know. All they knew is they had a long weekend and they couldn't go party and it held their career back and it was a way for the government to keep the poor poor right.
Speaker 2:They think you're giving them something, but what they're giving you is a way to just climb the ladder and fall back down, yeah, right. So I kind of came in and said I want to work for a plumbing company, go, do that. You want to work for us? You're going to get education, exposure to tools, exposure to AI, which is not even now, but you're going to work in the American days, right, so it's a given again, right? Yeah, I think you know, you've probably seen that in Latin America they're more trained on, like, how to sue the employee than they are how to make a lot, because that's what they get. They're given they're not given the opportunity to move up the ladder. They're given opportunity to sue the employee, right, and and I was like yeah, you can't sue me, I'm an american, you know, like, like, you know like I'm not. You know, I'm not hiring an employment contractor, independent contractor, and you're gonna have to work hard and and earn skills.
Speaker 2:People are given things that distract them, right so I felt like the government was pulling the shades over the eyes of the general population. While the top 1% working and crushing weekends, the average person is partying and taking off and right, like, okay, if you're, you know, and it's backwards In this culture. A lot of the kids are taking care of the parents. The parents don't retire at 50. The parents get supported by the kids and there's one way to break that trend by somebody saving money and investing, right. So some of the guys I'm working with now have stock portfolios, they have Bitcoin, because I talked to them about that right, and I would say stuff like hey, it's not fair that now that you make more money, you give your family more money. And they retired at 50. Like like, where does it stop? Right, it's a never ending vicious cycle. And I just kind of like told them the truth. It hurt their feelings, but they could see that I kind of meant it from a point of like, empowering the next generation.
Speaker 1:You're right. Yeah, I like that. I think that's really good advice. Is there any other advice that you'd give maybe US CEOs? Yeah, yeah, if they were trying to build-.
Speaker 2:Fly down, meet your team, take them out to dinner, like I have, a company called Expensify. They had 48 account executives for five years. Well, guess what? They flew out. They met the team, they took them and they're still there, right, everybody who flew out to visit their team still has the team. Anybody who just hired it like an outsourced third party, fire them. Treat them like they might work with you for eight years. Get to know them and build real relationships in person.
Speaker 1:Yeah, that's great advice. I want to talk more, amir, about AI. You're very well versed in your company. What do you see? What are some of your predictions, and then maybe even how it might impact nearshoring.
Speaker 2:Yeah, faster, cheaper, more efficient. I see it making everything faster, cheaper, more efficient, and I see the fact that companies are going to have could probably be able to be leaner on the headcount and achieve more. But there also might be more startups, right? So instead of having bigger companies, I would predict that there's going to be many small, specialized companies, right? So if you need a million people employed, and that was in 500 companies now, it might be a million across 2,000.
Speaker 2:And I think that what I'm trying to do is just get the hands, get the tool. I have an example. I got this guy, danny Nadella. I joked around because on LinkedIn, I put some posts about how he didn't speak English when I met him, which is not true. He did, and now he programmed a candidate assessment of lovable and just letting and just like letting people know that, like you got to break things.
Speaker 2:If you want to learn something, just start using these tools use madnessim, use lovable, use chat, gpt, use Gemini, use perplexity and ask it questions. It's about the questions you ask it. If you ask it, how do I improve my career and protect myself for the next five years? It'll give you an answer that can help you If you ask it, you know who should I bet on in the next basketball game. You might get some good information, but it's not going to.
Speaker 2:So it's like anything is as good as the questions you're asking. We're just getting information faster, right? So just make pretend that you're using the tools the right way, and then there's going to be a big opportunity for you to be a transform agent, meaning like, hey, I'm going to come to your company and share everything I know with AI to make you do things faster, cheaper, more efficient, versus being replaced by it. So if you don't want to be replaced by it, you should be using it. If you're not going to use it, expect to be replaced by it. And I sent an email to my team basically saying hey guys, we're going to grow to a billion dollar company with 12 employees or less. You have a choice you can either use these tools and I'll pay for them, or you can resign. Nobody resigned and everybody's using the tools Awesome, I love it, I love it.
Speaker 2:And that even goes for me.
Speaker 1:Yeah, yeah, yeah. I'm sure you saw the email from, I think, the Fiverr CEO, right Like even even the CEO.
Speaker 2:Yeah, that was something similar. I saw that and it's true, right, because it's like you're not, like you're just, you're like telling them the truth, and it goes for me, too, right. Like like as a CEO, like there might come a day like a year from now, or like I can get replaced by AI right, I might own that AI in that point, right, which might still be beneficial is safe from innovation and change, and it's not a you versus them type of thing. It's like we're just innovating fast and you could be a leader or a laggard, right. What's your favorite?
Speaker 1:AI tool. Yeah, I've been having a lot of fun with a caption app. You know, where you can kind of grow your own avatars. Are you vibe coding? You vibe code? I'm not a vibe coder, but I'm seeing a lot of this vibe coder trend. Are you All right? No, I don't know. Maybe, yeah, I'm seeing the trend. Maybe, maybe I'll I'll become a vibe coder. It seems like, yeah, I think there's a lot of FOMO right now around vibe coding, so we'll see.
Speaker 2:Yeah, I'm like you know it's. I wouldn't say I vibe coded, but for me, to communicate with my CTO, my dev team, I was able to use Manus to get this prototype on a website, so it's technically vibe coding. So, yeah, I guess I am vibe coding.
Speaker 1:There you go. There you go Good, good stuff. Well, as we start to wind it down, I just want to ask a fun question. Yeah, what are some of your favorite must-go-to restaurants in Medellin?
Speaker 2:Favorite must-go-to restaurants in Medellin Somebody visit, yeah, don Diablo, best steak yeah, and then I go to Hakanami, which is the best sushi yeah, el Cielo is like a five-star restaurant, which is awesome, yeah, awesome.
Speaker 1:Awesome, cool. We'll definitely put those in the show notes for everybody.
Speaker 2:Yeah.
Speaker 1:Yeah Well, Amir, this has been super fun. I'm just really impressed with how you took the risk, built something really special, did it all in Colombia and embraced the culture. So kudos to you.
Speaker 2:Likewise to you, man. You did the same thing, so I'm also impressed.
Speaker 1:And I appreciate you having me on. Absolutely Well, you're listening to the Nearshore Cafe podcast. This is Amir Ryder from CloudTask. This podcast is sponsored by Plug Technologies pluggtech Great way to connect talent from all over Latin America to growing US companies. We'll see you next time on the Nearshore Cafe podcast. Thanks for listening.