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Setting the Foundation for Built-to-Last Companies | TechCrunch Early Stage

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Rajeev Batra and Manny Medina standing on the stage in front of audience at TechCrunch Early Stage

Rajeev Batra:

Welcome everybody. My name is Rajeev Batra. I’m a partner at Mayfield, a venture firm that’s been supporting early stage entrepreneurs for over 50 years and has invested and partnered with over 500 entrepreneurs such as Manny Medina here. He’s co-founder and CEO of Outreach. Our journey together began, I think, over 10 years ago, maybe 10 or 11 years ago.

Manny Medina:

Yeah.

Rajeev Batra:

When we first met, I told Manny that I really loved-

Manny Medina:

You voted against me.

Rajeev Batra:

I voted against him. There you go.

Manny Medina:

That’s right. That’s how we met.

Rajeev Batra:

We had a spirited conversation where I was like-

Manny Medina:

You didn’t want me to find out that you voted against me. That’s how it went.

Rajeev Batra:

That’s how it went. That’s how our relationship started. We’ve talked about it often in public and written about it, but the reality was, here was an entrepreneur with an incredible story, a personal story going down the path of innovation and has a really interesting, fascinating background that he’ll get into. I was just struck by that and his desire to change and impact the world, I just wasn’t crazy about the first idea he pitched me. We stayed in touch and Outreach has been an incredible journey since we started working together about seven years ago this month.

Manny Medina:

Thank you. I’m Manny Medina. I’m co-founder of Outreach. Outreach is a sales execution platform. For those who don’t know what that means – you’re going to run into this a lot if you’re starting your own categoryt’s a place where a rep lives, takes all their actions and the execution platform helps the rep perform better and achieve their full revenue potential. What drives us is the fact that we’re changing rep’s lives. Sales is one of those functions that is important to an organization because it’s important to anyone who’s B2B and selling something, but it’s a great equalizer in society. To be a great rep, you don’t need a degree, you don’t need to be poor or rich, you can be an immigrant, you can be of any color, you can see yourself as anything you want and you deliver the number and you win. When reps win, especially those who come from humble backgrounds, they elevate their families or communities and they really pay back. For us, making the rep, the sales profession greater, making them achieve their full potential was our true north and it’s always been.

Raise your hand if you’ve heard of PLG. Everybody’s heard of PLG? Yeah. Everybody wants to be PLG, that’s the new thing. Before PLG, there was a lot of talk about how to ramp sales and run sales teams, et cetera. We did the worst of both worlds. We were selling products to individuals when it’s not supposed to be that way. You’re supposed to be self-serve for individuals and sell products to companies, but we sold products to individuals because we were selling to salespeople. To salespeople, if you make them successful, they buy. Not only do they buy, they tell their friends. In my mind, that was the best way to build a company because, by selling to individuals, they also call you when something doesn’t work, they also call you when something is working, they also refer their friends directly to you. That allowed us to build a really good product really early on that took off once we hit scale and that’s the genesis in short of what we do.

Rajeev Batra:

That’s great. Manny, let’s talk a little bit about the backstory. How did you actually come to do Outreach? Outreach has an inception story and a pivot story. All startups, all great startups have some sort of inception and pivot – can you comment a little bit on that phase?

Manny Medina:

Yeah. Outreach is a pivot. Outreach is a pivot and very few investors invest in pivots. That’s what makes Rajeev special, that he invested in a pivot, which means that your cap table is dirty with a bunch of other people who invested in a company that is no longer. The founders don’t have as much equity because you got diluted on the way. There’s a lot of hair in pivots. It takes courage to invest in a pivot, but pivots work out. Slack was a pivot.

Outreach began in 2011. I met my co-founders and we decided to crack the problem of recruiting. We decided that we were going to be building a marketplace and that marketplace was going to have profiles and we were going to attract employers and things were going to spin out of control and we’re all going to be great and rich and change the world. In December 2013 we found ourselves with two months of cash left. As I mentioned before, people don’t like to fund pivots so I couldn’t raise to get ourselves out of trouble. We looked at the four of us co-founders and we decided that we’re going to stop developing features and try to solve our way out of features, learn how to develop things that allow us to sell more. We did the math and we figured out that, if we 10x-ed the number of meetings that our two reps were driving, the conversion rates would allow us to generate enough cash to make payroll.

We did that. We built a workflow that did two things: it personalized emails at scale, and I can get into that if you want to at the end of the session, and then it did follow-up automatically so that it felt like we were reaching out in a personalized way. We built this workflow and we did 10x our meeting generation, but we could not close these meetings fast enough and generate cash. Now I have one month left of cash. I turned around and I went to agency recruiters who get paid for placement and I said, “I can generate meetings for you. If you do the conversion, this could be very profitable.” Meeting generation works in sales as a service, it doesn’t work in recruiting as a service. Every agency recruiter would look at us and be like, “Why? How do you do this? We don’t do that, we don’t buy meetings.” I told them, “Well, we built this workflow that does this thing and generates a lot of meetings.” They were like, “Stop. I want to buy that workflow, I don’t want to buy your service.”

I had about 50 meetings like that and I went back to my co-founders and said, “Hey guys, we have a shot here of pivoting the company to build a workflow engine for recruiting.” We did that and that’s when we met Rajeev. We went and rebuilt it and now I’m trying to get money to finish the job. We went to pitch at the Harvard … what was it? The entrepreneur competition or something?

Rajeev Batra:

Yeah, yeah. Harvard Business School Entrepreneurship Fund.

Manny Medina:

I was confident I was winning because everybody else in there had really bad ideas. Mine was bad, but the other ones were worse. You’ve heard the term I don’t have to outrun the bear, I have to outrun you – you just have to be better than that low bar that was in the room and my friend Rajeev voted against me which was the deciding vote. I swore to everyone that I will never talk to him again. Matter of fact, not only will I never talk to him again, whatever he invested in I will make sure that I will compete with him.

Fast forward, now we’re trying to sell this recruiting engine to recruiters and recruiters are really hard to sell to. Then one company that did buy was AppDynamics. AppDynamics, their recruiting team bought us and I’m trying to get more out of them. I’m like, “Are there more seats? Is there something else I can do for you?” They were like, “No, but what you do is very similar to what SDRs do.” The recruiter literally grabbed my hand, walked me over to the SDR pit, called the SDR manager over and he’s like, “Do a demo for him.” I did a demo for him and they bought 50 seats on the spot. I went back to my co-founders like, “Guess what we’re doing? We’re doing workflows for sales.” That really took off.

It took off because the whole sales stack began being evangelized by the likes of LinkedIn and so on and so forth that started posting about what’s your stack? What are you doing? I was selling door-to-door. That’s the other thing that I advise founders to do. I was crashing somebody’s office and using a desk in Union Square. I would set up meetings in the financial district and people would be like, “When are you sending a video conferencing link?” I’m like, “No, I’m downstairs.” When you pitch to a person in person it’s really hard to say no. It’s really hard to say, “No, I’m not going to try it.” I would make people part with their money on the regular just by selling face-to-face. That’s what got us to about half a million in ARR and that’s when Rajeev and I re-met. I’ll let you tell your own story.

Rajeev Batra:

Yeah. My impression of meeting Manny was first being struck by this incredible energy of somebody wanting to change the world and not taking no for an answer, one incredible quality of an entrepreneur. Most great entrepreneurs don’t like hearing that their idea is not necessarily great, but in Manny’s case he was open to a real thorough conversation. The first time we met around the recruiting marketplace idea, a 45 minute meeting turned into a two hour conversation/debate – heated, but a conversation nevertheless.

Manny Medina:

Just to give you context, he was sitting at this long mahogany table kind of like Putin. He was on the other end of the table, I’m over here. We’re having this vigorous debate on a very long distance table.

Rajeev Batra:

That’s right. That’s right. It looked like a scene out of a James Bond movie.

Manny Medina:

Yeah.

Rajeev Batra:

Actually it only felt like that to you, we were actually sitting right next to each other. Fast forward a couple of years when they were working on this pivot and the HBS competition…he still won’t actually ever get the real reason why I said no, I never will tell him that, but the reality was he was still going up into the recruiting world. And in the past 3, 4 years, obviously recruiting technology has seen an incredible resurgence, but seven, eight years ago it was a really difficult place to be. Everybody talked about recruiting tech, but nobody wanted to invest in it. I knew something about that because I was involved with a couple of companies in that space that are actually doing quite well now, but it was a really, really hard grind.

Now moving to salespeople, now that’s a world that I love having been involved with companies like Marketo and the first generation of CRM predating Salesforce. Now Manny was applying what they knew into a market that really truly deserved innovation, real innovation. Nobody had really invested truly in sales tech until 2013, ’14, ’15. It sounds like everything is now sales tech, but seven, eight years ago, if entrepreneurs were starting something in sales tech, most people would be skeptical and they’d say, “Well Salesforce would do it. Their name is Salesforce.” That market really needed innovation and it needed outside-in thinking which is what Manny and the team were bringing to the table, a completely new way of thinking about engagement and building something for the reps and changing their lives and changing the lives of their customers and ushering in innovation through bringing revenue generating technology to the table.

That’s when I literally chased Manny and said, “The past is the past. We can only look forward. Let’s really truly team up together.” This actually speaks to Manny and the values of Outreach and how they started creating the foundation very early on in terms of the values informing the culture. Manny and the team really think about different ideas and competing ideas coming from all different places – including somebody who had said no twice, taking their call seriously and saying, “Okay, what do you have to say?” 

Maybe we can talk a little bit about how you thought about building the culture of the company. Has this been an afterthought or something that started early in the journey of Outreach?

Manny Medina:

Yeah. There was a panel here before, I don’t know if everybody saw it, I overheard them saying what’s the right number of co-founders. When we started Outreach there were four of us and we were all told that we were going to fail, that there’s no such thing as four co-founders. There’s always two, tops three, but four is just not possible. It turns out having four co-founders was the best thing that could have happened to us because it forced me to take a step back. I’m the CEO because I’m the worst coder out of the four co-founders. Everybody else was busy so I got to do what everybody else was not doing. That’s called the CEO in the early stage. Much later you get the glory, the benefit of being a CEO, but early on it doesn’t mean anything.

Having my co-founders meant that I had to explain to them why we do what we do and I was also the bearer of energy. Early startups are founded on energy, meaning there’s going to be a lot of downs, there’s going to be a lot of bad news, there’s going to be a lot of rough spots and if you as a leader, you’re not bringing it, you’re not getting everybody up, you’re not making everyone believe, you’re not re-centering everyone on the vision, the startup fails and it falls apart. Having three other co-founders really cemented that everything that we do, even now that we have over 1,200 people, has to come from a point of empathy, has to come from a point of caring for you, meaning my coworker, our customer and the business as a whole. 

Rajeev Batra:

Your VCs sometimes.

Manny Medina:

The VCs? Yeah, when they’re behaving.

Rajeev Batra:

Sometimes.

Manny Medina:

Sometimes. If you do all that, it’s like the Johnson & Johnson thing. If you take care of the people, if you take care of your customers, everything else takes care of itself. VCs will make money on that. Having four co-founders really forced me to sell everything that I wanted to get done. I couldn’t just walk around and tell people what to do because my co-founders would just look at me like, “No.” Then what? That practice of selling internally even at the early stages, of really caring for each other, of really taking turns lifting each other up is essential. We are a diverse bunch. I’m a Latino immigrant, my co-founders are all in their 20s, or they were in their 20s at the time and from Washington state so there were three white guys and myself, that really made us more powerful.

We hit about 25 or 50 million ARR and we decided that we really needed to keep this. Actually it was less, it was 10. We really need to keep this and lock it and make sure that we cement this foundation so that, when we grow much bigger, we continue to live these values even at 1000 people. We did it out of respect for each other and honoring what we had built on the back of each other’s work. We have grit as a core value for instance, that is very important. But we have another core value that is not as well-known which is having each other’s back. That’s a true core value. People have been fired at Outreach if you cannot demonstrate that you have done that in the past.

Having that codified in your early DNA allows you to scale it out and tell stories when you have somebody’s back and somebody else is having each other’s back. Now that we are in 10 countries and 1,200 people, the stories keep repeating themselves and people tell each other stories of what they’re doing when having each other’s back. That was one of the attributes of starting with four co-founders and really locking in on who we wanted to be when we grew up.

Rajeev Batra:

There’s a lot to talk about with DEI, right? People from diverse backgrounds and ideas and being inclusive. How has Outreach been intentional about this? Has it been something that just fell in your lap because you’re a Latino immigrant or was there intentionality? Was it random chance meeting intentionality? What has that journey been about and how has that actually informed building great products and great performance? 

Manny Medina:

Yeah. It began with us and the fact that we are different, we come from different walks of life. When we were about 50 people we sat down and we decided to lock the values. One of the values that we locked was the fact that we found strength in diversity, meaning we need diversity of thought, of walks of life, of color, of experiences to really be able to add to the culture but also to the product and to our success. We’re also very fortunate in that we sell to salespeople. Salespeople can come from all walks of life. You can’t have a homogeneous culture selling to a heterogeneous market because it’s not going to fit. We have to align who we are to the people that we’re selling to.

Second of all, because we’re a pivot, when we raised our seed round, the previous board members were like, “All right. I’m out because that’s not the company I funded,” so we were left without a board. I asked Sarah Imbach to be on my board and she was transformational. Having that experience made me realize, what if I have an entire staff that looks like her? Fast forward to today, half of my direct reports are female. 45% of the executive team at Outreach is female. Almost 50% of the entire company is female, but it begins at the top. If you’re intentional about the kind of people that you want to bring in, what you are getting from them and why you want to build it that way, then it propagates your company values as you’re building it. It’s really hard to retrofit that later, meaning if you’re 100 dudes and then you want to be diverse, it’s really hard to bring somebody in who is not from your background because they’re not going to be accepted. There’s going to be a rejection in their tissue.

In tech companies the word that we use is cultural fit. The culture fit could be poisonous if your culture is homogeneous and everyone looks the same.That just means I’m going to bring in people who look just like me and then you’re going to propagate the problem even further. You have to be intentional. Intentionality means two things. First, intentionality means that you think about who you want to be when you’re 1,000 people and you start solving that today. Second of all, it’s important that you allow yourself to make mistakes. If you’re really trying to push the boundaries of who belongs in your company, you will make mistakes. It will show up on Glassdoor and that’s okay. If you are not making mistakes, then you’re a homogeneous culture. The easiest way to get a great Glassdoor review is to fill the room with people who look the same because everybody’s going to be super happy to be there. If you’re really intentional about bringing in people from diverse backgrounds, then you’re going to make mistakes and that has to be okay because you learn. You treat it very humanly and you move forward but you need to grow.

Rajeev Batra:

We often think about three pillars for companies that have this inception to iconic arc. One is some unique technology product insight to a market that changes the dynamics of that industry and you’re doing that with sales engagement and execution. The second is a unique business model. You’re changing the unit economics, the margin structure, the industry and how people actually get value. Outreach is a product that reps live in four days out of five, they’re in it throughout the whole day, that’s truly the power of software. The third most important pillar is the people operating system, the culture. That outlasts probably everything because the markets are going to keep evolving and changing.

You’re building this incredible culture that’s inclusive and we talked a lot about empathy and having each other’s backs, so how do you think about accountability and performance? We talk about empathetic performance cultures, do you think the two are mutually exclusive? There are a lot of shows out there these days on Uber and Theranos etc, and they tend to take one point of view or the other, that either you can be empathetic or performance driven but not necessarily both, let’s talk a little bit about that. What do you think?

Manny Medina:

Yeah, that’s a great question but I think it’s a false dichotomy. As a startup by definition, you need to push the boundaries. I remember this one conversation that we had at the very beginning. We had some amount of churn in our base and we were really worried about it, we were trying to solve the problem, trying to figure it out and you told us in a board meeting that if you didn’t have some amount of churn when you’re early, you’re not trying hard enough. You always sell this big TAM, everybody has a massive TAM of billions and whatever, but that TAM is not really addressable to you until you go and sell it, until they’re using your product and somehow getting benefit of it. If you’re not going outside of your TAM and experimenting with things, you’re not going to learn how big your TAM is.

For instance, we tried to sell into automotive really early on. Clearly we didn’t have a fit because automotive uses different CRMs in the lots, et cetera. There are a number of reasons why it was hard. We signed a few customers, we lost a few and we were really worried about that churn. The culture is really what propagated the fact that we went and tried it. If I would have gone and yelled at the person who went and sold against automotive, “Why didn’t you stick the landing? Why didn’t you call us when you did it?” I would’ve created a culture of fear and that propagates quickly. When that happens early, that becomes an ethos and then that ethos propagates. That doesn’t mean that we’re not accountable, but it means that, by having each other’s back, by making sure that we’re giving it our best, that we’re gritting it out, then you can still be grateful for the effort even if you did not get the result. That’s what’s really important.

Performance is a series of things that lead to a result. Any breakage in that series of things causes non-performance. That doesn’t mean that we’re not caring about performance. We’ve been one of the fastest growing B2B SaaS companies in the world. You don’t become that by under performing, but you can be that and have each other’s back. You can be that and fail. You can be that and grow people instead of churning and firing everybody as you’re growing and hiring that VP that has been there and done that. The question is how much work are you willing to put into it? The advice that you see out there mostly comes from people who’ve never run a company before or built anything. Don’t take it. Talk to your team, go and think about who you want to be. What are your principles? What are trade-offs and what is not a trade off? Then build that company.

At the beginning, we were optimizing for one metric which was revenue. As a matter of fact it wasn’t even revenue, it was cash. When Rajeev got involved, we were running the company on a cash basis. There was no accrual. We didn’t count the revenue until somebody swiped a credit card, like a drug dealer operation if you know what I’m saying. Cash came in, cash went out, that was it. Being focused on that element of survival got everyone aligned and got everyone incentivized into one thing. Then we became revenue driven, then we became ARR driven, et cetera, et cetera, but we were always clear about what we were trying to optimize. We were also clear about our values. Sometimes when you have those things together you can build a big, great company that is also very caring and empathetic.

Rajeev Batra:

Talking about building big companies, they often require you to innovate and create a category. How has all of what you just discussed set you up to define and create the category you operate in? You’re starting to even operate in and lead multiple categories now. How important was this whole process? What is the category you’re in today?

Manny Medina:

The category that we have created now for ourselves is called sales execution. Before then we invented a category called sales engagement. We decided that category wasn’t encompassing enough of the problem that we were solving. Our customers were asking us to solve a bigger problem so we redefined the category to something that solved every customer problem. When you start a company, you will have a decision as to whether you’re going to disrupt a category or you’re going to invent your own one. I don’t know, if you’ve read Frank Slootman’s book, it’s a great read, you should go and read it because there’s a lot of nuggets there. He advises against founding new categories. He tells you to go and disrupt the current category. Category creation is for lunatics.

I’m not a young founder so I’ve only got one shot in me. I’m not going to go and build a disruptor, I’m going to build my own thing because I’ve only got one shot. My perspective from the category building was that we’re going to build a category because that’s what’s more exciting. I can get my founders behind that rallying cry. We were also inventing based on what the customer was saying, not what the market was saying but what the customer needed. If you follow the customer and they pay you for it, you can call that whatever you want.

As a matter of fact, if you call it something special, all of a sudden your customers become part of that special thing and you’re creating a community. Not only do you have a business now, but you have a community. If you bring those two things together you call it a category.

Now our customers are part of the sales engagement category. There’s no rep that believes that they’re part of the CRM category. They don’t wake up thinking, “I’m going to CRM today.” They all wake up thinking, “I’m going to engage them and I’m going to make some money.” If you call that a name that is special and they belong to that, now all of a sudden you create a tribe and a tribe becomes a movement and the movement becomes something that raises you and allows you to expand, to evangelize your product for free. That’s why it’s worthwhile doing it, but it’s a long journey.

Rajeev Batra:

A lot of people are floating around now, suddenly sales tech is hot, it’s exciting. What do you think has set you up for success today? Is there some special sauce that Outreach has?

Manny Medina:

I think we just f*** up less every day and that sets us apart. 

Rajeev Batra:

That’s a technical term.

Manny Medina:

Yes. Right. Again, I think that, because of our roots of needing to survive and needing to have our customers pay us for the product to survive, we developed this innate need of customer validation. We need to have everything customer validated for us to put more wood behind it. Customer validation, there’s a lot of ways to do it but for us it’s a question of “Would the customer pay for it?” The customer only pays for it if the customer gets value from it. I think there’s a lot of distraction around the usage funnel and all these metrics. The metrics abstract the real feedback, from a real human touching your product, getting value from it and swiping a credit card and paying you for it or going to their boss and saying, “Can I please buy this?”

I think it’s that obsession of making sure that we’re aligned with the customer that has propagated to the culture and now the product managers do that, the engineers think about it that way, our customer success people think about it that way. Our reps are a little different, they really want to get into the weeds. If you get into a customer conversation and it gets technical, the rep wants to be able to navigate that herself. I think that, again, that’s a cultural thing and it came from the fact that we almost died as a company. If it wasn’t for the few customers that paid us, we would not be here. We have this tremendous amount of gratitude towards the customers that kept us alive and now to the customers that keep us growing.

Rajeev Batra:

Talk a little bit about the categories. You’re not just in one category, you’re in multiple categories. How do you maintain leadership now that you have multiple products, multiple categories? Arguably you’re doing this sooner than a lot of other companies tend to do at their stage of growth. Do they inform each other? Are they part of a bigger whole? How do you think about that?

Manny Medina:

For us, I think my co-founder, Andrew Kinzer, used to put it this way…how many people have kids here? Not that many. All right. This may be the wrong analogy but it’s like Alice in Wonderland going down the rabbit hole. You solve a problem for the customer and the customer likes it so much and it’s such a big deal that the customer asks, “Hey, I have this other problem. Do you mind solving it for me?” You go and sit down with your co-founders, with your technical team. If you solve that problem, they ask you to solve the next problem.

There is a children’s book called If You Give a Mouse a Cookie and it’s a beautiful book. If you have children, buy it for them. You give the mouse a cookie and the mouse asks you for milk and then he asks you for a napkin and then he wants to take a bath. It’s a very long book that is easy to follow, but it’s the same thing. You give the customer a cookie and all of a sudden the customer says, “Do you have milk?” Then after you have milk it’s like, “Let’s go play after that.” The customer pulls you in one direction and as long as you think that direction is something you can deliver and be differentiated, you follow the customer. If you follow the customer, you’ve solved this problem.

We called the first problem that we solved engagement and engagement for us was pipeline generation for reps. Pipeline generation for reps means that either you’re an SDR or you’re a rep that needs to generate some pipeline and that’s hugely valuable, right? If you’re not generating enough pipeline, you’re not going to make your number. We solved a little bit of new business insurance for us. Then, after we solved that problem, then our customers were like, “Can you help us forecast that problem? Can you help us close that pipeline?” We continued to add products. We failed, we added new products, some products worked, some products didn’t work, but then at some point you have to realize that, to really encompass the whole of the problem, you need to redefine the problem and then redefine the category.

The first problem that we solved was engagement, but then the next problem we called the sales execution gap, which is all these different things that are keeping you from delivering the number that you want to deliver that are gaps in execution. They’re all over the place. If you really start looking closely there could be gaps in pipeline, there could be gaps in conversion, there could be gaps in how you run a meeting, there could be gaps in how many people you’re enrolling. There’s all these gaps in sales. We decided to call the whole thing the sales execution gap. Once we named the problem, and this is literally out of Christopher Lochhead’s book, once you name and frame the problem you can name and frame the category. The first thing you do is you look for the problems that you’re solving for the customer based on customer feedback and then you name the category based on what you think you’re solving.

Once you solve it and you go for it, then you look for two points of evidence. Are your competitors calling it that too? Then you’ve won because you’ve got momentum. Two, are the analysts calling it that? At that point you’re made. You’re king, you’ve won, you’re going to the next round.

Rajeev Batra:

That’s great. Manny, let’s shift topics slightly to your development evolution as a leader, as a founder and CEO. This is your first time as CEO. You started the company with three other people so you were four people. I think when we met up and got involved, maybe 10, 12 people, something like that, now over 1,000.

Manny Medina:

1,200.

Rajeev Batra:

1,200. How has your own journey as a leader been? How have you adapted, evolved?

Manny Medina:

Yeah. One of the things that I talk about is how your motivation and what gives you energy changes. When we started Outreach, our motivation was not to die. We were motivated out of fear, out of running out of cash, out of “would our customers churn”. That really kept us alive. It’s this panic that we would just have to go and get a real job somewhere else. Once we started generating enough revenue and we realized that dying is not going to be the next thing, the next thing that came into our mind was raising a round. Rajeev comes in and brings these partners and gives a term sheet. I’m like, “Oh my God, this is real. We can be rich.” Then you get into this mode of how big can this be? What are we going to do with all this wealth?

Sometimes you take your four founders and you go for a drink and you dream about the things that you’re going to do with the money you have. That’s very short lived. We were coming in to the office one morning and we got a call from a customer. It’s 8:00 AM Pacific, 11:00 AM East Coast time, for customers in New York and the system is down. The customer said, “I just sent my entire sales team out to lunch early because they can’t sell if they’re not on Outreach. You’d better fix it in the next hour because that’s when they’re coming back.” Then we went back to that first panic of, “Oh my God, we’re going to die. Everyone’s going to churn. We’re done.”

We went into this deep panic mode, solve the problem, get the customers back up. We solved it an hour-and-a-half and we avoided this problem. At the end of the day, we’re reflecting and we’re realizing that, when the customers call in and say, “We’re running on Outreach,” that’s people’s livelihoods. That means that rep is not making their commission number, they’re not buying whatever they want to buy, they’re not sending their kids to college. There’s something they’re not doing if they’re not on Outreach. All of a sudden we grew from that sense of greed to a sense of duty. Now we have people relying on Outreach and it’s our duty to keep them up. It’s our duty to educate them, it’s our duty to make them better. I feel like that’s a stronger sense of motivation.

This category creation thing is something that we really, really, really love because it’s like a white canvas, you get to invent what’s next. That sense of motivation of going from fear to greed to duty and love has been our journey as we grow and my journey as a leader, because now my job is to instill that sense of duty to the entire organization in the form of stories, in speeches, in quarterly announcements and whatever it is. I’m the Pied Piper of a very large group that needs to run on this next level sense of energy. That’s how I’ve grown as a leader myself.

Rajeev Batra:

Do you still take support tickets once in a while?

Manny Medina:

I still take support tickets once in a while.

Rajeev Batra:

Sales calls?

Manny Medina:

I prospect once a month.

Rajeev Batra:

Prospect once a month. Still living in the product?

Manny Medina:

Of course, but that’s an important lesson. You develop your own leadership style as a founder, but mine was that I would never ask anybody to do something I wouldn’t do myself.

Rajeev Batra:

The full stack.

Manny Medina:

Even if I didn’t know what I was doing. I needed to learn to be able to really commiserate at the most fundamental level of the job to be done, otherwise I don’t think I would be an appropriate leader. Taking a ticket to really understand how support is doing earns me the credibility of support that I’ve been there with them. Successing a customer with the success team, the same thing. If I’m prospecting along with my sales team, they know that a leader has their back. You do you, but that’s how my leadership style has evolved over time.

Rajeev Batra:

Any last words for the audience? You’ve got seven seconds.

Manny Medina:

Do it for the love of the game. Look at yourself internally and make sure that you pour your life into something that you’re really going to love. Do it for somebody else and do it for yourself.

Rajeev Batra:

Great. Thank you, Manny.

Manny Medina:

Thank you.

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