Manny Medina, Outreach — Founder Story

DFJ Growth
Apr 2 · 7 min read

I was blown away by the opportunity I found in the US, with the amount of available capital and freedom of ideas. The fact that you can be whatever you wanted.

Talk about the roads not taken.

If Manny Medina had listened to his parents, he would never have left his native Ecuador to study in the US. Years later, while at the helm of his first company, a talent recruitment startup, if he had just doubled down and kept plugging away — he would have gone out of business.

Chalk it up either to brilliant insight or just having a knack for lucky hunches, Medina wound up making choices that subsequently led to extraordinary business success.

After getting an MS in computer science from the University of Pennsylvania and an MBA from Harvard, Medina worked his way up the ladder at both Amazon and Microsoft. But when he started his first company, GroupTalent, Medina’s charmed career almost had an abrupt end when he encountered a whisker’s-close brush with bankruptcy.

“We were literally two months from going out of business,” Medina recalled.

But that wasn’t the end of the story. Medina escaped that initial disaster when necessity literally became the mother of invention. We caught up with Medina to learn more about his journey and the subsequent founding of Outreach, a fast-growing developer of sales engagement software tools, where today he is its CEO.

Q: Your parents were both engineers and the expectation was that you would also be an engineer. Did that turn out according to plan?

Yes, but I did what every rebellious kid does in their teenage years. I told them that I didn’t want to be an engineer. I told them that I wanted to be an economist. Of course, my parents completely ignored me. Later on, when I actually became serious about becoming an engineer, they were like, `No, that’s not even an option. You need to figure out what kind of engineer you want to be.’

Q: Were you a computer geek?

No. My family was well-educated but we didn’t have a lot of money. I was sent to private schools and there wasn’t money left to buy a computer. I only really got into computers when I went to college.

Q: You’ve been quoted as saying that in Ecuador entrepreneurship was generally not something many people did when you were growing up. So, where do you think your entrepreneurial interest stems from?

Right. My plan was to go to university, get a job, and die working the rest of my life for The Man. But the word “entrepreneur” is loaded. It has this persona that you are always starting something, maybe multiple times. I am not that guy and I don’t think about myself in that sense. I don’t have 10 great ideas; I have one and this is my one shot.

Q: So, what motivated you to leave home and come to the US to study?

I realized that if I stayed in Ecuador, my success as a programmer would be writing modules supporting SAP or Oracle systems. That was the last thing that I wanted to do. The original plan was to go to Germany. My parents put a higher value on the education you could get in Europe when it came to engineering. I think that I came to the US mostly because I was fighting with my dad.

Q: When you arrived here, what did you find to be the hardest thing about leaving home?

The food as well as the environment. When I came to the US, I was living in Hoboken, New Jersey, which is very close to other places where you can find food from Ecuador. But it’s not the same eating a ceviche in Manhattan as it is eating a ceviche on the beach in Ecuador. That’s the thing I missed the most.

Q: But you stuck with it and you eventually got your MBA from Harvard. What resonated with you about being there?

Q: You worked several years at both Amazon and Microsoft. What motivated you to launch GroupTalent?

My partners and I were looking for ideas that were broken and that software could fix. We were looking for things with very high friction, and very high price. One was real estate, but Redfin was already disrupting that market. The other was recruiting. The original idea behind the business was to use technology to match job hunters and businesses. We weren’t able to solve that with a product. The people who you try to recruit are humans, so you have to get in front of them and understand who they are, and what they read.

Q: That idea nearly put you out of business. How did that experience change you?

It made me fearless. When you have a successful career where everything goes right — you go to all the right schools, you get all the right jobs — and then to have a company and run it to the ground and may need to shut it down. Once you stare down that situation, nothing else will break you. Now, nothing fazes me personally or freaks me out.

Q: So your talent recruitment company was a flop, but the product you developed out of necessity turned out to be a sleeper hit. How did that get you on the path to Outreach?

We had been selling the product to a few recruiters and the reason they bought it was to learn how someone was getting such a high commission rate with candidates. They were asking us things like, `How is it that your software is getting a 40% reply rate on email when we get 5%?’ That’s when it dawned on me. What if we turned around and took this tool and sold it to the people who are actually doing the selling? My partners agreed that we should go for it.

Q: Your grandfather was the head of Ecuador’s Communist party. What do you think he would say if he knew that his grandson embodied the textbook example of capitalist success?

His political conviction came from the fact that he really cared about people and wanted to help create a just society. Communism was just the tool that he used to try to get there. With me starting a company and making sure that everybody here has great opportunities and the ability to participate — I think he would be fine with that. I think that he would have been proud.

Q: Play the role of futurist. You run a sales automation company. Five or 10 years into the future, how do you think your part of the business is going to change as we come to rely more on automation and perhaps even robots?

I think about that a lot. In the next hundred years, I think there is still going to be interaction between humans and computer-generated life-forms. Humans will remain very much part of the fabric. I think that the human connection, this problem-solving ability we have to create trust and problem-solve, that’s a quintessential human faculty. Sales is basically one human making another human aware of exchanging goods and getting money for it. An innovator can go out and build something, but eventually you have to get it into somebody’s hands. You have to sell it. Facebook is great but at the end of the day somebody is selling Facebook advertising.

Q: You came to the US from another country. When you look at the immigration debate, how does it make you feel?

It’s hard not to listen to it because it’s everywhere. It makes me sad because the US has all the right ingredients. I’m not just talking about Silicon Valley but the US as a whole. It has everything to retain the status of being one of the greatest countries in the world. It has educational institutions; it has free capital and the history of people coming here to build. It has none of the stigma that you see in Europe, where if you fail, you’re considered a loser or where there’s over-protection and regulation that makes it harder to start companies. We have it all here and the vicious attacks against immigrants are just unfounded. It goes against the fabric of what built this nation. And we should remember that capital is not just flowing here; it’s also flowing to Canada and Europe, where there also are great scientific institutions. For instance, this revolution around machine learning started at the University of Toronto where the work they did is powering everything from AI to self-driving cars. So, greatness is everywhere and if the US is not the place where greatness can land, it will land somewhere else.

Q: On a lighter note, do you still sit on an uncomfortable wooden chair to encourage you to get up and walk around the office regularly?

Yes, I do. It’s a banker’s chair. And it must be the most uncomfortable, hardest chair ever.

Q: Do you still start off each morning giving fist bumps to all the employees at Outreach?

Still do. It takes a lot of time, but everybody’s not in the office at the same time. I only do it with the people who are there when I show up.

Q: How did that start?

Frankly, I don’t remember, but one day I started going around fist bumping everybody and I just never stopped.

Q: Do you have a favorite quote that you try to live by?

There are so many that it’s hard to choose. The thing that I do try to do is to learn something new every day.

Q: Any particular individual who you most admire?

Jeff Bezos. Nothing was obvious about Amazon’s success back in 2003; not retail, not AWS [Amazon Web Services]. He is just an inspiration to me.

Q: Do you have a favorite book?

“Thinking, Fast and Slow,” by Daniel Kahneman. Everyone should read that one.

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