Sales Playbooks that Land Investment - The Formal Discipline Investors Expect to See

Automated Transcript

Alastair Cole 0:08

Hello and welcome to The Sales Scoop. This is a weekly live show for the founders, and senior leaders of technology businesses who want to improve how they sell. My name's Alastair Cole. I'm a computer scientist and a software engineer with two decades experience in sales and marketing, and I'm delighted to say that I'm joined today by my co host, Kiran Gill. Hi, Kiran.

Kiran Gill 0:38

Hello, everybody. Good to speak to you. My name is Kiran Gill. I am the co-founder of the operative partnership. I've got 25 years worth of experience now in sales ops. I've done many different roles, mainly in corporate finance and in sales operations in big tech.

Alastair Cole 0:59

Thanks, Kiran. And I know you're a busy, very busy man on camera for most of today, so we're delighted to have you with us today and share your expertise. I mean, both of us are heavily in sales playbooks at the moment, both creating new ones for clients and amending and taking sales teams through existing ones. So it's a really, really great topic that we're talking about today, sales playbooks, and specifically their ability to land investment. For anybody watching live on LinkedIn, please feel free to leave us a comment. We'll see if we can get to it today. So I mean, sales playbooks, you know, you might think that they are, you know, just a boring document in their original format, but so much more than that. What's your experience, my friend, in terms of the importance of sales playbooks for businesses.

Kiran Gill 1:56

The thing is, it depends on the kind of sales organization you are, the more complex. I think the sales playbook tends to be very, very fundamental to the way your business is run. If you're more of a SAS business, it's tiny. Kind of changes the product. The Playbook kind of changes. But pretty much it's fundamental. It's a cornerstone to your business. And also, if you want to land an investment, it shows clearly to the investor where you're spending your money, and how you're doing. How will you do what you will do with their money? And how are you going to make money for them? Basically,

Alastair Cole 2:34

yeah, I think that bringing the investors straight in, we see such a connection between the discipline that is brought through, you know, really robust sales practices with business and investors landing money. We're averaging 1.3 million pounds raised for all of our clients over the five years. That uplifts have been going so we've had a number of successes, and often there's been a you're able to draw a line directly from the investment round to the sales playbook, and one of our clients said that it sealed the deal for them on a $350,000 investment. So it's a really, really big deal. Your playbook sits for us as one of the five core foundations of being a confident founder seller, you know, after assessment and strategy. So it's, it's absolutely critical. These eight areas are actually part of our white paper, our 12 page white paper that we'll touch on later. But sales, that playbook is a really important strategic element. And there's so many, so many things that go into it, and we want to touch on as many as possible. We're going to break it down today into three, three big things. One, the sales playbook as the cornerstone of your sales engine. Number two, how to keep it simple and friendly, right, so that it can be a working document. And three, the third area is that, how to make it a living document that isn't just made once and then and then, never referred to, never updated or never used again. I don't know if I want to put you on the spot and hear any kind of bad or good examples. You've got Kiran from people who you know didn't have a playbook or hadn't had an absolute killer one, and it was a massive success for them. Any stories from the trenches, from you on, on, clients past or present? Yo,

Kiran Gill 4:28

The client's past is there was a client that I can remember not too long ago that had a playbook and hadn't revisited it for a long while, and you know, they dusted it off and had a look at it. And tell you the truth, it wasn't actually worth the paper it was printed on because it no longer was. It was no longer current. It had no understanding of what's happening. And the weird thing is, actually, if you do have a sales playbook at the moment that. Answers are, it is already outdated, mainly because of what's happening in the market at the moment, because everything is constantly changing. And that means, potentially, the customer that you're selling to is constantly changing, meaning that your ideal customer profile, your metrics, all the things that you've got in there, the way you're selling to these people, everything's constantly changing. So your playbook, realistically needs to be always changing with you and clients get, you know, a lot of our clients do get caught at by this. Yes, I've got one. When was the last time you looked at it? Three months ago? Probably not good enough any longer.

Alastair Cole 5:36

Yeah. And, and, you know, we, the playbooks that we create are often 3040 pages long. And obviously there are ways to, you know, accelerate the creation of that content. But ultimately, you're talking about defining some really key things, you know, business basics, the sales strategy is front and center in that document. You know, including numeric targets and growth plans, the sales playbook should have, you know, deep target market analysis, value propositions. You know buying journeys and definitions, competitor analysis. You know your processes and methodology, the team, other documents that you can refer to. So it's really, it really should be the, the cornerstone, right, the cornerstone of your sales team, your sales HQ, and it's about like real world usage, and like you say, keeping it updated. One of the things we talked about there was target market analysis and buyers. What kind of you know, what kind of detail would you expect a playbook to go into? If it is to be the cornerstone in terms of target market and ideal customer profiles, what should be in there? Well,

Kiran Gill 6:46

fundamentally, like you said, I think the market opportunity or an understanding of what the market is for that playbook. Now, if you're selling complex IT or solutions, or whatever it is, and to multiple markets, your playbooks are probably going to be fundamental, because it's going to be a lot bigger. However, remember, it has to be a usable document for the person who's looking at it, so parts of the sales playbook probably won't get touched as much. So your IT stack, probably will stay the same for 12 months, and there's no need to update that, and there's no need for that to be overly living. However, your sales process, your demand generation, part of the book is continuously changing. So the major thing here is to remember that parts of it probably will be static. Parts of it will be very organic and constantly changing. But somebody needs to take ownership, and that's where the problems tend to be. Somebody puts it together and then never touches it again, or passes it on to somebody else who never really cares about it, because they never developed it. So there has to be a handover, and there has to be ownership, and I think that's key when it comes to a document like this, because otherwise it just turns into another document that tells you the truth, just sits in another shared folder that no one ever opens ever again. Yeah,

Alastair Cole 8:06

and we'll get on to how we make sure that it's, it is opened regularly and used regularly, but, but you're right. It's really about the journey. It isn't really about the document. It's really about the time that people invest in, in work, collaborating together to get to the answer, and then having it defined right, people contribute. And then that becomes the single source of truth for your sales strategy and your plays. And people must be encouraged to, kind of, like, go back and use it right. It should be the single source of truth. Your kind of sales, HQ, and you know, that's where, you know, given the number of buyers that are involved in a B to B deal, now they need to be mapped. They need to be defined. You know, buyers need to have their definitions really clearly written down in the sales playbook, because the detail is critical. You know, almost 90% of B to B buyers expect to be delighted before and after purchase, right? So if you, if you haven't written down exactly who you're going after and how you're going to get to them, then you're, it's very unlikely that it's going to be a kind of quality outreach or a quality message or a quality document. So that detail is really important. And also in that cornerstone document comes the value, right through the value propositions and other information, the value that your offering brings. And you know, HBr is very clear that it's a 30% likelihood of a higher quality deal where you're able to clarify the value. And we all, we all know this in sales, right? The better you can articulate the benefits that solution is going to bring, the more likely you are to get a quality deal. So it is the cornerstone is, is really, really important before we skip on to the next, the next stage, which is how to make it simple and friendly the document and. Which you know has many, many pages, and you know can run to 50 or 60 pages. And like you said, parts of it are more static. Other parts of it, like your sales strategy and your ICPs, are moving quite regularly, right? As you, as you come as things don't work or you need to change, you come back to the playbook. We're talking about playbooks that land investments, right? You're our finance and investment specialist. While we've got you, could you just run through quickly your take on kind of early funding rounds for the kind of tech businesses that are looking for investment?

Kiran Gill 10:35

Yeah. So if you're if you've got a playbook, or if you're developing a playbook, depending on where you're looking for investment, I would expect it to be in a different kind of estate. So if you're pre seed, the chances are you're still trying to figure out whether your product has any product market fit. There's probably you've got the initial investment and understanding how big the market is, there's competition in there, and you know you're at that point, your playbook probably isn't overly defined when it comes to the seed round. By that time, you really should know who your customer is, what your product actually does, what problems does it solve? Who is, who is the competition, what your sales process is, and realistically, what you're looking to do there is scale, and that's where you're probably going to be asking for quite a generous amount of money from the investor to start thinking about scaling your sales operation in your market operation. So that's where your sales playbook becomes critical earlier in the pre seed point. I'd say it's probably less likely. But when you then look at series A and when you're getting into that point, your sales playbook needs to be reading like a hymn sheet by that time, because if it's not, it's a red flag. Let's beware, because it's pretty much the document that any investor is going to hold you to account, and they're going to look at you and say, Hey, this is what you said. It was going to happen. This is what's happening. This is where the book is. This is what the deck looks like. This is what you've said to me, what was going to happen? What? Where did you go wrong? What's happened here? So,

Alastair Cole 12:05

yeah, and you know, the playbooks a playbook that sits at the heart of your organization, right? That needs to be simple and friendly and easy to use. And we're going to come on to that in a minute. That obviously isn't something that you're going to, you know, present to investors. What that is, is, is your kind of investment deck, really, which is the kind of distillation and the presentation of a lot of the information and the thinking that's in the playbook. But that is, that's something that we produce as well, and that helps our clients raise, you know, 1.3 million annually. So let's, let's skip into the second section, right, keeping it, you know, in order that it's reused. How do you keep it simple and friendly? You know, it's something that needs to, you know, be accessible, easy to open really quickly, you know, plain language, written, mobile, friendly, you know, ideally, and a tone and structure that makes it usable and inviting. What are your what kind of tools of choice for the playbook? Kiran, what would you recommend somebody if they were looking to up their playbook game? Where should that sit? What kind of tools would you use?

Kiran Gill 13:14

So theoretically, it should be in a shared folder that everybody can get to different levels of access within the shared folder, certain parts will be accessible to all, and especially if you've got a low level sales team or a BDR team or SDRs who need to make sure that their messaging and everything, this is probably going to be a part you know, this potentially could be just PowerPoint, but it's all going to be a part of the main document. Certain parts of the strategy, you're probably not going to open that up to all the team members that's going to be again over to other places. So a central document that is kind of sliced up into places that different people can work on and should have ownership over your value propositions, and also when it comes to your kind of market definitions and all your kind of understanding of your ICPs, maybe your marketing departments working on this sector, and they have that ownership, and they also have a look at this. Like I said, overall, there needs to be one person who's looking at the whole thing, smaller the company, more sections that you're probably overlooking, larger the company, smaller the sections you're looking after. But it needs to be somewhere. That is, it's not static. It's a living document. It needs to be I, what I would want to see is the last time that document was opened was yesterday. So it's very easy to see on a share, on Google Drive, or on Microsoft SharePoint, or wherever you're going to keep it. It's very easy to see when somebody last looked in it. Another major red flag for me when I go into look at companies, kind of sales playbooks, or whatever they want to call it, sales plays, or different words for different companies, is when you know that it hasn't been touched for several months and you're thinking, Hmm, I wonder how you're doing that. Then, if no one's looking at this,

Alastair Cole 14:59

yeah. And that's interesting you talk about, you know, a range of documents, because it can get unwieldy when there's too much in there. And there is a right moment when when sections or other documents come out and and often at the back end of the the sales playbooks that we create, there are links out to other things, you know, marketing strategy assets that you can go and get. So not everything needs to live there. And ideally it needs to be quick to open. You know, I think our preference probably is a Google as a Google Drive Doc, you know, quite simple. Okay, it might not look that, you know, fantastic, but that opens fast. It's quick to update. Everybody can see it. And the complexity, additional complexity can go elsewhere, right? It is. It's possible to move, move things out. And you know that it's really about the details. One of the big areas that we help define is the right funnel mix for businesses, you know, across cold, warm, outreach in real life events and inbound, and put down the metrics and the details and the plays for how we're going out to those different, those different bits of the funnel, so that that's a really, a really core area as well, in terms of, you know, keeping it simple and friendly. It's a challenge, right? But like you say, it's about when people used it recently. And I think, like most things, it's about trying to build a habit, right? And habit stackings in a kind of James clear way, right? And getting into it on a daily basis. So it is, it is a journey right to make it together, but it has to be a living document. And you've touched on some of those, some of those things. What kind of cadence would you like? Would you suggest, not in terms of looking at it, but in terms of reviewing that document in sections or overall. How often should it be? You know, should somebody take a step back and have a look at how the document is?

Kiran Gill 17:08

Well, if you're looking at the metrics, I think probably weekly is where you need to be, and that's where, because your metrics are going to be telling you whether your sales playbook is actually working. You know, are the plays that you've got in there being executed, if they're not being executed, where things are going wrong. So that for me as a sales manager, that's where I would be living. Maybe my metrics are going to be on my CRM, however, my overall metrics, the metrics that I've been set for this quarter, this year, whatever it is, where, however you're looking at your your your your metrics, that's where they're going to be. So am I hitting the numbers I'm expected to hit? Are my numbers off? If they're off, why are they off? Is it because I didn't understand my market properly? Is it because we haven't got enough sales people? What is it, you know? So this part of the sales doc, the sales playbook, I would be living in other parts, such as the value proposition and the messaging, probably not so much, because once I've got the messaging out there and it's been created, I'm going to have that in my own CRM or in my own email, wherever I'm going to keep and I'm going to go keep that messaging to myself as a salesperson so and I only need to go in there Every so often, if marketing suddenly alert me to say, new value proposition, new messaging involved, new documents here for you to download, to send out to you. So you need to think about how you're going to use this. And it comes back to how many people are going to be involved in this document. Because the more people involved in the document, the more likely it might become more unwieldy and harder to use, because you've got different authors doing different things. So everybody needs to have a very clear designation of what they're doing and what they're actually, you know, what's their kind of remit in the book itself? So you try to make it easy for yourself to understand who does what and when they should do it.

Alastair Cole 19:03

Yeah, and like you say, there are challenges, right? With lots of people having access, and people with different levels of access, that is hard, which is why it's good to keep the format simple, so that it's easy to use. But really, that's where the juice is. I mean, the number of times where you and I will have it open in different locations, and we'll start writing a kind of new thoughts, new ideas that kind of expand, and they grow and other people comment, and then either that becomes its own kind of element, or it gets, gets, you know, gets exported into something else. But it's often the place where we are because it's the HQ for our sales strategy and all the definitions of our of our buyers, that's often where we go. And, you know, start tinkering and start making new stuff. So it must be a highly collaborative document, and that makes it easy. You know, rather than opening something fresh is because you can refer up and down to, you know, previous strategies go to more. Market strategies, ICPs and all that good stuff. So, you know, I mean, look at, back at our notes that we recommend for clients. It's about, kind of almost keeping it open, right? Really, almost keeping it open in another tab. Certainly, when you open a tab and you try and get to it, you know, it should, it should be recommended by your browser as something that you're going into regularly. And it should be almost that, that kind of the playbook that's just open permanently, that's good habits, right? Not always possible. But, you know, if we can remove the barriers, then it becomes incredibly powerful. And I think some of the barriers that I've seen are people choosing the wrong format, forcing it to go down, say, a slide route where it looks better, but actually extending is hard, and getting stuff on one slide is hard. Any other kind of watch outs from you about things that prevent it from being a living document.

Kiran Gill 21:01

I think, I think you've touched on it there Alastair, it's got to be accessible. You've got to make sure that the people who are supposed to have it are in there. The one thing that I will go back to is that if you're going to then use a third party potentially to do lead gen for you your sales playbook. And I know this for a fact, speaking to companies that I'm speaking to at the moment, a sales play book has helped them save up to 10,000 euros worth of extra costs, because that's what a demand generation or a marketing company will say, that's their first piece of work they'll do with you. It's guaranteed. Okay, let's sit down and figure out where this mark and this is just money that they're spending, where, if you've already got a sales playbook that you've developed, and maybe you haven't got a marketing department, maybe it's just you and the other founders, or whoever it is, suddenly you've got the fundamental corners, you've got the foundations of what you need to do. And you can go to that agency and say we're ready to go. We need to know this. We don't need to do this. And if you don't know your customer, how do you expect somebody else to know your customer? So that's why I think every company in some such way should have a sales playbook. No matter where they are, whether they're pre seed, seed or series A you should have a sales playbook that's in development that will slowly, slowly build into something more and more.

Alastair Cole 22:26

Yeah, great shout. And if you're early on in that investment round, you're kind of a pre seed, or you don't have a sales playbook. And we talk to a lot of people, you know, they've kind of got it. Some of it's in their head, and some of it's on post and some of it's in a spreadsheet. Actually opening a fresh document now and starting to write, you know, the headline of what is your sales strategy is a great place to start. And there are, you know, myriad ways to accelerate the creation of a sales playbook, and we're some of the tools that we build for ourselves and our clients. Are using cutting edge AI and our frameworks and our frameworks and our experience in order to accelerate the creation of assets, including the sales playbook, which is, you know, saving us bags of time. Gartner here suggests that sellers could create an extra 27% bandwidth for themselves using AI, which equates to, you know, a day and a third, almost of the week. So AI very much. Can help in all areas of sales, and especially in the creation of playbooks. And I would say that's kind of it sits at that top level here. So these are our three AI levels of AI used for sales in this kind of everyday utility, which is just better oil in your engine, all round specialist operational firepower, where we're using AI for specialist jobs, but they're larger and then really the kind of playbook sits at the top here. You know, AI can function as an army of assistants that we've created with specialist roles. They operate as strategy partners for us and our clients, and help us accelerate the creation of sales playbooks. And I know the world of AI and certainly AI and sales can get overwhelming. It's everywhere at the moment, and unsurprisingly, those people, those sellers who feel overwhelmed by tech, end up with a 43% lower quota, right, compared to those who can harness it positively as research from harvest Harvard Business Review. So, you know, AI can be too much for some people, but it's something that we feel like we're able to harness and share with our clients to accelerate the creation of quality playbooks. We touched on one other document earlier, Kiran, which was the kind of investment deck, right? That's helped us raise, helped our clients raise. What you know, obviously that looks different than. Kind of an internal playbook, what gets, what else gets added into those investment pitch decks. From your point of view, that is beyond what's in a play. Internal playbook in order to close, close income,

Kiran Gill 25:13

A playbook realistically is about what you're going to do or what you're trying to do. The investment deck is also a part of what's happened. So you need to show a little bit more about, okay, this is where we were, and this is where we're going, and this is where we are, kind of, it becomes this kind of story, and that present moment is, well, we're asking for investment, because your investment is going to come into us, and this is what we're going to do with this. So theoretically, you're going to show, you, know, probably two different kind of strategies within there with this kind of if we get this much money, this is what we're going to do with it fair, where are you going to spend it, and how is that going to affect the business, and what's going to happen to the business if you get that money? Yeah, now remember, this investment deck might be also for people who are already invested in you to say, do they want to keep on investing in you, or have they had enough now? So it also has to show the people who have already invested into you, and it's something that you're sending out to them. This is where we have been, and this is a snapshot of what we're going to be doing in the next 12 months, 36 months, 48 months. So remember that this document tends to be more visual. It is something that kind of comes from the sales playbook. But it's not going to be only from the sales playbook. There's probably going to be a lot more finance in there, a lot more accounts data. And then parts of the playbook that will be in there would be, you know, what's your go to market plan, what's your sales process? You know, those kinds of thoughts, those kinds of things that you need to explain to your investors of what you're going to do. So they're the parts that, they're the some of it's in there, some of it's not. So you just need to make sure that whoever looks at it gets an understanding of what your business is going to do in the next however long that you want that investment for

Alastair Cole 27:07

Super thanks. And you know, the creation of the playbook, and which is heavily, you know, highly strategic we're talking about, you know, the definitions and the thinking and the work that's gone into who you going to target, how you going to get to them, what that message is going to be that all sits for us within the first of the seven core area sales, which are sales strategy, the other six are team structure, tech stack, lead gen deal, closing, customer success and continuous improvement. For us, those are the seven core areas of of sales success for technology businesses, and we assess those, those seven and 52 underlying metrics through our 360 sales diagnostic tool that creates an overall score with breakdown scores in those different areas, personalized recommendations and A revenue roadmap about where your business could go income wise over the next 12 months, so that that's one of our products that is aimed specifically at people early on in their their their sales journey. Maybe they don't have a playbook, or they do, but it's pretty nascent. And as I mentioned, the playbook is one of those five foundations of our kind of stack of how to become a confident founder, seller, and that is part of our current and relatively new white paper. It's just 12 pages short. It's available on our website, at the operative partnership.com, forward slash white paper. Or you can scan this QR Cole code, if you happen to have your mobile out in front of you, that's all from us today on sales playbooks that land investment. If you enjoyed today's show and you are interested in watching previous recordings or seeing what's coming next, there's a myriad of interviews with highly experienced sellers and loads of topics focusing on technology sales. And you can follow the URL below the sales group.com to see those that's us for today. Bang on time. Thank you so much for joining Kiran. Much appreciate your time and expertise.

Kiran Gill 29:23

Thank you very much. Alastair for having me.

Alastair Cole 29:26

Okay, we'll leave it there. Thanks everybody. Bye, bye, bye for now, bye for now. Bye.