Oliver Jay: How To Create and Execute a World-Class Sales Playbook | 20VC #889

1. 0:00 – 4:35

   Entry into Sales

   1. OJOliver Jay0:00

      Three, two, one, zero. You have now arrived at your destination.

   2. HSHarry Stebbings0:09

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

   3. OJOliver Jay0:17

      Oh, I'm so happy to be here.

   4. HSHarry Stebbings0:19

      That is very, very kind of you. I've been looking forward to this one. But I wanna 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?

   5. OJOliver Jay0:34

      Uh, you know, I... First couple of years my, in my career was in finance. I, I, I was in first starting equity research at Morgan Stanley and covering tech companies. That was my first exposure to how the, sort of the intersection of tech and business. Um, then I went over to venture, uh, and, and I worked at NEA for a bit. Uh, loved, loved my time there. In that experience, I really saw how amazing some, uh, investors were bas- sort of leveraging their operating background to help founders.

   6. HSHarry Stebbings1:06

      Mm-hmm.

   7. OJOliver Jay1:06

      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 gonna operate, you either build product or you sell product. Everything else is supporting one of those two." And I was like, "Oh, interesting." And, and just one thing led to another. I just hap- ... It was like 50/50. I went down the sales path, and that was the, that was the path I ended up on.

   8. HSHarry Stebbings1:30

      I love that. I love that kind of simplicity of you either build or you sell. Um, I do wanna ask that, you know, when we look back at the time, six years Asana, 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 each, what would you say they would be, looking back and reflecting?

   9. OJOliver Jay1:49

      So, drop- Dropbox, I think for me, number one, is that, uh, technology is just fundamentally diff- uh, adopted differently in businesses. B2B businesses, uh, are, uh, no longer by the traditional top-down way in terms of how technology is used in, in companies. Uh, employees get to pick, right? And that started with Apple with the iPhone in, in probably around, what, 2000 and, 2010, right, when people had this BYOD move, and Dropbox was the, was the company that shattered and started the BYOA move. And so th- I think that's number one. And so as a result, number two is that, you know, 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. 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. You know, at, 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 can, you got to pick one or the other. And, at Asana, we pioneered, and we, we try to do both at the same time. And, and I think the results were quite positive, and I think it dem- My takeaway is that it is possible. Uh, it's hard, but it is possible.

   10. HSHarry Stebbings3:15

       I, I speak to a lot of found- and we're kind of diving straight in, kind of ignoring schedule, but I speak to a lot of founders today who are like, "Well, you know, if we have product-led growth, we, we don't need a sales team 'cause the product sells itself." How do you respond and advise those founders? At what point does it asymptote or plateau? How do you think about that?

   11. OJOliver Jay3:33

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

   12. HSHarry Stebbings4:25

       Listen, I, I totally agree, and I actually think it's like Karl Parrish at Figma, who I think's done it very well in a PLG motion, uh, and layered it on top. We- we're gonna get into that. I do wanna start though,

2. 4:35 – 12:23

   The Playbook

   1. HSHarry Stebbings4:35

      if we kinda go back to the beginning of a company life cycle 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?

   2. OJOliver Jay4:49

      So, it's a, it's a question I get a bit. And the first thing I wanna say is, I want- Let's talk about what a pl- What, what is a playbook? 'Cause in the world of sales, hiring and such, people talk about the word playbook all- this P word. I, I don't even wanna u- I, I sometimes don't even wanna use it, because it means different things to different people. So, like, for me-

   3. HSHarry Stebbings5:09

      Okay. So to me, to me, to me it means something that's repeatable and, uh, scalable, having been tried and tested, and it's like a process that you can cookie-cut and replicate.

   4. OJOliver Jay5:21

      Okay. Uh, so I think that is a... 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 gotta figure out, especially if you're a product-led growth company, is what personas are you really wanna sell to? Does your product really resonate with and drive amazing, incredible value? This playbook also tells you how, what is the best way of reaching these personas? Because every persona, uh, acquires technology differently, right? And then third is like, how do you, uh, 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.... or these are big, open questions that you may not have answered. And if that is a- it... Right? And so, if that playbook hasn't been written, the founder must be involved, because you have to, you have to, you have to talk to the customers to learn, "Hey, this is where it's go-" This- The- To hear the feedback firsthand, so that you can then incorporate it into your product and you eventually get to product market fit. Uh, so to me that is higher order priority. Once you figure that out it's actually quite easy to figure out the more, "Hey, uh, you know, we're gonna do three calls here. We're gonna use this email template to ping this person, and then we're gonna text this person's mom," you know? (laughs) Like, you can figure that out, uh, later. It's not rocket science. The harder part is that- is the who you sell to and what are you selling?

   5. HSHarry Stebbings6:52

      So, 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 and articulation, that's founder. And then stage two is more plastic, is that correct? Like, the head of sales can work on that?

   6. OJOliver Jay7:07

      Yeah. So the second th- uh, the second thing, right, around the basically you're selling process, the repeatable thing that everybody dreams about, like, I want to just demystify that first. I don't think you create that playbook until you have at least 20 ramped AEs.

   7. HSHarry Stebbings7:27

      Wow.

   8. OJOliver Jay7:27

      Right? Where you can- 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- 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 not- you just don't know. You have to figure out a lot, right? And so 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 f- you hire your first head of sales, you're piloting it, right? Like, y- uh, you, you may not even know is- if your product really resonates with, I don't know, uh, is- should you st- are y- is your primary persona here the CIO or is it some functional leader, like a VP of HR? Right? That- You don't know that. And if you don't know that, the- going after either of those requires a different play, right? And, and so I, I, I think that's the, that's the danger.

   9. HSHarry Stebbings8:28

      I-

   10. OJOliver Jay8:28

       It's like, a lot of focus on the repeatability. I rather focus on agility.

   11. HSHarry Stebbings8:33

       Okay. Let's, let's... Sorry. Let's go down that end. I mean, I've got loads (laughs) of questions for you. Uh, but when you say you rather focus on agility, double down that. What do you mean about- by that?

   12. OJOliver Jay8:43

       I rather focus on instead of like, "Hey," trying to get people to f- like, write up some playbook, uh, "Hey, actually be really nimble. This month we're gonna focus, right, on answering these questions," right? Like for now, let's focus on which persona actually resonates most with our product. Who does our product resonate with most? Right? And let's, this, this month let's do a deep dive, and sprint, and like really focus there. Take that learning. All right, next month, let's learn, what does it take to engage with some of these people? Right? Is it, is it through a referral, uh, uh, program that we should do this? Is it cold outbounding? Is it, um, you know, do we, do we- can, can we cold email these people? Right? Like, because I'll tell you some personas you can. Some, probably not so much, right? Okay. After you answer these questions, then you can piece it together. Then it's very, very, very obvious. Uh, so that's, that's what I mean by agility. Wh- When I'm hiring my first leader or first couple people, I'm not telling them to come back with, uh, a playbook. I'm telling them to come back with learnings and insights.

   13. HSHarry Stebbings9:46

       This is the first time I've actually had to get out like a notebook and a pen to, to write questions so I don't forget them while you talk. (laughs) Um, my, my question to you f- first And again, I said there's many. First is like I always say to founders and, man, this is why I think VCs are so dangerous, 'cause we actually give shit advice. But, um, 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. Um, they come in without a playbook. They don't have anything to execute on. They don't hit numbers 'cause 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. H- How am I wrong then if the playbook isn't created 'til much later on? How would you change my advice? I actually need help here, 'cause I use that advice a lot. (laughs)

   14. OJOliver Jay10:42

       Uh, I would say, look, you need to s- you need to start with something, right? You need to like, yeah... The f- and the founder, for the founder to have gotten enough traction to raise a seed or s- or A round, they must have had some enough traction, uh, to have something to start with, right? And so I think you can call that your first playbook. I think the- I think playbooks should be dynamic. And so it should be something where, okay, "Hey, I hired my first two, three Aes. They may be junior people. You're gonna, you're gonna start with this, right? But I also expect you to make it better constantly," right? "Tell me how, how to actually be more effective. How do you improve this part of the funnel? How do you improve this messaging?" Right? "Go test out these different copies and you tell me what's- what makes better." And I think that playbook, instead of thinking about it as a V2 or V3, it's just- it's constantly improving. It should be improving every single week. All right? And so I would rather make... As a founder I would say, "Hey," like, "I want you to close a... you know, drive revenue, drive logos. I also want you to bring me insights. Every week, how can we make kinda the V1 playbook better?"

   15. HSHarry Stebbings11:52

       I, 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 (laughs) kind of first iteration of it. You know, I had Mitch Teriko 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 rep 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

3. 12:23 – 27:50

   The Hiring Process

   1. HSHarry Stebbings12:23

      Seed Series A, do I hire reps first or head of sales first?

   2. OJOliver Jay12:28

      ... it depends, as you, like most of my answers always depends.

   3. HSHarry Stebbings12:32

      (laughs)

   4. OJOliver Jay12:32

      Yeah, that's

   5. NANarrator12:32

      (laughs)

   6. OJOliver Jay12:33

      ... why people sometimes (inaudible) . Everyone's like, "OJ, what's your playbook?" I'm like, "Well, it depends."

   7. HSHarry Stebbings12:37

      (laughs)

   8. OJOliver Jay12:37

      Okay, so here's how I think about it. If you are, if your product and your business is going after an existing category, and you're just a much better version of it, right? So, there's already, sometimes already budget, but certainly it's pretty clear who the buyer is and what, what are you solving. I would lean towards hiring a head of sales.

   9. HSHarry Stebbings13:00

      Mm-hmm.

   10. OJOliver Jay13:00

       Because that tells me that you, you probably can, uh, grow faster. You're probably on the hire, fast hiring scaling path, like soon, in the near future. And so hire a good head of sales, like can, can really accelerate things. On the other hand, if you're trying to actually create a new category, right? What you're selling is fundamentally the first piece of that kind of software, solving that unmet 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, that you gotta learn. You gotta learn who are you actually selling to? What should be your motion, like, uh, are you, should you go enterprise? Should you go top down? Should you go bottoms down? Up? Should you go middle down? Up? You know, and so, uh, only after that will you actually know what to look for in a head of sales, right? Uh, and so I think it kind of depends on your ca- category, uh, and, and your product.

   11. HSHarry Stebbings14:02

       I, I tend to... Yeah, I do like that categorization though between, you know, when there's existing budget, when there's existing consumer or customer education head of sales and when it's less, um, solid in terms of its packaging, that may be the wrap route. (laughs) On the wrap route, Jason Lamkin always says, "Hey, hire two reps at a time." Kind of, you know, pit them against each other kind of, um, Hunger Game style. (laughs) Um, 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?

   12. OJOliver Jay14:34

       Yeah, uh, I don't, is... Uh, uh, gosh, I would love to talk to Jason live about this and kind of understand like exactly what, what, what, what he had in mind. I, you know, for me, there are elements I like, that I agree. There are elements that I would not agree, like based on, you know, the, the snippet, right? Uh, uh, that you just mentioned. I agree that 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, uh, good people. If you can batch them, great, right? Lots, lots of benefits, onboarding, you know, right? You can actually like, kind of, uh, uh, uh, have basically an A/B test. Uh, I, I think though, a couple of things. Around competition, I think if you need to rely on sort of like having people with the same cohort to drive competition, I think you may have hired the wrong people, in my opinion.

   13. HSHarry Stebbings15:25

       Hmm.

   14. OJOliver Jay15:26

       Right?

   15. HSHarry Stebbings15:26

       Yeah.

   16. OJOliver Jay15:26

       Uh, 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. And so, if I hire the right people, I will hire people who are intrinsically competitive and hate being num- 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, uh, and work together and share their best practices, right? That's what I would want.

   17. HSHarry Stebbings16:07

       So, we're, we're gonna dive into the traits of those reps. Final impossible question, which will likely, uh, lead to it depends. Um, but, uh, 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, when do I hire? I'm, I don't know.

   18. OJOliver Jay16:32

       Number one, I don't know if your first hire needs to, necessarily has to be sales, right? It can... I, I think a lot of times, I'm just gonna say a customer-facing person, right? Could be, could be a little bit more CS than sales, could be very sales eng, kind of, uh, you know, almost like a dev rel kind of a persona if, if you're selling a DevOps product. Uh, but, but I think that is, um, uh... So, so 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. Uh, in terms of timing, I think my answer is a little different today than it would have been two years ago. Because today, capital-

   19. HSHarry Stebbings17:23

       Okay.

   20. OJOliver Jay17:23

       ... is not that big of an issue, right? Like these seed rounds are massive, these series A rounds are massive, and so are the valuations that you have to grow into. They're also massive. And so, like I, I'm just, uh, my answer is assuming that you're not that resource constrained. If you're not that resource constrained, spending that much money to hire like a junior customer-facing person as early as you can is actually would be my advice. Again, not necessarily to drive those revenue, but to get those insights, right? The more customer reps you get-

   21. HSHarry Stebbings17:57

       Yeah.

   22. OJOliver Jay17:57

       ... and, and you talk to, the more you'll learn. Uh, and, um, and I think that should be the approach. If your approach, "I'm just gonna hire, I'm, I need to hire some, a head of sales person 'cause I needed someone to just drive logos and drive revenue," then I might not be as aggressive. But for me, I'm, I wanna be very aggressive upfront about learning insights about the market and my potential buyers. That's why I would hire someone ASAP.

   23. HSHarry Stebbings18:21

       Uh, okay, so we're gonna hire someone really early. I, I embraced a chunky ass seed round at a ridiculous price, so I'm just like everyone else in the market right now. Um, and, uh, I need to hire these first reps. How do I structure the process? Do, (laughs) what does the interview stage look like? Can you walk me through it?

   24. OJOliver Jay18:39

       Uh, well, number one, right, you mentioned process. I think it's extremely important, I think, be- and the reason why is, um...Number one reason I think it's actually, if you, over time, if you care about 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 the right, a process from the start is critical, so that you make sure that you iron out as many potential unbiased, uh, unconscious biases as possible.

   25. HSHarry Stebbings19:12

       Yeah.

   26. OJOliver Jay19:13

       And for that process, I think number, number one, be really clear about what you're looking for. Right? Be really clear about what are the competencies and the behavioral traits that, and 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? All right?

   27. HSHarry Stebbings19:36

       Okay. So let- let's just, let- let's just pause there and go through them. I'm writing as well. We're an early stage startup. We're sub-a-millionaire. What, um ... I know it's difficult 'cause there, there's nuance, but if we think back to those, what are we looking for? What, 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?

   28. OJOliver Jay20:02

       Yeah. So I'm not gonna talk about like the obvious stuff, right? Which is like someone has to be, someone has to-

   29. HSHarry Stebbings20:07

       Yeah. Yeah. Yeah.

   30. OJOliver Jay20:07

       ... like be, be conversative and, you know, be hungry and all that.
4. 27:50 – 32:09

   Sales Compensation

   1. HSHarry Stebbings27:50

      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?

   2. OJOliver Jay28:01

      I'm gonna start with what I think is a common mistake, which is... Okay, the first sales hires they're hiring from Twilio and Amazon, they are on these crazy... Like, 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, and early in your life cycle, I think is very, potentially very detrimental. And it-

   3. HSHarry Stebbings28:25

      Wh- wh- why is that?

   4. OJOliver Jay28:26

      Because, number one, once you put in, like, a sales commission plan, there's, like, a... There's a whole bunch of, like, legal, uh... I mean, you have to sign a legal... Like, there, there are, like, legal, uh, repercussions that are hard to go back on, especially in a time when you're just starting. How do you know how to set targets? You don't have a track record. I can... The, the only thing I can usually guarantee you is 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. So, if I'm going to figure out a commission plan, I'm almost guaranteed to get it wrong, because how do I calculate the commissioner rate? And I can ship two features in the next quarter that changes that significantly, right? So, I think it's just... The... It is something where I would say my biggest lesson here learned is there are many, many, many, many different forms of variable compensation. 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 v- uh, 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. And so, there are many ways. I think it's imp-... 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, to, uh, uh, sort of, uh, earn that variable compensation.

   5. HSHarry Stebbings30:07

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

   6. OJOliver Jay30:10

      Specifically on sales comp? Well, I think it would be a mistake not to, not to give equity. I think sometimes, I- it's... 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 their product can sell itself. And so, you know, why should sales? And, and they're just, like, so incredibly cheap on the equity part.

   7. HSHarry Stebbings30:30

      Mm-hmm.

   8. OJOliver Jay30:31

      Um, huge mistake. And, 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 want to build sales teams, that scale, and you need that customer relationship, right? Uh, that the sales and CS f- uh, team, uh, personnel can help you drive. In my experience, your first 20 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.And these are also the people who you will end up sending as ambassadors around the world to start local offices, right? 'Cause you wanna k- keep in a cohesive culture and such. And so these initial people, like I- I've seen, I've seen situations where, uh, there, it's a, it's more of a transactional relationship between the company and the initial salespeople.

   9. HSHarry Stebbings31:35

      Yeah.

   10. OJOliver Jay31:35

       Salespeople do well, ... as well. That's great. And then they, and then they leave to go to some other company because they don't feel like they're really foundational to the company. So that's the mistake is, like if you lose these in your initial batch, what you have is you have your playbook that you know is somewhat gonna be outdated within the next quarter, and it's really become transactional. Uh, and it's very hard to create that, those deep ties in a, in a, in a team.

   11. HSHarry Stebbings32:00

       Okay. So we've got the right com plan. We've got the right people. We now need to onboard them. And I think, you know, onboarding is something universally (laughs) companies suck and fail.

5. 32:09 – 43:55

   Sales Onboarding

   1. HSHarry Stebbings32:09

      When we think about ideal onboarding p- processes, what does that look like in your mind? And what would you advise me when it comes to onboarding new sales reps?

   2. OJOliver Jay32:21

      And we're talking about like, you're still at early stage. You're hiring-

   3. HSHarry Stebbings32:24

      Not early stage. I am series A seed.

   4. OJOliver Jay32:27

      Yep. Okay. Uh, I would sequence product knowledge first and then sales knowledge, right? You know, kind of like, and then, uh, s- so I would do product first, market fir- second, and s- sales last.

   5. HSHarry Stebbings32:44

      Okay.

   6. OJOliver Jay32:44

      So product first, right? Like in the beginning, you're not gonna have a full-fledged sales team where you have SEs, sales engineers who can, you know, handle the technical things. You don't even, you may not even know, um, you may not even know what, what pro- what gotchas you have in your, whatever data model your company was built on. So in the beginning, I think it's super important that like whatever customer-facing people you hire, they, they have to play that role. They have to go two or- two orders of magnitude deeper on the technical side of the product, whether it's talking about the security, the infrastructure, you know, with like a, a CSO or a CIO, uh, than, than kind of your feature As, right? And so I think in the beginning, really important to, to, to build that product knowledge. Uh, a lot of times the best way to do that is actually get the, get the team exposed to support because the tickets that you get coming in is basically a reflection of li- your likely sales obstacles that you're gonna get, right? And so you want to be able to talk about it, understand, number one. Number two, the market, like I, I-

   7. HSHarry Stebbings33:55

      So, so, so just, 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 s- dumb question.

   8. OJOliver Jay34:04

      Uh, I actually say is n- is less product in the beginning. It's actually more you start with support-

   9. HSHarry Stebbings34:10

      Huh.

   10. OJOliver Jay34:10

       ... because everyone's gonna be filing all your bugs. Then you, you as AA go, go get some answers. Understand like not just how we answer it. Like, go and find the engineer to understand why things are built a certain way, right? That's how I would actually have it is like figure out what the, what will likely be your most more difficult product questions, and you go find the answers-

   11. HSHarry Stebbings34:38

       Gotcha.

   12. OJOliver Jay34:38

       ... 'cause you don't have a playbook yet. Right?

   13. HSHarry Stebbings34:40

       Gotcha. Okay. So then we, we put them in support. They understand from the tickets and from the knowledge they get from the feedback. Then market.

   14. OJOliver Jay34:47

       Yeah.

   15. HSHarry Stebbings34:48

       W- what do we do for market knowledge? How do we ad- an- educate them there?

   16. OJOliver Jay34:53

       Yeah. So that, that is like, that to me is probably like at this point probably going through your fundraising deck.

   17. HSHarry Stebbings35:00

       Huh.

   18. OJOliver Jay35:01

       Right? Because at this point, you probably don't have a sales pitch.

   19. HSHarry Stebbings35:03

       Hmm.

   20. OJOliver Jay35:04

       I mean, I, I, I remember at Asana when I joined it, when I joined Asana we had 20 million in revenue, mainly driven from our self-service business, right? And, uh, there was no, we didn't have a, we didn't have a sales deck. Okay? So, so it's very common that you don't. And so at that point you, you're probably taking your fundraising deck, right? And you're just like educating on like here's, here are the players. This is what we're trying to s- this is, you know, here are, here's the competition, right? And you, that, you're kind of like ba- getting your one on one that way. Why I think it's important to do market first is, uh, I, I think it's, well, put it this way. I want to put the sales stuff last because that's the stuff that like you will d- the, the, 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 gonna be there. Plus, I actually think that s- people are, will be, uh, higher performers if they actually understand broadly what's happening. What's, what are the drivers, right? 'Cause you wanna 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? Uh, that's why.

   21. HSHarry Stebbings36:22

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

   22. OJOliver Jay36:39

       Yeah. My, my guess is if you're hiring your first couple people, right? Y- th- it is like you're, you're, you're shadowing the founder-

   23. HSHarry Stebbings36:47

       Uh-huh.

   24. OJOliver Jay36:48

       ... on couple, uh, conversations. I think absolutely you go talk to your top 10 customers and you develop a relationship there. I mean, these are probably pretty friendly customers. And, and really ask like, "Hey, w- w-" You start asking like the questions in, around like, "Hey, how," you can even ask a customer like, "H- like, w- we haven't run a case study yet, but like how, how would you quantify the value that we've provided to you?" Right? Uh, you, you probably have to do that because no one has done that yet, if they hasn't done that. So you basically shadow the founder for a little bit.Um, and then what I do is I- it culminates for me. This is where- where I mentioned a demo earlier. Like, you may not need to do a demo during an interview process. Absolutely, I want someone to demo the product at the end of whatever onboarding period you designate as reasonable. Um, and it is in this... And like this is kind of like a- the equivalent of a PhD defending their thesis for me. You're coming in, you're gonna d- you're- you're going to present your demo of our product, and we are going to actually role play. And- and- and I invite... It would be like, you know, if I'm the founder, right? That would be found- one founder, it would be a PM, right? And like whatever the other peop- the other two, three people you- you have in the customer facing team. So it's high stakes, right? 'Cause you gotta get... If you can't even like present to your own team, you forget about customers. So it gives, it's, 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 the you're- you're- you're buying, right? You're trying to imi- you're trying to role play. So like someone's like the CISO, someone's the CIO, someone's the actual champion. Uh, and- and you see how they, you know, you- you see how that acts. Um, and that's basically a certification process.

   25. HSHarry Stebbings38:38

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

   26. OJOliver Jay38:49

       I'm just like, I have to like go back in time to think about this super early stage, right? I feel like two months is reasonable, uh, at this stage to- to get to, hey, 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 good flow of, reasonable flow of inbound, or you're an open source company where you can like sort of tap into a community, I- I think, I think within- within- within three weeks, they can start talking to customers. They may not, they may not need to be selling, right? Because like, again, I just wanna hire some c- 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 don't you like about the product? What's your issues?" Right? Just like, get more reps. I do think it's important to get- 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 diff- one difference between PLG company and non-PLG companies. You can actually start doing that, uh, and it helps with accelerating their ramp.

   27. HSHarry Stebbings40:01

       Uh, you mentioning the difference between PLG and non-PLG. You know, in terms of for new reps, um, often when it's PLG, they just have a lot of inbound to- to service, and it's- it's a lot more on a plate bluntly. When that plateaus, 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?

   28. OJOliver Jay40:23

       Yeah, yeah. I see this pattern everywhere. Uh, so let me just start by saying this. Like, I love PLG. I breathe and bleed PLG. At the same time, I love outbound. Outbound's way easier. It's like, it's like, I- I love going outbound, okay? But I think going out... For outbound to be successful, generally speaking, you're selling to a different buyer, probably a more senior persona. You're probably selling a different value. Uh, 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 up for that, your deal size needs to be commensurately bigger. And generally speaking, that will require a different type of talent to execute that. Okay? So what I see a lot happening is sometimes people's initial inbound thing goes, it's, you hit that S-curve, it's amazing. And then suddenly it just like starts plateauing. You're like, "What the heck's going on?" I don't know. The answer I always hear is, "Well, we're just gonna start going outbound now." 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, right? Converting at a higher speed and a smaller deals. So if you want to go outbound, I'm all for it, right? I say, but what you need to do is you gotta make sure your marketing team is aligned, right? To actually generate and work with you to develop the right messaging for this different persona. Your product probably needs some augmentation to- to sell a bigger deal. So if you're gonna go outbound, just make it comp- a company in- initiative, not just hire some salespeople to go outbound, because I don't think it's gonna work. I don't think it's gonna work. Uh, and so that- that- that's what I mean. Um, I- I- I... A- 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." It- it's- it's 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," right? What else can we do to drive more inbound, right? I mean, is it, whether it's how can you generate more word of mouth? How can we have a more performant, uh, uh, conversion, you know, converting website, you know, whatever that is, I mean, there's-

   29. HSHarry Stebbings43:05

       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."

   30. OJOliver Jay43:17

       Yeah. Like just bec- I would say this, like yeah, exactly. Just because you see some signs of initial like, like plateauing of- of- of your initial PLG playbook, right? For the company...... doesn't mean that it's ... The party's over, right, and therefore you need to go outbound. Like, that's like the last thing you should do, because it takes so much to, company-wide, to make it work.
6. 43:55 – 45:46

   Head of Sales relationship with the CEO

   1. HSHarry Stebbings43:55

      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?

   2. OJOliver Jay44:05

      Yeah, uh, my relationship with the CEO is super important, and for me it's, it's one of partnership, right? Like, I, my job is to bring in, I gotta bring in the, I gotta bring home the bacon. I gotta get, get the cash in, right? Get, I get that. But there's a bigger play here, which, that, that I, I have in my head which is, I see one of, 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 need to, I am responsible to bring back the right amount and type and in the right form of feedback, right, uh, to my CEO, so that he or she can make the best decisions.

   3. HSHarry Stebbings44:55

      Mm-hmm.

   4. OJOliver Jay44:55

      It's my responsibility to make sure that I and my team don't have recency bias, right, based on the last deal that wasn't able to close. Like, I, it's my job to tell, make sure that the CEO knows what's working and what's not working, for the purpose of his or her decision-making. And so, uh, I think that's really important. I s- I, and, and to do that, um-

   5. HSHarry Stebbings45:17

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

   6. OJOliver Jay45:22

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

   7. HSHarry Stebbings45:26

      Okay.

   8. OJOliver Jay45:27

      Minimum. Yeah. I mean, at the end of the, in, in the early stage I think it, it ought to be quite frequent. And if you're not, that means that you're just not getting enough, uh, you're not collecting enough learnings and insights for your CEO.

   9. HSHarry Stebbings45:44

      Can I ask-

   10. OJOliver Jay45:44

       That's how I would see it.

7. 45:46 – 49:33

   Postmortem Reviews

   1. OJOliver Jay45:46

   2. HSHarry Stebbings45:46

      ... do you do deal r- do you do deal reviews and postmortems, and if so, how do you structure them?

   3. OJOliver Jay45:53

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

   4. HSHarry Stebbings46:27

      Wh- what are Five Whys?

   5. OJOliver Jay46:29

      Five Whys, like when something goes wrong.

   6. HSHarry Stebbings46:31

      What are the Five Whys?

   7. OJOliver Jay46:32

      Basically saying when something goes wrong, you wanna get to like the fifth level of, "Okay, why did, why did this fail? Oh, because someone messed up. Okay, well why does the person mess up? Well, because this person wasn't trained well enough. Well, 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 the, the, the, enough bandwidth, and so we deliberately chose to prioritize something else." So, it's important to, when you do this postmortems, you really understand if something doesn't go well, right, really like why you lost a deal, there usually are multiple layers, um, as opposed to what you normally first hear, which is that like, "Oh, uh, bad timing. Bad timing. Got pushed to next month." You know, you hear that-

   8. HSHarry Stebbings47:28

      What's, what's the answer to that one? Because I often, I often have this where it's like, "Ah yeah, they pushed it. Not a priority. Bad timing." How do you respond to that? What, why is it bad timing? Like, w- what would you respond?

   9. OJOliver Jay47:39

      Why is it, why is it, why is it not urgent? And you normally, normally we just end there, because normally the, the, the, the rep may not actually have the answer. Right? "Oh, why is it not urgent?" Well, they think that it is the, it is the, uh, always the responsibility of the customer to, to, to make timing work. But, hey, it's also part of our job to try to create that urgency. Right? And so you j- it, it's ... 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, you will, through that process, find one or two big like core root problems that you can address.

   10. HSHarry Stebbings48:27

       Uh, my, my, and fi- final one, my favorite is, um, we lost our champion, so there was nothing that we could do internally. It's just that, you know, the person who wanted it left. How would you like analyze that with the five whys? Like, why didn't we have a broader base of supporters?

   11. OJOliver Jay48:44

       Yeah. Well, yeah-

   12. HSHarry Stebbings48:44

       Exactly.

   13. OJOliver Jay48:45

       ... exactly. Like some, some ... Yeah, you know, start, I would start with like, "Why did this person leave?" Sometimes this person left, you know, and, and, and you realize that you were actually always talking to the wrong person. So when you, right? "Okay, why didn't we have more gen- why weren't we multi..." Multi-threaded is the, is the lingo. "Why weren't we multi-threaded in this account?"

   14. HSHarry Stebbings49:03

       (laughs)

   15. OJOliver Jay49:03

       Right? Uh, "Oh," usually it's like, "Oh, we just, you know, did we ..." Usually it's just like, "We didn't get to it." It's usually thing that we get but, but, but then, and it stops there. But it's interesting to be like, "Well, why didn't we get through it?" It could be that, "Oh, well, we didn't get through because we have so many friggin' accounts." Right? 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."

   16. HSHarry Stebbings49:30

       I love it. Um, listen, I could talk to you all day,

8. 49:33 – 54:17

   Oliver Jay: AMA

   1. HSHarry Stebbings49:33

      OJ. I wanna 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?

   2. OJOliver Jay49:40

      Yeah.

   3. HSHarry Stebbings49:41

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

   4. OJOliver Jay49:47

      The need to articulate the... your, your business impact and value.

   5. HSHarry Stebbings49:53

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

   6. OJOliver Jay49:59

      Emails.

   7. HSHarry Stebbings50:01

      Expand on that.

   8. OJOliver Jay50:02

      Emails. Cold email. Uh, I, I think this idea... Like, the, the predominant motion now is, I'm just gonna blast email, you know, a bunch of people, see who responds, you know? I mean, this starts even with like, ear- early days of 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 r- read my white paper." Like, I, I don't... I just don't believe in that anymore. I don't think people download white papers and, and do that anymore. Like, there, there's way too much rich content and information in the... on the internet now. They're reviewing different products, like, no one's gonna be doing that anymore. So, that whole, like, MQL to PQL... to MQL to SQL, all that, I just think that's, that's done.

   9. HSHarry Stebbings50:50

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

   10. OJOliver Jay50:56

       I think the mistake is not investing much in thinking about the bridge between the, the customer facing teams and the product teams.

   11. HSHarry Stebbings51:06

       Mm-hmm.

   12. OJOliver Jay51:06

       Like, thinking through how does the voice of customer gets captured, brought back to product. Uh, and to me, I think companies should spend as much time on that as they should on, like, their, their sales playbook.

   13. HSHarry Stebbings51:21

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

   14. OJOliver Jay51:25

       Well, today's environment's really tough for new sales leaders. Because a- it almost... 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 grow. You need to prove, uh, progress very quickly. So with that context, today I would say most sales leaders forget to manage up. Most sales leaders who come in, they focus so much on building their own team, writing that playbook, um, you know, 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 wanna succeed.

   15. HSHarry Stebbings52:11

       Now-

   16. OJOliver Jay52:11

       And managing up doesn't mean, like, managing lower expectations. It just means, it just means you make sure your dialogue with the founder, CEO and the board is, um, is, is really clear.

   17. HSHarry Stebbings52:23

       Final one. What one company sales strategy have you most been impressed by over the last couple of years?

   18. OJOliver Jay52:35

       Hmm. I, I need to get back to you (laughs) . I've, I've been so focused on Asana, I have not explored outside that much. Um-

   19. HSHarry Stebbings52:52

       We can switch it up for a different one, which is, what would you most like to change about the world of sales?

   20. OJOliver Jay53:01

       Uh, what would I change? I think sales... still, today, when people think of sales, they still have this picture of some, some used car salesman image. And I think salespe- what salespeople do at the core is they help customers solve their problems. They happen to do that sometimes because the pro- your product actually does that really well, right? 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 go about it differently. And so, I think a lot of times in tech, frankly, I think salespeople are second class citizens, uh, because they're not building product and all that. And I think... I would love to change that. Because I think the best companies are, are, are the ones where sales, collecting customer feedback, working with customers directly, are on equal footing with the, uh, with product.

   21. HSHarry Stebbings54:08

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

Episode duration: 54:17