Oliver Jay - Head of Global Sales & Partnerships @Asana (Formerly @Dropbox, @NEA, @HBS) - Top Talent: 4 Hiring Criteria & Step x Step Recruiting Process, The International Expansion Playbook, Freemium to Enterprise, Picking Great Companies, Unit Economics

Guest:

Oliver Jay - Head of Global Sales & Partnerships @Asana

(Board Director @Grab; Formerly @Dropbox, @NEA, @HBS)

Guest Background:

Oliver Jay is the Head of Global Sales & Partnerships at Asana. Prior to Asana, he scaled the Dropbox sales team from 20 to 100 people across multiple geographies. Previously, Oliver worked at Morgan Stanley and New Enterprise Associates (NEA) where he invested and worked alongside entrepreneurs in consumer internet, cleantech and enterprise SaaS companies. Oliver earned his B.A. from the University of Pennsylvania and his MBA from Harvard Business School.

 Guest Links:

Website | LinkedIn | Twitter

Episode Summary:

In this episode, we cover:

- Top Talent: 4 Hiring Criteria & Step x Step Recruiting Process

- The International Expansion Playbook

- Upstream: Product-Market Fit to Freemium to Enterprise

- Building Sales Engines - Self Serve, Online Sales, Enterprise, Partnerships & Channel

- 3 Criteria for Picking Horses (the Right Hypergrowth Companies)

- The Role of Unit Economics for Sales & Marketing Leaders

Full Interview Transcript:

Naber:  Hello friends around the world. My name is Brandon Naber. Welcome to The Naberhood, where we have switched on, fun discussions with some of the most brilliant, successful, experienced, talented and highly skilled Sales and Marketing minds on the planet, from the world's fastest-growing companies. Enjoy!

Naber:  Hey everybody. Today we have Oliver Jay on the show. OJ is they call him. OJ is the Head of Global Sales at Asana, a $1.5 billion valuation company, a Unicorn with $213 million capital raised. Prior to joining Asana, he scaled the Dropbox Sales team from 20 to 100 people across multiple geographies. Dropbox IPO in 2018 $9.6 billion valuation. Previously Oliver worked at Morgan Stanley and New Enterprise Associates, NEA. We invested and worked alongside entrepreneurs in consumer internet, clean tech and enterprise SaaS companies. OJ is also on the Board of Directors for Grab, who has a $14 billion valuation and $9.1 billion capital raised. OJ earned his BA from the University of Pennsylvania and his MBA from Harvard Business School. Here we go.

Naber:  Oliver Jay, awesome to have you on the show. Thank you so much for joining us.

Oliver Jay (OJ):  I'm so glad to be here, Brandon.

Naber:  Excellent. Thank you. It's July 4th. I'm sure you don't have anything better to do, so I'm really glad that you're spending it with me this morning. and I really appreciate your time. So we've got a lot to talk about. We're lucky enough to know each other personally and professionally, so I get to talk about some of my favorite things and hear about your story personally, and we'll hop into professional as well, hop through some of your career journey and ultimately, spend the bulk of our time in your professional journey, talking about a lot of the strengths, experiences, and ultimately superpowers that you've built up over time, that you've been able to study about, but also execute on that at several different, really, really high growth businesses. So let's start with on the personal side, little bit about you growing up, a little bit about what you were like as a kid. I mean, Hong Kong, Concord, New Hampshire, Philadelphia, New York, Boston, San Francisco, Sydney, San Francisco 2.0, been all over the planet. And I'd love to walk through you as a kiddo and talk about some of your interests, some of the things you're interested in, and then your journey through school. And then we can get into some professional stuff. Maybe in five to seven minutes, et's talk through what was OJ as a kid?

Oliver Jay (OJ):  Awesome. Yeah. Well, so I grew up in Hong Kong. My parents are still there. And, I think even as a child I was always, I was the Lego kid, I was the builder. I was a total nerd throughout. And I excelled in math and science. Not a surprise. And it got to a point where my parents were , okay, math is only going to get you so much here. So they then sent me to boarding school in New Hampshire.

Naber:  And that was St Paul's?

Oliver Jay (OJ):  And that would be St Paul's. So I went there. That was my entry to the US was a ninth grade.

Naber:  Nice. Excellent. So, what were some of the interests you had or the hobbies you had when you were a kid?

Oliver Jay (OJ):  My main thing was tennis. Tennis was my major hobby growing up. And I think a lot of who I am came from just that sport, because that sport, just like any sport, requires you to be excellent. You just have to be, continue to grind away. A lot of, how I think actually came from that sport and competing, learning how to lose graciously, learning how to stay calm when there's, when it's things are looking rough. When you're down a set, what do you do? I'm thinking about how do you change your tactics in real time? That all comes from tennis.

Naber:  Absolutely. Especially in an individual sport. We have to be so iterative. Where you do things a thousand times in practice, and it just becomes a transaction when you're in the actual match. That makes a lot of sense. So when you moved to St Paul's, and you were in Concord, New Hampshire, out of your comfort zone, tell us about that transition. And then let's talk about some of the things that you were interested in when you were in New Hampshire and high school.

Oliver Jay (OJ):  Boy, so the interesting thing was Saint Paul's is one of the top high schools in the US, and that's pretty much all my parents knew. And my parents said, you're very strong in math and science, but your English sucks, and it's just really bad. And they're like, you need to supercharge that. And so they looked at the list, I think it was a US News and World Report list. And they had a couple rankings and some names that people have heard of, Exeter, St Paul's, whatever. And then so I applied and got in. And I mean St Paul's is a real school, in that it's academics is intense. And it's in the middle of nowhere. I mean, you're literally in the woods. I grew up in Hong Kong, I grew up in the heart of the jungle, a concrete jungle, and then I'm literally moved into a jungle. The school had, I think 200 acres. And I mean, it was nuts. But I learned to adapt. I learned about the American way. Yeah, it was tough, but it was certainly, also the best four years of my academic career.

Naber:  Nice. Very cool. And did you play tennis when you were there? Or what were some of the activities that you were doing?

Oliver Jay (OJ):  Yeah, yeah. I was on the tennis team, I was captain of the tennis team there. We were decent, we were decent. I did that, and then I was just lots of part of lots of clubs. But honestly, high school was tough for me. I didn't have that much spare time. Obviously, it should be clear, I have tiger parents, right? Obvious. So I did play a violin as well, but I was terrible at it. But I did the orchestra thing, but I was, I was so bad, so bad. But I survived, and I was okay. But I mean, I just, I worked so hard because my English level was far, far, far, behind my peers at school.

Naber:  That must have been so challenging. Learning all that curriculum at such a high level, while you're learning how to master the English language yourself. That is immensely complex.

Oliver Jay (OJ):  It was crazy. It was crazy. But, it changed my life. Because when I went to college, I studied philosophy, politics and economics. I went to Penn, right? So I didn't go to Wharton and just do a bunch of math and talking about strategy. I mean it's funny, I'm in business now. It's so easy compared to a career, or studying old philosophy texts, and debating, and writing papers or why you disagree with Socrates. I mean that's...But if I didn't go to St Paul's, and then of gotten out of my comfort zone, I wouldn't have done that.

Naber:  That's cool. That's actually a really good way of looking at it. The most challenging class I think I've ever had in Uni was my logic class, my philosophy class - deductive reasoning, and logic, and going through all those different frameworks, and squaring everyone from old philosophers, and folks that...it's just almost, it feels it's impossible with their life experiences to contend and debate with. But that's, that's really interesting. You moved to U Penn. Why did you decide to choose U Penn?

Oliver Jay (OJ):  Actually it was specifically because I really liked this program. So PPE, philosophy, politics and economics, is the most popular major in Oxford, in the UK. And Penn was one of two schools that adopted this program. It sounds fancy. Sometimes when I tell people that, it sounds I tri-majored. It's not true. It's more than one, but, it's this integrated curriculum of three disciplines that I think are really, really tied together. So that's why I went to Penn, for that program specifically.

Naber:  Got It. So I won't tell anyone you didn't tri-major, but it sounds really, really stimulating. So you were at U Penn, What were some of the things you're interested in at U Penn? Before we get into your first job.

Oliver Jay (OJ):  Like I said, Saint Paul's really opened my eyes to the world of humanities, and that's why I really loved that. But my interest had always been in business. You grow up in Hong Kong, you're going to be in business or you're a doctor, right? Or maybe a lawyer. It's just what you do, and it's in my blood. And so even when I was in high school, I was reading Peter Lynch books on how to invest. And so I've always been interested in business, but I took a couple of business classes and I was like, especially the management ones, and I was like, this is ridiculous. I'm not gonna pay this tuition to learn how to work as a team. Not to dismiss it, but I'm like, I don't think I'm going to have a chance again to, to read about Immanuel Kant, and how he thinks about the world. So in college, what I did was I spent most of my time academically on humanities, and then extracurricular was where I got scratch my itch on business. And my biggest thing there is I started the Wharton China Business Society. And back then, it was 2000. China had just gotten into the World Trade Organization, this was before China is the China we know it as today. But you knew it was going to be big. And it's cool, that society is still running now. I'm still getting their emails. Well they keep asking me to for donations.

Naber:  That's how you know you made it. All right, cool. So you're you go through UPenn, you tri-major, obviously we talked about that. And you're interested also in studying business. I know you've always been interested in studying companies. I don't know if that's at the cost of studying people, but I know you've always been interested in studying companies. Is that when that started? Or did you get more practical with investing at Morgan Stanley, at NEA, at Harvard, before you started studying companies a lot?

Oliver Jay (OJ):  I think the turning point was Morgan Stanley. I mean it was probably that summer internship. I just find it really fascinating. So when I got to Morgan Stanley, and I picked Morgan Stanley because I always liked tech as well. So I've always been a geeky, nerdy guy. And so at Morgan Stanley, I joined the tech team. And I ended up joining team that covered hardware. So companies Cisco, Juniper, and all the companies that died, Nokia, Motorola, they don't exist anymore, Nortel. But I just found it so fascinating to think about how a lot of these companies basically sell commodity hardware. A Cisco router is not that much better than Juniper router, or vice versa back then, at that point.

Naber:  That's like a nightmare for software, I mean you're selling on features and pricing.

Oliver Jay (OJ):  Exactly, exactly. And, but you were able to see very, very different trajectories. A lot of these companies no longer exist. A lot of them are still strong today. And that's just because of a different strategy that companies took. And I had the opportunity to go really deep. So that's why I joined equity research as opposed to a lot of my colleagues that joined investment banking to work on IPO's and deals. Because, it's probably my humanities background in education that I had led me to want to dig in deep, as opposed to more of a transactional finance job. And that's why I ended up in equity research. And through that experience I've really got to learn how to dig into companies.

Naber:  Yeah. Very cool. That's a great transition. So while you're at Morgan Stanley...What's the top thing you learned from Morgan Stanley? The top learning you had, before you moved into NEA. And then we'll hop into NEA after that.

Oliver Jay (OJ):  Ooh, top thing from Morgan Stanley. I actually, I have two things in my mind. So can I give you two?

Naber:  Give me 10 if you want to, I've got time.

Naber:  Yeah. Yeah. So the first, is I think of all places, I was extremely fortunate. And I had two great Managers at Morgan Stanley. They were my first bosses. And they say your first Manager really impacts you and your career, more than any other, right? I was just so fortunate because normally you don't get that on Wall Street.

Naber:  Yeah. Statistics aren't on your side.

Oliver Jay (OJ):  And I got placed with Scott Coleman and John Marchetti, and they were up and comers. And they rose through the ranks, and so they know what it took to move up. And they just had a very empowering mentality from the beginning. So they just pushed me, and I always asked for more. But every time, they just really gave me great feedback, pushed me, I learned so much. And they empowered me so much that by the second year I was they put me on stage at the Morgan Stanley tech conference, interviewing tech CEOs. And I was like 2 years out of school. And I think that was a very formative experience because I got to benefit from that, and I know what that did for me, and my career, and my confidence. And we'll talk more later about building teams and managing teams, but I've taken a lot of that philosophy from them. I was so lucky. I mean, that would be the number one thing. I will give you that, that was my number one thing I got from Morgan Stanley.

Naber:  Nice. That's great. I mean, you're going to talk us through NEA. I mean you've worked for incredible companies, and you're on team building. Let's talk about that. Hiring great teams. One of the things that I know is your superpower from hearing from other people, from talking to you personally, talking to you professionally. But the result speak for themselves. You've hired incredible individuals that I know, because I used to work with them, or I know people that used to work with them, are just the best at what they do. And you consistently do it time, over time, over time. What's I'd love to hear is one, what's that hiring philosophy that you took away from those guys, as well as any additional things you've applied today? And then we can talk a little bit about your actual process. Because clearly there's something you're doing in execution that is better than most, if not better than almost all. So what is your philosophy around hiring that you took away from those guys as well as how you think about it? And then we'll talk through the process like, candidate profiling strategy, how do you attract and recruit, how do you close? So we'll talk about those things as well. So, what's on your mind?

Naber:  I love building teams. I mean, it starts there...let me start with why I care about it. And I think for me, that's literally why I think...That's where I find meaning in my life. Bringing in high potential talent and seeing it grow, and creating opportunities. And I've always thought of myself, on my deathbed if I'm seen as the Y-Combinator of talent, I'll be really, really happy. And so because of that, I think that it impacts what I look for, because I really look for people who I believe we can go on a journey together, and they can learn from me and I can learn from them, and we're going to achieve great things together. That's the high level mentality that I have. I really don't look at...no matter how senior or whether someone's a fresh-out-of-school graduate. I think I can learn something. If I can't learn something from you, then I don't think you're a good fit. But that's how I see it. And so it's interesting, at Asana, we recently distilled down what are our Sales attributes, the hiring profile, not profile, but what are the attributes or values, depending on how you define it, that we look for. And I was very, very involved you can imagine, because in many ways I think I codified the things that I really value. So there are four pieces that I really care about in every single person that I hired. No matter, again, fresh out of school or you're going to run EMEA. The first is someone who really "pursues excellence". What I mean by that is, I want to see evidence that someone knows what excellence means. Because in high growth companies, you're growing 100%, 200% early on, 300% in the super early days. Every knows...information is everywhere now. So you can imagine you've got great competition. And so, you gotta go for people who really, really...Well, if you're not excellent, you don't even have a chance. You don't even have a chance to survive. And so, if you're fresh out of school, and I'm digging into your profile, and I don't see one thing...And I don't care, it could be a violin. If you've gotten really good at violin, I'm like, oh yeah. And this is sometimes why I think some of my best hires have been teachers. Because, gosh, if you can teach, especially if people from Teach for America, if you can teach math to inner city kids who have no interest in math, okay, you've pursued excellence here. And I think in this world, you either get it or you don't. You've either seen excellence, and you know what that means, and what it takes to be great, or you just don't. And it's very binary, and you can tell very quickly. So someone who does that is something I value a lot. The second piece is, we're calling it, you "lead with empathy". And in Sales, of course, if you don't have empathy, you're not going to understand your customer's needs, and you're not going to relate to them. You're not going to build a good relationship with them. But I think a lot of this is also empathy just in terms of how you work together, right? Like in Sales...you never win because of Sales. This is a huge thing, where a lot of times I've talked to other founders and they're like, oh, okay, it's time to monetize, but I need to hire some Salespeople. Those Sales people are gonna fail, right? Because Sales is just a part of a bigger engine, because you've got to work together. And working together is fricking hard. It's really hard. So if you don't lead with empathy, you're not going to know how to work together cross-functionally. In Sales, what do Sales people say all the time, every single Sales person, every single Sales leader, I need more leads. Marketing's not developing more leads for me. I'm like, okay, great. Tell me more. How could they be developing more leads for you? And why? Most people can't answer that. If you can't answer that, just like with a customer, you're not going to be able to partner with Marketing to generate the leads that you actually want, right? It's not transactional. So anyways, so leading with empathy I think is something really important. And really behind that, what I'm looking for is self awareness, right? In a fast growing company, you don't have the time to coach every single person. You really don't. I've got some Managers right now who are managing 14 people because we're just growing that fast. And I couldn't hire Managers fast enough. That means that of the 14 people, honestly, they're not each individually getting the top quality mentorship that, say, I got from two guys at Morgan Stanley. But, if I hire people who are self-aware, they're going to teach themselves. They're going to look for ways to learn. And that combined with pursuing excellence, you're going to get good people. The third piece is what I call, someone on our team defined it as, "do the hard". And this is simple, this is like, you've got to grind. I mean, no one has achieved excellence without grinding away. And Sales is really tough. I mean, literally it is the definition of a grinder job. But also, do you take shortcuts? Sometimes the hard way now is actually the easy way long term. And that's what I look for. Are you willing to do, the hard work today so they easier for you later. And the last thing we call it "ascending together", which is your ability to work as on a team. It's like, thinking like an owner, right? That's something LinkedIn, I think it was one of Jeff's big things. It's one of my big things too. I remember when I was Morgan Stanley, that's what John Mack said when he was running the company. Now this is a big bank, Morgan Stanley. When he first said that, I was like, yeah, how am I going to change the trajectory of Morgan Stanley as a first year analyst. But, I did think that way, I really did, and I love that. So, those are some of the high level qualities that I look for in anybody.

Naber:  Nice. That's awesome. One follow up on that, that was really well articulated, thanks. And the one follow-up on that...Do you have a particular process you go through? Let's talk about hiring directly on your team, your team, your directs. Do you have a particular process you go through around candidate profiling, attracting that candidate, and you reaching out to them either personally, or the message that you craft? Going through the recruitment, and interviewing process, and then closing. Do you have any tactics that you think completely set you apart from, maybe what other people do, just based on the results that you've gotten? You know that they work.

Oliver Jay (OJ):  I don't know if it's differentiated, but I'll tell you how I approach it. I think the first step is you really have to understand the nuances of the role that you're trying to hire for. This is a mistake I see a lot in companies. Especially early stage companies, at some point they have like 10 Salespeople, they're hitting quota, kind of. And then the Board's like, you need a VP of Sales. And then they go and the hire some kind of recruiting firm, and they load them up with VP Sales candidates, and they just hire someone to do VP Sales. And that happens every day. And, I think there's so many nuances to the rule. What kind of Sales? How do you want to build it? And, what types of talent would you want this person to bring in? And, so I am a big believer that you don't know how to hire for that role unless you've done that job yourself, for at least a quarter or two. I think as you get better, you use pattern matching and shortcut. But in the beginning, you have to do it yourself...in the Sales world, so you know what type of companies are you really, really going after and such. And so that's my first step. Because even though I'm desperate for bandwidth, and I would just love to hire someone right now to just take the job, if I don't dig in myself, I don't think I'll hire her right, the best person for that job. So that's first, and I think that helps a lot downstream, and I'll come back to it. Second is, I leveraged my network. So I leverage my network, and I go talk to people. You and I have talked. I'm like, hey, I'm looking for this person. And now I know what I'm looking for, right? Who's the best two people you know? And I don't need to recruit them, but I want to talk to them.

Naber:  You do this a lot. You do this a lot. To the point where sometimes I know you're in the market for someone because either I'm close with someone that might be one of the best in the market, and I'm hearing that you had a conversation because he or she and I will talk, and hear that, OJ had a conversation. You do this, it is perpetual, it is in your nature, perpetually to do this all the time.

Oliver Jay (OJ):  And I think part of it is, I find it interesting, right? It's like, you get to learn. It's free education, why not? And so I constantly do that, that's true. And then I get referrals. I remember when I moved out to Australia to run, to start Dropbox APAC, and back then LinkedIn when you were there, LinkedIn was one of the top SaaS organization. Smaller than Salesforce, but the talent was super high quality, right? I canvas the top three layers. I talked to every single person across Sales, Marketing, Talent Solutions, everybody...and that's how I met great people Gareth. So, that's step two. Step three is then obviously building that list and talking to people. And I think this is one where, I don't know if it's different, but I do it myself. I do it myself. I reach out. I mean, I'm looking for a Head of BD right now. I'm the one who's InMail'ing people. I don't outsource it to a recruiter. And I think that makes a big difference. Because if you're a top talent, you want to hear from...you want your best shot at this person, right? So I do it myself. And when I get in touch with these people, and I think this is where having done the job yourself for at least a quarter to really, really make a difference, because then now you can talk about the role in a much more sophisticated way. You're not like, I'm just hiring someone to run east coast...Someone is interested it when you're able to map the distinct qualities needed for someone to be successful in a certain role, and why that candidate is a perfect fit.

Naber:  There's something ultra sexy about that. There's something ultra sexy about that from a candidate perspective.

Oliver Jay (OJ):  Because the candidate, people have choices. There's so many great companies out there. And what candidates want to know, ultimately no matter where and who, is that they're going to be set up for success. And so I think that comes across when you actually know what you're looking for, and then you can talk about why that person...Hey Brandon, I'm talking about you, and you specifically, because of XYZ, and that XYZ is exactly what I'm looking for. And that makes it a lot better. And then I also think a lot, again, you gotta develop that relationship, especially if you're hiring General Managers...If you treat it as just a process, that's where I've seen these things fail. I mean, I've seen bad hiring practices, even at Dropbox where I was, where you meet a lot of hiring mistakes. It was when you make these critical roles that you just rush through a process. I'm gonna go find an executive recruiter from, they're gonna bring me 20, and then I'm going to whittle it down to three, bring people back onsite, pick one. Those almost never work out because you don't have that trust developed, or you can't close. Because that trust has not been built up throughout the process.

Oliver Jay (OJ):  Those are great. Those are great. All right. I feel people are going to be furiously writing down notes in audience, much slower than you can talk about this stuff. All right, let's move into NEA...So you're at Morgan Stanley, you make the jump to NEA. Why do you make that jump? What are you doing there? And then I've got a couple of questions for you.

Naber:  Cool. NEA was the world's largest venture capital fund. And back then they were, they had never hired pre MBA analysts before, so I was a guinea pig of the first class. Essentially all of these partners just wanted people to do their work for them. And fast forward, now NEA I think has 20 analysts because it's like, wow, that's great to get people to do great work, do all that work for them. NEA - why did I join NEA? Well, first why did I join venture, go into venture capital. And when I was in equity research, I got into the business of studying companies, and giving buy, sell, neutral ratings on every stock, right? You go to CNBC, and there's someone talking about their stock, that was me. Well, that wasn't me, I didn't go on TV, but that's the work I did. Behind that analyst on TV, there's some baby, junior OJ who is crunching numbers. What I realized about my job that I liked was actually understanding the company, the strategy of companies, and the technology of companies. Back then, that was right when iPhone came out. And I made a bad call, by the way. I was like, Blackberry, RIM, remember Research in Motion? Blackberry is for consumers. Remember this company called Palm - PalmPilot remember? Palm is for prosumers. When the iPhone came out, I was like, this is for consumers. Don't worry. Buy more Blackberry. Buy, buy, buy. Obviously I was wrong. But anyways, I love that analyses. What I did not care about was the actual finance. I can do the job, but whether Cisco is going to trade to 35 or 33, I just didn't care. It was almost too easy. It was like, okay, I can look at a stock chart, after a month be like, okay, it's going to pop back up.

Naber:  Humanities OJ comes out again.

Oliver Jay (OJ):  I think so. It's just not for me. It wasn't fulfilling. if I made a really great call, and I helped a client make a ton of money, I just didn't find that rewarding. So, venture sounded interesting because it sounded it was like, okay, I'm still leveraging some of my analytical background, but I can dig deep into strategy and technology. So that's why I learned to venture. And there was a really a crazy adventure where I got to work with a great farm. Also, so fortunate work with some such great Managers, who empowered me and challenged me. And that's when I got closer to entrepreneurs, and founders. And my job there was due diligence for deals that came in. NEA got great deal flow because it was one of the best firms. So the pressure was more on diligence, and then working with companies, which is great. And then as I worked more with companies, and if we fast forward, that's why I ended up working as, becoming an operator. I was like, wow, that seems fun. It was funny because it gave me that kind of exposure.

Naber:  Nice. I read a quote that you had mentioned, in a couple places, that you saw the fun the operators were having, and you wanted to hop on that side of the coin. And I think it's well said. So when you were there at NEA, I've got two particular things that over your career, you've been good at...But since we're on NEA, and you've had a ton of exposure to a lot of different types of companies and deals, it could have been one of the places where the seeds were planted for these two things. The first one is around picking horses, picking the right companies that are going to take off, and understanding the process you need to go through in your mind for one, picking that business, and two, evaluating as to whether or not you would want to hop on board. You've done an amazing job with evaluating them for the companies that you've joined, Dropbox and Asana as an operator, as well as a bunch of businesses you've helped, either been a Board Observer, or you've been a Board Director on a bunch of different types of companies. So when you're thinking about picking horses, what is the criteria you think about for joining a company? And like you said, people have options that are the best...that it being worthy of one, you looking at it, and two, you hopping on board?

Oliver Jay (OJ):  Yeah, it's I absolutely learned that from venture. And as a result of that, I look at everything from a investor lens now. When it comes to picking horses, I think...two of the most legendary investors in the valley, Dick Kramlich was a founder of NEA, and Forest Baskett who is still a GP there and just incredibly smart. Basically, when Tableau was founded, he worked with the early founders in the NEA offices to start Tableau. And I asked them, hey, what's what's the secret? Because there are some venture investors that are just clearly better than others. What's the secret?

Naber:  Yeah, top quartile year over year.

Oliver Jay (OJ):  What's the secret? I mean, when I asked them, I was amazed...Dick was like, find companies that are going after really large markets. And you're like, okay, duh.

Naber:  Let me just write that down.

Oliver Jay (OJ):  But as I've matured, and I've looked into different companies, and how markets have matured, I can't tell you how many times I've told people on my teams who want to go to some company gave them some VP Sales job, and it sounds great, but the category is just not that big. And I think that's number one, you have to pick a company that has an exploding market, and most importantly is timing. Is the market about to explode now. Let's take a couple of examples. Let's look at Zoom and Slack, two examples recently. Zoom was one of the best IPO's of all time. I mean incredible IPO. Messaging, I mean, I remember the days in 95 when we were using ICQ. I don't know if you ever used ICQ. I still remember my ICQ number, right? We were messaging. Slack versus ICQ, or later MS Messenger, is honestly not that different. And then there was Skype in the middle. So, why is this so different? Do I really believe that the UI is so amazing that that's the reason. Like, okay, maybe, but I don't know if that's a $20 billion difference. It's just that somewhere, in the B2B world around 2014, the market tipped. There was a need in the market for more dynamic communications because the pain of email was just too high, for that use case. And CIO's started believing in it. And that's when it tipped. And that market, the enterprise messaging market, basically tipped in 2014 to 2016, I would say. In those two years the winner, it's a winner take all market...There's good research that shows that when a category tips, you get a flood of competitors, and then within two years, 18 to 24 months, the leader ends up taking I think 78%, something that, call it 80% market share of the market. But if the market is huge, you can go into a big market and you'll still be okay, right? Remember there's a company called Jive, right? And remember Yammer? Remember there was a Chatter? All the still did okay, but if you want the get the $20 billion market cap that Slack got, you have to be the winner during that window when the market is ready to tip. And I would say the same thing about video conferencing. Zoom...this is nothing new. I mean, that's how my wife and I developed a relationship, right, over video conferencing, over Instand Messenger - AOL, by the way, another messaging tool. And look, somewhere between 2015 to 2017, maybe even later, was when the need really, really tiped, and now you see Zoom taking off. And you and I now, we're doing this podcast via Zoom, and we use it all the time. Same thing with file storage. Dropbox, is generating $1.4 billion in recurring revenue for file sharing.

Naber:  Fastest company to $1 billion for a SaaS business ever? Is that right?...ARR.

Oliver Jay (OJ):  That's right. That's right. And they didn't invent file storage. I remember when I first used Yahoo in 1995, I got to upload a file into Yahoo, and then download it when I was in the library. It was life changing. Yeah, it was amazing. So it's not new. Cloud storage wasn't new. It's just that the market tipped at that point where people were starting to move away from servers. And in 2013 to 2014 was when mobile adoption in the enterprise had hit a certain rate, and that's when you needed cloud storage. Because on mobile, you can't access files anyway. So number one, you've got to pick a huge market, and most importantly, you've got to join that market right before the market tips. And so you have to make a call. I joined Asana when people were like, what is this project management thing? I don't know what it is. Forrester and Gartner haven't written reports on it yet. But I asked the most progressive CIOs, what's next? They're like, well, I just put in Slack, and now all my work is fragmented even in more places than before. I need something to pull it back together. So I'm going to look into this project management, work management space. And I'm like, oh, interesting. So I developed this hypothesis that the capstone of the new modern collaboration stack is going to be something like Asana that pulls things back together, at least for the things that I really did matter to that company. And I'm seeing that market...we are in the heart of the race right now, that 18 to 24 month window. So that's number one. Number two is obviously what people generally look for which is technology, right? If this market is going to tip, does this company have the right technology to win? And this is very much a venture thing, where you need to some make some calls on the architecture, how they built it. What are customers saying about the product, right? That's when you get some feedback. So the second thing is, does this company have the right product to win the market. Because I do think, especially in the B2B now, SaaS more and more, is dictated by the end user and what they use. So you gotta make sure you're the one that people are gonna pick. And then the last part is, do you have the right team? Does this company have the right team that you're going to back? And that's probably the number one thing, besides the size of market, that venture capitalists bet on, is the people. Because early stage you don't really have much of a business yet. Or even a product. And I think in terms of picking companies to join, same thing, right? Let's say you join a Series C company, what is the management team? What are the dynamics? When things go south, which always happens, how does that management team work together to solve them? Or is there finger pointing? 90% of the time it's fingerpointing. 90% of the time Sales says Marketing didn't generate enough leads. Well, no, let me start...Customer Success and Support says Sales as closing crappy deals. Sales says well, what do you expect? Marketing is driving these bad leaves? Marketing goes, well, what do you expect our Product is missing all this stuff. Product goes well, that's because design is a bottleneck, and it's not shipping. We're not shipping fast enough because design is not ready. Design is like, well, you know what, it's not my fault. I can't hire enough designers, it's recruiting, right? Recruiting..it just goes on. And when I say 9 our of 10, I think that it's 9.8 out of 10. And I made this mistake myself. Before Dropbox, I joined a company that I probably shouldn't have. So a lot of people look at the company profile, and the executives, and where they came from. Oh, this person was at Google for 20 years. Well, you know what, so have like 10,000 other people. And you've seen this at LinkedIn, not everyone's a star at LinkedIn buddy. A lot of stars. But, quite a few duds too.

Naber:  Totally. I mean, nature of large numbers like that, for every one of those businesses.

Oliver Jay (OJ):  Totally. Totally. Or they haven't seen the right stage that's relevant for your company. So, finding the right team that you think you can bank on just to get through the hard times is really, really important. Don't just look at the profile.

Naber:  Nice. Awesome. Great answer. Okay. So, we've gotten through NEA right now. At this point, I believe you jump into Harvard, correct? HBS.

Oliver Jay (OJ):  Yeah.

Naber:  Cool. So take us through the reason you decided to go get your MBA. Why Harvard, which may be self-explanatory. And then take us all the way up through your decision to join Dropbox. So through that period, Scientific Conservation, Harvard, etc, up through the point where you're joining Dropbox. And then we'll talk about what you were responsible for there. And I've got some, a couple of questions for that.

Oliver Jay (OJ):  Yeah, sure. So I decided when I was at NEA that I wanted to be on the operating side. So I was like, they have all the fun. I didn't understand how much pain they had either, honestly, but I was like, it sure seems fun. And, the short answer of why I decided to get my MBA...I was like, okay, well if I got into a great school, I might as well take a break because I'm going to make this career switch anyways. So I'll just do it. And that's literally the logic. And this was mainly...I remember one of my mentors at NEA, John S., who's a fantastic guy, fantastic...Remember remember there was this company called The Ladders?

Naber:  Yeah, of course. Yeah. The $100K+ jobs is their thing, right?

Oliver Jay (OJ):  Yeah, yeah, yeah. What happened with them?

Naber:  They died. I have no idea. It was almost overnight. Because I remember, I mean, I did a lot of research on ladders for at some point in my career. Anyways, I don't know, they just died at some point.

Oliver Jay (OJ):  So we we're going to meet with The Ladders in New York. I remember this clearly. This was right around the recession starting, and John's just like, you need to apply to business school. And this was October, and the deadline was coming up in December. So I was like, all right. He convinced me that would be good. I mean, I might as well, I'm going to try it. John's like, you're probably not going to get in, and that's cool, but why not try? Because getting into business school, certainly getting into HBS, is a total crapshoot. It's a total lottery. Yeah. I got some friends who were way more qualified than I am and didn't get in. And I now know it's for sure a crap shoot. So anyways, I applied. And I only had time to apply to one school, and that was not the plan, but I just didn't have time because I had to take the GMAT, write the essays, get the recommendation, all that. I only applied to Harvard assuming that I didn't get in. And then I got in.

Naber:  Stop it. Hold on. This is unbelievable. Hold on, hold on. So you only applied to Harvard and you got end up...

Oliver Jay (OJ):  Yeah, it wasn't because I had so much confidence or that it was the only school that I would go to. I was gonna apply to like five. But dang it, man, these essays, they take like...I haven't written these essays in a long time, and they go back to humanities OJ. It took forever. I just didn't have time. I think the the application was due January 1st or something, and I remember over Christmas I was writing these essays and I was just like, I don't have time for this. And I just applied one. I really didn't think I was going to go to business school, and then I got it in. And I'm like, oh, okay. I guess I'm going.

Naber:  No one can see me losing a right now. Laughing silently while I'm listening to this, and not believing it. This is a great story about getting into Harvard Business School. Such a good story. All right, so you're at Harvard, what's the biggest thing you learned there? And then take us through up to you joining Dropbox.

Oliver Jay (OJ):  Ah, man. Yeah. So Harvard was great.

Naber:  You must have met some really cool, interesting people.

Oliver Jay (OJ):  I met some amazing people. And people that I considered to be my best friends today. That's where I met the co-founders of Grab, I'm on their board now. I met a lot of great professors.Look, I think the thing about business school...A lot of people poo poo on business school. They're like, it's expensive, you don't learn anything, it's just networking. I mean, I call bullshit on that. Because I'm a nerd, I to learn. And so I studied. I'm like, wow, this is interesting. And I'll tell you at that point I was going through this big clean tech phase in my life. I was really interested in clean tech. I was doing clean tech investments at NEA. I was part of the environment group at HBS. I was super active. I thought I was going to build a career in clean tech. And now that I'm selling productivity software for the past seven years, it's given me a different kind of perspective looking back. But I was so into clean tech. And I met some great people through that, through other who have similar interests. But I'll tell you, so my first job was Scientific Conversation - they basically sell building automation software to help optimize the equipment in commercial buildings to optimize their energy spend. Think of it as HVAC optimization software. I would not have been able...and I took a Sales role coming out of school, which is interesting because very few people go to HBS to come out to be a Sales guy. It's pretty rare. And I sold to real estate developers. And if I did not take a real estate class at HBS, I wouldn't know how to speak that lingo. Cap rates, and TNI, and whatever. I mean it's just, there's different things. I learned that from school. And then what was really interesting was then Scientific Conversation went through a big period of restructuring. And I had to be a big part of that. I took this class called turn arounds, because it's a new topic, when you learn about - how to turn around companies? How do you learn about bankruptcy law? You learn about how to negotiate with your creditors so you can live to die another day, so to speak. And then I used those skills. I literally looked up my notes on bankruptcy. Because I would call our creditors, and it'd be like, hey man, we're about to go under here. I'm going to give you, I know I owe you $2 million, I'm gonna give you $2,000, or you can have a shot at bankruptcy court. Anyways, long story short, business school was awesome. I met great people, and I learned a ton, got great exposure, and I actually implement the things that I learned.

Naber:  Wow. That's great. Great Story. Okay. So Boston, Beantown, you leave. Scientific Conversationis next, you join in a Sales and Partnerships capacity. Every Harvard Business Schoolers dream, joining Sales right after that.

Oliver Jay (OJ):  That's why you go to HBS.

Naber:  That's right. #HBS. So what is the biggest thing that you learn at that business, and why did you join Dropbox?

Oliver Jay (OJ):  Well, a lot of my lessons learned around the people, in part, was what I learned at Scientific Conservation. It had on paper, all the things that most people look for, right? I said, oh, pre rocket ship, hot industry, a team that looked really, really strong on paper. That's what I went for. You know, hypergrowth. I remember Kleiner Perkins, NEA, Accel. Everybody was like, this is the next one, this is the next OPOWER. This is the commercial version of OPOWER. I thought it was the best thing. But you know what, just didn't have the right team to execute going through the tough times. and that's what I learned. That's honestly the biggest lesson I learned. I met a lot of great people. But that's where I really realized, wow, so much of execution is the people, and the chemistry of those people. And that's what I learned there. So why did I Dropbox? Honestly, I mean...we had to do a big turn around in Scientific Conservation. Within a year we went from 30 people, to 180 people, and then I had to play a big part in restructuring down back to 90 people, and then down to 50 people. I mean it was a year that felt 10 years. So Dropbox, I showed up, people on scooters, drinking from coconuts...you've been to the office. It was just a different world. I'm over here trying to make payroll, literally. There was a payroll period where I...

Naber:  And letting people go daily.

Oliver Jay (OJ):  Ugh, brutal. People always ask, what's the biggest done, whatever. I'll say the biggest deal I've done was in...I broke my lease, the Scientific Conservation lease with a real estate developer...Because we had signed this Embarcadero Bay Bridge View Office for a seven year lease, even though the company was making zero in revenue, so that tells you something. But thankfully, the one thing that went in our favor was the rental rates have actually gone up in SF. Far, far greater than our committed rate of increase in her seven year lease. So they way I made payroll was, I went to the developer and I said, I will break the lease if you give me x amount of money. Well, they didn't know it was how we were going to make payroll. It was hilarious. And then negotiation, at the end the thing that clinched the deal was office furniture. I was like, I'll throw in the office furniture.

Naber:  Stop it. I always find it mind blowing when in residential, someone rents someplace for like, a few grand more a month just because the furniture's included. And that was your deal with the developer. That guy has done tons of deals, tons of deals, and this guy closes over the furniture.

Oliver Jay (OJ):  Honestly, I probably would have gotten it done anyways. I was actually in my head thinking, I don't want to pay to get rid of the furniture. That was what was going to be my head.

Naber:  Oh, that's a good win-win. All right, so you join Dropbox. There's coconuts, there's cupcakes, there's all of it. So walk us through in one or two minutes, what you were responsible for and the jumps that you made at Dropbox. And then I've got a few questions around some of your super powers, okay?

Oliver Jay (OJ):  Yeah. So Dropbox I went in as one of the first business generalists. There wasn't a role, it really just do everything. So, looking to our payments gateway infrastructure, looked into capital financing for our data center to help raise capital. I looked into real estate because they're like, oh, now you're a real estate pro from my background. So I had to try to figure out finding office space. Andthis was all in the first three months. We were moving so fast. And and then there was this business called Dropbox for Teams that was starting to grow really, really quickly. And the Head of Business, our COO was like, can you just take a look at that. Basically, do the Sales Ops work to see what's going on. And that's how I got into it. And then one thing led to another. So took that role on, started adding some visibility into the business. And then moved into actually managing part of it. And ended up running a lot of it, growing the North America Online and Inside Sales teams to 70 or so people. And then got the opportunity to co lead our APEC expansion efforts.

Naber:  With Tony, is that right?

Oliver Jay (OJ):  With Tony, that's right. And they're like, all right, figure it out. I mean, that was it. Figure out APAC, period. So then we did that, that led to both of us moving out to APAC for a year and a half. Started the Australia office, Japan office, I was gonna think about Singapore, but didn't end up doing Singapore. Also looked at Latin America, when the new CEO joined. He's like, well, there's another continent. Someone's going to look at it. And they just put it on our plate. And then did that for a while. And then when I came back to the US, transitioned into the Corp Dev team, so think about M&A at Dropbox. And then through that experience I realized I really missed building teams. Which is why I went back to the Sales world at Asana.

Naber:  Nice. After hearing your story, and I saw a lot of firsthand when I was working with teams at Dropbox and I'm working with teams at Asana, now I get that, why you made that jump. Or at least why that was the right time in your life, and in missing teams to want to make that jump. Wow. That's really interesting. Okay. So a couple things about Dropbox. There is a theme, and you've done this really interestingly coming at it from, let's call it the Sales Ops angle first, and then jumping into manage these teams. Which some of the best operators I know from a Sales and Marketing perspective, have come from the Ops side. I look at them as the Ying to my Yang. They speak a beautiful language and I want to hear all of it. So as you're doing that, you're building things from scratch. And you are building at one phase at Dropbox, and you go through a lot of different phases of growth in your international expansion playbook. You're also going through phases you've been in before at Asana, and planning for phases that are things you've seen before, and things you know a lot about. So let's talk about your international expansion playbook. As you're going through phase by phase, and one, making the decision as to whether or not you should do it in the first place - Expanding outside of, let's call it the US for now, into other markets? And then two, once you decide yes through that evaluation process, you want to go about doing it. What's your step by step process you're going through in order to expand internationally? You can use the Dropbox example or the Asana example, or both, If you just want to say, hey, this is what we did then and this is what we did then. But either way, what's your phase by phase and step by step approach as you're executing on this expansion playbook.

Oliver Jay (OJ):  So I think the first is understanding that international operations is not...Adding international operations is, honestly from management overhead perspective, it's the minute you go international, for every new region and office you add is equivalent of adding two, and the next one you add is like adding three. There's a complexity, the overhead is so much more, and sophistication is so much greater. And that's not to say it's not worth it, right? Obviously I do it, but it's something that I think you need to be really, really honest with yourself, with your teams on whether or when are you ready for that? Because honestly, one of the things that I think about is, most companies go international too late, right? I think Slack is a good example. Slack to me, and I have a lot of good friends at Slack, so maybe you have to delete this. But, international is only 30% of their revenue, or 35% of their revenue at this scale. And I think Microsoft got a jump on them internationally. Well Microsoft has a jump on everybody, but especially internationally. And so, you want to go fast, but you got to make sure you commit. So step one, before you commit 100%, what you can do is just play the digital game. Localize your product, localize your ads, localize your website. And I would say probably even in that order. Again, it depends on what product you have, right? But if you have a user facing product...and in Enterprise it starts with the product. In many countries you may have one or two people who aren't very comfortable with English, but the rest of the team may not be. And you're not going to get good adoption that way. So I think that's important, localize your product, as long as you feel you have enough confidence that it's worth the engineering investment. Because it's a big investment. There's a certain threshold where you're going to start seeing...Whether it's tickets that come in asking for your language, or your community, you'll get that ask. Yeah, I mean, maybe French and Spanish, the website, that's as an obvious one. But what's interesting is you can some good lift from just localizing the ads, in Dutch or Japanese, and it points to an English website. You're still going to get some incremental dollars there. So play the digital game. And then at some point, and you have to come up with a framework, and it's different company to company, and you don't have to be that Scientific. But at what point do you feel you're ready to go open an additional office? And almost always, you'll see English speaking markets adopt first - UK, Australia, are the next two, and Canada. Large markets that, for many reasons, and we're not gonna have enough time talking about them, but they usually are the next to adopt technologies. And so your next move almost guaranteed is going to be somewhere in Europe, right? And you pick between Dublin, Amsterdam or London and we can talk about which one, why, but it's going to be one of those three almost guaranteed, right? So setup your Europe hub. And then depending on the type of company, you can think about growing from there. So then the most obvious, next markets would be France and Germany in Europe. And so then you got to make that decision on whether you want to service those markets in whichever hub you've picked, or you go even more local. And I think that depends on the type of company that you have. We talked about Australia, that makes a ton of sense already. The minute you're looking into the UK, if you have the bandwidth, you should look in Australia as well. I would think that the market demand would be equivalent in terms of the time. And then Japan. Japan, people forget, is the second largest IT market in the world. And they're early in their cloud adoption. But for SaaS companies, it's really starting to take off. And so Japan is a market where investing in early can pay off dividends three, four years down the road. Japan is Slack's number two market. It's Salesforce's number two market. But it takes years to build up that market. And so you can start thinking about that. So the order of sequencing, I guess I'm not even...I guess I've done it enough now to just know the sequence instead. I mean the first time I did this at Dropbox it was like, okay, how many users do we need to see before we go green light here? How much revenue? How many businesses? How many domains we want to see? And, I've traveled so much in the last couple of years. This is the order that I would go in,

Naber:  Good one. Awesome. You know what's really interesting about that, is you mentioned you've looked at the data, and from the data side it says to do this, this, and this. What you're saying is don't necessarily do the work that everyone else has has done. This is an all likelihood, the chronology of the markets that you will go into next. And that's really interesting. Don't redo all the work. Do not reinvent the wheel. I have two follow-up questions to that. One is how do you know whether to hire local, even more local, versus doing it from a regional hub? How do I know whether or not I should sell from Dublin or London or Amsterdam into France, Germany, Spain, Italy, some of the Nordic countries, etc? Or hire local in that particular market? And by that I mean, when do I do it? And I'll ask the other question after that.

Oliver Jay (OJ):  Yeah. To me it all depends on your target audience. Who are you trying to go after and how? So if you're going after SMBs, this is primarily going to be Inside Sales function. You're not showing up. It's not a relationship sale. Then there is so much value in centralizing to the last minute that you can because you're still trying to figure it out. So Asana is small deals, we start with small teams and then we expand them. And, we essentially have a big machine in Dublin. Why? Because the French rep who has learned some new insight selling to Mid-market & SMB companies in France can share with the Nordic Rep, and those best practices when you're early in a region, you got to learn quickly, and you're gonna to learn from the field. And that information transfer is so valuable. And then eventually you go the other way. You launch a new product, you've got to enable the team. There's a lot of operational overhead to enabling lots of people in the field, versus you just fly into in one office, and you basically enable a team all at once. So huge, huge advantage to centralizing. However, if your Sales cycle and process relies a lot on relationship building, whether it's for bigger deals, whether it's a complex deal that relies on partners, then you need to go in the field. And that's where showing up makes a ton of sense. And what changes is the unit economics of that office, where if you open an office in Paris, now showing up at a mid-market opportunity of a 10K Pounds deal, normally is not going to justify a flight in, hotels, make it work. But now it's just, down the street. I mean not down the street, but now you can justify making that visit, and absolutely everything that increases the conversion rate. So there is benefit there too. But balancing operational overhead, learning earlier, I am a big believer that you should hold off as long as you can. Because once you're decentralized, there's no way you can centralize again. Or you can, but it's very painful. You gotta shut down offices, and it's really painful. So you want to wait as long as possible.

Naber:  Nice. Great answer. Thank you. And then, second question is...So you're going through this process of massive expansion, within Dropbox and Asana, and you're going through different stages of growth. One of the things that you need to constantly think about...which I don't necessarily believe that a large number of Heads of Sales and Heads of Marketing are very good at this. One of the things you need to constantly be aware of...and coming from VC, you've got interesting perspective on this, and not all the people who have gone from VC to operator and done it with the amount of, not only success, but the amount of speed that you've done it...So a Head of Sales and Marketing needs have the right mindset, with planning and execution, with unit economics in mind. So how do you make sure that you have the right mindset? What is your mindset when you're thinking about balancing, things LTV to CAC ratios, versus booking in revenue growth rate expectations, versus the growing pains of teams and the engagement of those teams. How do you think about incorporating unit economics into your approach? And how do you think about that as a Head of Sales and Marketing?

Oliver Jay (OJ):  Okay. So I would say there's a couple of things. First in terms of mindset, if you're leading Sales and Marketing, let's say your company is growing at 100%, right? My mindset, and I tell this to all my Managers, is that my job is to plan and execute as if we were 12 months from now. My Manager's job is to execute and plan as if we were six months from now. Your IC's are the ones who were executing to quarter to quarter. And I think that's something that I always drill into my team, and my Manager because most people manage to the quarter. And by the time you manage to a quarter, you've already forgotten about the next one, and you're basically accumulating debt. And I think part of what's challenging and exciting about managing in high growth, is you've got to balance executing and the job at hand, but at the same time develop the vision of where you need to get to - So if you're a line Manager six months from now - and you've got to do both at the same time. So as my leads, they got the quarterly number, that's great. I just assume they're going to hit it. I mean just tell me if you're not going to hit it, but I'm assuming you're going to hit it. What are the programmatic things you're building in right now as if you're six months from now? Because that is going to take time to build it. And then once you build it, boom, now you're ready. My job is 12 months. So right now, I'm thinking about what my team needs to be doing this time next year. Because, well, my team is getting pretty big now. It's hard to steer a big ship. And so if I'm optimizing for something for the end of the year, not to say that's I don't do that, I do that. But I also push myself to think longer because for me, and from my angle, what's going to happen in the second half of this year has already been shipped. Our performance, our unit economics, our, whatever programmatic infrastructure we build is going to be, it's already too late to change that. So I'm thinking ahead. I think that's important because, you mentioned about unit economics, your unit economics need to change over time. And so you got to work with your management team, your finance team, to understand what unit economics you need to have this time next year. So that you can slowly migrate there. Otherwise you're just hiring heads, heads, heads, heads, heads, and eventually you're like, oh, one day you wake up and finance is like, okay, you're going to get three heads next year, but you have the grow revenue revenue by 50%. So that's the high level mindset that I think is really important, to understand end state first, and work with finance to understand what that looks like. And so I know next year what my unit economics need to be. Now, I can start back filling. And then this is what I do to backfill. So what I do is, I ask my teams to now start thinking about, not unit economics first though, strategy. First strategy, then tactics, then numbers. So for example, my team in Europe. Right now, it's July, and it's the end of our quarter this month. The leads are going to come over to the US and present their strategy for next year, so basically the next 18 month strategy. What do I mean by strategy? Who's our primary customer? Who are we trying to win over and outserve everybody else. Why? And where are we going to focus? Because you can't go after everything. And when I think about Europe as an example, a microcosm of the world, the UK is very different than Germany, which is very different than Spain, and very different than the Nordics. So, if someone calls me and tells me this is my EMEA blanket strategy, I'm like, that's not a strategy. I want you to define what winning looks in the Nordics, and define what winning looks in Spain. Portugal, not as important to me, lump it into that region. Iberia, right? Or something. But, I think it's important that to have a view where you define success. Okay, this is what I'm trying to accomplish in Germany. Align on that first. That's a strategy. Then the tactics. How are we going to do that? Okay. in Germany we're going to go after this segment hard. Now what's the tactics? How are we going to do it? What are what are the resources that we need to make that happen? How much revenue? Well, we won't get a numbers yet, but just tell me how are you going to get it done? For example, at Asana, we think in Germany there's a big digital transformation push, moreso than any other countries that we see, right? And there's historical reasons why that is, but it is moving. So to us, it makes sense that the tactic is to really build field, right? And that's why we're going to build field in Munich and not Berlin, because it has a lot more of in your more iconic traditional companies, Berlin's a tech hub. The strategy in Germany, for field, is to go after digital transformation opportunities. I would say a lot of companies make the mistake and they go tactics first. They go, oh, okay, this is what we're doing right now. And so the next year we're going to do this. And you don't actually understand what it ladders up to. And your tactics may not actually end up hitting the strategy that you actually really want. You got your strategy down, on a region by region basis. You got your tactics. Then you've got to figure out numbers. What is the target that you want to get? Because remember, we've already defined success region by region. Now we're going to deploy resources, and see what do you need for that? How much field Marketing do you need? Oh, I need to sponsor this conference, I need two Sales Engineer's, five AE's, three SDR's, and whatever. Okay, great. And then I can come in, and I know my unit economics 12 months from now, and I can see overall where are we over, where are we under, where can we push. Because some regions I'm okay with having poor unit economics because we just started, right? The Munich office, they'll have terrible unit economics for the first year. I'm okay with that. But I have a portfolio view, and I can make sure it happens. And once it happens, sometime later this half, I will start aggregating all of these different regions, and strategies, and then I'll be like, oh okay, I'm way over. And this always happens. This always always happens. Everybody wants 50 heads, and then basically we have to iterate them. Then we'd go back, and we prioritize, and we say, Hey, this is the unit economics we need to hit. We are this over. And so let's stack rank our priorities, and then we'll cut it. Right? So maybe we'll cut an office here, or maybe we'll cut some resources over here, that may impact top line. And so we just iterate and you go through a couple cycles.

Naber:  Wow. That is a great comprehensive, step by step answer. Nice moves, OJ. Thank you for that. All right, so we've gone to your phases that you went through at Dropbox. I've got one more major topic to cover, and it's a good segue, after you talk about Asana. So, why make the move to Asana? And tell us what you're up to there, up through now. And then, I've got one final topic to talk about. It's a bit meaty, but it's a good one.

Oliver Jay (OJ):  Okay. Hmm. Exciting. Cliffhanger. Asana's easy, right? I mean, I told you my criteria already, so, I made the call that this space is gonna blow up. It's going to explode. It's going to be huge. It's going to attract a lot of competitors. It's going to track a lot of interest. And I don't still know exactly what the category is being called. I mean, Forrester is now calling it collaborative work management. 451 is calling it enterprise work management. Gartner keeps cold calling us, I'm not sure where...but there is heat. I think that the technology is differentiated for many ways. I love the product. Our users love the product. And then the team, ultimately, the team. I've never worked with a team that is as committed to co-creation as Asana. And just great culture, starts from the top. Our founders really care about how we work, as important as the product itself, and the market. And so I feel we are going to be tested in battle, and we will win in the battle. So that's the short version of why Asana, and I feel very strongly about all three of those dimensions.

Naber:  No, go ahead. So, then let's talk about what you're responsible for there, and maybe one or two minutes and then, I'll hop in.

Oliver Jay (OJ):  Okay. So I run our Sales teams our BD practice. So on the Sales side, we have three lines of business. We have a big self-serve business. This is not what you think about traditionally when you think about Sales. This is a lot of working with product and Marketing to make sure your conversion funnel is really strong. Those of this as like Netflix. Netflix knowing which movies to pump in front of your face, so you buy them. Or Amazon, right? So a lot of this is Growth Marketing and Conversion Marketing. And that's a practice that is a strong one for Asana. We have another one called Online Sales, which is layers on top of self service, and this is high velocity Sales that takes advantage of our freemium model. And then we have enterprise Sales that is, more traditional. And their approach is really around driving big expansions in companies that we've already landed. And BD, there's two components. There's a component around channel, which is how do we develop an ecosystem of revenue partners who can help us? And then strategic partners. So how do we partner and build alliances with folks like Google, Microsoft, Salesforce, Adobe, just kind of more software partners.

Naber:  Awesome. Okay. This is great. And you guys have just grown, it's a massive rocket ship, and you've got enough cash, and you guys have all the right criteria for everything you mentioned earlier for how you're evaluating. Okay. And that's a great layout. So let's start with the topic, going from freemium to enterprise, and knowing when to do that, and we'll talk about how to do that. So you mentioned, and I was listening to a couple of your podcasts you'd done in the past, and there was a really interesting structure you laid out about going from freemium to enterprise, and the steps you take in order to do that. One of the first steps you've talked about in thinking about freemium was the right audience and the right product category. Can you explain those two concepts and how people should think about that?

Oliver Jay (OJ):  Yeah. Most freemium products start this way. They come out of Y Combinator, something didn't work, and then it didn't work a week before demo day, they pivot, and they figure out something that works. They copy and paste in the Stripe snippet. They get everybody else in the same y Combinator class to buy, it's like this thing. And then then demo goes well, and everyone's like, wow, look at the LTV to CAC. It's amazing. Usually that's what happens, right. And it's a product-first view based on an insight of potential perceived pain. Now 8 out of 10 of these don't make it out of the gate. The pain is obviously not big enough to warrant more funding and such. But 2 out of 10 are great...I mean, these are smart, smart, smart founders, a lot of them. And they find a pain that that's actually pretty big, and they put it on the website. You can do a free trial, or you can download for free, it's pretty easy. And you start getting data on people that are starting to starting to sign up. And the word of mouth effect is something that is extremely...you have to have lived in Silicon Valley to understand what that means. And this is something that I think is different globally. But boy, technology that comes out of Silicon Valley, that word of mouth is effect is very strong. And so, if you got something, it will go viral pretty quickly, and you can start seeing people starting to sign up. And then usually it's for one particular pain that you think you're solving. But the reality is the market is going to find your solution actually solves a number of different kinds of problems that you don't even know about. And so this is where I think it's super interesting. Once you get to a certain scale, right? Let's say you get into single digit millions in ACV, or maybe in terms of customers, or let's say you get over a thousand customers...You have enough information now to just look across, and just do an analysis of, hey, what kinds of companies are these? It's going to two hours. Okay. Because a lot of these will be SMBs, and you can't just run data, and match, and stuff. But you can start inferring what types of companies are getting value from your product, and to solve what pain. That second part is very, very important. A lot of companies misse that. But if you're doing it in a freemium model, just looking at which company uses you doesn't tell you anything. Because usually it's a small team, solving a small pain, within a bigger company. So you've got to pick up the phone, or you do a survey, and you understand. At some point you're like, okay, makes sense. I have some hypotheses on where I have great product market fit, and it's a big market, and I have a differentiator - to continue to double down on this pain, and do it in a differentiated way. Then I would start building, adding humans to the process. So the first piece I love is always Inbound Sales, or Inbound chat, or Inbound support, whatever. Basically get some humans in there to test your hypotheses, right? You've got some data now...hey, maybe government is where the sweet spot is in solving this type of thing. Okay, great. So then higher one or two Inbound Sales people, and their job is to do a couple of things. One, for the companies that you've identified to be in the middle of your bullseye, call them up, build a relationship, and you'll see that there's probably some good expansion opportunity right away. So again, because of the word of mouth dynamic should be pretty strong...If it's not strong, you gotta go back to the way, back to the whiteboard. If it is strong, you should be getting a reasonable amount of traffic on the website, right? It's not going to be thousands of leads every day, but maybe 10 a week and the the beginning, right? You want to man them, you want to take advantage of each one of them, validate your hypotheses. Obviously try to close the deal as well. But to me, revenue is secondary. And I do see this in a lot of management. They hire one Salesperson, and they're like, here's your quota. And that's, if that is your primary objective for that person, you're not gonna get the insights that you really want. And the insights are way more valuable. So your first couple of Sales people, I think you really drive the people to get you the insights. I'm like, hey, where's the sweet spot? What pain are we solving? What are the additional pains that we could solve. That is more valuable than whatever, 20k MRR that you're going to get...So you do that and...mainly you take that feedback, work with product to really improve or expand the problem that you're solving and make it excellent. And then that should bring in more people, and more people. And then at some point you can start building out the team more, and then you start segmenting more, and eventually you can start going outbound. And outbound I'll put in quotes. What does outbound mean? Does it mean you're just traditional outbound...and Linkedn...and I mean, you are the expert here. This is like, okay, I'm going to create opportunities. You figure out your persona, you know who you're targeting. You get them on the phone. People don't do phone anymore, people don't even do emails now. I don't even know, now people are sending books around. I don't know. But you find a way to get in there. You prospect. Yeah, that is traditional outbound. I think premium outbound, you'd have something kind of in between, whereby you can go after companies that you already have some traction, and let's say they're healthier. Those are essentially your leads for an Enterprise play. And I'm a big believer that if you can't even drive big expansion deals where you've already landed, it could be a small land, but if you can't even drive some big expansion there, you've got no business to go - let's call it true "outbound". So you know what, go outbound in accounts that you already have landed to some degree. And that motion, by the way, is not easy. You're at Nike, you're trying to get into Nike and you've got 50 people, super fans love Asana, and they want to use it more, and they're really happy. And you're like, okay, well how do I navigate that organization? Right? It's hard. There's a craft. It's a different art and science to how you go about doing that. You've got to get that motion down first. So that's the process that goes through my mind.

Naber:  Nice. Awesome. And so let's say that you get to that phase, and you're going to start building out your Sales Engine. You're going to start building out your team of humans. What are the first few phases you go through and steps you take in order to do that?

Oliver Jay (OJ):  So the way I think about it is, you gotta first understand what are the selling motions that you want to build. And I think this depends company by company. But for me, now, there's a selling motion...it's not really selling with humans, but just growth optimizations, right? How does your website convert? That is a motion that you're gonna have to get good at. So I built a team around that. I have a team called Online Sales, which basically uses a lot data process automation to intelligently know which are the teams that likely came in through a self-serve funnel, that have a high propensity to close or expand. That's another selling motion that's very different. We talked about that Enterprise expansion play. How do you go after companies where you've already landed and then you want to expand? That's another motion. So, I think depending on the company, this is I think more first principles, right? You've got to understand what are the motions that you really, really need to develop. And you basically organize and start developing these teams to start building out those practices. And then as you do that, you can sort of reallocate resources depending on which ones are doing better and not. But I think the critical piece here is you need to be able to articulate and identify what is the motion that you want to build.

Naber:  Yeah. Good one. Last last one, and then we'll wrap. You've been so generous with your time. I really appreciate it, OJ. Thank you. Now you just talked a little bit about your org and how you structure it, and you kinda just went through a few different motions that almost map, very closely, to the same org that you were just talking about. So within each one of the Self Serve, Online Sales, Enterprise Sales, BD, and Strategic Partnerships, can you give us one or two things you absolutely have to nail, or one or two best practices you absolutely have to think about if you're going to nail each one of those? Maybe we could start with Self Serve first.

Oliver Jay (OJ):  Sure. Self-Serve number one thing, you've got to get cross-functional alignment. You talked to many, many growth teams, this is what where it falls behind. This goes back to my earlier comment about, you got to find a team that actually works as a team. Because that Self Serve business touches upstream, acquisitions...I mean, you can even go more upstream with branding. So brand, to acquisitions, to conversion funnel, to the actual adoption of a product in the first first 30 days. That's this Self-Serve business...and then eventually, and also retention. So it touches everything. And so if you don't have a cross functional alignment, you can forget about it. Literally forget about it. Don't even waste time because most companies are so small, where you really need the whole full funnel to work together, otherwise you're not going to move the needle. So that's number one in this Self-Serve business, you gotta get that alignment, you gotta get that commitment, and that's hard. So it's hard. Before you even build it, you've got to spend a significant amount of time and energy to align with all the other functions around the company that Hey, do you all agree this is an important practice to build? And if so, this is how we're going to build it and how we're going to work together, otherwise not worth it. That is, Self Serve. Online Sales, so this is high velocity Inside Sales that sits on top of self service. A lot of this is depending on whether you have the systems, and operations, and data science to support that kind of velocity, right? On our Online Sales teams, each person closes above $1 million per person. That's a tremendous LTV to CAC, can't be that.

Naber:  Whoa, I just gave that my stank face. Ooh, Whoa, that's really good.

Oliver Jay (OJ):  It's real good, real good...and they're going after SMB and Mid-Market. You can only do that if you have really good automation, data science, that picks out which are the leads and contacts that you should invest your time in, and you get a bigger deal, right? Let's say each rep closes about 20 deals a month. So it's not a ton of deals. You've got to really, really make them count to retire that money. And so making sure you have invested in the Ops, and the Systems, and the Tooling to make that efficiency work, is something that I think most companies underestimate. I continually underestimate it actually. I thought I'm ahead of the game, and then a month later, I'm like, ugh, I'm still behind. So having that platform, thinking about the business as a platform, super important. Enterprise, for freemium businesses...I think the most important thing to tease out as a leader is understanding how much of the revenue is actually driven by the reps, versus how much revenue probably would have come in anyways. A lot of companies have the problem where the Enterprise reps essentially just piggy back, and put their name tied to an organic expansion, that likely would have happened anyways. So that's where I think people need to spend some time thinking about...Because that's not scalable.

Naber:  Right. Alright. Business Development, Strategic Partnerships. You've done this at multiple businesses and extremely well. What are some of the best practices when you're thinking about doing that?

Oliver Jay (OJ):  So with the Partnerships, you got to ask what is your North Star? Are you trying to use Partnerships to drive awareness, which is much more around co-Marketing and branding. Are you trying to use Partnerships to drive leads? Are you trying to leverage a Partnership program to address product gaps to get into a new vertical? Are you trying to use Partnerships to just drive more user engagement? These are the questions that you got to answer first as a company get. Because I think where a lot of Partnership programs fail is, Partnerships go out and try to find Partnerships, and then eventually they bring it back into the company and people are like, there's no resourcing for it. Marketing doesn't want to support it, Product doesn't want to build it, because people aren't aligned on what you're trying to build. What are you going to solve for? And that's kinda the age old thing with Partnerships. Partnership folks generally want to do deals. But do those deals map and ladder up to a important initiative? If it's not a top initiative at a company don't even bother. And so I would say that's the most important thing when you think about Partnerships, of any kind, whether it's Channel, whether it's Strategic, same thing.

Naber:  Hey everybody, thanks so much for listening. If you appreciated and enjoyed the episode, go ahead and make a comment on the post for the episode on LinkedIn. If you love The Naberhood Podcast, we'd love for you to subscribe, rate, and give us a five star review on iTunes. Until next time - go get it.