Solutions Driven

[PODCAST] Manny Medina, Outreach CEO, on Imposter Syndrome, Winning The Talent War, And Running Outreach Like a Well-Drilled Soccer Team

manny medina outreach

In episode 6 of The Talent Intelligence podcast, Solutions Driven’s Global Head of Business Growth, Nicki Paterson, sat down with Manny Medina, CEO of Outreach, soccer fanatic, and a man who feels his business in his bones.

From organising his elementary school football squad for success, to heading up cutting edge projects at Amazon, Manny has always known how to get the best from his teams.

Now, as funder and CEO at unicorn, Outreach, Manny is one of the leading figures in the SaaS business.

In this episode we discuss:

  • The challenges of being a CEO when “no one looks like you”
  • Finding great talent and winning the talent war
  • The importance of a net-positive energy dynamic
  • How his footballing background has set him up to build the Outreach team

And much (much) more. Both Nicki and Manny can talk…

Listen to the podcast episode here:

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Transcript, Manny Medina, Outreach:

Nicki Paterson, Solutions Driven: Great alright so hi everybody and welcome to the latest edition of our Talent Intelligence podcast. This is going to be a little bit about me, a little bit about Solutions Driven and then we’ll quickly get on to our guest for today Manny Medina, the CEO of Outreach.

So to start a little bit about me, I’m the Global Head of Business Growth here at Solutions Driven, which is a nice way of saying Head of Sales and responsible for all of our clients.

Solutions Driven are a global recruitment partner that serve into the stem industries. We’ve recruited in 59 countries and been going for 23 years now.

We also launched the category Recruitment Process Intelligence in 2020. It’s the intelligence and the process that guarantees results to hire the right hire first time everything. But enough about me and enough about us. I’m delighted today to welcome Manny Medina, who is the CEO and the founder of Outreach.

As a customer of Outreach ourselves having recruited for various positions, I’ve watched your amazing journey over the past two or three years. And you’ve been killing it recently – hundreds of millions of dollars of funding, a $4.4 billion valuation, a true unicorn. Paving the way for many companies to go on that growth journey, and allowing people to launch stellar careers. 

Manny, I believe you were employee number three at Amazon AWS and prior to that also led the mobile division at Microsoft. So today I am honored and delighted to welcome Manny. 

Manny Medina, Outreach: Thank you, thank you for having me appreciate it.

Nicki Paterson, Solutions Driven : So “Talent Intelligence Podcast”, what does it mean? I think today, Manny, I’d love to just get into the mind of the talented person that is Manny Medina. You are the leader and founder of a symbolic company now. There is so much top talent at Outreach and it would be really good to understand a little bit about you and about the company. How you hire and retain some of this amazing talent and just a future of the category and indeed Outreach itself 

The four areas I’d like to look at would be leadership, culture (I can’t wait to talk culture with you), hiring and retaining talent, and then indeed Outreach and the future of Outreach itself. 

So let’s start with leadership, what type of employee were you in the early days? 

Manny Medina, Outreach : I always felt that my superpower is in assembling the right team. You probably know this, I grew up in Ecuador and growing up in Ecuador football or soccer is very big and when I was in elementary school I would do my homework as quickly as I could, so I could go outside and play soccer with my friends. And the game of soccer was fascinating to me, but the picking of the team was actually more fascinating, so I spent most of the day in school, the teachers would be lecturing and I’d be thinking “what is my team going to be this afternoon?”

It wasn’t just picking the best players, it was also picking the right support staff that will want to play the entire afternoon supporting the best players. 

So the whole misconception of having an A team at all times, it’s actually a little bit off because what you want is an A team, not an A player. 

We’d regularly play this off in other neighborhoods. We’d play neighborhood against neighborhood right, so I live in one street and I will go and pick up a game with the street over.

As we were doing that, we’d try to pick the best player from the two streets over and find somebody super good and try to call them over. Whereas I would think about the team makeup not just one guy, all the people who are supporting. Who’s the striker, who’s in the midfield who’s going to be there’s going to be sitting in the back just to stop whatever comes through. So the ability to create the teams, based on what you want to get done was more important to me than picking the best players. 

A lot of people would show up in the street and would like to start doing some fancy moves to show off their skills. And I will not be doing that, I will be thinking what my team is going to be and what the structure is going to be the team.

I tried to take that into the rest of my career. It’s always been about who is around me to get the best outcome. Not just about me but who’s my team, who am I going to lean on to get the best out there. Who’s going to lean on me to get the best outcome, how do I make other people better? 

What kind of employee was I? I was an employee that always thought about that – how do I get into a leadership position, where I can be part of the team, I can be a team leader, and I can pick teams where talent would shine.

Even as I grew up as a programmer and then I moved on to become a manager and a leader, the leadership aspect of me was more about team building and consistency and finding the best environment for the team to grow in. That has been my growth as an employee in my life in general.

Nicki Paterson, Solutions Driven : I think anyone from Solutions Driven who listens to this will know as soon as you mention soccer, things go crazy, for me, because that is my passion. I’m too old now, I have one knee left but before that I was in Europe and then 12 years in North America. I totally appreciate the love for the game – I was the exact same as you. It was always about how I can influence others around me to get the best result on the pitch. At my sales launch kickoff this year I put all my team into positions on the park and actually gave them all a number and said “you’re the striker, you’re the midfield”. That got a laugh. 

In terms of early career, I can already see that you always wanted to get to that leadership position, but there was anyone early in your career that you looked up to from a leadership point of view.

Manny Medina, Outreach : There’s a few in particular, so my last boss at Amazon. He transitioned with me to Amazon web services, working on the 3S pricing etcetera. He was marvelous because he would smile and make light of the most tense situation. Amazon is a very hard charging culture.

A lot of people call it humanizing but it’s not really humanizing it’s the fact that everybody’s a top performing athlete and it’s expecting the best out of you.

And a lot of feelings and energy sort of flares up meetings and so on and so forth, so in light of that, if everybody’s type A and super emotional, very little shit is going to get done.

But you need somebody in that team, in this case my boss, who takes something and realizes that we’re not not saving the planet here. And we’re probably gonna be wrong, because nobody has done this before. Nobody has taken storage and priced it on a per kilobyte basis so chances are we’re going to be off and we got to be okay with that. You have to have a good laugh because at some point shit is gonna hit the fan we’re going to learn from it gotta move on. 

The ability to keep things in perspective, to have a ready smile and a ready joke when things get tense are incredibly powerful in leaders, especially in fast growth leadership.

Especially when you hire a passionate and committed team that have a lot of energy and bring their whole selves to work, you gotta be able to bring a good word, a calming sentence, sort of the opposite energy to keep things in balance. Being able to read the room was incredibly powerful in him and I took that through my whole life.

And the second was my boss right before I left Microsoft. He taught me the ability to think really big and test the edges of your thinking at all times because we were doing these massive deals for Windows Phone.

And, as you know, Windows Phone was not flying off the shelf, so we’re trying to figure out how do we create commercial agreements to get along with the carriers and a lot of things to get this unit volume to move.

The ability in him to give me a lot of rope and just expose me to bigger thinking was incredibly powerful, especially now, as they come in we get to in our luck.

So in a startup you’re always looking for the high Beta moment right because, even if you’re $100- $200 million you’re still small in the great context of things.

So you gotta put food on the table, but look for the high Beta moment that it’s going to give you the home run again. And then do it again and then do it again, so the ability to always think about that was something that I took away from that I think every startup photoshoot to carry with them.

Nicki Paterson, Solutions Driven : A lot of stuff resonates for me there too, I think, being a professional soccer player, you don’t win every game right, so you win some, you tie some, sometimes you lose a couple. And there are highs and lows. 

I’ve seen this happen to a lot of people that are massively over celebrated and got really depressed when things weren’t going right. Personally, I was always able to stay the same, it’s not that I wasn’t able to accept defeat, because I hate losing more than anyone or fear it pretty massively.

But I think as a leader is a really strong thing to have for everyone to look at you and you say some things that went wrong here, Manny’s calm, talking about the next thing in the future.  

I also think to be successful, you need to celebrate some of those small things, don’t get too carried away, but always have goals and you’ll get better at them, and they’ll get bigger. 

 I guess that takes me on to reach. In previous roles, your roles grew and grew and grew. How have you been able to set short and long term goals and manage them?

Manny Medina, Outreach : I don’t have an easy answer for you, I wish I did. Because I tend to go into this phase where I over dial in one direction or another, like you know.

I personally believe, and I may be wrong on this – there are two types of leaders in the business world. They’re the founder types who not only know how to run the business but they feel the business. It’s like they can feel the storm because their bones ache. 

Your back is killing you and something is wrong that you can’t put your finger on, so you’re going to dig in til you find out. And then there is the girl or the guy or the person that runs it by the numbers. A professional manager. With structures and frameworks and things that went to the best schools and blah blah.

I am the first. It is hard for me to explain, because a lot of it is gut feel. So sometimes I will go down in tangents of too long term thinking or too short term thinking.

Both are useful as long as you have a team that compensates for the other side and that puts up with your shit. So when I go too short term, I tend to get too into everyone’s business and I run a lot of inspections.  

My energy is diverted into getting into everybody’s faces, I call it understanding, but people sometimes don’t receive it that way, and that’s fine. 

But you have to have a team that appreciates you for that and sort of rolls with you and sort of humours you a bit, but also pushes back and says “look Manny I got this. I know you’re thinking a lot into this, but if I’m gonna do 10 things I’m not going to get anything done. So I’m going to focus on these two, and I know you’ve identified another eight but if I do this other eight that are broken we’re not going to get anything done.” 

Because we need to get shit done to be able to move the ball forward and we’ll take care of the other eight later because they’re less important. 

I also get into too much of a long term thinking when that happens, I tend to ship resources into long term projects right are three/four years out. We gotta put food on the table today, we’re a company that’s getting more and more public disability. My ratios have to be right. I can’t just burn money without a good plan to see it pop out of the other end. I only get one Gaia every three years or so, I don’t get it every year, so you’ve got to really pick those stats to like and I have a team that also reminds me and we’ve got to focus on the things that are on fire right now, we’ve got to put food on the table next year and stop thinking too longer term and bring me back into what we’re going to do to operate a business. 

I appreciate my team for letting me have time to go off and have escapades and go off into tangents and they allow me to do it and humour myself and make it easy. But eventually they bring me back in and are like “ok here’s how we’re going to run the company”. And it doesn’t affect the long term plan. 

Nicki Paterson, Solutions Driven : That’s so true because we speak to lots of multinational companies, but also startup and scale companies all the time and you find and you find companies are doing everything themselves.

The founder is recruiting, they’re selling, you’re turning the light off at the end of the night, you’re trying to do everything. It’s the ones that can build the best teams around them, it’s the ones that can delegate.

It’s the ones that maybe are worrying about the long term when others are worrying about the day to day and the short to medium term projects, those are the ones that are truly truly successful.

Manny Medina, Outreach : Let me put a point on that.

Because it is true that in small companies, you have to do everything. So when I was really early on as a CEO – and the CEO job is probably the one of the worst because as a CEO you are taking care of everything else right. So you’ve got a team of 10 each TIM has a position delivery and something to do and you’re doing everything in between like whatever falls through the cracks or your job right like.

Early on, we decided that we really wanted to land Docusign.

And when we got Docusign, we talked to the security team and we got this 50 page document of security requirements from Docusign. Alright, that’s clearly a barrier, we don’t have somebody here, no one has that job. 

So I’m going to take that job. I took off my CEO hat and put on my chief security officer hat, and I became the chief security officer for the company for three months. I told everybody “look guys if you need any leadership, anything like that, you’re gonna have to work with each other, because I am working on security to get Docusign through. That’s my job from now on.” 

Nicki Paterson, Solutions Driven : What you’ve subconsciously done is delegate the business to those guys, who have upscaled themself tuning that PDF together as a team.

Manny Medina, Outreach : Right, it works both ways right because they filled in and made it so that I’m able to just handle that. But I also felt better about recruiting than a chief security officer because i’d been in his shoes, and I have, I can talk the language I feel like every time I do it, I think, able to attract the higher level of talent than if I just have a job rec and then hope for the best. I did that with security, I did that with HR I did that in finance I’ve done that in a number of areas where the company needed a step change.  

You need to build muscle mass like not just the function but you need to build the function and the process and the rhythms and the accountability etc.

So the ability to step in and run it and then hand that over is the most important thing. Now if you don’t hand it over and you over dial in the inspection, two things are gonna happen. You’re gonna lose your best talents because they’re like “what are you hiring for?” and you’re going to burn out.

And, and this is the interesting thing about burning out. Burning out doesn’t show up in any way other than you being miserable and making everybody else miserable. Then you start losing all your people, you start losing your bearings, where is North etc, so you have to cut it to be able to do both. That has been my biggest learning at a startup. 

Nicki Paterson, Solutions Driven : Again awesome point because sometimes people will just say, I’ll get there, no matter what, but you will lose things along the way.

Manny Medina, Outreach : You become a little bit more miserable every day and everybody can tell. You’re not invisible, people know that you’re incredibly hard to deal with, and they just don’t tell you.

Nicki Paterson, Solutions Driven : So I want to maybe talk a lot about successes versus challenges so let’s start with the challenges.

Let’s just talk about Outreach for right now – you don’t get from a couple of employees to 1100 employees, without challenges. Would you mind sharing some of your early challenges in your business and some of your current challenges and telling me how they differ? Because the challenges in hiring early on for example, are different from later, it’s a completely different game. 

Manny Medina, Outreach : There is a catalog of challenges. Let me just pick a few. So early on, I feel like one of my biggest challenges ever was to understand the scale at which things beak. That was the first aha moment for me, we were hustling meetings, everyone was all hands on deck and closing. And it didn’t really matter the territories, we all have the account, you know. What matters was that we had a huge pipeline and that our number went up every quarter, so every quarter we added 20% growth above the last quarter. 

That gave me over 100% growth right. And it was a lot of brute force. We got a lot of dopamine release on the 11th hour deal on the last day of the quarter and it’s like 10pm and we’re celebrating, high fives. That’s a really bad sign. 

What happens is when we do that, the quarter comes in really hot. And I remember talking to one of my investors and them saying “you’re one or two quarters away from missing the quarter.”

And the moment you do that, nobody wants to invest in an early stage company that has had a slow down moment because you don’t know whether that’s systemic, was that executional, or was that the market going south. That scares the bejesus out of everybody. So for the first five or six rounds of funding, you want to be as clean as a whistle, no questions. You may be inefficient, there’s a lot of forgiveness for being inefficient but you do not want to miss growth. 

I remember one quarter that everything felt hard. Came in at the last minute and did some contortions to get it through. And I remember sitting down with that advisor and saying “I’m having this feeling, I have a little bit of evidence but I don’t have a ton.” And he’s like “dude you’re about to miss a quarter. Then when we miss a quarter it’s going to take a year to turn things back around.” 

So I panicked and I started inspecting and I realised there were just a ton of processes that we’re not following. And that’s when I started upgrading my go-to-market team to bring them up to where we are today. But I feel like not enough early startups, especially the ones that have product or marketing driven founders, pay attention to the fact you can’t miss growth. 

You can screw up on a lot of things, but growth allows you to play the next game. So that’s one. 

The other one is scaling the people in the organisation. At some point in the company you lose the ability to remember everyone’s name. I did it until 200 people then I started losing touch with the new person’s name. It’s impossible. Once you start losing some of that connection, that’s when the infrastructure for talent and culture kicks in. And if you don’t have that ready to snap into place, you’re going to lose a lot of people you don’t necessarily have to. 

So the ability to make every employee heard, make sure that they understand what makes them tick – do you want to be a manager, make more money, where do you want to be a year, two years from now. How are you feeling right now? Do you feel like the company values are aligned with your values? Those kinds of things – listening at scale. It’s super important to bring that in before you need it. Because by the time you realise you need it, it’s too late and you’re already in an emergency. 

That was something that if I were to do differently I would start a lot earlier. 

Nicki Paterson, Solutions Driven : And that’s key, I mean you clearly had product market fit with Outreach and probably knew in your bones “I am onto something special here” and could probably bring in decent sales people who could sell it for you. It wouldn’t have been difficult to sell but you thought you might not achieve success and you panicked. But you’ve been able to fix it. 

And that’s a challenge turned into a success and I think that’s really important. Leaders can just see another quarter of growth and think great, onto the next one, but eventually something will beat them.

I guess that takes me onto the next question – what is your biggest fear as a CEO? 

Manny Medina, Outreach : The problem for me is it’s actually the opposite of that. I have to pump myself up every morning to come in and be the CEO of Outreach because if you look at CEOs of companies our size, with our projected potential, they don’t look like me. They’re usually born in the US, located in the US, normally white. 

So, I don’t have a ton of support networks out there to make me feel good about myself. I feel like I’m sticking out, when the chopping comes it’s my head that gets shot. I always have a sense of anxiety and panic in my gut. There’s a sense of anxiety and panic and my gut of “what am I not thinking about?” “What about the true CEOs out there?” “What are they doing that I’m not doing?”.

Nicki Paterson, Solutions Driven : You probably fear failure, rather than have a biggest fear.

Manny Medina, Outreach: I have the constant reminder of potential failure, constant reminder, of inadequacy that on the one hand I have to control, because if I let it get out of control, I would just sit on a couch and not move.

On the other hand, it makes me never be full of myself, always questioning why that worked or how it worked, why are we not doubling down on that so a lot of a lot of I see a lot of a lot of leaders, do a lot of the spectrum and what’s not working.

But you should also do inspection of what’s working, because if it’s working, you need to actually increase the investment in what’s working to accelerate growth, so I’m always afraid that I’m not thinking that I’m not doing it right, that I’m missing something big.

So yeah I don’t have a biggest fear because every day, I have to fight the fear to come into work and be my best.

Nicki Paterson, Solutions Driven : You know, I guess, a lot of my leadership or how I learned about leadership was from soccer coaches growing up. They instilled that passion, that desire, that resilience. One would tell you “Nikki, work on your left foot because that’s not as good as your right. Then you had other coaches that said, “Forget your left foot, Messi doesn’t have a right foot, just use the one that’s the one that works.” 

Manny Medina, Outreach: Right, you only need a right foot to get on the bus and off the bus!

Nicki Paterson, Solutions Driven : Exactly! So let me come back to culture because that’s quite clearly one of the biggest things that stands out. But let’s maybe finish the leadership part around the successes.

How do you celebrate success? Because you’ve had so many milestones along the way, your first round valuations, winning big clients, or maybe one or two moments people might not know were vital for you. 

Manny Medina, Outreach: It has changed with size. We used to have, back when we were up to 200 people, this stand up on Fridays. We’d go around as a company and do our highs and lows.

We’d go round and talk about if they were individual in nature or part of the team. And we’d celebrate our lows, because they’re our learning moments. So they’re something you want to get out there because starting a company is hard. 

And growing a company is hard so you want to let it out, be real with each other. We had some hard moments and you learn from and by sharing them, my burden is a little lighter. 

As we grew it became harder to do this as a company all hands. We celebrated milestones financially or people-wise but we actually began to feel like we needed to do more in small teams. And the inability to get together inperson has a huge dampener on these things. 

On the one hand, I’m going to come and celebrate with you, on the other hand I don’t want to put another Zoom meeting in your calendar so how do I celebrate when we can’t get together? 

I’m a huge fan of being in the moment when I’m having a conversation with you. Like I want to listen. Not only to understand but I want to understand what is not being said. What is in your face and your posture. Like right now, you’re sitting back with open shoulders, I know you’re in receiving mode. 

I have a hard time not being present and not doing that. So we’re investigating ways to celebrate better in our remote team. Especially with the go-to-market culture we have here. 

Nicki Paterson, Solutions Driven: Awesome. Let’s talk about culture. I think one of the first parts of culture is the commitment to DE&I and bringing your whole self to work. We have a network of like 75 HR & TA people that came together during Covid. This was when people were asking “how is everyone dealing with hiring for diversity and mobility and we were quite siloed. 

All of a sudden, everybody wanted to share ideas and collaborate. It’s been amazing. One of our first guests, who we ended up hiring as our Chief Diversity Officer, was saying “okay everybody’s talking diversity, let’s do it. Let’s go on this journey with our clients.” 

It’s been amazing hearing people talk about diversity, hiring for diversity and high potential.

So talk to me about bringing your whole self and what that means to you? 

Manny Medina, Outreach: I fundamentally don’t believe I’m just hiring your hands and your head for the problem at hand for the eight hours you’re supposed to be at work. I believe our best hires are ones that own the problem. They think about it in the shower, think about it in the morning. 

I’ve just come back from two weeks in Italy and I spent a third of my time getting my six month old to sleep. And in the afternoons, I would take a long nap to give my wife a reprieve and just walk them to sleep and solve problems. I’m on vacation but I’m still solving a problem that I didn’t get to crack through the week. But I’m solving it in Rome trying to get my daughter to sleep and I feel like our best employees do that. They bring their problems home. 

And because they do that, I have to allow them to bring their social worries and energies into work as well. We need a constructive dialogue for people to bring these things to be heard, to be seen. 

Not to say that would be ridiculous. You’re hiring a whole human being, you should be getting a whole human being. And the more you allow this whole conversation to happen in a constructive and positive way, that’s a true differentiator. So that’s how I behave, that’s how my co-founders behave and it’s how we should behave all the time. 

But I’m also selfish because I think it’s a differentiated advantage. When you’re in a world where the CEO comes out and says you can only talk about work, I’m like ‘great, I can’t wait to go take your employees and tell them, you get to show up with your whole self to work when you work for us.” 

So the ability to create differentiation around what we do and represent is powerful in the marketplace. It’s not about being better, it’s about being different. So I’m not going to get into the same rat race of saying I’m going to pay a lot of money and you can drink all the beer you like, and you won’t ever have to come into work, blah blah blah. 

I’m going to be different by saying, you can bring your whole self to work. What you’ll find here is a group of people that want to talk about the things that are important to you outside of work. So you can grow as a human being and a professional and I think that’s just powerful. 

Nicki Paterson, Solutions Driven: I spoke before about getting comfortable with being uncomfortable and I think you’re more than happy to see the uncomfortable things and that probably gives freedom to your employees to talk about the things they maybe one didn’t want to talk about but they see you leading from the front the way you do.  

Manny Medina, Outreach: Exactly. At the end of the day, I’m hoping I’m cultivating 1000 CEOs here. That they’re all going to grow into their own leaders, whether that’s here or somewhere else. And by doing so, I feel like I’m moving humanity forwards because in the future of work it’s going to be bringing your whole self to work and moving the ball forwards in terms of efficiency and innovation for our customers. 

Nicki Paterson, Solutions Driven: It’s clear to see the way this filters down through the organization. I follow so many people from Outreach and they just constantly talk DE&I and they’re so authentic. You’ve really created this environment of self improvement, coaching, and mentorship. 

And obviously, having hired for some of those teams, I know there’s clear criteria for people who fit into what you have there. You have such good people in place and a strong culture at Outreach. 

Manny Medina, Outreach: I don’t know how I would not do this. It’s how I operate. I want to work at a place where I’m surrounded by people I admire, respect, and who fill me with energy.  So I have to hire accordingly and continue to hire accordingly and the only thing I’d be missing in the past is a system to inspect what is actually happening across our organisation. We have an office in Prague, London, Atlanta. And we need to be making sure it’s all happening at scale so we don’t lose that thread. 

It’s a lot of being out there and leading from the front and embodying the culture you want to drive. To be frank, I’m not sure at what scale it breaks, I’m sure at some point it does and I’m going to have to change what I’m doing. But so far it’s working so there’s no reason to stop. 

Nicki Paterson, Solutions Driven: You mentioned earlier, you like your employees to take problems home. My wife would probably say the opposite. I have two kids and when I finish, there’s nothing I’d love more than to turn my phone off but that doesn’t happen – I take it home. I coach soccer as well so I’m constantly thinking about something. 

But I read something last week around resilience. People that are successful are resilient, they think, I’m just going to punch through this little challenge, I’m going to walk that extra mile every day. But there’s a real balance between resilience and recovery. But how important is that work life balance? How do you get that balance between people going above and beyond, but also making sure they’re in a good space.

Manny Medina, Outreach: Relaxing is just changing the activity. It’s not doing nothing. A busy mind like yours or mine won’t just do nothing. You will fill that with something else. And the trick is to fill it with a different kind of activity that allows you to tackle the problem from a different angle. 

You see, what you’re doing if you bring your phone home is continuing to react to the typical   coming your way. You may want to stand back and work on something a little bit bigger.

Like pick a problem and needle in on that in the quiet of your brain, and when you’re with your kids. I’m not saying don’t be present, I’m saying in the times when your mind is wandering, and you’re only a little bit focused, you’ll wander into this particular problem. 

That’s what I did. I actually deleted my slack. I deleted my Linkedin. I looked at my email and now that’s it I kept my text going, because every once in a while I would have a really good idea.

I bring a notebook that I fill with ideas I mean, so I always have a notebook and a pen at hand so whenever the inspiration happens, I could sit down and write it out, doodling it out in charts and everything. That’s what’s important – the ability to shift how you’re tackling a problem. 

Manny Medina, Outreach: The other thing that I found powerful is keeping a little journal. If you wake up in the morning, before the condition of the day determines the rest of your day. So if you start your day jumping into the pool of your company, you’re going to just swim in it. Whereas if you get started prioritising and thinking big themes and thinking about big things for you personally and for the business that will allow you to set the priorities for your day. 

Nicki Paterson, Solutions Driven: I got some amazing advice from a coach and one of the things he said to me was when you’re a coach or a leader one day, when a session goes well go home and write down what you’ve done that was good.  

So for maybe 10 years, I wrote down every session that I thought was good. Why did we do that, who were we playing against, what was the success? And I thought I was going to be a soccer coach, not a recruitment leader right. But it set me up for lots of success and I think the same can be said for sales. Talent is changing, it’s evolving and I look at the SD of now compared to 10 years ago. They all want to be the best in the world. They’re on social media, they’re doing podcasts, they’re learning methodologies. I think it’s amazing to see – but it’s the ones that are doing that little bit extra, the ones that are getting ahead. 

So in terms of hiring for talent, when you can’t do interviews in person at the beginning and can’t learn everyone’s names, and all about their families, has that been a struggle for you?

Manny Medina, Outreach: It has been a bit of a struggle. I’ve missed the ability to sell Outreach to an individual personally. I missed that a lot because I love talking about the company. I feel my pitch to investors also resonates well with individuals because they’re investing their career and their life and I’ve missed that. I do think it’s untenable for me to continue at this scale and continue to be a leader so there’s a lot of picking my fights and figuring out what is the best activity I can take for the company. 

I think recruiting for sure is one of those but can I do it at scale? I have to figure out what the right levels are so I can make an impact. But the thing that’s important to me is to stay fresh with the class of people we’re hiring so we can impact the culture, impart my point of view of what we’re here to do and why we’re doing it. 

Nicki Paterson, Solutions Driven: This is where I see so much synergy and how we are versus how you operate. When I first joined, I listened to the CEO talk about the company. I was like “recruitment – there’s hundreds of thousands of recruitment companies globally. You can do what you say you’re going to do but when you join and realise what’s actually happening and see the passion the owner has for the business, it’s infectious. 

And a lot of the sales people on calls, I love to see it because they sell the company for us.  call right i’d love to see it speak to the client because they’ll sell this for me easily. It’s the trickling down and setting the standard, what do we stand for, where are we going. That’s what we see with a lot of successful companies – the Gongs, the Drifts, the Outreaches, everyone singing from the same hymn sheet. 

So, what are the one or two traits that you think make the difference between good talent and really, really great talent?

Manny Medina, Outreach: You know, assuming all else is equal, there’s two things I look for. One is energy. So you could be a great positional player, a great leader in terms of running a ship. But can you impart energy to people in your team, your peers, and your superiors. That’s a unique trait because energy is a bit of a balance sheet. There are people who are high energy, there are people who are neutral, and people who suck the energy. And the people who suck the energy, you sometimes need a few there but if you’re not net positive, you will start feeling it. 

And it will start draining the organisation. I remember, when we hired one of our early executives, they were kind of low energy and in a way they took a little bit from everyone else. And I took a trip for a week and got a note from my co-founder saying “Dude, the energy’s gone.” And I was like “shit, better do something about that.” There was nothing wrong per se, we just needed to feel the same. And you need to make sure you have a positive balance of energy that you bring. 

The second thing is that I tend to hire people who need a win, an unequivocal win on their terms. They will do anything to get that win on their terms at all costs. And they want to win with style. It’s like Brazilian soccer, you play beautifully and you win, if you don’t play beautifully and win you get panned by the press, they’ll say “that’s not our game”. 

Or like Germany can win a game with the structure right, but in Brazil, you need to have this flair right. I love to play with people that want to win on their terms with style and perfection.  That even though they may have won in the past, they want to do it in their own way. They’re artists in their own craft. Those are my favourite hires because they self perform and make everyone else perform better.   Even though they may have a win from the past, I went I went they went to do it, in with their own campus.

Nicki Paterson, Solutions Driven: That said, what you see in new people coming in at an SDR level, for example. They grow and they grow and they grow because of the learning from amazing leaders.

And I think back to the early days of the first couple of sales of yours coming in, or the first couple of leaders, they must have had that energy and really they’ve paved the way and now it’s almost like a machine? 

You need to evolve as well. I think if I just look at sales, you’ve been in business development and sales, that’s my area. So how do you see that area evolving? Have the characteristics of good salespeople changed from say, three years ago, to today? 

Manny Medina, Outreach: Oh for sure, I think the instinctual sales leader that sort of wins by bravado and force and their contact book then that’s going to go away, I think that sales is going to be a game of intelligence, a game of data, a game of Ai and prediction and using more signals than you had before, to be able to maximize growth and performance by the performance or the individual.

I think that the new rep who will become the new team leader will become the next manager, who will become the next VP is somebody who’s going to expect high performing, technologically savvy organisations that have a lot of intelligence and data and insights at their fingertips to operate faster. 

I think that ship has sailed and I think the big tsunami that’s coming to all of us is gen Z – zoomers, they’re the ones we’re hiring right now, some as leads, and you, as the organisation they are your future leaders and won’t stand for low tech.

Bravado – what worked in the past, isn’t going to work today. Let me read our own playbook that I used 10 years ago, to get 1000 dials a day and that’s not gonna work, but you, you will get, what used to be called a centaur in chess – someone who took all the power of the machines and the humans to drive incredibly high performance. 

Nicki Paterson, Solutions Driven: And then I guess the last question around talent really is, then, how do you retain them. It’s inevitable, you lose good people. Along the way people are going to offer them a lot more money to “come help me start this new rocket ship”.  How do you protect your talent? 

Manny Medina, Outreach: There’s two answers, it is a fairly complicated question, especially in this time of Covid. Everybody’s going through a great migration and everybody’s changing to some degree. 

The first of all is that you have to bet on people for who they’re going to become, not where they are right now. That is a significant shift, because every performance software or framework measures what they have done in the past so you can extrapolate where they end up in the future.

And the easiest thing to say is that you have the same job. But if you’re going to have the same job and be a leader, what is your potential and how does that potential align with your desire. 

Very few people do that even in my organisation. I’m not about to claim that I’m perfect but very few of our managers do that, and let people and themselves have the ability to take risks in their individual space on their future performance. Which is bad right, and whoever cracks that at scale is going to win the talent war straight away. 

That said, you can’t overdial for retention. Retention is only as good as your players are happy, the individual is fulfilled, and you’re getting the best out of the person and the person is getting the best from you. 

It’s a trade right. You come in and be like, we’re going to grow, you’re going to have fun, you’re going to be motivated by other people. The moment that stops, we fail, they fail, then you’ve got to be able to say “this is inevitable”. And dealing with that is healthy. But the higher up, it’s hard to replace someone with a new person. For playing the long term, you have to play with individuals who want to be around long terms. 

Nicki Paterson, Solutions Driven: That sometimes opens the door for the next person to fill the role that helps them achieve their potential. You see the growth within the organization that’s huge when people see I’m not always going to be an SDR or see “I can go somewhere here”. 

The ability to know is so important right, hiring for potential is one of the reasons why I think we have been so successful. It’s not just looking for the exact same carbon copy person again because not every SDR or sales leader you hire is the same, they all bring something unique and assessing for high potential is difficult but it’s possible but it’s taking a guess that a little bit of a calculated risk the areas where companies like yourself really really do well.

Manny Medina, Outreach: Right and so I was just hiring and retaining for high potential but you’ve got to assume that every six months, the contract is up. And we have to fall in love again with an individual, and an individual might have to fall in love again with us. That potential isn’t just how they have performed, because if all you’re doing is tracking current performance, you may get the wrong read and that’s what’s hard.  

Nicki Paterson, Solutions Driven: awesome so a couple of the last questions. You are by far the leader of your category. What do you see next for the category and what do you stand out differently to your competitors? 

Manny Medina, Outreach: We stand for the end user, for the rep, for the manager, for the people who have to deliver the goods and they have to put in the time, and effort to deliver those performances, deliver the meetings, deliver the revenue, deliver the retention of the app, the cross sell etc. So that’s our true north, we will always stand for them. As opposed to solutions like a CRM that started with the CEO and Demand VP and sort of worked their way down. We start with what is the individual workflow, what is it doing and what does the individual need to get their job done. How do we achieve that, how do we make that better which would mean more efficient scaling. 

How will we grow from being a sales engagement to being engagement and intelligence around anything that is customer facing and not making assumptions as something you do regularly. If you don’t regularly define your category, somebody else will. 

You have to be on top of it, so if you created the category, guess what congratulations, you get to do it again but on a bigger scale with more risk, and then you get to do it again and that’s it that’s the name of the game

Nicki Paterson, Solutions Driven: I think I could go on and talk to you for four hours Manny I think we need to book another call just to talk soccer at some point. I won’t keep you for too much longer, but thank you so much for all your time it was an absolute pleasure.

So, the brilliant Manny Medina with the rocket ship that is Outreach – I’m very excited to see the next thing that comes from you guys. Any sneak peeks into the future?

Manny Medina, Outreach: yeah we have a big platform announcement coming up in October that is going to redefine the game, how do we go to market, how do we scale our teams and get it to produce better, more and be happier with how they do it. So stay tuned. 

Nicki Paterson, Solutions Driven: Awesome. Well you’ve got my money already you’re probably going to get more. Hopefully we can continue to help hire high potential top talent people into the organization, but thank you so much Manny, it was an absolute pleasure.

Manny Medina, Outreach: It was an honor thanks, thank you.

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