YouSaid · the spoken record

Oliver Jay

lines on the record: 44
first: 2022-05-25
most recent: 2022-05-25
sittings or episodes: 1
sources: podcast

Every line below is reproduced as it was said and linked to the record it came from. Nothing here is summarised or generated. Directory · Search · Corrections

“Well, today's environment is really tough for new sales leaders because you're almost certain going to be walking into a situation where you have a valuation that is probably three years ahead.”
2022-05-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“I think the mistake is not investing much in thinking about the bridge between 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.”
2022-05-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“I think the predominant emotion now is I'm just gonna blast email a bunch of people, see who responds. I mean, this starts even with early days marketing automation, with like Marquetto and stuff like, oh, this person clicked on my link. It must be really interested. You know, oh, they read my white paper. 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 internet now. They're reviewing different products and no one's going to be doing that anymore. So that whole MQL to SQL, all that I just think that's done.”
2022-05-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, exactly. I'll start with why this person leaves sometimes this person left and you realize that you were actually always talking to the wrong person. Okay, why do we have more time? 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 like, oh, well, we didn't get through because we have so many friggins. 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.”
2022-05-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 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 Y's 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.”
2022-05-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“I was like when something goes Basically, saying, when something goes wrong, you want to 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 post-mortems 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.”
2022-05-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Deal review is for sure every week we have deal reviews even when we're really really small and usually you have a qualification framework and you kind of go through it and usually in the early stages everything is like unqualified but it's good to have that rigor to start postmortem Asana we had a practice called five Y's is adopted from Toyota that I think is very effective it's a practice where”
2022-05-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“An early stage, I would hope it's a weekly thing minimum. 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...”
2022-05-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“My relationship with CEO is super important for me, it's 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 response 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.”
2022-05-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, exactly. Just because you see some signs of initial 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.”
2022-05-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, I see this pattern everywhere. So let me start by just saying this. Like, I love PLG. I breathe and bleed PLG. At the same time, I love Alban. Outbound is way easier. I love going.”
2022-05-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“I feel like two months is reasonable at this stage to get to a point where they're really, really solid with 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 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 be 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. You can actually start doing that and it helps with accelerating the ramp.”
2022-05-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“And like the other two, three people you have in the customer facing team. So it's high stakes. You can't even 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 your 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.”
2022-05-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“My guess is if you're hiring your first couple of people, you're shadowing the founder on a couple conversations, I think absolutely you go talk to your top 10 customers and you develop a relationship there. These are probably pretty friendly customers and really ask like, hey, you can even ask a customer. 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 they hasn't done that. So you basically shadow the founder for a little bit. And then what I do is it culminates for me. I mentioned a demo earlier. Like you may not need to do a demo during the interview 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 the equivalent of a PhD defending their thesis. Coming 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 be one founder, it would be a piece.”
2022-05-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“That to me is at this point probably going through your fundraising deck because 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 of 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 101 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, but let me just educate you on the market. Like you just the absorption is not going to be there. Plus, I actually think that people are will be higher performers if they actually understand broadly what's happening. What are the drivers? Because 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”
2022-05-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“I actually say it's less product in the beginning. You start with support because everyone's going to be filing all your bugs. Then you as an AEA go get some answers. Understand 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. It's 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.”
2022-05-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“We're talking about you're still early stage. So I would do product first, market second, and sales last. Product first. In the beginning, you're not going to 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 a CIO, then kind of your future A's. 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 because the tickets that you get coming in is basically a reflection of your likely sales obstacles that you're going to get. So you want to be able to talk about it, understand number one.”
2022-05-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Where it's more of a transactional relationship between the company and the initial salespeople. Salespeople do, well, company as 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. It's like if you lose your initial badge, what you have is you have your playbook that you know is somewhat going to be outdated within the next quarter and it's really become transactional and it's very hard to create those deep ties in a team.”
2022-05-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Specifically on Sales 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 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 that does 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. And these are also the people who you will end up sending as ambassadors around the world to start local offices because you want to keep a cohesive culture and such. So these initial people I've seen situations.”
2022-05-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 in 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 at Learn is there are many, many, many, many different forms of variable compensation. 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.”
2022-05-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“I'm going to start with what I think is a common mistake, which is, okay, the first sales hires I was 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.”
2022-05-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“They're going to do great. But on the fly, that's something you can work on. I like to kind of 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 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.”
2022-05-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“My first step is I'm going to map out the competencies. Generally speaking, you're not going to be able to optimize for like 10. In fact, 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, no one's super polished. There are some people who are super polished, but they may not actually be that good. So I want to give people a chance and see how do they act if you give the time to prepare. Someone may bomb their on-the-fly interviews, but they may crush their prepared demo. It doesn't have to be 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 train,”
2022-05-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Just tell by the voice how they communicate it. That is to me a sign that while this person is someone who really cares about making people around them better.”
2022-05-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“I asked for a real example. I was gonna give you an example. So if you're a leader, I always ask, I'll let you 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 manufacture something that seems okay. But again, this is one where, again, you can tell by the passion. Someone 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 read. And then I asked 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 Huey when we were working at Dropbox together. Anyways, 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. And the people you want are people who take it personally. It's a personal failure of mine, they 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.”
2022-05-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Number two, if you are expecting this person to really build a team in scale and 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 an 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.”
2022-05-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, what I'm looking for at 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 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 logistics. And you'll see, is your 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.”
2022-05-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2022-05-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Well, number one, you mentioned process I think is extremely important. And the reason why is number one I think is actually if you over time if you care about diversity on your team, you want to 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. In terms of that process, I think number one, be really clear about what you're looking for and be really clear about what are the competencies in the behavioral traits that 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?”
2022-05-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 a hire as a head of salesperson, because I needed someone.”
2022-05-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Number one, I don't know if you're first hired needs to necessarily have 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 CS than sales, could be a very sales engine, 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. My answer is assuming that you're not that resource constraint. 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”
2022-05-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2022-05-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, gosh, I would love to talk to Jason Live about this and kind of understand exactly what he had in mind. There were elements 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 where it's so hard to hire good people, if you can bash them great, lots of benefits, onboarding, you can actually kind of have basically A-B tests. 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. 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.”
2022-05-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 fast hiring scaling path soon in the near future. So hire good 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 got to learn. What should be your motion? Should you go enterprise? Should you go top down? Should you go bottoms down? Up? Should you go middle down? Up? Only after that will you actually know what to look for in ahead of sales. I think it kind of depends on your category.”
2022-05-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“I would say, look, you need to start with something. For the founder, have gotten enough traction to have raised a seat 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 playbooks 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 going to 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, a 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. Every week, how can we make kind of a V1 playbook better?”
2022-05-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“I rather focus on instead of like, hey, trying to get people to write up some playbook, hey, actually be really nimble. This month we're going to focus on answering these questions. For example, let's focus on a wish persona actually resonates most with our product. Does our product resonate with most? And later this month, let's do a deep dive and sprint and really focus there. Take that learning. All right, 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't. Some probably not so much. Okay, after you answer these questions, then you can piece it together. Then it's very, very obvious. That's what I mean by agility. When I'm hiring my first leader or first couple people, I'm not telling them to come back with a playbook. I'm telling them to come back with learnings and insights.”
2022-05-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, so the second thing around basically you're selling process, the repeatable 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 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 playbook word is one that I just think has all these connotations associated with it. And I think like you just have to be practical. Like the reality is in the first your first two AEs, there is no playbook. Your higher 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 repeatability I rather focus on agility”
2022-05-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Like you can figure that out later. It's not rocket science. The harder part is that who you sell to and what are you selling?”
2022-05-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Yes, that is a play, but I think that's the second playbook you built. 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 a 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 it into your product and eventually get to your product market fit. So to me, that is higher order priority. 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.”
2022-05-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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. This P word. I sometimes don't even want to use it because it means different things to different people.”
2022-05-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 and 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 tick 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 decision to not have sales, you're just missing out on a lot of potential growth.”
2022-05-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“We pioneered and we try to do both at the same time. And I think the results were quite positive. And I think my takeaway is that it is positive. It's hard, but it is possible.”
2022-05-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Dropbox, I think, for me, number one, is technology is just fundamentally adopted differently in businesses. B2B 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 in probably around 2010 when people had this BYOD move and Dropbox was the company that shattered and started the BYOA move. 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. And I think what I learned at Asana was if I had to pick one thing, it would be this concept of product 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.”
2022-05-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“First couple years of my career was in finance. I was first starting equity research at Morgan Stanley 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. And 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 we 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.”
2022-05-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source