Becoming a Confident Founder-Seller: Core Sales Skills to Develop

Automated Transcript

Alastair Cole 0:03

Hello, good afternoon, and welcome to The Sales Scoop. This is a weekly live show for tech startup founders who want to improve how they sell. We tackle the hottest topics in sales and bring you the shiniest pearls of wisdom from experienced sellers. I'm Alastair Cole, your host for today. I'm a computer scientist and ex Software Engineer with two decades experience in sales and marketing, and I'm delighted to say that I'm joined today by Kiran Gill, B2B sales expert, hi Kiran.

Kiran Gill 0:43

Good afternoon. Alastair, welcome everyone. My name is Kiran. I am a B2B, sales professional with 25 years worth of experience in technology and also in corporate finance, and I've worked over loads of different positions in sales, whether it's frontline operational and management.

Alastair Cole 1:04

Thank you, Kiran, so today's topic is about becoming a confident founder seller. Really, really important. A lot of the founders that we meet are experts in their fields, whether that's engineering or product, and they're keen to develop their confidence and become better at selling. Is why we've picked this topic. We want to say straight away that if you're if you've got any questions, feel free to put them in the comments. We'll maybe answer them right away. We'll leave them until the end of the show. We'll have some time for questions. So if you've got some thoughts as we progress through this important topic, chime in please on the questions. So Kiran, what are your thoughts on, on the importance of confidence for founders and founder sellers?

Kiran Gill 1:57

I think it's fundamental. When you think about business, that as you start your business, normally, the founders have to be people who are confident in selling their product and being confident in selling so I've been fortunate enough through my career to train a lot of sales people, coached a lot of salespeople and tell you the one, tell you the truth. The ones who are confident are the ones that tend to be, you know, the ones Hit, hit the numbers and and, you know, make sure they're successful in what they're doing,

Alastair Cole 2:31

yeah. And it's, you know, it's just one word, but it, you can't just imbue or give confidence to somebody. It comes through, you know, repeated actions and behaviours and foundations, it's absolutely critical to the startup world, and we've seen through our research and our work with startups that confidence and increase in confidence comes from clarity, right? When things are clearer, confidence rates increase and win rates quadruple as a result. You know, there's a really big impact, impact of confidence on closing new business that leads to the positive stats at the bottom. And as well as clarity, it's also about having the right foundations and taking the right repeated actions, right? So, and those are two areas that we're going to cover, foundations and actions. I'm just going to dive straight into foundation number one, of becoming a competent founder seller. And this is, this is the assessment stage. Right? You've got to undertake an assessment, a rapid analysis of the strengths and weaknesses of your sales function. So that assessment, Kiran, how important it is that that's the first bedrock, the first foundation. And what are your thoughts on assessment analysis? It's,

Kiran Gill 3:57

yeah, it's, I think it's the foundation of understanding what you need to improve on, or what you need to do as a seller. So some people, there's lots of aspects of selling, but whether you're frontline selling or whether you're managing a team of sellers, you need to understand where you need to grow and where you need to, you know, expand or get better at and where you you know you might not need to train as much. So when it comes to that kind of understanding of where you are, that assessment will give you an understanding of what are you missing, where should you be, you know, putting your time and effort to get that confidence up, to make sure that you know you won't train yourself across everything. And when you're starting the journey, you need to know where, where should you start? You know, it's such a lot of things that you've got to cover. So you might not be everything. You know when it comes to selling, there's so many aspects. There might be only a few things that you need to do at the start to get yourself to be confident in those and then. You move on to the next and build, build the foundations as you go along,

Alastair Cole 5:05

and within assessment a couple of key areas here. One is getting a holistic view of the capability, the maturity of your sales function. One of the ways that we do this, right at the beginning of all of our journey with clients, is through our 360 degree sales diagnostic. We look at seven areas of sales and 52 metrics underneath that, but picking one of the elements out, you know, sales teams versus SaaS Kiran, what? How? How should startups go about assessing where they fit on the grid? And what are these? How would you describe this, these different areas of self service versus sales teams. So

Kiran Gill 5:48

First of all, you know, to become confident at something or become confident at selling, first you need to understand how you need to sell. So if you're selling self service, that means probably less time in front of the customer, but this is more web based stuff, and it'll be like videos and content creation, all those things. That's where you're probably going to be expanding, or putting a vast amount of your time into doing those things. If you're more of a traditional sales and you're going in front of customers, what most of us will do at the start, and where you're speaking to people, you're probably going to be then going more the traditional route, and probably having a full coverage is where you're probably going to end up. So all founders, whether you are going to be sitting in the background in self service or you're going to be in the foreground, you're going to get out there, and you're probably going to be a hybrid of both.

Alastair Cole 6:39

Assessment, the foundation number one, the second foundation moving into is strategy, right? The creation of a truly biassed centric strategy. Right? Is, you know, easy to say, difficult to do, but absolutely paramount. What are you seeing in the startups that we met at sifted two weeks ago, my friend, or in the startups that we're working with as clients, where do you see their how can they build confidence in that buyer centric strategy,

Kiran Gill 7:08

always getting out there and speaking to their customers or potential customers, finding out that their product, their service, is going to do something for the people that they're who have got these problems and challenges or wants or needs, and that that the more you more time you spend with the customer or your potential customer, the better understanding you have, and the better confidence you have that you actually know what you're speaking about. A lot of founders tend to come from the industry that they're solving the problem of. So they already have a confidence there of understanding what their potential customers' needs and wants are. And from there, you can then have, you can have that conversation. You know, whenever you meet somebody, the confidence someone oozes when they know the subject, when they know what their service or product is solving , so you can just feel it, can't you? Sometimes these people just ooze that confidence. They speak about it, but are not arrogant. They're not arrogant about it. They're not telling you that you don't know enough. What they do is they give you the confidence of thinking, wow, actually, you're somebody I should speak to, because you seem to know a lot about this subject, and you seem very sincere the way you speak about it. So I want to continue conversing with you to figure out whether you can help us with this problem that we have in our business.

Alastair Cole 8:23

Yeah, you talked about sitting down with clients there. It's about, you know, immersing, observing, asking questions and the four key documents that we recommend when looking at strategy, you know, that's the ideal customer profile definition, by personas, value propositions and buying journeys for absolutely critical documents that we work with clients to build, to give them that foundational confidence. And you know, don't just take our word for it. You know, hubspot's sales trend report from less than a year ago found that, you know, you won more than two thirds more accounts when you had a strong ideal custom profile. So those elements of strategy are absolutely key. Let's move on to the third Foundation, which is a playbook, right? Some would say your most important sales asset. Would you agree? My friend,

Kiran Gill 9:18

it is totally the most important sales asset you will have in your company. And it's amazing how many companies don't even have one. It is crazy. How many come and even those, the ones that do have it don't even use it. That's the best thing about it. So having a sales playbook that you as a founder, you know are building yourself, and then you can pass it on to the people you bring on in your company to say, this is the way we sell in our company. Remember, this document is never finished. It's a work in progress. It'll never, it'll never be finished. You're always putting things in there and changing things around and buying you know, it's always changing. You know, your buyers are changing. Your way of selling is changing. Technology is changing. So this, this document, is a living, breathing thing that is continuously moving. But like I just said, Alastair, it's crazy, isn't it? How many customers we run into and you say, Do you have a sales playbook? And they go, No. And you think, oh, okay, so how are you going to pass that knowledge on to other people, how you're going to become confident in selling if you haven't documented it in something,

Alastair Cole 10:27

Yeah, and I think a lot of founders are, you know, they're naturally ambitious, they're kind of confident individuals and they think, well, it's just me, I don't need to write it down. But actually, what we see is, when they do, you know, go through that process of writing stuff down, even using chat GPT. A client recently was sitting down for the weekend to work with GPT and kind of document the way that they go about sales, even writing it down, the process of that helps them consider it. So even if you're just a single founder seller, getting a playbook is really important. Let's add the fourth sorry for it for a skip on the inside that plays with a couple of big, big things to think about. One is the definitions right of your funnel mix, and also your growth plan, the details that you want to bring into the playbook about how you're going to grow so beyond playbook, technology absolutely core, foundational. It's got to be the right tools at the right time. What are you seeing that's making a difference right now? Kiran, and what should an approach be for founders, seller founders, and startup founders. Sellers thinking about bringing in technology,

Kiran Gill 11:44

just be confident in what you're using. Don't rush. Bring one tool on as it goes along. Don't panic. You know, if you made a decision on using a particular tool, understand that tool and understand its functionalities before you start adding other things on there. So, you know, just take your time with these things, because there is so much out there, and everything is the next best thing. And it's easy to get thrown into this world where you just continuously. Are you never really getting fun, or, you know, you never become competent on one tool. What you do is you kind of jump around from tool to tool, and you don't really understand what you're using. So use one tool. Get used to it. It might not be the best, but once you're competent in that, then you can add another one, or maybe even change to a different one, saying, You know what? That doesn't do enough for me. I need something more. But sometimes, the mistakes that I see are that there's too many tools, and most of them aren't even being used properly. So less is more in this kind of world that I would say,

Alastair Cole 12:50

Yeah, I totally agree. You know, you wouldn't, you know, you wouldn't stop your lead generation strategy or lead generation campaign after just a few weeks, right? These things, sales are a long game. It takes time to get results, and it's the same with technology. You need to do your research, pick something and then like, like you've just said, you know, commit to using it for, you know, a number of months in order to get the value out. That's really important, and there are huge gains to be made. Gartner predicts that 27% extra bandwidth can be created for sellers harnessing AI. You know, how would you like to have all of Wednesday and the first third of Thursday? You know, to do other things, because I was helping with your sounds like the promised land. And if that's interesting. One of our previous shows was on our top 10 AI tools for sales. You can see them here. You can see them in more detail and watch the show back on our website. The technology tools, right? Absolutely critical foundation, and the last one, the fifth Foundation, is collateral, right? The assets that you need, the essential sales and marketing content, and it's so important right now, isn't it, with a competitive set out there, my friend and all the noise, what's your view? On, on, on, on what, what is best in class collateral for you,

Kiran Gill 14:23

it's having collateral that your prospects or your potential customers want to actually, you know, engage with or want to actually have. So you know, again, it doesn't need to be life changing content. You don't need to feel like you have to continuously make new videos or have white papers, but it does help to have those assets, because when you're selling, the customer sometimes wants something, just to show that you have the expertise in that area, that you have an understanding. Now, this could be just a basic thing from your website, but it could be cloud. Collateral that you're building. The thing about sales assets is, again, less is more, and the quality is important. It needs to be about not what you think the customer should have. It's more about what the customer might find useful. So again, collateral so important, but if the other foundations are done correctly, your collateral will actually be engaging, and it will be you'll you'll feel confident that your cut, your your collateral, is bringing something to the party, and it's not something that you know is just a waste of time, really.

Alastair Cole 15:32

Yeah, and, and, and, I think it really can help with confidence when you know it right. When you've gone back to the drawing board, you've reconsidered your customer profile. You've done all that work, and you realise that, you know, there are three assets that you really need in order to help the process along and help the buyers along. The creation of those assets, sitting down with a, you know, blank sheet of paper and actually thinking about what should go in from from previous assets, what needs to be created from new that process naturally builds confidence, because you're, you're right in there, you're, you know, sleeves rolled up, pencil sharpened, and you're, you know, you're actually making the assets. And I think the creation of those assets just does build confidence. And, you know, there are, it's different for different businesses. Some might need, you know, one page, two pages and five pages. Others are relying heavily on white papers. There's all kinds of social media posts, all kinds of assets that need to be created. And the truth is, they've got to be good, right? You've got to go back to the drawing board, because, you know, almost 90% of B2B buyers, According to Forrester, expect to be delighted, right, not just before the purchase, but after the purchase. The pressure is on to delight them, and so your sales and marketing collateral has to be, you know, has to be fantastic, and you have to be confident about which one to share at the right time. So, really, really important. That's the last Foundation, the fifth, the fifth foundation things that need to be done. You know, they don't need to be done on a daily basis, right? The playbook is being updated, you know, relatively regularly, but not daily. But we're going to move now into the first actions, right? And the actions we're talking about are, you know, the actions that need to be undertaken on a daily basis, right, in order for the sales engine to work. And the first one, no surprises, is prospecting. So daily outreach and community engagement. You're the king of prospecting, in my eyes. Kiran, you what? Tell us a little bit about the importance of regular prospecting, how often it should be done, and what your tips would be for startup founders. Yeah,

Kiran Gill 17:53

Thanks for the compliment. So from the way I look at it, it's like anything in life. Confidence comes by repeating things and understanding that you're competent in doing something. So if you're prospecting, you should prospect every day, in my view. And the people or the salespeople that are successful, they do, or the companies that are successful, they have people who do this continuously, and they understand their process, and they'll go through the process, and however, if they see that the process isn't working in places, they come back. So doing it every day gives you the confidence of understanding that you're doing this, and the more you do this, the more kind of understanding and the more skills that you build up. So when you do hit a roadblock, or that customer comes in with an awkward question, or somebody doesn't respond to your email, or somebody does respond to your email, but responds in a way that you didn't expect you have the knowledge and the confidence to be able to deal with that situation. Because remember, prospecting, the whole point of prospecting is to try to get a meeting. That's what you're trying to do now, and it's hard out there. It is really, really hard because most of the time, the doors get slammed in your face, and people don't pick up your phone calls, and no one answers your emails, and it's horrible, and it feels dissent, you know, you just lose all your confidence, and it's all gone. However, it's those little moments where you do get somebody replying to you in an email, somebody does pick up the phone, somebody does engage with you. That's where you think you know what. I know what I'm doing here, and I can continue doing this. Yeah, it's going to be hard, but hey, if it was easy, then everybody would be good at it, wouldn't they?

Alastair Cole 19:36

Yeah. I mean, it can feel like a thankless task, shouting into the void, but the result, the rewards are amazing when they come through. And, you know, there's the question I think we get asked most is, is, how much should I be doing? You know, how many hours should I be spending a day prospecting? How? What different types of prospecting should I be doing? And we have a bit of. A formula for this, tell me and the results in the number 618 which is a big number for us, right? It's a sales actions number. Do you want to talk a little bit about what 618 Kiran is, and how you got there? Yeah.

Kiran Gill 20:16

So 618 is our number. So the number that we created for ourselves at uplift in an understanding of how many actions that we have to do per month to generate so many meetings, and 12 meetings a month. Of those 12 meetings a month, we're expecting to close potentially four clients a month, and that's what we're looking at because of the ticket size we sell for, and what we're doing and our capacity, that's our number. Everybody has a different number, however. So your number, if you're selling something that's only five pounds, you might have a lot of sales actions doing however. You might say, well, actually, we don't need to, we don't need to turn over that much. So your sales actions come down. It's all about the calculation. So understanding how many things you have to do per day gives you a great understanding of am I on track? I run a lot. So the thing is, understanding how quickly you just ran that last kilometre gives you a good understanding of what you need to do in the next four to finish your 25. You know your five kilometres within 25 minutes, or whatever you're trying to aim to do, and that's the same with sales. You know, you've got to get your actions out there. So if you don't do your actions, you're not going to get your sales and if you don't do enough actions, then chances are you're probably not going to hit sales again. So you've got to record what you're doing, and then from recording what you're doing, you need to understand that they are the right things that you're doing, but they will be because you followed all the other foundations. So your prospecting will become better, and you'll become more confident in your prospecting, because you'll think, you know what, I know what I'm doing here.

Alastair Cole 21:54

Yeah, and you know, 618, our number might feel like a big number. They don't all have to be done by humans. You know, AI can free up loads of time, extra bandwidth, and so those 618, or whatever your number is, a lot of that's going to be handled by automation and semi automation as well. So that makes it less scary, right? The second group of actions that you need to be taking after prospecting is meetings, you know, sitting down with buyers face to face. This is what it's all been about. And you know, depending on your price point and what you're selling, the number of meetings you need each month in order to reach your targets is going to be different. Talk to me about sitting down with Kiran with clients. How important is that?

Kiran Gill 22:50

Well, again, if you're self service, you're probably not going to sit down in front of a lot of clients, unless you're selling a lot of units to one person, then you're going to be sitting down with somebody, I can guarantee. But if you're in the world of consultancy, or you're selling something high ticket, the chances are that you're aiming to after your prospect, to have multiple meetings with a client to make sure that they get the product or the service that they want. Being confident in the meeting means a lot, because if you come across that you don't understand what you're doing, or you know, whatever it is, and I have been in some car crashes when it comes to meetings with clients. Honestly, I could tell you some great stories about people not coming in prepared. I have been on both sides. I have prepared teams to go and sell that have come in overly prepared and are amazing. But I've also worked on the other side, where teams are totally shambles, coming and trying to get you know with a client in their meeting. And it honestly makes a difference. You can see again, some someone who is confident in the way they talk about their product, their service, about your problems and challenges. It all comes out to play there. Remember, all those things that we've done so far in the foundations are leading up to this one moment. All these things we do all day long in sales is to get meetings, and then when we do get the meeting, we're not prepared. And it absolutely makes me go mental when I see that, that people, you know, they turn up, and you think you've done all the hard work, and now you're about to drop the ball now all the time. So meetings are super important. Alastair,

Alastair Cole 24:28

yeah, and you know, if you are trying to close bigger deals, which we're seeing a lot of the moment, startups going for enterprise, then you've got to map out and understand your buying personas and the large and complex buying group who's going to be at that meeting, who do you need to satisfy? Absolutely critical you get a big view there and of everybody involved. And I think HubSpot recently published the average as turning out to be about five. I think 551, Individuals at the buyer's end involved in a complex sale are so really important that they are mapped out. Our third and final group of actions is closing, getting deals over the line. You know, this is where you know, the money arrives. The deal is signed. Everybody's happy. It's time to celebrate. And you know, for me, I think value, value is absolutely key. Value affirmation closes deals. You know, we know this from great research from the Harvard Business Review, it's a 30% higher likelihood of a high quality deal, if you can talk about value. And I think you know, really, life is so competitive now in sales that you need to be demonstrating value every single step of the way, from the collateral you make to you know, the leads you're generating. What's your take on how startups can build confidence in closing deals. Kiran,

Kiran Gill 26:04

Well, closing deals is, if you're closing deals, your confidence is continuously going up, because you know that what you're doing is actually making a change. So it's as simple as that, you know, if you're closing deals, you know you're doing the right thing. If you're if you then do your statistics, and you certainly find out that you're you're creating the meetings, you're doing the meetings, but you're not closing that's where you probably need to start looking at what the problems tend to be in your business, or you're in your sales process, because if you're not converting, and that's why I'm a, you know, a massive advocate to stats and all the kind of statistics you get around sales. So that's why you should be using a CRM, and that CRM needs to be up to date, because then it will get all the information. And once you know where you are, you can then start making changes. Now, even if you're closing and your win rate is at 25-30% and that's quite good in B2B, could you be even better? Because a few percent higher in win rate could be a few 100,000 more in generation, you know, at that kind of level. So, yeah, you know, 1% here, 1% there, suddenly starts making a massive difference,

Alastair Cole 27:15

totally. So closing the last of the three key actions. Those are for us, the foundations and actions needed to become a confident founder seller. If I referred to a couple of things there, not least the 10 AI tools for sales. You can go and read or watch that particular show, and a host of other shows over at the sales scoop.com just want to answer the live question we got from Mario Rivas, thanks for that, Mario. You asked about the best sales act of creating leads for startups, right, versus those that are going to go out in the next few months, so new ones and those that are already established. And I'd say Mario, there are myriad tools out there that you can use, some fantastic and we have a small list that we use. But really the difference there is about the quality of the leads that you're able to generate, because a startup that is absolutely fresh, you know, has fewer contacts, less credibility, newer sales assets, whereas those that are more established, you've got a bigger network already. So actually, the messaging is going to be different, and potentially the sales tool as well. So it really depends on lots of factors. So and also, we referred in the assessment stage, right at the beginning to our 360 sales diagnostic, which is a fantastic place to start if you're looking for a rapid analysis of the capability of your sales function. It includes a full score breakdown recommendation and a revenue roadmap. Take a look at the uplift partnership.com, forward slash 360 for that spot on time. Amazingly, there's a new development for the show. The first one in November is going to be a new format. We're going to be interviewing our first inaugural guest, Dan Hammond, who's the co-founder of Squadify. That's on Tuesday, the fifth of November. And we're starting to bring in guests alongside or in between, interspersed between shows that Kiran and I do, the next one of which is a very exciting topic on the 29th of October. So two weeks today, high touch versus low touch, selling Kiran, what's what peaks you just about that,

Kiran Gill 29:44

oh, everything. I just love the topic of understanding whether you should be high touch or low touch or a combination. And I think this is that, this is, this is where the rubber hits the road for a lot of startups, you know, the kind of trouble or the kind. Challenges or problems that we're trying to solve with our clients is understanding what their business model should be or what their sales model should be. So join us in a few weeks, because that's going to be a fun show. Yeah,

Alastair Cole 30:13

i look forward to that. Well, spot on time. Thanks for your expertise today, my friend. It's really good to chat with you about how to build confidence in founder sellers. That's it for us. And so until next time Bye, for now, see you soon. Bye, bye.