20 Sales: How To Create and Execute a World-Class Sales Playbook, Why You Should Do Both PLG and Enterprise Sales at the Same Time, Three Non-Obvious Qualities the Best Sales Reps Have & The Four Steps To Sales Team Onboarding with Oliver Jay, Former CRO

Oliver Jay (OJ) is one of the most successful sales leaders of the last decade. Most recently, OJ spent 6 years at Asana where he was hired as the company's first revenue leader. As CRO, OJ was responsible for product-led and sales-led revenue and grew the team from less than 20 to over 450. Before Asana, OJ spent 4 years at Dropbox in a period of hyper-scaling for the business where OJ was Head of APAC and LATAM. At Dropbox, OJ scaled the sales team from 0 to 50 while tripling ARR. If that was not enough, OJ is also an independent board member at Grab, the leading Super app in Southeast Asia. In Today’s Episode with Oliver Jay You Will Learn: 1.) Entry into Sales: How did OJ make his way into sales with Dropbox? If OJ were to choose 1-2 lessons from his time at Dropbox and Asana that have stayed with him, what would they be? How did they impact his mindset? What were some of the non-obvious but crucial things Asana and Dropbox did in sales that led to success? 2.) The Playbook: Why does OG disagree with so many definitions of "the sales playbook"? What is the sales playbook to OJ? What are the different chapters? Should the founder be the one to create the sales playbook? What are the signs that the founder has a repeatable and scalable playbook? When is the right time to hire the first sales rep? Should it be a Head of Sales or Sales Rep? How does the first hire depend on whether you are PLG or enterprise sales led? 3.) The Hiring Process: How does OJ structure the hiring process? How does OJ know the qualities that he wants to uncover in each candidate? What questions does OJ ask to unpack whether the candidate has those qualities? How does this differ when hiring sales reps vs sales leaders? How does OJ use the sales demo to test the quality of a candidate? What does he want to see? Who does OJ bring into the interview process? When do they get involved? What are two questions that will immediately tell whether someone is a good manager? 4.) Sales Onboarding: How does OJ segment sales onboarding into 3 crucial steps? Chapter 1: Support: Why does OJ believe it is so important for reps to spend their first week with support? What should they look to learn? What questions should they be asking? Chapter 2: Market Knowledge: How can sales leaders teach and educate new reps on market landscape, dynamics and competition? Why does this have to come before sales training? Chapter 3: Sales Training: In the final step, what does the sales training process? What does OJ look for in the final sales demo? When does OJ let reps speak to customers? How does this differ when comparing enterprise to PLG?

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Harry Stebbings?

  Welcome to 20 Sales with me, Harry Stebbings. Now, this is the show where we take you inside the minds of some of the greatest sales leaders to reveal their tips, tactics and strategies. When it comes to scaling the best sales teams on the planet, and I'm so thrilled to be joined today by Oliver Jay, one of the most successful sales leaders of the last decade. Most recently, Oliver spent six years at Asana, where he was hired as the company's first revenue leader. As CRO, Oliver was responsible for product-led and sales-led revenue and grew the team from less than 20 to over 450. Before Asana, Oliver spent four years at Dropbox in a period of hyperscaling for the business, where OJ was head of APAC and Latam. At Dropbox, Oliver scaled the sales team from nought to 50 while also tripling ARR.

• 0:40Harry Stebbings?

  And if that wasn't enough, Oliver's also an independent board member at Grab, the leading super app in Southeast Asia. This is an incredible discussion. We go very, very deep in many different parts of the sales process. I want to say huge thanks to Carl Parrish at Figma for the intro today, without which this episode would not have been possible. But before we dive into the show today, here's an alarming stat for sales leaders out there. According to research done by Zand.com, only 28% of deals are forecasted accurately. 28%! Why is that? Either you don't have enough reliable data to draw from in Salesforce, or you based your forecast on wishful thinking instead of facts. So how do you get your team to input all the data you need without hounding them around every corner and taking away their sailing time?

• 1:22Harry Stebbings?

  Well, that's where Dooley comes in. Dooley is what top-performing sales reps use day-to-day instead of Salesforce. It's the fastest, easiest way for sellers to input deal data in real-time, update their pipeline in a snap, and manage every deal at once, so nothing falls through the cracks. It's a dream for sales teams because reps save hours of admin grunt work, and managers get up to 60% more accurate deal data in Salesforce, so you can build a sales forecast you can feel confident about. Visit dooley.ai/demo to speak with a Dooley rep today. And speaking of up-leveling your team with incredible tools like Dooley there, SalesLoft is the leading sales engagement platform, helping sales teams drive more revenue with the modern revenue workspace.

• 2:03Harry Stebbings?

  It's the one place sales teams can go to prospect, manage active deals, and get the insights they need to Coach seller performance, forecast with accuracy and find out what steps to take to close more deals. Some of the world's leading companies like IBM, Shopify and Stripe all love a new SalesLoft and so can you. It's the new way to sell. Find out more at salesloft.com. But that is enough from me. So now I'm so excited to hand over to the one and only Oliver J, or as we refer to him in this episode, OJ.

• 2:37Speaker 01

  You have now arrived at your destination.

• 2:40Harry Stebbings?

  OJ, this is such a joy to do. I heard so many good things from Danny Hersberg before this show and many other guests. So thank you so much for joining me today.

• 2:48Speaker 02

  Oh, I'm so happy to be here.

• 2:49Harry Stebbings?

  That is very, very kind of you. I've been looking forward to this one, but I want to start with some context. So you've worked in some of the most incredible hypergrowth companies from Dropbox to Asana. Tell me, how did you make your way into sales and come to lead some of these incredible sales orgs?

• 3:02Speaker 02

  First couple of years of my career was in finance. I was in first starting equity research at Morgan Stanley and covering tech companies. That was my first exposure to how sort of the intersection of tech and business. Then I went over to venture and I worked at NEA for a bit. In that experience, I really saw how amazing some investors were sort of leveraging their operating background to help founders. So I got that curious about operating and all the GPs I really admired, they were like, hey, you should operate. And if you're going to operate, you either build product or you sell product. Everything else is supporting one of those two. And I was like, oh, interesting. And one thing led to another. It was like 50 50. I went down the sales path and that was a path I ended up on.

• 3:40Harry Stebbings?

  I love that kind of simplicity of you either build or you sell. I do want to ask that when we look back at the time, six years of Sana, four years Dropbox at pivotal moments of scaling for both companies. When you think back to that, and if you isolate one or two key takeaways from me, what would you say they would be looking back and reflecting?

• 3:56Speaker 02

  So Dropbox, I think for me, number one is technology is just fundamentally adopted differently in businesses. B two B businesses are no longer by the traditional top down way in terms of how technology is used in companies. Employees get to pick and that started with Apple with the iPhone and probably around what 2010? When people had this BYOD move and Dropbox was the company that shattered and started. The BYOA move, but I think that's number one. And so as a result, number two is that PLG is fundamentally is a very different kind of go to market than traditional B2B sales. I think that's the main thing I took from Dropbox, had the opportunity to then apply that to Asana.

• 4:33Speaker 02

  And I think what I learned at Asana was if I had to pick one thing, it would be this concept of product-led growth sales and traditional enterprise sales. When I first joined Asana, and even today, when I talk to a lot of people, I think there is this predominant view of that you have to pick one or the other. And at Asana, we pioneered, and we tried to do both at the same time. And I think the results were quite positive. And I think my takeaway is that it is possible. It's hard, but it is possible.

• 5:00Harry Stebbings?

  I speak to a lot of founders today who are like, well, if we have product-led growth, we don't need a sales team because the product sells itself. How do you respond and advise those founders? At what point does it asymptot or plateau? How do you think about that?

• 5:13Speaker 02

  Well, I think it depends a little bit on your product category and who you're trying to sell to. There are some categories where you can get really far with a self-serve only model. I think about Atlassian and how far they went in the sort of in that DevOps world, it makes total sense. No developer really wants to get on a phone or get a cold call or whatever, even pick up a phone call from a random salesperson. Makes a ton of sense. Almost every other persona, sales makes sense to complement, not to say that you have to lead with sales, but sales can really help you move up and get to the larger, more strategic conversations. So I think it depends on your product, but generally speaking, I think the decision to not have sales, you're just missing out on a lot of potential growth.

• 5:54Harry Stebbings?

  I totally agree. And I actually think to like Carl Parrish at Figma, who I think has done it very well in a PLG motion and layered it on top. But we're going to get into that. I do want to start though, if we kind of go back to the beginning of a company lifecycle and sales cycle, really, which is I always think that founders are the ones that need to create the sales playbook. Do you agree that the founder needs to be the person to create the playbook or can they bring someone in to do it?

• 6:16Speaker 02

  So it's a question I get a bit. And the first thing I want to say is let's talk about what is a playbook? Because in the world of sales hiring and such, people talk about the word playbook, all this P word. I sometimes don't even want to use it because it means different things to different people.

• 6:31Harry Stebbings?

  To me, it means something that's repeatable and scalable, having been tried and tested. And it's like a process that you can cookie cut and replicate.

• 6:40Speaker 02

  Cut. Yes, that is a playbook. I think that's the second playbook you build and that's a much easier playbook to build. I think the first one you got to figure out, especially if you're a product like Growth Company, is what personas are you really want to sell to? Does your product really resonate with and drive amazing, incredible value? This playbook also tells you what is the best way of reaching these personas? Because every persona acquires technology differently. What is the actual business value and how do you articulate it? So for me, that's like the initial playbook. When I think about, hey, if you're thinking about hiring your first salesperson, you're probably at that stage where these are big, open questions that you may not have answered. If that playbook hasn't been written, founder must be involved. You have to talk to the customer to hear the feedback firsthand so that you can then incorporate that into your product and eventually get your product market fit. So to me, that is higher order priority.

• 7:25Speaker 02

  Once you figure that out, it's actually quite easy to figure out the more, hey, we're going to do three calls here. We're going to use this email template to ping this person and then we're going to text this person's mom. You know, like you can figure that out later. It's not rocket science. The harder part is the who you sell to and what are you selling?

• 7:42Harry Stebbings?

  Step one being that who we sell to, what we're selling and how we're selling it in terms of like the words that we use in articulation. That's founder. And then stage two is more plastic. Is that correct? Like the head of sales can work on that?

• 7:55Speaker 02

  Yeah, so the second thing around the basically your selling process, the repeatable thing that everybody dreams about. Like I wanted to demystify that first. I don't think you create that playbook until you have at least 20 ramped AEs.

• 8:10Harry Stebbings?

  Wow.

• 8:10Speaker 02

  Where you have the right to say this is a playbook. Any sales leader says, I got a playbook, I got five AEs and look at them like they're just doing my repeatable process. Look, it is, it may be repeatable for the next month. It will not be scalable as you build more people because you just don't know. You have to figure out a lot. That's why this like playbook word is one that I just think it has all these connotations associated with it. And I think like you just have to be practical. Look, the reality is in the first, your first two AEs, there is no playbook. You hire your first head of sales, you're piloting it. You may not even know if your product really resonates with, is your primary persona here the CIO? Or is it some functional leader like a VP of HR? You don't know that. And if you don't know that, going after either of those requires a different play. And so I think that's the danger. A lot of focus on the

• 8:54Speaker 02

  Repeatability, I rather focus on agility.

• 8:57Harry Stebbings?

  Okay, let's sorry, let's go down that then. I mean, I've got loads of questions for you. But when you say you rather focus on agility, double down there. What do you mean by that?

• 9:04Speaker 02

  I rather focus on, instead of like, hey, trying to get people to like, write up some playbook. Hey, actually be really nimble. This month, we're gonna focus on answering these questions. Right, like for example, let's focus on which persona actually resonates most with our product. Does our product resonate with most? And this month, let's do a deep dive and sprint and like really focus there. Take that learning. Alright, next month, let's learn, what does it take to engage with some of these people? Is it through a referral program that we should do this? Is it cold outbounding? Is it, can we cold email these people? Because I'll tell you, some personas you can, some probably not so much. Okay, after you answer these questions, then you can piece it together. That is very, very obvious. That's what I mean by agility. When I'm hiring my first leader or first couple of people,

• 9:45Speaker 02

  I'm not telling them to come back with a playbook, I'm telling them to come back with learnings and insights.

• 9:50Harry Stebbings?

  This is the first time I've actually had to get out like a notebook and a pen to write questions so I don't forget them while you talk. My question to you at first, and again, I said there's many. I always say to them, founders, you need to create stage two also, stage one and stage two of the playbook. Because if you don't, you hire reps, the reps generally are more junior. They come in without a playbook, they don't have anything to execute on, they don't hit numbers because they don't have a playbook to work against, they churn, and morale sucks, and that's very, very bad and toxic to get out of. How am I wrong then, if the playbook isn't created till much later on? How would you change my advice? I actually need help here because I use that advice a lot.

• 10:31Speaker 02

  I would say, look, you need to start with something. For the founder have gotten enough traction to raise a seed or a round, they must have had some enough traction to have something to start with. And so I think you can call that your first playbook. I think playbook should be dynamic. And so it should be something where, hey, I hired my first two, three AEs, they may be junior people. You're gonna start with this, but I also expect you to make it better constantly. Tell me how to actually be more effective. How do you improve this part of the funnel? How do you improve this messaging? Go test out these different copies and you tell me what makes better. And I think that Playbook instead of thinking about it as a V2 or V3, it's just constantly improving. It should be improving every single week. As a founder, I would say, hey, I want you to drive revenue, drive logos. I also want you to bring me insights.

• 11:16Speaker 02

  Every week, how can we make kind of a V1 playbook better?

• 11:19Harry Stebbings?

  I totally agree with you on kind of the dynamic nature of the playbook. I do want to get to that element of, you know, you have those two reps kind of executing on that kind of first iteration of it. I had Mitch Tariqah from Zoom on and I've had some prior guests on the show who say always start with a head of sales. They can then hire the team that they want and build their rap base. And then others say, hey, get jack of all trades reps in and roll with the first iteration of the playbook. Where do you advise me as a founder, early stage seed, series A, do I hire reps first or head of sales first?

• 11:50Speaker 02

  If your product and your business is going after an existing category and you're just a much better version of it. So there's already sometimes already budget, but certainly it's pretty clear who the buyer is and what are you solving? I would lean towards hiring a head of sales because that tells me that you probably can grow faster. You're probably on the high fast hiring scaling path soon in the near future. So hiring a head of sales can really accelerate things. On the other hand, if you're trying to actually create a new category, what you're selling is fundamentally the first piece of that kind of software, solving that admit problem at a company. I think you're better off with hiring some hungry and smart customer facing people first. Why? Again, talk about that playbook thing, you gotta learn. What should be your motion?

• 12:35Speaker 02

  Should you go enterprise? Should you go top down? Should you go bottoms down, up? Should you go middle, down, up? Only after that would you actually know what to look for in a head of sales. I think it kind of depends on your category and your product.

• 12:46Harry Stebbings?

  I intend to get, I do like that. On the rap route, Jason Lemkin always says, hey, hire two reps at a time, kind of pit them against each other, kind of Hunger Games style. Do you agree with that suggestion? And how do you think about creating competition and urgency in those first reps that you bring on board?

• 13:02Speaker 02

  Yeah, gosh, I would love to talk to Jason live about this and can understand exactly what he had in mind. There are elements I like that I agree there are elements that I would not agree based on the snippet that you just mentioned. I agree you should hire in batches. If you have the privilege to be able to time your hiring in this environment that where it's so hard to hire good people. If you can batch them, great. Lots of benefits, onboarding, you can actually kind of have basically an A B test. I think though, a couple of things around competition. I think if you really need to rely on having people with the same cohort to drive competition. I think you may have hired the wrong people, in my opinion, because in that early stage, I'm actually trying to foster more than anything, a culture of collaboration. I want us to learn. I want us to co-create that playbook together.

• 13:45Speaker 02

  If I hire the right people, I will hire people who are intrinsically competitive and hate not being number one. That I don't need to manufacture that environment. Everyone should want to intrinsically want to be number one. I don't need to overtly make it even more so. If anything, I want people to actually come together and work together and share their best practices. That's what I would want.

• 14:05Harry Stebbings?

  We're going to dive into the traits of those reps. Final impossible question, which will likely lead to it depends. But if we think about timing, a lot of founders are like, when the fuck do I hire this head of sales or first sales reps? In terms of timing, again, take us back to that coffee shop you advising me, when do I hire?

• 14:23Speaker 02

  Number one, I don't know if your first hire needs to necessarily has to be sales. I think a lot of times, I'm just going to say a customer facing person. Could be a little bit more C S than sales, could be very sales eng, almost like a DevRel kind of persona if you're selling a DevOps product. So that's one first clarification, right? It's like, I don't think your first person has to be sales. Just make them customer facing, so they can get feedback, serve the customer and help you make better decisions. In terms of timing, I think answer is a little different today than it would have been two years ago. Because today, capital is not that big of an issue. These seed rounds are massive, these series A rounds are massive. So are the valuations that you have to grow into, they're also massive.

• 15:06Speaker 02

  My answer is assuming that you're not that resource constrained. If you're not that resource constrained, spending that much When I need to hire like a junior customer facing person as early as you can is actually would be my advice. Again, not necessarily drive those revenue, but to get those insights. The more customer reps you get and you talk to, the more you'll learn. And I think that should be the approach. If your approach, I need hires, have a salesperson because I needed someone to just drive logos and drive revenue. Then I might not be as aggressive, but for me, I want to be very aggressive upfront about learning insights about the market and my potential buyers. That's why I would hire someone ASAP.

• 15:40Harry Stebbings?

  Okay, so we're gonna hire someone really early. I embraced a chunky ass seed round at a ridiculous price. And I need to hire these first reps. How do I structure the process? What does the interview stage look like? Can you walk me through it?

• 15:53Speaker 02

  Well, number one, you mentioned process. I think it's extremely important. And the reason why is number one, I think it's actually if you over time, you're cared by diversity on your team. You wanna get your initial hires right because so much of hiring comes through referrals and such. And so like, I think building a process from the start is critical. So that you make sure that you iron out as many potential unconscious biases as possible. And through that process, I think number one, be really clear about what you're looking for. And be really clear about what are the competencies and the behavioral traits that I think the characteristics that you want to test for. Write them down. Number two, make it really clear what are the questions that we are using to assess them? And what does a great answer look like? What does a mediocre answer look like?

• 16:36Harry Stebbings?

  Let's just pause there and go through them. I'm writing as well. We're an early stage startup, sub a million in AR. I know it's difficult because there's nuance, but if we think back to those, what sort of things would you say we should all be looking for? And then what questions would you say are brilliant or you always like to really tease out whether that person has those characteristics?

• 16:55Speaker 02

  I think the things that I always look for in whether you're a leader or just any of my customer facing folks. Number one, reverence for the product. You can tell when someone really appreciates the product, the intricacies, what it can do. I think nowadays, especially in an increasing PLG is on the rise. I want this person to convey this passion and this love for the product to their customers as opposed to just following some playbook. That reverence for your product or for. Any kind of product is something I look for.

• 17:24Harry Stebbings?

  How do you test that? We're gonna do it one by one. So we're in the interview. What questions do you ask to tease out whether they have that reverence for product?

• 17:31Speaker 02

  Yeah, what I'm looking for in most of my answers is not your answer, but how you answer. In this case, I will ask you to tell me about your product. Tell me about your product. Very simple. And you will see, there's like, either it's amazing. Let me tell you, all the amazing lives it has changed because it was able to do this and this and this. It is by far the best. Then you have the other ones, they just, they give you the playbook. They treat you like you are, they called you and you're like, I accept. Tell me about your product, please. And then they go, okay, we are a platform for increasing the efficiency of your, for logistics. And you'll see, is there passion for the product itself? Or is there just passion for executing a generic thing? It's very obvious. So it's the how, it's not the question.

• 18:13Harry Stebbings?

  Okay, so number one is reverence of products, and I like that. What's number two?

• 18:17Speaker 02

  Number two, if you are expecting this person to like really build a team and scale in time, is does this person make people around them better? Obviously, if you're a leader, then you should have a track record of like growing talent. But if not, just like even a IC. I want people who, especially in the beginning, because every single hire really contributes to your culture, very important that everybody makes everybody else better.

• 18:40Harry Stebbings?

  How do we test that in the interview?

• 18:41Speaker 02

  I ask for real examples. I'll give you an example. So if you're a leader, I'll always ask, I like to know, give me an example of someone whose career you impacted personally. And usually, everybody has one or two examples, or they're able to like manufacture something. That seems okay. But again, this is one where, again, you can tell by the passion. Someone will talk about, oh, my gosh, Harry was a disaster when I met him, but he has so much potential. We worked on it. Or someone would just like talk more factually. So that's already one, one read. And then I ask another one, and this is the key one, which is, I learned this from probably the best interviewer I know, which is this guy called Tony Hui when we were working at Dropbox together. And it was, hey, tell me about someone who you were not able to get them to reach their fullest potential. And again, it's about how they answer for me in terms of reading it.

• 19:26Speaker 02

  And the people you want are people who take it personally. It's a personal failure of mine, that Harry, I wasn't able to get Harry to reach so much potential. I saw so much potential. But I wasn't able to get there and you could just tell by the voice how they communicated. That is to me a sign that wow, this person is someone who really cares about making people around them better.

• 19:44Harry Stebbings?

  No, I like that. And a red flag in that one would be if they shy away from responsibility and blame the person or blame someone else.

• 19:51Speaker 02

  Absolutely. I have had interviews, so many, but I have some where people say I get the best out of everybody.

• 19:57Harry Stebbings?

  My Veritas, what are your challenges today? And this is like an early, early stage startup and they're like, honestly, we don't have that many. And you're like, really? Really? I would like to be you. Okay. So I like that in terms of traits. And any more that we've missed there?

• 20:11Speaker 02

  Those two, I think it'll get you pretty far.

• 20:13Harry Stebbings?

  And again, I'm asking dumb questions. How many interviews does it take? Who do I bring into the interviews from the wider team? How should I play those two questions?

• 20:23Speaker 02

  My first step is I'm gonna map all the competencies. Generally speaking, you're not gonna be optimized for like ten. In fact, like for me, I would optimize for like four to five. Each interview slot, right, is designed to test for that specific competency. Now, you can merge it. You can do maybe two in the same one or something, but I want four or five people to have been able to meet someone. Again, each person tests a different competency. So that's one dimension. Second dimension, the final round for me has always been for someone to give a demo. I love people giving demos. You can tell so much about how they prepare asynchronous. Here's the thing, like especially when you're hiring young talent, like no one's super polished. There are some people who are super polished, but they may not actually be that good. So I wanna give people a chance and see how do they act if you give them time to prepare.

• 21:07Speaker 02

  Someone may bomb their on the fly interviews, but they may crush their prepared demo. Doesn't have to be a demo. It could just be like a pitch. And that tells you that this is someone has potential. If you give them the time and space and training, they're gonna do great. But on the fly, that's something you can work on. I like to kinda have that as well. And then in terms of like the mix of interviewers, number one, I think it's important to make sure your your interview slate represents the kind of diversity you want on your team. Don't just have all dudes on a panel. And I think it's important to have at least one, if not two, cross-functional partner in that process. It could be product, it could be marketing.

• 21:40Harry Stebbings?

  Sales compensation. We like the person. We want it to happen. How do we approach? Constructing the right sales comp plan. Again, I've never done this before. I have no idea what to do here. What have been some big lessons for you in constructing the right sales comp?

• 21:53Speaker 02

  I'm gonna start with what I think is a common mistake, which is, okay, the first sales hires I'm hiring from Twilio and Amazon, they are on these sales commission plans. Everybody has sales commission plans. I need a commission plan. Putting in place a commission plan when you're really young and early in your life cycle, I think is very, potentially very detrimental.

• 22:11Harry Stebbings?

  Why so?

• 22:11Speaker 02

  Because, number one, once you put in like a sales commission plan, there's a whole bunch of legal repercussions that are hard to go back on. Especially at a time when you're just starting. How do you know how to set targets? You don't have a track record. The only thing I can usually guarantee you, you're either going to massively exceed your target, or you're going to massively miss your target. Generally speaking, that's what happens in the beginning. If I'm going to figure out a commission plan, I'm almost guaranteed to get it wrong. Because how do I calculate the commission rate? And I can ship two features in the next quarter that changes that significantly. I think it is something where I would say my biggest lesson here learned is there are many, many, many, many different forms of variable compensation.

• 22:53Speaker 02

  It doesn't have to be just commission. You can do a bonus structure. You can do team comp. You can do team competitions. You don't even have to use variable comp on ARR. In the beginning, you might wanna do logos, or you may wanna do a number of deals of a certain size. I think variable comp is a very, very powerful lever, and it also makes the job fun for sales teams. But again, you don't have to do commissions. You can find different ways to earn that variable compensation.

• 23:19Harry Stebbings?

  Any other big mistakes? Any other big nudges or piece of advice?

• 23:23Speaker 02

  Specifically on sales comp?

• 23:25Harry Stebbings?

  Yeah.

• 23:25Speaker 02

  Well, I think it would be a mistake not to give equity. I think sometimes, I don't know why, but sometimes I talk to founders and I feel like they treat salespeople as second-class citizens because they feel like the product can sell itself, and they're just like so incredibly cheap on the equity part. Huge mistake. And it may sound obvious, but like, let me explain a little bit more why it's a big mistake. Over time, many companies will wanna build sales teams that scale, and you need that customer relationship that the sales and CS personnel can help you drive. In my experience, your first twenty People you hire, they are the heart and soul of the team. These are the people who understand the intricacies of the product. They understand who to go to on the product team or the engineering team if things are off. They understand how things are done.

• 24:08Speaker 02

  And these are also the people who you will end up sending as ambassadors around the world to start local offices. Cause you wanna keep a cohesive culture and such. So these initial people, I've seen situations where it's more of a transactional relationship between the company and the initial salespeople. Salespeople do well, company does well, that's great. And then they leave to go to some other company because they don't feel like they're really foundational to the company. That's the mistake is like, if you lose these, your initial badge, what you have is you have your playbook that you know is somewhat gonna be outdated within the next quarter. And it's become transactional and it's very hard to create those deep ties in a team.

• 24:45Harry Stebbings?

  Okay, so we've got the right comp plan, we've got the right people. We now need to onboard them and I think, you know, onboarding is something university where companies suck and fail. When we think about ideal onboarding processes, what does that look like in your mind? And what would you advise me when it comes to onboarding new sales reps?

• 25:03Speaker 02

  We're talking about like you're still at early stage. So I would do product first, market second, and sales last. Product first, in the beginning, you're not gonna have a full-fledged sales team where you have SEs, sales engineers who can handle the technical things. You may not even know what gotchas you have in your, whatever data model your company was built on. In the beginning, I think it's super important that whatever customer-facing people you hire, they have to play that role. They have to go two orders of magnitude deeper on the technical side of the product. Whether it's talking about the security, the infrastructure with like a CISO or CIO, then kind of your future aides. I think in the beginning, it's really important to build that product knowledge. A lot of times, the best way to do that is actually get the team exposed to support.

• 25:47Speaker 02

  Because the tickets that you get coming in is basically a reflection of your likely sales obstacles that you're gonna get. So you want to be able to talk about it, understand, number one.

• 25:57Harry Stebbings?

  Just so I get that right, so we put them with product, they sit with product for a week, a day? What sort of level of exposure? Just dumb question.

• 26:03Speaker 02

  I actually say it's less. Product in the beginning, you start with support because everyone's gonna be filing all your bugs. Then you as an A A go get some answers, understand like not just how we answer it. Go and find the engineer to understand why things are built a certain way. That's how I would actually have it is like figure out what will likely be your most more difficult product questions. And you go find the answers because we don't have a playbook yet.

• 26:29Harry Stebbings?

  Got you. Okay. So then we put them in support. They understand from the tickets and from the knowledge they get from the feedback. Then market, what do we do for market knowledge? How do we educate in that?

• 26:38Speaker 02

  That to me is at this point, probably going through your fundraising deck. Cause at this point, you probably don't have a sales pitch. I remember at Asana when I joined it, when I joined Asana, we had 20 million in revenue, mainly driven from our self-serve business. And we didn't have a sales deck. So it's very common that you don't. So at that point, you're probably taking your fundraising deck and you're just like educating on like, here are the players. Here's a competition. You're getting your one-on-one that way. Why I think is important to do a market first is I think I want to put the sales stuff last. Because that's the stuff that the team will hone in on forever. It's really hard to like, okay, you're in the middle, you're ramping, you're fully ramped to like, then suddenly come back and be like, let me just educate you on the market. Like you just, the absorption is not going to be there.

• 27:19Speaker 02

  Plus, I actually think that people are, will be higher performers if they actually understand broadly what's happening. What are the drivers? Cause you want to educate them, not in terms of like your sales messaging and value articulation yet. But hey, just like this is what's going on in the world. This is why we exist. What's the mission that we're trying to do? That's why.

• 27:35Harry Stebbings?

  And so we've got the kind of first area in customer support, known support. Second, they're going through the decks, understanding the market competition. Third being the sales, the last component, what is involved in that third component being the sales orientation?

• 27:48Speaker 02

  My guess is if you're hiring your first couple of people, you're shadowing the founder on a couple of conversations. I think absolutely you go talk to your top 10 customers and you develop a relationship there. And these are probably pretty friendly customers and really ask like, hey, you can even ask a customer like, we haven't written case study yet, but like, how would you quantify the value that we provided to you? You probably have to do that because no one has done that yet, if it hasn't done that. So you basically shadow the founder for a little bit. And then what I do is like it culminates for me, this is what I mentioned a demo earlier. Like you may not need to do a demo during any of your process. Absolutely, I want someone to demo the product at the end of whatever onboarding period you designate is reasonable. This is kind of like a the equivalent of a PhD defending their thesis.

• 28:33Speaker 02

  Going in, you're going to present your demo of our product and we are going to actually role play. And I invite, it would be like if I'm the founder, I would found one founder, it would be a PM. And like the other two, three people you you have in the customer facing team. So it's high stakes. You can't even like present to your own team. You forget about customers. It ends up being a good forcing function to wrap up everything that someone has learned. And in that demo, someone plays a role of a depending on that you're buying, right? You're trying to role play. So like someone's like a CISO, someone's a CIO, someone's the actual champion. And you see how they act and that's basically a certification process.

• 29:08Harry Stebbings?

  How long is this three stage process number one? And when do we allow these new reps to speak to their first customers?

• 29:14Speaker 02

  I feel like two months is reasonable at this stage to get to a point where like they're really, really solid with like a great demo. They have acquired all this knowledge. That doesn't mean that they can't talk to customers earlier. If you're a PLG company where you have a reasonable flow of inbound or you're an open source company where you can like sort of tap into a community. I think within three weeks, they can start talking to customers. They may not need to be selling because again, I just want to hire some good customer facing people at first. So that in the beginning, they might just be talking to existing customers, just being like checking in. What do you love about the product? What do you like about the product? What's your issues? Just like get more reps. I do think it's important to get reps, but just because you're talking to customers at that point, doesn't mean you're truly ready yet. So this is the different one difference between PLG companies and non PLG companies.

• 29:58Speaker 02

  You can actually start doing that and it helps with accelerating the ramp.

• 30:02Harry Stebbings?

  You mentioned the difference between PLG and non PLG. In terms of for new reps, often when it's PLG, they just have a lot of inbound to service and it's a lot more on a plate bluntly. When that plateau is, you said before to me that you can't just kind of go outbound. What did you mean by this, like not being able to just go outbound?

• 30:19Speaker 02

  Yeah, I see this pattern everywhere. So let me just start by this thing that's like, I love PLG. I breathe. And bleed PLG. At the same time, I love outbound. Outbound's way easier. I love going outbound, okay? But I think for outbound to be successful, generally speaking, you're selling to a different buyer, probably a more senior persona. Probably selling a different value and so therefore you need different messaging. In terms of the sales process, absolutely you'll have a much lower conversion rate. And to make it for that, your deal size needs to be commensurately bigger. And generally speaking, that will require a different type of talent to execute that. So what I see a lot happening is people's initial inbound thing, it's like you hit that S curve, it's amazing. And then suddenly it just like starts plateauing, you're like, what the heck is going on? I don't know. The answer I always hear is, well, we're just gonna start going outbound now.

• 31:04Speaker 02

  Again, outbound's fine, but if what you mean by going outbound is you're just going to get some salespeople to go buy some lists and just start cold emailing, LinkedIn bombing people, it won't gonna work. Because your entire conversion process is designed around a different buyer, articulating a different value, converting at a higher speed and a smaller deals. So if you wanna go outbound, I'm all for it. But what you need to do is you gotta make sure your marketing team is aligned to actually generate and work with you to develop the right messaging for this different persona. Your product probably needs some augmentation to sell a bigger deal. So if you're gonna go outbound, just make it a company initiative. Not just hire some salespeople that go outbound, because I don't think it's gonna work. I don't think it's gonna work. That's what I mean.

• 31:48Speaker 02

  And then what happens, I see there is like, it becomes a crutch because a lot of companies go, I'm just waiting for my VP of Sales to show me that outbound works to like continue the inbound lead funnel. Apples and oranges. What I wish I see more is, hey, our inbound funnel seems to be not growing at the same rate of our expectation. How can we inflect that? What else can we do to drive more inbound? Whether it's how can you generate more word of mouth? How can we have a more performant conversion or converting website, whatever that is, I think.

• 32:16Harry Stebbings?

  So it's not waiting until that plateau really hits, it's being diversified enough where you go, okay, we're starting to see a tail off in terms of the PLG motion. Now's a good time to start layering on.

• 32:26Speaker 02

  Yeah, exactly. Just because you see some signs of initial like plateauing of your initial PLG playbook for the company doesn't mean that it's the party's over. And therefore you need to go outbound. That's like the last thing you should do because it takes so much to company want to make it work.

• 32:41Harry Stebbings?

  I totally agree. I think people consistently underappreciate what it takes to go outbound effectively. I think one area that I would love to dig into in particular though, is really the relationship between head of sales and the CEO. For me as the first time CEO, what should that ideal relationship look like? And what can I do to get the best out of my head of sales?

• 33:00Speaker 02

  My relationship with CEOs is super important for me is one of partnership. My job, I gotta bring home the bacon. I gotta get the cash in. I get that. But there's a bigger play here that I have in my head, which is I see an equally important part of my responsibility as a CRO, head of sales, whatever, is to help my CEO make the best decisions that he or she can. And to do that, that means that I am responsible to bring back the right amount and type and in the right form of feedback to my CEO so that he or she can make the best decisions. It's my responsibility to make sure that I and my team don't have recency bias based on the last deal that wasn't able to close. It's my job to make sure that the CEO knows what's working, what's not working for the purpose of his or her decision making.

• 33:44Harry Stebbings?

  How often do we meet, OJ? Is this a weekly thing? Is this a monthly thing?

• 33:48Speaker 02

  At an early stage, I would hope it's a weekly thing, minimum.

• 33:50Harry Stebbings?

  Okay.

• 33:50Speaker 02

  In the early stage, I think it ought to be quite frequent. And if you're not, that means that you're just not getting enough, you're not collecting enough learnings and insights for your CEO. That's how I was.

• 34:00Harry Stebbings?

  Do you do deal reviews and postmortems? And if so, how do you structure them?

• 34:05Speaker 02

  Deal reviews for sure, for sure. Every week we have deal reviews, even when we're really, really small. And usually you have a qualification framework and you're gonna go through it. And usually in the early stages, everything is like unqualified, but it's good to have that rigor to start. Postmortem, at Asana, we had a practice called five whys, is adopted from Toyota, that I think is very effective. It's a practice where-

• 34:26Harry Stebbings?

  What are five whys?

• 34:27Speaker 02

  Five whys, like when something goes wrong. Basically it's saying when something goes wrong, you wanna get to the fifth level of, okay, why did this fail? Because someone messed up. Okay, well, why does the person mess up? Well, because this person wasn't trained well enough. Why didn't this, why wasn't this person trained well enough? Oh, because we- Didn't hire sales enablement. Well, why didn't we hire sales enablement earlier? Oh, recruiting didn't have enough bandwidth. And so we deliberately chose to prioritize something else. It's important to, when you do this postmortems, to really understand if something doesn't go well. Why you lost a deal, there usually are multiple layers. As opposed to what you normally first hear, which is that like, oh, bad timing, bad timing, got pushed to next month.

• 35:10Harry Stebbings?

  What's the answer to that one? Cause I often have this where I say, oh yeah, they pushed it. Not a priority, bad timing. How do you respond to that? Why is it bad timing? What would you respond?

• 35:19Speaker 02

  Why is it not urgent? Normally we just end there because normally the rep may not actually have the answer. Oh, why is it not urgent? They think that it is the always the responsibility of the customer to make timing work. But hey, it's also part of our job to try to create that urgency. Five whys is really not about getting to the answer. I think it's about really like creating the right level of discussion. It's a framework to create the right conversations so that you will, through that process, find one or two big like core root problems that you can address.

• 35:49Harry Stebbings?

  Final one, my favorite is we lost our champion. So there was nothing that we could do internally. It's just that the person who wanted it left. How would you like analyze that with the five whys? Why didn't we have a broader base of supporters?

• 36:01Speaker 02

  Yeah, exactly. I'll start with like, why did this person leave? Sometimes this person left and you realize that you were actually always talking to the wrong person. Okay. Why didn't we have more? Multi-threaded is the lingo. Why weren't we multi-threaded in this account? Usually it's just like, we didn't get to it. It's usually the thing, but then it stops there. But it's interesting to be like, why didn't we get through it? It could be that, oh, we didn't get through it because we have so many frigging accounts. And so what you realize that, oh, you need to actually work on a prioritization system. As opposed to just being, oh, well, we didn't do it. Okay. We should do it next time.

• 36:29Harry Stebbings?

  I love it. Listen, I could talk to you all day, OJ. I want to move into my favorite, which is a quick fire round. So I say a short statement and you give me your immediate thoughts. Does that sound okay?

• 36:37Speaker 02

  Yeah.

• 36:37Harry Stebbings?

  Okay. So let's do what sales tactics have not changed over the last five years?

• 36:42Speaker 02

  The need to articulate your business impact and value.

• 36:46Harry Stebbings?

  What sales tactic has died a death over the last five years?

• 36:49Speaker 02

  Emails.

• 36:50Harry Stebbings?

  Expand on that one.

• 36:51Speaker 02

  I think the predominant motion now is I'm just gonna blast. Email a bunch of people, see who responds. I mean, this starts even with like early days, marketing automation with like Marketo and stuff. It's like, oh, this person like clicked on my link. They must be really interested, you know? Oh, they read my white paper. Like, I just don't believe in that anymore. I don't think people download white papers and do that anymore. There's way too much rich content and information in the, on the internet now. They're reviewing different products and no one's gonna be doing that anymore. So that whole to MQL, to SQL, all that, I just think that's done.

• 37:24Harry Stebbings?

  Tell me, what's the biggest mistake you see founders make when hiring their first sales teams?

• 37:29Speaker 02

  I think the mistake is not investing much in thinking about the bridge between the, the customer facing teams and the product teams. Thinking through how does the voice of the customer gets captured, brought back to product. I think companies should spend as much time on that as they should on their sales playbook.

• 37:47Harry Stebbings?

  What piece of advice would you give to a sales leader starting a new position today?

• 37:51Speaker 02

  Well, today's environment is really tough for new sales leaders because you're almost certain you're gonna be walking into a situation where you have a valuation that is probably three years ahead, crazy multiple. And you need to prove progress very quickly. So with that context, today, most sales leaders forget to manage up. Most sales leaders come in, they focus so much on building their own team, writing that playbook, some cross-functional stuff. But they just like, they don't have the experience to manage up. And I think you have to manage up really well, especially in this environment, if you want to succeed. And managing up doesn't mean like managing lower expectations. It just means you make sure your dialogue with the founder, CEO and the board is really clear.

• 38:29Harry Stebbings?

  Final one, what would you most like to change about the world of sales?

• 38:33Speaker 02

  What would I change? I think sales still, when people think of sales, they still have this picture of some used car salesman image. What salespeople do at the core is they help customers solve their problems. They happen to do that sometimes because your product actually does that really well. But that is what sales is about, you're solving problems for customers. It's not that different than that of a product manager. It's just how you do about it differently. A lot of times in tech, frankly, I think sales people are second-class citizens because they're not building a product and all that. I would love to change that. The best companies are the ones where sales, collecting customer feedback, working with customers directly are on equal footing with product.

• 39:12Harry Stebbings?

  OJ, this was so much fun to do, as you can tell from the run over. I love this. So thank you so much for joining me and I can't thank you enough for giving me the time.

• 39:19Speaker 02

  Oh, that was really fun. I wanna do it again.

• 39:24Harry Stebbings?

  Well, I mean, OJ is my new favourite person. I absolutely love that. I love how granular we went with the interview process, with the onboarding process. So much to learn there from OJ. Huge thanks to him for that. But before we leave you today, here's an alarming stat for sales leaders out there. According to research done by Zand.com, only 28% of deals are forecasted accurately. 28%. Why is that? Either you don't have enough reliable data to draw from in Salesforce, or you based your forecast on wishful thinking instead of facts. So how do you get your team to input all the data you need without hounding them around every corner and taking away their selling time? Well, that's where Dooley comes in. Dooley is what top performing sales reps use day to day instead of Salesforce.

• 40:05Harry Stebbings?

  It's the fastest, easiest way for sellers to input deal data in real time, update their pipeline in a snap, and manage every deal at once. So nothing falls through the cracks. It's a dream for sales teams because reps save hours of admin grunt work and managers get up to 60% more accurate deal data in Salesforce. So you can build a sales forecast you can feel confident about. Visit dooley.ai/demo to speak with a Dooley rep today. And speaking of upleveling your team with incredible tools like Dooley there, Salesloft is the leading sales engagement platform, helping sales teams drive more revenue with the modern revenue workspace. It's the one place sales teams can go to prospect, manage active deals, and get the insights they need to coach seller performance, forecast with

• 40:48Harry Stebbings?

  accuracy, and find out what steps to take to close more deals. Some of the world's leading companies like IBM, Shopify, and Stripe all love a new Salesloft, and so can you. It's the new way to sell. Find out more at salesloft.com. As always, I so appreciate all your support. We've got an incredible episode with Iden at Felices coming out on Friday. Stay tuned for that, and it's incredible.