Marylou:    Kevin knows what it takes to build a tech sales team. As Manager of Sales and Operations at Digital Ocean, he was charged with building the company’s first ever team of outreach sales reps. His insights on building a team are beneficial for anyone either tech startup or an established small business alike. You can find him on LinkedIn where he’s built quite the following with his unique and telling pulse blog posts.    In this podcast, Kevin reveals insights on building a strong sales team, tips to find and keep ideal customers, and utilizing social selling in the tech world. Essentially what’s happening is I’ve known Mark and Manny. I don’t even know how we connected. I think they reached out to me a while ago but the success of Predictable Revenue, everybody was sort of wow, this is a really cool channel, I think it would work for our company. They started implementing or assembling it together to get a little bit of success and then things sort of fall apart. It’s the fault of the book because the book made it seem as though it’s a magic pill that you could take and then all of a sudden you start getting all these great referrals. They reached out to me and we started talking and I started mentoring them. It was very clear that the book was great for its time but it’s severely outdated. Also, when you got further into the pipeline, you started going to the working status and then maybe towards qualification or the are we a fit sequence. You really needed to rely on selling skills or at least a good understanding of where your position in the marketplace, why you matter, why people should change, why you, why now. We started working together and then I realized I need to write a new book because it was a disservice to all of my clients who were trying to use Predictable Revenue as a bible. They called it that which is kind of scary. To use that book in order to be able to create an outreach channel and an outbound prospecting system that they could scale or that was consistent and predictable. Fast forward, wrote another book. I’m blessed because it was picked up by McGraw Hill. Now, they’re gonna launch it in August and I thought, “Let’s start talking to our people.” People who’ve been embracing this, trying to get to work, making it better.  I wanted to hear everybody’s story so I started doing that then I realized, we should probably put a podcast together so that’s where we’re at right now. I’m interviewing people who have embraced the idea, the concept, the framework, the process, whatever it is. Listening to them on how they’ve adapted it to make it better or what pieces of it they thought were just brilliant, what pieces of it do they struggle through, how they overcome those struggles. I started interviewing people, and I interviewed Mark, and he’d recommended that I speak with you. Kevin:    Wow. That’s awesome. I’m really very honored that Mark would think of me and I’m honored to be speaking here with you here as well. Marylou:    Oh, good. Kevin:    What’s the name of the book that you launched on Amazon? Marylou:    It’s on Amazon, it’s called Predictable Prospecting. It’s not a stretch from Predictable Revenue. It was picked up by McGraw Hill. I think that’s kind of like, oh my gosh. It’s now a publisher that actually put money into it because they believed that this was still a missing hole for a lot of businesses. We try to cram it full as much as possible but can’t really do justice with the written word. I thought let’s take that book and then let’s build an ecosystem around it of people who have either done it, of people who are still working through it, of people who started with Predictable Revenue and thought there’s got to be more to this and actually created the more to it part so that we can share our stories together and embrace what’s working and what’s not, why it worked, why it didn’t. For me, Predictable Prospecting really talks about embracing the content pieces that were missing or absent in Predictable Revenue and actually taking a piece of content that we may use for inbound, turning it sideways, and then saying, “Okay, where is my buyer in his thought process?” I looked back and studied for years the greats of direct response. Eugene Schwartz, I read all of his level of awareness stuff. Drayton Bird, David Ogilvy, Rosser Reeves, all these people who are able to get people to buy product and services and having a cold conversation to do so. I took those concepts and I brought them into the fold of Predictable Revenues’ framework and it ended up morphing into this 28 step assemble, activate and optimize framework that is Predictable Prospecting. Kevin:    Wow, I love it. I’m definitely going to preorder it right now. I have my one click purchase on with Amazon and I kind of have like what they call this happy finger or trigger finger. Just been buying a ton of books. I think being a part of the reason why Mark might have pointed you in my direction is I try to be very proactive in my learning and I think there’s so much content and knowledge out there that one thing you can do as young selves leaders is be proactive about absorbing all the knowledge from all of the sales leaders out there who have that track record of success. They’re sharing their stories whether it’s online through a blog or through a book. This is the one thing that I kinda knew going into reading Predictable Revenue is that it’s not gonna be a one size shoe fits all especially when everyone is trying to use that same sales played book all the way to the extent where they’re calling it a Bible. That it might be outplayed but I think that there’s definitely little nuggets out there and you have to absorb all the knowledge you can and then look at your sales process, your market that you’re going after and your ideal customer profile. Molding all the best pieces of everything into what’s going to work for you, that’s how you become more successful rather than just copying something from somebody and applying it exactly. Not all markets are the same and not all businesses are the same. You gotta have to sell and adapt to the buyer that presents itself to you, not someone else. Marylou:    Right. Tell me, what is the type of business that you’re in right now? What do you guys do? Kevin:     This is a very, very interesting story, cause I think that not a lot of people in SAAS are very familiar with DigitalOcean. I think we actually just made a recent name for ourselves in the SAAS base because we sponsored Saastr which you probably or might have been at, which is one of the biggest sales conf in San Francisco that’s hosted by Jason McCann and Max with Sales Hacker. We sponsored that event. We’ve been picking up a lot of traction because we’ve built a very, very successful business that’s now going up against Amazon web services. You can technically still consider some storages because we’ve only been around for less that or around four years. Marylou:    Okay. Kevin:    We built a very, very successful business off of selling or simplifying the cloud infrastructures experience for developers. When you take a look at Amazon web services, they offer everything and anything that you could imagine about infrastructure. What we wanted to do was simplify that and just take us to what they’re offering and patch it up for the developer markets in a way they can deploy their own server web application in less than a minute. Marylou:    Wow. Kevin:    We’re not necessarily in the service base. If you take a look at the three tiers, you have software as a service, you have platform as a service, and then you have infrastructure as a service where it’s like the bare bones virtual machine. Every SAAS application is hosted on something whether it’s DigitalOcean or Amazon Web Services. We’re selling it to developers and the developers build the applications and then we sell it to the consumer market. It’s been really, really interesting because DigitalOcean has become that unicorn essentially and has had no sales. Everything has been organic sign up and solely just on product execution that has really projected our growth from zero to the unicorn status that we are today. There’s not a lot of companies like that in the market. The one that I can really think top of my list that’s still doing it that way is Wack. They’ve built a very successful business not focused on sales whatsoever, it’s really just organic signup and then kind of up selling from there I believe. The interesting part is you can think of decision very like B to C and now we’re transitioning, B to C because we have over six hundred thousand customers. A lot of that is the developer market or the individual developers but we have definitely tons of customers and teams of developers that are now migrating from Amazon Web Services over to Digital Ocean from companies like ZenDesk, Docker. It’s just crazy because they’re starting to see that DigitalOcean is just as viable a solution as Amazon Web Services and we’ve really been only around for a short amount of years. When most people who are in a work decision think that there’s just really AWS or Microsoft or Google. When I heard about the opportunity, it’s actually pretty crazy because I actually work with my brother, he’s the one who told me to leave Greenhouse which is the company I was at and I absolutely loved working at Greenhouse. They’re the leading tracking system in the space right now that’s taking on some of the legacy players like Oracle. Marylou:    Right. Kevin:    Some other notable ones might be like Smart Recruiter or Lever. They’re working with just really, really big companies and they’re growing really fast. It’s tough for me to leave but when I heard about Digital Ocean, where they came with no sales team, I knew that it was an opportunity that I cannot turn down. To be the first sales person joining that and build that team from scratch was something that I’ve been wanting to do my entire life. I wanted to pursue that opportunity. That’s what brought me here today Marylou:    That’s great. You step in the door and you look around, what’s your next step? What did you do first to try to figure out the ideal team that you put together, that you eventually put together. What was step one? Kevin:    Step one was definitely thinking about or learning about the product. I left Greenhouse just around early December before this past winter. I was supposed to start DigitalOcean on January 4th but literally, that entire two weeks, I already had homework assignments technically so my brother had assigned me some stuff to do. There’s definitely no Christmas break for me. It was dive right in and make sure that my first day with DigitalOcean did not seem like my first day at all. I spent the first two weeks just studying the product day and night, making sure that I could come in on day one and not feel flushed. I wanted to make sure that I knew the product really well especially because I didn’t have that advantage of moving from one SAAS company to another. Marylou:    Yeah. Kevin:    I definitely got to give the executive team props for bringing me on because it’s tough. It’s hard to find someone in the infrastructure background because it’s not as easy as like picking a SAAS sales leaders because there’s not that many players in the infrastructure’s place. They kind of brought me on with my background in SAAS and I do have that track record there. Before I used to say that, that’s gonna easily translate into infrastructure service because it just doesn’t. That was my first thing,  I wanted to make sure I understood the product because by understanding the product and the market you’re in, by understanding the ideal customer profile, understanding the customer base, you can start to figure out who that ICP is and by that, ideal customer profile, I’m referring to ideal candidate profile. You want to make sure the people you bring on, they’re going to be people that can sell into the developer market. I knew that I had a decent sized network because I also run a meetup for Sales Hacker in New York where we have over a hundred attendees and I’ve seen most SAAS sales reps are very well rated. They probably attend, you’re not gonna want to hire six of the same types of people that do really well in SAAS sales and just bring them over into an environment like DigitalOcean. I spent a lot of time researching, building a really big candidate pipeline. I probably interviewed over 300 people and this is me actually looking at the Greenhouse reporting. We use Greenhouse. I interviewed over three hundred people to get to the first six. I’ve been here for almost three months. I would spend I spent my good first month and a half, 90% of time probably sourcing and interviewing. They originally wanted me to have six people by February 1 which I’m sure you’ve had a ton of experience probably hiring by now. It’s pretty impossible hiring six people on one month that you obviously want them to be the perfect fit, right? Marylou:    Right. Kevin:    You might hire six people but you can easily turn and burn them because they’re going to figure out that these weren’t the right candidates. I’m very, very confident in the team that I built, I hired a lot of account executive that they were the number one AE on their team. One rep that we have here is the fourth best rep in the company and they had a hundred plus sales reps. Another person we have was a team lead, SPR that was about to get promoted to manager but left that company to come to DigitalOcean because everyone we hire is a very, very rigorous process and they believe in a mission of at least the same reason why I came to DigitalOcean. It’s not about the money, it’s not about the title, it’s strictly on opportunity. If what we do here becomes very successful, then this first six is going to be the reason or the future of sales of DigitalOcean. The company will remember the first six people that left what they were doing to come on. A lot of people could say is it is a little bit of a risky venture but to build up a sales team for company that has had no sales is definitely not easy by any means. Marylou:     I can imagine, where do you begin? If you look at your customer base, I just was having this conversation with one of my colleagues, do you want to look at your customer base as the foundation for the future or is your customer base exactly opposite of where you want to go. The case study for Sales Force was all about the fact that they wanted to get into the enterprise market. Their client base was more wanted to licensed type of client but they wanted to grow into the other market. How do you juggle that? Have you thought about, what is your plan as you think through now you have these great sales people. What do you have in mind in terms of the ideal customer going forward? Kevin:    Yeah, definitely. I think that’s one of the things that I want to touch upon before we dig deep. I read this really great article from First Round Capital that really resonated with me and it’s something that I hold true to this day. They say that I believe I might have a background but I’m almost positive that they say hiring the builder versus hiring the architect. When I first came in in this kind of road, I really just interviewed with the executive team. One of the questions is what is it about you that essentially makes you have a competitive advantage of people who have more experience than you? Someone that has the experience in infrastructure. I think that, the advantage that I have is I’m always trying to build, I’m very process oriented. I want to build a predictable and scalable process, very similar to the title of Predictable Prospect and Predictable Revenue. That kind of resonated with me because in the article or the blog shared by Elizabeth, you can hire a builder who can go in there and they can get the first couple sales. They’re great as a contributor, they might have moved up to a manager, but they’re not good at setting up a sale for the future. What I told them was that where DigitalOcean is today. You can hire someone who can make that sale with the product that you guys have and all that, sure they might have infrastructure background. They’ll have that have advantage over me. But, what they’re not going to do and what you’re trying to do is you’re trying to build a team very quickly and you’re trying to set up a process and set yourself up for the sale that’s going to come six months and twelve months down the line. What a lot of companies have done in the past is they try and grow, grow, grow, grow, grow, grow very quickly and just hire that person that they think is perfect on paper right there, twenty years experience that came from that top company, a brand name company that everybody knows. They start to realize that they built it so fast that they didn’t really architect the sales process correctly and they didn’t set themselves up for success six months down the line, twelve months down the line. They were able to crush in the first five months but everything broke after that six month mark. That’s kind of the way I like to look at things. The reason why I want to talk about that first is when you look at DigitalOcean, where we are today, is that most of our customer base is, sure they’re spending $5 here and there which is why we have over $600 customers and we’re signing up over thousand customers each day. But you want to make sure that you’re building on a sales process that can help evolve that and turning those into some much larger customers. A good side of our customer base is actually we have customers that will pay us over six figures a month in infrastructure cost. Those are million dollars deals each year. The question that I’m kind of Facebook today, and my team’s space, how do we find more of those customers and get them to sign up with DigitalOcean and not go with something like Amazon Web Services. The upside is that the total address market is really wide open for DigitalOcean. We have all the brand recognition that we need. One of the interesting things and why we become so successful is we have a community team here that does a really great job of helping brand DigitalOcean. One of our core values, it sounds cheesy but it’s really true, is love. We’ve been able to build a huge customer base by really just caring about the developers that sign up. Our customers’ success team have less than 1% chance. When you’re looking at 600,000 plus customers, that’s very, very little people spinning down service on DigitalOcean. On top of that, we have a tutorials and community website where we get over six million hits a month. That’s a tutorials website on how to do anything technical, any type of application on not just DigitalOcean’s infrastructure but also Amazon, Microsoft or Google or any other vendors out there. We really just want to be a resource and the go to hub where the other technical question. It’s essentially like kind of the Yahoo! Answers for technical developers to come find a legitimate tutorial on step by step instructions on how to do something. Marylou:    I love that. Kevin:    It’s pretty awesome, right? Marylou:    Yeah. Kevin:    It’s actually when going back to the question of what did you first do when first got there. I was able to teach myself the product by going through our tutorials website. There wasn’t a sales playbook. It wasn’t watching this play book or the stack or this demo because when you’re selling infrastructure, you don’t have a deck or some sort of a user interface. Yes, we have a control panel but it’s not like a SAAS Application where it’s very robust and you can navigate yourself through the product and teach yourself that infrastructure is very, very complex. You have all these different types of applications, web applications that architect their infrastructure in many, many different ways. Our tutorials website does a phenomenal job of teaching even non-technical people how to understand it at the highest level. It’s really awesome. Marylou:    That sounds great. I think having that open forum for people establishes more of your credibility, establishes your thought leadership, so that people feel comfortable and trust that if they join your company that they’re going to be in great hands. Kevin:    Yup, absolutely. Going back to your question about what do we do to reach out to those customers. We do lots of different types. Whether it’s phone, email, social selling on Twitter, LinkedIn, whatever the case might be. The responses back have been phenomenal. The upside to joining DigitalOcean right now is that the light at the end of tunnel it’s kind of the same when you join a [00:23:23] sales person, right? It’s going to pay out dividend that you’re making and it’s obviously really risky. The growth that you’ll get because the FedEx is higher when the sales is now hundred. It is second to not going to be amazing, you won’t really get that opportunity elsewhere. The branding that we have when we are reaching out to these prospective customers is really, really amazing. Most of them are saying, “Hey, I really love DigitalOcean. Have you reached out to me three months ago, I definitely would have went with you guys. I didn’t even know that you guys were for production use. I thought you guys were more staging or testing environment.” The way the market’s been reacting to us when we’ve been reaching out to them has been really, really positive. We set up tons of meaning close it and selling up tons of deals that are going to close. How’s it really been like, “Oh, I’m not interested at all,” but it’s more been like, “I love what you guys are doing, I’ve actually used your tutorials to set up infrastructure on Amazon or Google. I didn’t even know that we could use you guys.” It’s really about prodding and knocking on the door and saying, “Hey, DigitalOcean is in fact ready for production use case, we’re not just built for developers, we’re actually built for larger teams of developers. That’s what we’re doing today. Marylou:    Right. What’s nice about the outreach channel is those awareness campaigns to show or gain understanding of where people are in their level of awareness is what Predictable Prospecting is all about. It’s really taking the content you have, taking the messaging you have and creating the actual touches so that you’re spanning across the different levels of awareness. One of the things we talk about in the book is there are multiple levels of awareness that you’ve really got to organize your content around so that you can bread crumb people and gently pull them through to the point where they want to have a conversation with you. I think that’s one of the biggest differences now that we can leverage a lot of the great content that was built for inbound knowing that inbound is really only addressing two levels of a five level awareness, latter. They generally, working with people who are interested because you have now taking the action as an inbound person to fill out a form, to engage with the website, to download a white paper. There is some level of interest, there is some level of excitement around it. But for outreach, we have three more levels that we have to write for and deal with. Like you said before, people weren’t aware that you did X. The content with process allows you to touch these people in a way that’s authentic, that’s respectable, and resonates with them at the level that they’re at.  And then you can track where they are so that you know when the optimal time is to place that phone call or to nudge as you said, to get the point where, “Hey this is something that you want to look at,” and they will actually be ready to do that. Kevin:    Absolutely. I think what you’re talking about is a little bit with just what account based selling is about. I know it’s a super hot topic but it’s just kind of selling smart. It’s looking at an account from a holistic perspective, taking all those different five pieces that you’re talking about and putting them together so that way you’re reaching out at the right time and really just trying to make things less, less cold, which is really the right way to do things. Marylou:    Exactly. We take it even the account based selling, the word account is account. But what we say is, I know it sounds like your culture is that we take it to the people within the account. Not everybody is going to be in the same level of awareness from a personal point of view either, the buyers. Now, granted if you have one or two buyers that you know you’re going to always have entering at certain points in the pipeline, then you want to make sure that your content is written for that person at that point in the pipeline for entry. We really look holistically at the people. Who am I sitting across a table from? When do I first meet them in the sales cycle? Is it early on? Is it mid? Is it late? Where is it? How can I warm up that chill, meaning that they don’t know about me or know how great things can be if they were as if a client of mine. Where are those points in the pipeline that I can insert content and leverage technology so that it drips to them in a way that’s meaningful? That’s what we have now which is just phenomenal but you have to sort of like you said, you have to have that process, not mindset, of mapping out. It almost looks like a transit map, like the Gartner Transit Map. It’s like where do these people enter? At what level of awareness are they at? What relevant content should we squirrel feed them and bread crumb them so that we move them along to the point where they’re sort of, “Oh, wait a minute, I need to talk to somebody now. I want to raise my hand and talk to someone.” That’s the beauty of outreach. That’s what we love about this particular channel is that A, we’re controlling who it is that we want to talk to which is what you said on account based selling. We’re also controlling the conversation of where we’re going to be talking to them and at what level we’re going to be talk to them Kevin:    I 100% agree. I think that one topic that kind of is very similar to what you’re discussing right now is sales and marketing alignment. With us over at DigitalOcean, we kind of even go one step beyond that, sales and marketing success alignment making sure that the entire buyer process has been moved along to the journey, that were hitting them at all the touchpoints, make sure that we’re extracting the most value out of them as possible. What I mean by that is you always want to get a holistic look into what’s going on in the account. The account use worth a million dollars and there’s things that you don’t see, you might not get all million dollars, that’s just something that we find unacceptable over here. One of the first things that I did when I got here is I met with the Director of Marketing and also the manager of customer success. We’ve very, very closely to get insights into each account. If you have five potential decision makers because it’s a much larger organization, we know which one of those decision makers have ever spun out what we call a drop foot which is a virtual machine at DigitalOcean. We know who’s interacted with marketing material, we know who to add retarget because they’ve never interacted with anything, we know who to reach out to because they’re interacting with some report material. It’s a very, very strategic outreach process. The only way to do that is really by getting yourself involved in account based selling process but also making sure that it’s not very one sided. You want to make sure that you’re online on all departments that are involved with this customer or this prospect before they become a customer. That’s always going to include sales marketing. More often than not, we’re seeing clues to customer’s success. That customer, they’re going to renew at some point, they might add up more licenses. In our situation, they’re going to be scaling their infrastructure. You want to make sure that there’s alignment across the board and that you’re getting visibility into that. Marylou:    Not only that. When you have customers on boarded, you’re learning how they describe why they chose you, why they went now. Those language snippets, those long term key words, whatever it is. That, when collected in a database, can be directly transportable to the top of pipeline conversations. I think that that’s an area that I’m sure that you guys since you’re focused on the account itself and you’re doing process based work will take that language and essentially recreate, modify, iterate the content at the top of the pipeline so that you’re reducing the lag of getting people to raise the hand. Kevin:     Beautiful point. I was just trying to not give away all of our secrets. Perhaps that’s definitely something that’s really important and we strive to do here as well. Marylou:    Yeah, that’s great. Tell us what’s in store for the next six months? How do we follow you to see what’s going on and where you’ve grown from here to there? Kevin:    You can follow me in a few different ways or follow DigitalOcean. We have a huge following on Twitter but I think if you are trying to get more following the sales process and see how it’s evolved is I’m trying to do a lot more blocking and talking about the team, where it was when I joined on day one, where we’re at on month six and where we’re going to be at on month twelve. I also run a Sales Hacker meetup in New York where we talk about a lot of this stuff. I’m available on Twitter. I’m also very, very active on LinkedIn. If anyone has a question, you can always shoot me a mail and I’m happy to give you more insight into what’s going on over here. Marylou:    Okay, perfect. Kevin:    We can always schedule a follow up call as well. Marylou:    A lot of what I’d like to do since the book is coming out in August and there’s a conference coming up in June I think in New York for Sales Hacker, right? Kevin:    Oh! That’s actually, I totally forgot to mention that, but yes, there is a Sales Hacker, Max will kill me if he found out that I forgot to mention that. But yeah, there’s an amazing sales conference, Sales Machine. We’ve partnered up with Sales Force. Lots and lots of good speakers going to be on there including guys like Gary Vaynerchuk, we also have all the traditional SAAS people going to be like John Barrows, Joe Conrad, and couple of other people on there so you definitely want to make it out there. I’m not entirely sure if we’re sponsoring the event but if we do, then you’ll definitely be able to get some updates on us there Marylou:    Perfect, so that’s coming up in June 2016, why don’t you give us your Twitter handle so that we have it? Kevin:    Yeah definitely. My Twitter handle is @kvn_chiu. Marylou:    Okay, very good. Thank you so much for your time. We really appreciate you sharing an exciting journey to walk in the door and start from scratch. I love that. Kevin:    Definitely. I really appreciate your time and having me on. I really enjoyed that. I really enjoyed this.