Outreach CEO & Co-Founder: Manny Medina


Manny grew up in Ecuador, where his father is originally from, and where his mother immigrated to from Russia.  From a young age, Manny has always had a desire to build something special that contributes to the society around him. After high school, he had interests in becoming an economist, but his father strongly recommended that he go to Eastern (communist) Germany to study engineering.  Manny would end up moving to New Jersey to get his bachelor's degree in computer engineering from the Stevens Institute of Technology. Soon after, he got his master’s in computer science from the University of Pennsylvania.

Manny would eventually join Amazon as just the 3rd employee on what is now known as the Amazon Web Services (AWS) team and created the compensation system for Amazon associates.  Two years later, he joined Microsoft as a business development manager and would work there for 6 years, eventually becoming the director of business development handling Canada and Latin America.

Then, he realized he was into his forties, and decided it was time to begin building something special, something he had always had a desire to do since he was a just a kid.

In 2011, Manny left his job at Microsoft without a plan, and just three years later in 2014...

Outreach, the #1 sales engagement platform, now valued at over $1 Billion, was born.

Podcast Transcript

Note:  There may be errors to this transcript (some funny, some confusing - we used an automated transcription software!)

00:00:00 Manny Medina: …entrepreneurs are out to get rich.  I was talking to another CEO, who’s been CEO several times, and he’s like, “I got four years to make eight figures, and then I do it again. I do it four times, and then I’ll retire. That’s my plan.” I’m like, “Okay, it’s a good plan. You’ll get rich with that plan.” I don’t have that plan. I have a plan of building something that is meaningful for a lot of people: ourselves, our customers, the community, and then…


00:00:28 Ash Faraj: Hey! Welcome to the ExecuTalks Podcast. It’s the show that gives you insight to the personal stories of today’s top executives.  In this episode, you will hear from Manny Medina, current CEO and co-founder of Outreach, the world’s leading sales engagement platform valued at over $1 billion. You want to stick around to the end to hear where Manny shares the basis of his decision to leave his job and eventually co-found Outreach.

00:01:00 Ash Faraj: Hey guys. We initially had this conversation a little over a year ago. At the time, we recorded in an open space where there may have been some background noise. We apologize in advance for the audio quality.


00:01:20 Ash Faraj: Manny grew up in Ecuador, where his father is originally from, and where his mother immigrated to from Russia. From a young age, Manny has always had a desire to build something that is greater than himself. To build something that would outlive him. After high school, he had interests in becoming an economist. But his father strongly recommended that he’d go to Eastern Germany (the communist part of Germany) to study engineering, a career that is deeply rooted in Manny’s family. Manny’s interests had shifted to software engineering. He had dreams to move to the United States to pursue an education, but Manny’s father had to be convinced that he was going to obtain at least a master’s degree.

00:02:03 Manny Medina: You know, the desire to build something greater than yourself has always been in either my DNA or my life experiences. I’m from Ecuador to begin with but, even in Ecuador, I was the child of an immigrant. My mom was Russian. My mom immigrated to Ecuador with my dad. My dad is Ecuadorian. I always felt a little bit out of place. But a little bit with a higher calling to do better for the sake of everybody else. Russia, as you know, at that time was a deep communist country, and my family was deeply socialist. I always knew that whatever I did, I didn’t have to do it for myself. I’d have to do it for a larger group of people. The benefit was you not only have to prove to me, but I have to prove to everybody. How do I raise people out of poverty? How do you educate the masses? How do you provide healthcare for a lot of people? I always had to live with those questions. How do you do what you do, but you do it for a lot of people, which is counterintuitive if you think about the entrepreneurial journey. Like a lot of people think that entrepreneurs are out to get rich. I was talking to another CEO, who’s been CEO several times, and he’s like, “I got four years to make eight figures, and then I do it again. I do it four times, and then I’ll retire. That’s my plan.” I’m like, “Okay, good plan. You’ll get rich with that plan.” I don’t have that plan. I have a plan of building something that is meaningful for a lot of people: ourselves, our customers, the community, and then leave that behind as a legacy. That’s my goal. It’s a different kind of motivation. That’s what my childhood has inspired me to do what I do right now.

00:03:49 Male Voice 1: Awesome. You were in Ecuador, and your parents wanted you to become engineer. You wanted to be an economist, right?

00:03:56 Manny Medina: Yeah, it’s funny you remember that. Not a lot people know that.

00:03:59 Male Voice 1: Yeah, absolutely. I read somewhere that your parents were not on board for you to be moving to the States --

00:04:05 Manny Medina: -- Correct.

00:04:06 Male Voice 1: -- and specifically your dad. What was it that they wanted you to do, and what was going through your head at that time?

00:04:13 Manny Medina: I went to high school in Ecuador in six years, unlike here which is only three. So high school in Ecuador is kind of like from the age of 12 all the way to the age of 18. I went to a German school in Ecuador. My parents were hoping that I would continue moving on to Germany. That I would study in Eastern Germany, because that’s the communist part of Germany, and become an engineer just like my dad was and my aunt. I was going on that path, but then the Wall fell. Eastern Germany stopped being Eastern Germany and it sort of went into this turmoil. And then we’re like, all right, what are you going to do?  I started school in Ecuador, and they were like, “Well, you can finish it here and then you go to Europe.” And I’m like, “I don’t know anything about Europe.” It wasn’t a place where I grew up. All the movies come from the US. All the technology started coming from the US. All the software technologies that I’m in love with that I’m buying at that point, like Microsoft and IBM, etc., are US companies. I hated the prospect of -- You know, when you graduate as a software engineer in Ecuador, you end up maintaining somebody else’s software, right? You end up working on the support team in country at Oracle or whatever. I’m like, that’s the last thing I want to do. I want to write the software that people obtain. That shortens the list very significantly to the US. So that was my pitch to my parents. I want to be in software, and I want to be where software is made. All the software at that point was made in the US.

00:05:54 Ash Faraj: When you first told your dad that, when you first brought up the idea, what was his reaction?

00:06:00 Manny Medina: My dad at that time was living in Venezuela, so I was going back and forth to Venezuela. He started growing a little bit warmer once he realized that Ecuador wasn’t on the cards anyway, and that I wanted to leave. He started becoming warmer to the idea of, you know -- “As long as you study engineering!” [laughter] The US was not a terrible place to end up.  

00:06:23 Male Voice 1: We feel you. [ laughter]

00:06:26 Manny Medina: Anything less than that, was a no, no. I had to stop talking I was becoming an economist, put that aside, and talk about engineering. And just talk about the [indiscernible] is going to be greater on the engineering side. And so, he bought into that, and that’s how I ended up in the US. [laughter] It took a little bit to understand his real motivation.


00:06:54 Ash Faraj: After Manny got the okay from his father to move to the United States, he went to New Jersey and earned a bachelor’s in computer engineering from the Stevens Institute of Technology and attended the University of Pennsylvania to get his master’s in computer science, right after he graduated with a bachelors. In Ecuador, Manny had gotten through English courses and thought he was proficient in English. But getting his social life up and going was an initial struggle when he first moved to New Jersey as there was a language barrier that he did not expect.

00:07:30 Male Voice 1: What kind of struggles did you have to overcome when moving here, all alone I know. Was it New Jersey?

00:07:35 Manny Medina: Yeah, the port of entry was Newark, New Jersey. First of all, it was English. I took classes in English Academy in Ecuador.  I did it all the way to the end and got the degree that says I am fluent in English. Then I came here, and I was not fluent in English. I was really good at writing and I was really good at reading, but my conversational English was pretty terrible. It took me, I think, like a year to be able to hold a conversation on the street in New Jersey. I was very good technically. I could participate in classes in math or whatever, but if I were to go out to a bar or to a party and engage in small talk with loud noises it was not happening, for that entire first year. It was really hard to get acquaintances and make friends, to get girlfriends. That entire circle of social life became pretty hard because I couldn’t communicate, you know, to the degree where [indiscernible]. There’s a lot of like subtleties in the language that makes it more attractive. I didn’t word drop at the right time, or a thoughtful thing. [laughter] All of a sudden you go from here to here, right? [laughter] I couldn’t execute that stuff because my spoken word wasn’t at par. That kind of sucked at the very beginning. That keeps you kind of focused, so I did really well in school. I had almost zero distractions, but eventually something funny happened. I think Ricky Martin became popular like my second year in the US.  All of a sudden, having a Hispanic or Spanish accent was hot. [laughter] That was my step into starting [crosstalk/laughter] All right, perfect timing. [laughter] So that helped out quite a bit. But getting my social life up and going was hard, especially when you’re in engineering school. I also come from a family that -- the second thing that I had to promise my parents was, that if I were to come here, the school would not be done until my graduate degree. For him, an undergraduate wasn’t enough. You have to go and get your master’s in something. I have to enroll in UPenn to get my master’s in computer science so that I can get my parents off my back. That was the move. Once I was done with that, then I was released. Now you can go be your own person. Other than that, I don’t have to hear from my dad, and like, oh, you know, [indiscernible] but it’s not.

00:10:17 Ash Faraj: When I try to explain that, most of my friends are like, “What? Your parents are telling you what to study?” Nobody understands that.

00:10:22 Manny Medina: Right, right, right. Now, for me, it’s hard being a parent here, because whenever I hear people that tell me, “Oh, you need to let him go find himself.” No, you don’t! Do something useful. You know what I mean? Save a life! Become a doctor. Be an engineer. Anything else. Maybe write something. But, yeah, I have the same emphasis and the same thing with my kids, like, go be an engineer.

00:10:51 [music]

00:10:53 Ash Faraj: Manny would eventually join Amazon as just the third employee on what is now known as Amazon Web Services. He created the compensation system for Amazon Associates. Then two years later in 2005, he joined Microsoft as a Business Development Manager and would work there for about six years, eventually becoming the Director of Business Development handling Canada and Latin America. Things were going great for Manny, but the desire to build something greater than himself that had been in him since he was a child, wouldn’t go away. He would have to now face a difficult decision; leave Microsoft and build a business or remain on course at Microsoft.

00:11:40 Ash Faraj: You attribute a lot of your success to empathy, right? I read that somewhere online. Can you expand on that a little bit? What makes you feel like empathy really contributes to your success?

00:11:54 Manny Medina: Sometimes this holds me back, but I have a natural curiosity for understanding people’s motivations. That background processing is always on for me. You know what I mean? I always want to steer the conversation. Why are you guys here? What motivated you to do whatever you do? I do that all the time. I do it almost unconsciously. And because of that it allows me, it helps me, get into deeper conversations with pretty much anybody that I interact with. It’s really hard for me not to get serious. It’s really hard for me to just have small talk. I’m more interested in where are you coming from, and where are you going, and why. Everybody has a “why” for their existence. I’m always interested in that why. That’s a rubric of empathy in my mind. I’m empathetic, but I’m empathetic because I’m naturally curious about what drives you. I feel like I’m a collector of motivations. That’s what I do. My memory is very good because I associate you with what motivates you, and I create better memories because of that.

00:13:13 Ash Faraj: Interesting. Do you feel like that is a trait that helped you become successful in a way?

00:13:21 Manny Medina: I think that trait has helped me make deeper relationships that have helped me later in life. People who know me really know me. Nobody would say Manny is… People will always associate a set of attributes to me. Nobody would say, “Yeah, I kind of know him, but I’m not really sure about him.” People would be like, “Oh yeah, it’s Manny” and Manny has these things. If you get into conversation with me, we will both walk out with a bunch of stuff around each other that will allow you to identify me and me you. Would you be here in memory if I’m reaching out to you? I literally reached out to somebody, who I haven’t talked to in 10 years, yesterday. That person got back to me right away because he knew who I was. He knew the interaction that we had because you are able to lock that into peoples’ memories when you get down into their motivations.

00:14:13 Male Voice 1: That’s very interesting. That’s very cool. So getting to your career after graduating. You started with Amazon, and then you moved on to Microsoft. After leaving Microsoft, you had no plan for starting your own company. You just kind of did it. What was your thought process on that?

00:14:41 Manny Medina: I make a lot of decisions based on principles as opposed to -- You can take two angles or three angles. You can pattern match. You can say great people have done these things. If I do those things, I’ll be like great people or great companies or great anything, right? You match the pattern based on where you want to go. That’s one way of doing it. The other way of doing it is probabilistically. Meaning, if I were to start a company, it has a 99% chance of failure. Or you can do it based on principles. I had a few principles for me in that I felt that I was at that point in my career in which I can contribute a lot more than I was learning at Microsoft. And I was not contributing at Microsoft because Windows Phone had incredible amounts of layers of management and infighting politics.  It was a great product, but in a really complex market. I just didn’t see a way out of that, and I felt like I wasn’t contributing. I was in a career in which I felt like I didn’t contribute a lot. That’s point number one. Point number two, if I didn’t contribute from a point of where I can control the outcome, I wasn’t going to capture value. I think I did that right around when I was turning 40. I thought if I don’t do it now, I am never going to do it. Based on literally those two principles I decided to quit. If I didn’t quit, then I wouldn’t have enough space to figure out what it was that I wanted to do.

00:16:35 Ash Faraj: What I’m taking away from this is don’t be afraid to quit without a plan but just understanding why you’re doing something?

00:16:48 Manny Medina: Exactly. You need to understand why you’re doing it and if that “why” is strong enough that matches who you are. One of the biggest forces in personality is to have agreement with yourself. If you’re making something that sounds crazy, but it agrees with your view of yourself -- you’re strong, you’re smart, you’re energetic, you’re driven -- you can take something and make it happen, then you’re good. Of course, there is risk. I have three degrees. I can find a job. You’re good. But if you’re not being your best self, you’ll never forgive yourself for not trying. So you go ahead and do it.

00:17:31 Ash Faraj: The regret of not trying is greater than the regret of failure.

00:17:35 Manny Medina: Correct. You’d eventually develop with time; you’re filling up time that you develop, sort of like, a healthy balance and a healthy sort of relationship with failure. Failure is a thing that you expect. You’ll deal with it ahead of time. You’re mentally prepared to take it and learn from it and just move on.

00:18:00 Ash Faraj: We’re just going to switch gears a little bit. We’re going to turn to rapid fire questions. [laughter/crosstalk] Whatever comes off the top of your head and just say it.

00:18:11 Manny Medina: Okay.

00:18:12 Ash Faraj: In your opinion, what is the most important life skill?

00:18:17 Manny Medina: Curiosity. Whatever satisfies your curiosity. Be curious.

00:18:26 Ash Faraj: What was the most life-changing advice you have ever gotten?

00:18:33 Manny Medina: When you start a company make sure that you get one metric to go up and to the right. If it’s profiting even better.

00:18:42 Ash Faraj: What is your life-long dream?

00:18:46 Manny Medina: I’m living it. Being at my own company.

00:18:48 Ash Faraj: Right on. What advice would you give to 15-year old Manny?

00:18:53 Manny Medina: Quit earlier.

00:18:57 Ash Faraj: Okay, Microsoft or Amazon?

00:19:59 Manny Medina: At Microsoft.

00:19:01 Ash Faraj: Oh, really?


00:19:05 Ash Faraj: Thank you for tuning into this episode. If you enjoyed listening, please subscribe on Spotify or Apple Podcasts, and please leave a review so we that we can better serve you. Take care, dream big, and we’ll see you next Monday.

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