I am CEO

CEO Helps Bridge the Gap Between Tech Talent and Opportunities

Full Episode from I AM CEO Podcast - IAM1978

In this episode, Jacqueline Samira, the founder and CEO of Howdy. Shares her journey as an entrepreneur, her success in building her startup, and the unique approach Howdy takes in connecting tech companies with talented developers in South America.

In the world of business and entrepreneurship, it's not uncommon to hear stories of individuals who have overcome challenges and built successful companies. One such individual is Jacqueline Samira.

With her unique approach to connecting tech talent with companies in need, Jacqueline has become a recognized figure in the industry.

Jacqueline shared her experiences of witnessing a growing problem in the tech industry. While more and more companies were coming to Austin, there was a scarcity of tech talent to support their growth. Developers were being poached left and right, creating an imbalance of supply and demand.

Jacqueline is revolutionizing the tech industry by connecting talent with opportunities. Her innovative approach to hiring and fostering community has enabled Howdy to grow rapidly and make a significant impact. By addressing the scarcity of tech talent and creating a support system for developers, Jacqueline is setting a benchmark for other tech companies to follow.

Website: howdy.com

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Full Interview:


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Jacqueline Samira Teaser 00:00

And they're like, can you help us find more? So I ended up opening up a foreign entity in Uruguay so that I could hire these people underneath that foreign entity and then essentially pass on their employment contract to the companies in the U S it ended up working so well that.

I got just through word-of-mouth referrals, more and more companies were coming to me.

Intro 00:18

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This is the I AM CEO podcast.

Gresham Harkless 00:47

Hello, hello, hello. This is Gresh from the I AM CEO podcast. I have a very special guest on the show today. I have Jacqueline Samira. Jacqueline, super excited

Jacqueline Samira 00:54

to have you on the show. Thank you, Gresh. I'm so excited to be here.

Gresham Harkless 00:57

Yes. Excited to have you on and all the awesome things that you're doing.

So of course, before we jump into having a great conversation, I want to read a little bit more about Jacqueline so you can hear about some of those awesome things.

Jacqueline is the founder and CEO of Howdy, a successful people-centric entrepreneur who is building her startup into a unicorn, a keynote speaker, a voracious reader, a disrupter. of dollar-driven mainstream narratives and with a strong background in bringing equality, balance and empathy into the tech industry.

And just reading and learning more about Jacqueline, she has an awesome amount of success and a phenomenal story including having 100 million valuation for her company.

And, but the thing I love most is that she has a wealth of knowledge and experience that she shares freely. The word that phrase that came up for me was realistic positivity because she's the person that's going to tell you, Hey, you need to get what you need to get done, but also understand that it's not an easy journeys.

And 1 final thing. I think I found out Jacqueline is that you bought a piece of farmland. And as much as you would grind and do all these things I think it's so important to be able to have space to be able to recharge to make sure we remember what it is and why we're doing the awesome things that we're doing.

So super awesome that, you shared that super awesome that you're here today. Are you ready to speak to the I Am CEO podcast?

Jacqueline Samira 02:11

Oh my gosh, I am so excited. And the realistic positivity, I'm going to use that in a banner because I swear that's like the best accurate description of it. So thank you for giving me that little anecdote. I can now use.

[restrict paid=”true”]

Gresham Harkless 02:23

There you go. Look, it's easy to come up with a phrase a little bit harder to be able to get the great advice. So I love that you've been able to do the hard part to make it easy on me. So I guess just to kick everything off, what I wanted to do is just rewind the clock a little bit more on how you got started when I call your CEO story.

Jacqueline Samira 02:37

Yeah. Oh my gosh. So I, for the audience members out there, I'm going to age myself. I'm 37 years old. So I am, this isn't really my first foray into work. I've been working for a very, very long time. And just growing up, I always thought I was going to be a lifelong employee. The like right hand woman or of the person in charge, because I'm just such a people pleaser.

I want to help. I want to create solutions and I want to make folks happy. But what I ended up realizing just throughout my journey, throughout my life was that I was just very good at problem-solving and I would see problems and I'd come up with solutions and I would be excited to give the solutions to folks.

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And. In around 2015, 2016, here in Austin, there was a huge problem that I just kept seeing over and over and over again. And that problem was there was more and more capital coming to Austin, more and more companies coming to Austin, but there wasn't more and more tech talent coming here. And it started to create this imbalance of supply and demand.

And there was. So much toxicity in corporations and companies because developers were getting poached left and right. They were getting these crazy offers and it was really, really hard for the small business. It was really hard for small startups because one, they couldn't hire. Talented folks, if they didn't have a half a million dollar compensation package, and then two, if they were able to hire folks, they were very afraid that the person would vest and leave invest and leave.

And so there was just like, always this constant undercurrent of insecurity. And I was like, man, this is this is wild to me. This is so wild that there's all of these opportunities. And I'm sure that there are people all over the world who would be desperate for these opportunities. And I would love to just be the bridge to connect the folks that don't necessarily have access with the opportunities.

And that was the birth of Howdy. And I got started in 2018 and it really was just. From a problem that I was seeing over and over and over and not so much from the, Oh yeah, I'm an entrepreneur. I'm going to do this, but it's been a really amazing journey.

Gresham Harkless 04:46

Yeah. I appreciate you sharing that so much. And, what has led you, to the success that you have.

So I wanted to drill down a little bit more and hear a little bit more about howdy, how it works and how you're creating that impact.

Jacqueline Samira 04:57

Yeah. So, the funny thing is when I first started the business, I was not thinking big the way that I'm thinking now.

I was really just trying to help the people I was working with in trying to find. Talented individuals that could work with them and at the time, all of the solutions for being able to hire people outside of, your city or outside of your country, existed in Eastern Europe or in Asia or in India and for small companies that wasn't really conducive because small startups, they don't have really great processes.

They don't have really strong communication. And what we found is Once you hit a technical bar, the biggest risk is not if they are smart or if they can figure it out, or if they can build the product, the biggest risk comes from communication and having communication overlap. And so at the time I was just trying to find, Hey, where can we find existing talented people that have the same hours that we have?

Oh my gosh. Obviously, there's a whole continent to the South of us. Let's find these solutions at the time. Nothing existed down there that really would work well for tech companies. And what works well for tech companies is they're not going to basically throw their product over the fence right now.

Or at the time, when I started the company, there was outsourced product development companies, meaning you would give them the specs and then they would build the product. But if your core competency is technology, you want to build it. You don't want other people to build it. And then the other thing that they had was like staffing agencies and staffing agencies tend to give you talent on more of the junior level components.

And that's great and all. But if you're looking for architects to help you build it from the ground up, you need someone that has experience building things. And so I was like, man, where are the companies that are connected with the technical architects in South America, I went down there, I backpacked around, I went to a few different countries.

We, and I got connected to an individual in Montevideo, Uruguay, and he seemed like the perfect profile. And I was like, gosh, I know just the company for you. I know like you're going to be a perfect fit for them. And so I ended up connecting him with the company and then they had a really great success.

And they're like, can you help us find more? And so I went down there and I was looking and I found more people, but what I realized very quickly is in the very beginning. They wanted to work for a Uruguayan company. They didn't want to work for a U S company because at the time you have to understand like all of their benefits come from working for a local company.

So their healthcare, their, time off of their paid time, everything. So I ended up opening up a foreign entity in Uruguay so that I could hire these people underneath that foreign entity and then essentially pass on their employment contract to the companies in the U S it ended up working so well that.

I got just through word-of-mouth referrals, more and more companies were coming to me. It was like, Hey, that thing you did for that company, can you do it for me too? Can you do it for me too? And then it just started to spread. And I was like, wow, this is like so much bigger than I thought it was. Let me like rethink everything we're doing here.

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And it was around 20, it was like right after COVID happened. And then. Gosh, things just exploded from there. And that was when we really changed the focus from being more of a lifestyle business to one now that, we're swinging for the fences and trying to get that unicorn valuation.

Gresham Harkless 08:12

Nice. I absolutely love that. So would you consider that to be maybe part of your secret sauce? And this could be for yourself individually, the company or a combination of both, but isn't that ability to. I want to say maybe sift through all the noise and the distractions and really understand I think the core, you talked about that problem-solving.

Do you think that really makes your company unique and make you unique and be able to understand that? And of course, be able to do that?

Jacqueline Samira 08:37

Yes, totally. I think it's my secret sauce in 2 ways. I think it's a secret sauce in the sense that when you have kids, especially newborns, and you're the mom, Like you're, even if you have an equal partner, it's hard, right?

If you're breastfeeding, you're the main caregiver in that time period. And the most beautiful thing that happened that I didn't anticipate happening was the fact that it gave me the conviction to say no to most things. And I recently heard on a podcast that no is a complete sentence. And that's truly what it did for me.

It allowed me to say no to everything that wasn't absolutely business critical or crucial to what it is that we were trying to do, and it gave me the structure and foundation to say, okay, when I'm working, I'm completely working. I'm completely engaged. And when I'm not, I'm with my kids, but there was no time wasted.

Gresham Harkless 09:22

Yeah, that's so powerful. So I guess, how does how do you work? Can you take us through a little bit more on like how, companies or organizations might be listening to it now? And even on the other side, how might the people who are the developers and the people in the country is be able to I guess apply and go through that process.


Jacqueline Samira 09:38

So I'll give you like a little bit more background too, on the company. So one of the, my things I was trying to do was hire top technical, talented people. Now you can go to a freelancer platform. You can go to an online marketplace. You can go to Upwork. You can hire people through those platforms, real product companies.

Want people that are not freelancers because they don't want that mercenary type develop. And it's not to say that one is good or one is bad. It's just a different, it's just a different individual. The way they think through building product is more holistic. They're more a part of a team. They want to be a part of a team.

And so this whole idea of remote work, or if you think of the stereotypical developer, that's like in a dark room and they're playing video games is not necessarily the case in the places that we work at. And so what we do at Howdy is we actually have. Seven offices throughout South America.

We even did this during COVID. We call them howdy houses. And these are like future of work, community-centric event spaces, coworking spaces, really more just gathering spaces where people can work out of, we hire people only in select areas rather than just throwing a big map, because what we want people to be able to do is we help us tech companies.

Hire their team members in Latin. That's like the, like an elevator pitch. But how we do that is we have seven offices where we hire them locally so that they can work together. So you can have a cohort in Buenos Aires, or you can have a cohort in Lima, Peru or cohort in Brazil. And they have their space.

They have their community. They have their team members. They can work there. They can work from home, but we also will throw meetups and events because what we're also trying to do is give back to the local community and attract other like-minded developers to be a part of our mission. I want to be that social seal of approval for us tech companies looking to hire developers. And it's been awesome because our biggest growth has been through word-of-mouth referrals. So if you were a us tech company and you wanted to hire developers, what you would do is you'd come to us.

We'd help source a developer for you based on your specs. They join your team. We helped you all their payroll. We do all the legal compliance equipment, you name it. And it's a very, very easy all-in price. People pay week to week and it's a mutual two-week out. People can cancel anytime. So we really try and set it up like an at will employment agreement.

Gresham Harkless 11:57

Nice. I love that. So I wanted to switch gears a little bit, and I wanted to ask you for what I call a CEO hack. So this could be like an app, a book, or a habit that you have, but what's something that you feel like makes you more maybe effective or efficient?

Jacqueline Samira 12:11

One hack is I address things right away. It does not matter what time or if something even bothers me remotely, I address it right away. And what that does and what that gives my team is safety and security because they never have to question if I'm annoyed or if I'm mad or if I'm whatever, because I will tell them and I will always tell them like, Hey, I know it's 11 PM.

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But here's why I'm frustrated right now, or here's why I'm happy. I'm very, very, very vocal about where everybody stands at any given moment to give them the safety and security to never have to question what I'm thinking.

Gresham Harkless 12:41

Yeah. And that's so powerful.

Jacqueline Samira 12:42

Yeah. Another hack to, for all the CEOs out there listening is the beauty about being the CEO is you get to select everybody on your team. So if there's somebody you don't like either fix that relationship. Or move on, like it doesn't do you any favors and it doesn't do the employee any favors. If you are going to harbor any kind of animosity towards that individual.

Gresham Harkless 13:04

Yeah. And I feel like that's, definitely a subset of what you said about sometimes that we have those feelings and we feel like somebody might not be the right fit rather than, waiting, waiting, waiting. And, not only are you giving them an opportunity to maybe find a better situation, but you're also creating space for that next person or whatever it is that you're going to be you're going to do to be able to solve that problem.

Jacqueline Samira 13:23

Yeah. And then, okay. I've got another hack. Go for it. Your sales team is most likely not moving fast enough. And the reason why I know this is I've had years and years and years of sales experience. And the number one thing that a sales manager can do is create urgency.

Gresham Harkless 13:37

And so what would you consider to be what I like to call a CEO nugget?

You might have already session this. So this is a little bit more word of wisdom or piece of advice It's something that you might tell somebody that's maybe getting started more in business, or if you were to hop into a time machine, you might tell your younger business self.

Jacqueline Samira 13:51

You have to inspect what you expect.

It doesn't mean that you should micromanage people. It means that if you expect something to happen, then set measurable, quantifiable things around that thing and just track it either daily, weekly, monthly, just to make sure it's happening, but never assume. Because I assure you, even if it is happening, it's probably not happening the way that you want it to be happening.

Gresham Harkless 14:13

Yeah. So now I want to ask you my absolute favorite question, which is the definition of what it means to be a CEO. We're hoping to have different quote-unquote CEOs on this show. So Jacqueline, what does being a CEO mean to you?

Jacqueline Samira 14:23

The first answer that came to mind. Is like the true definition of it as it relates to being the CEO of a C corporation, which is to maximize shareholder value. That's the way I think about it. And the reason why I have to think about it in this way is because a lot of times. One of my, like I said, like I've said this a few times, I'm a people pleaser.

And so it can be at a detriment to me being the CEO sometimes because I want to make sure that everybody's happy and everybody's okay. But what I have to tell myself, knowing that is not necessarily like the best attribute in being a CEO is that a business is an unfeeling entity. And the role of the CEO is to maximize shareholder value.

So this business that has no feelings, how do they perceive this problem or this situation? And then what would that, this third-party CEO, that's not me do to maximize the value of the company.

Gresham Harkless 15:22

Yeah, I love that.

Jacqueline truly appreciate that definition. Of course, I appreciate your time even more. So what I want to do now is pass you the mic, so to speak, just to see if there's anything additional that you can let our readers and listeners know. And of course, how best people can get out of view, find out about all the awesome things you and team are working on.

Jacqueline Samira 15:40

Thank you so much. I really appreciate the time for being here today.

Yeah, go to, you can go to howdy. com. You can go to my LinkedIn, Jacqueline Samira, or you can find me at Howdy Jax, J A X on the socials.

Gresham Harkless 15:55

Awesome. Awesome. Make it even easier. We'll have the links and information in the show notes so that people can find out about all the awesome things that you're doing.

I truly appreciate you for blazing trails. I appreciate you even more for reminding us of how important that is. And I hope you have a phenomenal rest of the day.

Jacqueline Samira 16:06

Thank you so much.

Outro 16:07

Thank you for listening to the I Am CEO podcast. Powered by CB Nation and Blue 16 Media. Tune in next time and visit us at iamceo.co. I Am CEO is not just a phrase. It's a community. Be sure to follow us on social media and subscribe to our podcast on Apple podcast, Spotify, Google podcasts, and everywhere you listen to podcasts. Subscribe and leave us a five-star rating. This has been the I Am CEO Podcast with Gresham Harkless Jr. Thank you for listening.


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