Sales Playbook 2024: What Are the Essentials for Startups? - Podcast Recording

Automated Transcript

Alastair Cole 0:06

Hello, good afternoon and welcome. Welcome to the sales scoop. This is a show for startups who want to improve how they sell. We tackle the hottest topics in sales, and bring you the shiniest pearls of wisdom from the most experienced sellers. I'm Alastair Cole, your host for today and co-founder of a partnership. I'm a computer scientist and an ex Software Engineer with 20 years experience in sales and marketing. And I'm delighted to be joined today by my co host, and co founder.

Kiran Gill 0:42

Hi everybody, my name is Kiran Gill, also co-founder of the uplift partnership. I've got 25 years worth of experience in business development, and in frontline b2b sales.

Alastair Cole 0:55

Thanks, Kiran. So cutting straight in today's focus is the sales playbook for 2024. What are the essentials for startups, and a great place to start is where we see the sales playbook setting in the pantheon of the sales function for startups and, and other businesses. For us, it's fairly and squarely in the sales strategy section. And one of the things that we look for to measure and audit when we talk to startups is their overall sales methodology. And the playbook is a cornerstone of that, of that area. And we're gonna get into what we see as the future for that asset next year, and what startups can be doing to make sure that it's working hard for them. Before we dive into our three sections. Kiran, I'm sure you've got some thoughts on the importance, the relevance of a playbook for a sales team from your many years of experience.

Kiran Gill 2:02

Yeah, we've spoken about this a lot. Alastair ourselves, and when we speak to our clients, for the years that we've been working, and even prior to that, in my in my former life, as a salesperson, you could tell the difference between success and failure, depending on the playbooks it came down to that's That was how simple it was. Some companies had a very detailed, very structured way of selling. And that playbook was something that they really looked after, and made sure that it was complete. And then other times you went into some companies, and it was, you know, written well, it wasn't even written. So you know, it is, like you said, the cornerstone of your success. And if you want to be successful in 2024, I think that's where we start. Yeah.

Alastair Cole 2:48

So we're gonna break it down today into three sections. The first is looking at the sales playbook as the cornerstone, it's the see the kernel for kind of everything that you should be doing. It is HQ, the second section is how it needs to be simple and friendly. And the third section is how it should be a living, breathing, ongoing document. So we're going to get into those three sections. And to give you a bit of a flavour of how we see startups in this area, how mature they are, from our research over the last eight months and working with startups, actually the schools for sales methodology where the playbook lives, they're not strong, you know, even though sales strategy is a strong element within the sales function as you'd expect, because without a good sales strategy, your business isn't alive. We're only seeing a score of a mere 42.8% for sales methodology across the near 50 startups that we've scored over the last few months. And it's, it's so fundamental. And often, as Kevin said, it's missing or it's ad hoc, that that whole methodology, and actually, having a playbook written down having it as an existing document is absolutely paramount. And then across the different sectors that we've worked with, unsurprisingly, see that professional services outsourcing the other sectors much more disciplined, much more organised, much more mature across the board. Sadly, IT and software services and nonprofits are the back of the pack there. But that 42.8 I was surprised, you know, to see that number as we work through with startups because you you think that the sales methodology is is so important, but I think a lot of people care and don't realise that that playbook needs to be, you know, a collection of the definitions and descriptions. So let's talk about that first part, right. The fact that it's the cornerstone, the see the king of the curve of everything you should be doing from a sales point of view. I would argue that it's the most important document you should have. If you don't, if you have one sales document, it should be your playbook. Kevin, what? For a startup? Watching listening back to this session? What would you say were the absolutely critical things, the essentials that should be in that playbook document?

Kiran Gill 5:26

Well, if you go from the basics, so when we designed the 360, sales diagnostic, pretty much this 360 sales diagnostic was based on a playbook. That's what a playbook should really contain. Now, that's a very detailed playbook all the way through the sales process. And all the way through your sales strategy. You're looking at your tech strategy, you're looking at your team, the way you train them, you're looking at your sales processes, you're looking at your lead gen your deal closing, you're looking at, you know, the customer success, and all the way down to you know, even to the continuous improvement that you're doing in your sales. So that playbook within that you're going to have lots of little things. Now, fundamentally, where you want to start is that you just want to have your matrix, you want to know what you're going to be, what's your target for next year. And then when you're going to go down to it, who's your target market, and you need to get into detail. And these are all things that you know, you can easily do. But this is going to be the core, like we've said, Cornerstone keeps on saying the same thing cornerstone that is fundamentally going to help you understand what you're going to be doing. And that brings you back, it always brings you back the more detailed and the better. Your playbook is actually designed, the easier it becomes for you to stay on the straight. And it's your North Star that guides you and makes sure that you're going there. And also as you're bringing on new people, it's also the place that they can go and onboard themselves to say, Oh, this is how we do sales here. Now, as a startup, I'm not surprised when I think about startups not being that, you know, when it comes to their playbooks not being that sophisticated. I would expect people to have certain parts of their playbook or certain companies to have certain parts of their playbook documented properly, and other parts to be a little less, especially in the startup world. The surprising thing is Aleister, and we've worked with some of these companies, companies that aren't even startups that are established, don't have playbooks in place. And they're still making money, that's great. But you know, they could be even more successful by having it structured and having it down on a document where they can easily access it and make sure that it's always been updated and everything else.

Alastair Cole 7:51

Yeah, often the where we start with startups is they'll have, they start with the ideal customer profile, for example. So that's something they don't have, they kind of have a vague idea about who their customers are, but they don't have it written down, which means they can't refine it, they can't improve it, they can't share it. So often, we'll start with ideal customer sexual ideal customer profile, three slides, and a single slide on value proposition. And they write those individual things down. And obviously, that stimulates debates and discussion and refinement and improvement. And then that, as you've said, It's the place where others can come and see it either new sales teams, or new individuals, or people outside the company and outside the sales team, sorry. And we were chatting ahead of the session talking about how important it is to have the company's vision, mission and vision in there because that should be connected to your sales strategy. So often with these online documents, you know, you can have a slide or a paragraph or something that's linked to the company objectives and vision not going to change rapidly. But everything should be in that document that you need to get started as a salesperson, often we start with an ideal customer profile, and value proposition. And then that document expands, doesn't it my friend, you know, we extra sections come extra slides come. And then other documents come as well and other tools and resources. Obviously, you're not going to be running your entire business from one document. You need other platforms, other tools, marketing tools, sales tools, but that document should be the collection of the most important bits of your, your sales DNA.

Kiran Gill 9:40

Yeah, a lot of the one thing I would go back and say is there's certain parts of your sales playbook. You don't have to update continuously. But there are certain things within the playbook like your sales plays, the plays that you're going to use when you go and try to sell that are continuously being updated because you'll get In new data, so, you know, when when you look at your sales, there'll be certain sections of it where like your mission and vision, like you said, Alastair, you know, once that's done, you don't have to keep on refining that. That's basically your guiding star, however your sales play to a particular market. With that messaging that you're having in the back, what's your value proposition, and also your marketing collateral is continuously being updated. Now, and the great thing about a sales playbook, it's all in one place. You're not hunting around looking for things. And if people from marketing are building new collateral, they've got one place where they can put it where the sales team can go and pick it up from Yeah,

Alastair Cole 10:39

yeah. And it's hard to get everybody to agree on, you know, formats of documents or sections within documents. But actually, it doesn't, you just have to pick something and get started. And often, the startups that we're working with, they don't have anything. And so actually, we just say Open a new document, write down the ideal customer profile. Number one, add some details, and you're away. And from there, you'll improve, you'll extend, you'll take bits of it and move it elsewhere when it gets too large. But your sales playbook is that cornerstone document. Which brings us on to that second kind of section that we want to talk about, which is how important it is that it's simple and friendly. And you talked about being able to invite others in and onboarding for new starters and being able to share and refine and that is only possible. If it is simple, right? It needs to be a simple document format, not a multi worksheet, hyper spreadsheet, right that. So it needs to be legible, easy to read, easy to understand, easy to share and easy to comment on. And only the necessary sections. So one of the things that we've learned is not bombarding startups with 72 sections. Actually, if they're missing the ideal customer profile, that's what they should start with. If they've got that, but they're missing, their value proposition isn't clear, then that's a section that needs to focus on. So it doesn't need to be, it shouldn't be 100 pages, right, because that's going to take a long time to load. It's not simple. It's not accessible. And in terms of accessibility, you know, having something in the cloud is fantastic, because it's easily shareable you can get to it on your phone. Because this is a friendly document that you want to get into. I mean, I have mine open all the time, you'll be happy to hear that my sales boss is permanently open in a kind of group of tabs. And I'm referring to it all the time I'm copying templates for, for emails for direct messages. I'm using that to search audiences in Sales Navigator and other tools. So it's going to be really, really simple. And when we hand out when we give our templates away, often to startups. The Playbook, which we have as a slides document, is a Google Slides document. Actually, it comes with a couple of siblings, which is a Google Sheets pipeline document. And then we have a planner as well, which is a doc with some details in terms of calendars and diary dates and how plans happen. So the sales book can't be the only thing. It has a couple of siblings and then and then your methodology, the tools and documents used for your sales methodology will grow over time. And that's natural. What are your thoughts on keeping it simple, caring and Keeping it friendly? What have you learned over the last few years about what works and what doesn't work for startups in terms of that playbook and ease of use?

Kiran Gill 13:51

It has to be easy for the companies that are successful in having their playbooks, like I said, you know, there are parts of the playbook that don't need to be touched continuously. And there are certain parts of the playbook that you would go into. If you're an SDR or sales development representative, you're probably going to spend a lot of the time in the lead generation part of your sales book. Because that's where you're going to have all your messages, you're going to have all your templates, and it's probably somewhere that you're always referring to. And you're always going back to continuously. And there will be other parts for other parts of the team that will be going into their part of the playbook continuously. So keep it simple. And make sure that people have access to it that they need to have access to. And also make sure that they understand that they've got access to their part. And that keeps it down you know, that makes it manageable. So for as an SDR or somebody working in lead gen. The lead generation part of the playbook is important to me. And that's the part that I should be concentrating on. I might need to look at them occasionally but not today. So try to keep it easy. And then also think about the amount of things that you have inside of it sometimes means there can be a lot of legacy documents within Site. I've seen some, sometimes when I've gone into companies, and I've had to clean up playbooks. There is a lot of legacy in there because people don't like getting rid of certain things. Oh, yeah, we might need that again. And you think to yourself, are you really you don't even know what that is. So it's surprising, even companies that haven't documented their playbook, how much material they have to start a playbook. And not all of it is relevant. So keep it simple. And the friendly part is, think about how you've designed it and the way it looks, because it needs to be usable, it has to be a document that everybody feels that they can get something out of it.

Alastair Cole 15:45

Yeah, you made a couple of great points there. That legacy piece and larger, more established organisations. That's one of the things that startups don't have to worry about, right, they normally sign for a blank sheet of paper, or they're relatively immature. And so actually, you know, if startups are listening to this session, they think that that is a big challenge, actually, it's a massive result to be able to create a blank sheet of paper, and then start adding in doesn't have to have 1000 slides on day one. And actually the complexity, if there's complexity, which you will get to and you'll need that can go somewhere else, I can give other documents, it can go in other tools and templates, it doesn't have to be part of your, your, your , your playbook. And actually, you could argue that your playbook is the one of the early one of the cornerstones of your tech strategy, your tech stack, because it needs to be a living, breathing document work all the time. And we know that making it onerous making that one document difficult to engage with is a tech problem if you're sending people out to other tools. And we know from research that technology choices do impact sales quota attainment, when tech overwhelms sellers, they're their quotas, they hit a 43%. Lower. So you know, it's worth bearing in mind that you don't need a sledgehammer to crack a nut when it comes to the playbook. And that if you're using other tools to manage complexity in other areas, if you're your sales function, then that's fantastic. And that actually too can save you time. And then that last bit in the second one about it being simple and friendly. We it's about culture, right sales playbook, ideally, should be fun. I know that sounds weird. And sounds like it is a misnomer. But actually, the document should look good should be something that you're in regularly. And it should be welcoming, place it on people not opening it because they're scared about it. So it needs to, it needs to be friendly. It needs to be inviting. And people need to be encouraged to refine and improve, it needs to be somewhere where people feel like I want to make this better. I like this document, I love the information that's in here, it makes it easy for me. I want to improve it and refine it and make it better. And then the third and final section is on it being a living document. Right. We've touched on some of those points already, not least the fact that I've got mine permanently open and we're immersed in it. What would be your tips, Kiran in terms of startups who, who might create it and then just leave it alone? And they're not referring to or updating it? What would you recommend the how do they how do they keep it as a living document my friend,

Kiran Gill 19:00

start, like we said, Make it simple. And I know that not everybody's gonna go into everyday if you're a startup or any kind of company, you know, day to day business takes over, you're not going to just because we work in the world of playbooks, obviously ours is open and we're always telling people to have their eyes open, but it's not practical. So if you think about it this way, you need to review certain sections and have a cadence to review certain sections just to make sure that they're updated and they're okay and then everything's in the right place. And if you have got an account executive or an SDR or you are that themselves, that playbook should be open because realistically, that's where that's going to guide you. So your deal closing section of your playbook where you know, you're going through your process of client closing a client or you know, making sure that you you've got everything you need, you know, where you have all your documents stored by the client, what documents you need, you know, different companies will have different ways to sell there is Now one way to build a, you know your playbook is, is your recipe to selling to your clients selling your product. So it's not going to be the same as somebody else's. However, the fundamentals of that recipe are very similar for all companies. But the way you make your recipe on the move, the way you make your meal is going to be slightly different for your clients in different markets. And I would say a good county executive will always have an eye on their account of their playbook and will always be refining that with their sales manager. And it could be the same person as a startup normally is. And they're always refining it, because they want to make sure that that's up to date. Because if you leave it too long, it then becomes a very, very big test of time to update it, and then it gets left behind. And then what you have is something that hasn't been touched for 12 months, and then you're thinking to yourself, we just know randomly an ad hoc Lee selling things. And we don't actually know how we sell them. But because we're not documenting it any longer.

I've lost you on audio there. Aleister, I'm not sure if it's me

Alastair Cole 21:10

at once. So you make a good point, because once it's lost, or once that document isn't used, then people aren't going in there to get us the templates and the definitions and descriptions of how you're going to sell and, and what happens is people start making it up on their own. And so you have an inconsistency in terms of the selling experience, and people start doing their own thing. So you know, good habits are staying in the playbook. And that hopefully will support the habits of consistent approach to prospecting to deal closing to customer success. And as it grows, something that we've noticed, as well as that, as a section will grow IQ that can be taken out and removed and turned into another document, write another supporting document that you might use for three months, six months, 12 months, or it might live forever. If and when that dies, you know the playbook continues. So as it expands and grows, you can take sections and information out. We use it as well as a list of the tools that we've got for the different platforms. So there's easy access to get to those platforms. We have repositories of important prompts that are working for us when we're engaging with generative creation of AI images and large language models. So promising that all the kinds of helpful tips and tricks that you need to sell in 2024 are in there. And you talked about the 360, you know that that product that we've got is a great way to assess your overall sales methodology and dig into how well your playbook is working for you, or otherwise. So one of the things we chatted about ahead of the call was kind of craziness, sales playbook craziness. And mine, one of the most interesting things I've seen in the last few years is working with startups where we'll hand over the playbook and actually live on the call during the session. And watching as the sales leader is updating the ideal customer profile, like right in front of my eyes, because we because it's a shared document. And I found that, you know, I didn't expect to see that. But actually, a lot of the founders that we work with are super ambitious, they're fired up, they're, they're really keen to keep their business thriving, and in some cases, just surviving. And having them see it update live and running was fantastic. Because that then spawns a discussion with me and that's where the juice is, that's where the benefit comes out. Have you got any, any anecdotes from your, your, your life as a playbook coach?

Kiran Gill 24:15

A lot of the time, what you'll find is what I said before, it's that there are a lot of companies out there that sell in a particular way. And we tell in that particular way, because it's all in our heads. You know, we know what we're doing, because it's there and we keep all that information inside. And you say oh, where's your playbook and it'll be like, Oh, it's here. That's great. That's easy. That's great if we can share that around, because what that happens is that's where the random and the ad hoc behaviour starts coming in. And there's that fear of documenting it because that, that fear of and also what I've said, flipping that around. I've also seen a very, very expansive, detailed playbook If that had never been executed, because people will just go in there, and they'll create this amazing document, and it's got all this detail. And however, the sales team isn't executing the sales document that that playbook is not being used, because they're doing something totally different from what's in the playbook because no one's actually executing using the playbook for what it's supposed to be. Your plays are in there. You know, and that's the other thing, you know, if you're gonna have a playbook, make sure that you're executing it, and you're keeping you updated. And everybody uses that as that single point of truth?

Alastair Cole 25:35

Yeah, I think that's a great shout. Because you people can get into the, into that loop where they get stuck, where they're constantly just refining and updating and stuff. And, and so that's why you have to keep tabs on how you're how you're using it. And that is the sweet spot, right? It can't be up in your head, and it can't, and it shouldn't be, you know, 500,000 pages, it needs to be a kind of sweet spot. And, and if you don't have a sales playbook right now, if you're watching or listening, you don't have a sales playbook. Just open a new document, open a Google document in the cloud, and call it a sales playbook and write your ideal customer profile and your value proposition down. And that's it, you've started, you're off on your journey. So Kevin's referenced as have I 360, sales diagnostic product that we launched over the summer. And that is a lightweight audit, to create a snapshot of where you are and a roadmap for the next 12 months. It's a 75 minute meeting, you get a score and a personalised 25 page report. And then we do a final follow up session with presentation and questions. And that, like I said, it takes about a week for us to produce the report. And that lays out your next four quarters of recommended improvements that should be made to your sales function. And what we see with our clients is that it gives them a clearer view of the road ahead. And you can get more information at the uplift partnership.com forward slash 360. So really, that's that's that's us for today. That's us for the sales playbook. If you've got any questions about our playbook or you'd like to see an example, for startups, then you can get in touch with me or you can find Kiran, both of us on LinkedIn. And we can help you in that area. The last thing really to mention is that our next live event is Tuesday, January the ninth, where we're going to have our first guest, our first external guest on the podcast, Louise military who is a talent acquisition partner for startups and experts in talent strategy and recruitment for startups. Louisa will be with us live at midday UK time 1300 Central European on Tuesday, the ninth of January, very much looking forward to having her on the show. Before we wrap it up and and head off any any final thoughts from you, my friend

Kiran Gill 28:23

just reiterates what you said there. You know, to be successful, you need a sales playbook. And you need to start putting that together. It might be daunting if you've already started your company. But you'll be surprised how much information you already have and how quickly you can start creating it. So if you want to be successful, if you want to make your sales into a process where you don't have to think about it too much, and you can just repeat it. A sales playbook is the most important document you can have in your sales team. So don't don't not have one.

Alastair Cole 28:56

Brilliant, fantastic advice. Thanks for your time. Kieran. Thanks very much.

Kiran Gill 29:01

Thanks for that. How does it talk to you soon? All right.

Alastair Cole 29:04

Thanks, everybody. Bye bye.