Selling Into Enterprise: 5 Golden Rules for Startups - Podcast Recording

Automated Transcript

Alastair Cole 0:06

Hello, good afternoon, and welcome to the sales scoop. This is a show for startups who want to improve how they sell. I'm Alastair Cole, your co host and co founder of the partnership. My background is as a computer scientist, ex software engineer, and I have 25 years experience in sales and marketing. And I'm joined today by my co founder and the man with almost three decades experience of complex b2b Selling specifically into enterprise. Kiran, welcome, my friend.

Kiran Gill 0:47

Thank you very much, Alastair. Hello, everybody. My name is Kiran Gill, I've got Alastair says nearly three decades worth of complex b2b Selling behind me. I've worked in finance, also in technology, and also in the startup, a startup environment. So it's great to be here today. Yeah,

Alastair Cole 1:04

wonderful. I can't wait to get tap into your brains and experience in the world of enterprise. Selling into it. The reason that we're, we've chosen this topic for today, selling in the enterprise, five golden rules for startups, is because it's a really different game, selling into enterprise, you know, we've both done it, we've both sold into smaller businesses we've sold into large enterprises, it is it's a tough game, it's hard work. And it's really important right now, because you see a lot in the news at the moment of the struggle that some of the larger consulting firms are having. And that's a result of questions about the value and the price they bring. And so the opportunity is ripe now for smaller businesses to try and get into enterprises. And that's what we're going to cover in the show today. So my background is, of selling into enterprises, selling into some of the largest banks, energy providers and law firms in the world. Tell us a little bit about your experience, specifically with enterprises, Kiran?

Kiran Gill 2:18

Yeah, so I started off my sales career and started off in finance. And in finance, I was working in central London, doing very, very large deals, or structured finance deals with very multinational corporations. So based around globally, so that worked, that's where I started, I then moved off into the world of management consultancy, and was on the other side of things where I wasn't supported by a large company who had the all the mechanics and everything to do, you know, like large banks to attend to working for a management consultancy what was more like a startup and selling into enterprises as a startup was a totally different kind of feeling for myself. And then after that, I was fortunate enough then to work with other startups in building operations or sales operations for them to sell into enterprises themselves.

Alastair Cole 3:14

Yeah, and we've, as uplift, we've sold into smaller businesses medium size, and we've we've had some success selling into enterprises as well, which is what we did for Sydney dine and actually got one of their new a new product for them and you SDK product into enterprise corporates, delivering four times when rates 251% ROI. And over the last eight months, we've been working with about 50 startups through our 360 sales diagnostic. And we take data when we work with these companies. And we found that the average score in terms of the maturity of a sales process is under 50%, for startups under five years. So most startups have a kind of a fairly poor score when it comes to the sales process and that discipline and that process lead approach is so important in sales, and that's something that hopefully we're going to change now. So before we get started, just so everyone is clear, clear, and how would you define enterprise enterprise when we talk about selling into enterprises?

Kiran Gill 4:23

So an enterprise is a company that is a large corporation. So what you're looking at is a company that's probably got multiple branches or multiple offices in different countries. You're talking anywhere from 5000 people plus I would always say some people might call that large corporation, I would call that an enterprise, because it's going to be a complex sale. And that's the definition that I would always bring it down to a complex sale, something that's going to take a little bit longer, and it's probably going to be multiple meetings. To get the sale across the line.

Alastair Cole 5:03

Okay, that's really helpful. And we talked a little bit before the show about the pros and cons, right? The fact that enterprise selling advice can be so rewarding, and also so dangerous, right, we'll come on, we'll come back to that later, we're going to start straight in with the first of our five golden rules. And the first one is, do your homework. So let's dive into that a little bit, my friend we're talking about right at the start, before you even get out there and knock on any doors. It's about that homework, what would be your first things that you would recommend a startup do if they're thinking about moving into enterprise selling?

Kiran Gill 5:49

Okay, so notoriously enterprise selling is different to selling to the smaller kind of end of the market. So you need to have an understanding, because of this complexity of selling into these companies, you need a different sales approach, that sales approach will tend to be and should be more of a targeted approach. Because what will happen with these companies is that you'll need to target multiple different people within that, within that organisation. So you need to have a very clear, ideal customer profile, and also an understanding of the buying group or the buying personas that are going to be influenced in the background. With not that done, you're gonna have a problem straightaway, because enterprises are different and they're very large. And if you get that wrong, you might not even be getting in touch with the right people.

Alastair Cole 6:43

Yeah, so that homework starts right out the door, doesn't it with those definitions you talked about? You mentioned ideal customer profile, buying personas, the target market analysis, value proposition for each one of those ideal customer profiles. So and then, you know, we haven't even touched on competition analysis and buyers journey analysis. So there's a whole amount of research that needs to be done. I am most interested in something we talked about earlier, which is this kind of targeted account strategy, right? When we're talking about thinking about doing outbound in terms of your homework, how should startups think about target account strategy?

Kiran Gill 7:21

Okay, so let's take an example, let's say we're trying to sell into a bank, we'll just take an easy kind of an example of not really easy. Lending into a bank is an absolute nightmare. Anybody who's tried to do that, elongated sales cycles, different people with different names in departments, large corporations that are based over, you know, multiple offices. So trying to get all these people into one place. So your target is account strategy. First of all, you need to do a stakeholder analysis of who the people you're trying to approach are. Now, there might be different groups of people in different departments based in all different locations. And unless you have that kind of work done, you're going to struggle, you're going to struggle to even understand. So that's your starting point. So your target account strategy is where you have all your homework done, you know, that you're trying to get in contact with, where they're based, and all the other work that you tend to do in sales. Also, from that side, knowing the industry that you're selling into, I've seen it so often, where people are unprepared, they don't even really know what's happening in the industry, before they've gone in there. So that is what we mean by doing the homework.

Alastair Cole 8:38

Yeah, I think you're bang on though, we're talking about the kind of deep research we've seen, we've been asked to come in and help startups out with it, maybe move too quickly. They haven't done enough research that they don't understand the challenges that are going on, either in the industry or with the enterprises that are trying to sell into. So it is really important to think about who might be a champion, who are those key stakeholders, lots of research, lots of crunching, lots of writing down and formulating that plan. So that's step one. Do your homework. Number two, we'll move on immediately and knock on many doors, right? And there's a bit of a double meaning here. Kick off. So what do you mean by knocking on many doors?

Kiran Gill 9:25

Notoriously, what happens is because enterprise deals tend to be larger. As salespeople, we all have our kind of metrics that we're looking at. So let's say we're chasing or we have an enterprise that tends to be interested in what we're doing. Now, notoriously, what happens there is that instead of having multiple deals in your pipeline that are enterprise and it takes so much effort to win an Enterprise Client, so it might be easy just to turn off there and just concentrate on that one account because you think You know what, if I get this one account over the over the over the line? Well, you know, that's it, we're done, you know, we're gonna win. However, what happens, and I've seen it so often. First of all, it's really hard to win an enterprise account. The other thing is, there's still going to be a win rate here involved. So if your win rate is around about four to one in four, you're probably going to have to be entertaining at least four different enterprise accounts at the same time to win one of them. Now, hopefully, you will all fall, but you need to have more than just one account that you're chasing. And also, it's so dangerous, just relying on one account to do your numbers for the year.

Alastair Cole 10:40

And this is what we talked about at the start: the kind of reward and the danger, the reward of, of the enterprise account being so large that if you land one, you're sorted. And then the danger, you know, if you rely on too few, and they don't come through, that can destroy your whole year as a salesperson, and then the other half the other part knocks on many doors. So one is about having multiple opportunities in the pipeline. And then what about once you've you've you've picked a client, what do we mean, that was the second meaning of knocking on multiple doors, many doors?

Kiran Gill 11:15

Well, you've got multiple stakeholders within an enterprise client. Remember, there's lots of people working in the same department, maybe like I've said before, in different locations. And you know, instead of concentrating on just one person, now, you might have an entry point in the sense that there's one person who's going to introduce you into the account or give you the information. However, the sensible way to sell into enterprises is that you will be targeting lots of different people in different departments. And that's what we mean by knocking on multiple doors.

Alastair Cole 11:50

Yeah, and so you've got to be out there, you've got to map a larger potential buying group, because you're working for an enterprise and not for a smaller business, more people involved in the decision making process. I mean, we've seen the size of buying groups growing over the last few years accelerated by COVID, people at home making more of their decisions online in their groups, less time with individual sellers, so that and so that accelerated things. And now we're in a situation where the buying groups seem to be getting larger and larger, and you have to hit multiple people in order to convince them that your solution, your product, is the right thing. So once assuming we're knocking on many doors, right, the thing that we're going to take to those doors or take to those individuals is our third point, which is not that one is sharing your point of view, right. And this is about the expertise and the opinion that you're going to take when you knock on those many doors that need to be tailored. Talk to us a little bit more about why sharing your opinion is so important in enterprise selling.

Kiran Gill 13:04

So one, you need the credibility to get into an account. So you might have a relationship that might get you in at the starting point. However, there are other people within an account, who are going to make this decision. And remember, the thing about buying committees or buying groups being larger as, as we were speaking about, is that people buy by consensus. No one, one person wants to take the responsibility of purchasing something. So you might have a champion that might get you into an account or somebody who's going to champion your cause or your solution. However, they're not probably going to take that decision on their own, they won't be taking that, actually, they'll never take that decision on their own, because there's too much risk. So what you do is you buy by consensus. Now, the other people in that group won't know you. So you need to have that, that authority to be able to show everybody else, we are the right people to do this. And we have the right expertise. And we have the right, you know, understanding of your business. So that's why the conversation should continue with us.

Alastair Cole 14:14

Yeah, and that demonstrates their expertise and authority. So important, right, as a smaller entity, as a startup trying to sell in, you've got to show that you know what you're talking about. It's also an opportunity to differentiate yourself from the competition. And it's worth bearing in mind that most startups are bought or they're purchased based on the founder, the founders expertise and founders reputation, right. People want to buy from the founder, they want to hear the founder's stories. But as we try to sell into larger organisations, it can't just be about the phone really more than it needs to be the authority of the other people on the team and the kind of company profile and the company brand, not just that founder. And what about the regularity with which kind of expertise and authority should be shared with prospects Kiran.

Kiran Gill 15:07

It's about the buyer journey, I think we'll be touching on that in a bit. Each of these different individuals will require an understanding of what your solution is, and also your expertise, and that information needs to be given to those people as and when they require it. So not everybody is always going to be in the position to purchase straight away, and different information and different, you know, assets will be required at different times with different stakeholders to make sure that they understand what you do and how you do it, is exactly why they, you know, the challenge that they face in their company is going to be sold by your solution that you're selling.

Alastair Cole 15:54

And this is where the whole why the homeworks so important, and then working out what your opinion is, because a different piece of content or a different opinion piece or a different piece of thought leadership is going to work for a different prospect. And, you know, it feels quite challenging for startups to establish themselves as thought leaders, and that doesn't happen overnight. But it doesn't have to be an original piece of content that a startup has created, you know, to share something that's in the public domain that's newsworthy and recent to share that with the buying group, or people in the buying group at enterprise with your opinion is a great way to demonstrate expertise and authority without having to need to write a 20 page, white paper. So it needs to be coming regularly with your thoughts and your opinions. But that's, that's really, really important. And then, let's move on to the fourth golden rule, which is mapping the route to success, right, we've done the homework have been out there knocking on multiple doors, multiple clients, but also multiple individuals within each client, we're sharing our expertise on a continuous basis, now we've kind of got our foot in the door, we need to map the route to success. So talk to us a little bit about what's involved, why that's important, and what's involved in that, please.

Kiran Gill 17:19

So it's all about being professional. Remember, you're you're selling into a corporate and and those of you who've worked in corporate, and also, you know, for my toll, you know, understanding of being in corporate and understanding how things work, if you're not prepared, and if you miss your opportunities, the deal can suddenly slip away from you. So mapping and understanding exactly what you do in your process exactly when you're supposed to do it will make sure that you look as professional as possible. Now, like I was saying before, not all your clients are going to be in the buying window, at the time you're speaking to them, and are a part of your sales process will be trying to push these people or convince these people that this is the right opportunity, this is the right moment for them to purchase your solutions or service. And you have got the right things for them to make sure that they're going to be successful. So not mapping those routes or understanding how the customer purchases. And so there's so many nuances here because people in different companies call themselves one of the different job titles. And I've seen it so many times, that when you're mapping an account and your understanding of all the different dynamics and different people who are in the account, suddenly you can miss a key stakeholder. And at the 11th hour, you lose the deal. And you suddenly realise that there's this one person who was based somewhere else that you didn't even know was involved. So this is all about understanding or understanding the buying process within the company. And also being prepared and having a process yourself that you can then match with the client exactly the speed of purchase or the speed of decision that needs to be made.

Alastair Cole 19:08

Yeah, and if you've done your homework and you've knocked on doors, and you're sharing your point of view, you'll be gathering feedback, right gathering information. And, you know, I love this, this phase. And for me, this is about a really sharp pencil and a big piece of a three paper and I'm sketching out, you know, stakeholders gatekeepers influences, looking at the decision making unit climbing into things like the the procurement process and the fine details and trying to work out what is that route from where we are through which individuals all the way through to, to closing that deal. Really interesting. He talks about buying windows, because it's worth bearing in mind that something like only 15% of your ideal customer profiles are going to be wanting to buy at any one stage just because of net Trouble movements. So you've got a smaller group. And like you've just said care and you have to wait until they are ready to strike. Because when you get in, it might be that moment immediately. And if you haven't done your homework and got your, your, your game sorted, you might miss that, that buying window. The other thing that I really like is this idea about matching speeds, you talked about being professional, and corporates and enterprises work at a slower speed and startups do right naturally, because they're different beasts. And so as a startup, you have to slow down a bit, or be prepared to kind of slow down and operate at their pace, otherwise, you're gonna get frustrated. And obviously, that has issues when it comes to things like payment terms, and they can be different, but you have to slow down and match their speed. So that's, that's mapping out that route to success. And it's something you have to do constantly, because your point about people moving on, is a really big deal, carrying a hat. And if somebody does move on or move out of the decision making process, then who are you in touch with the person who's likely to fill their shoes? Let's get on to the fifth and final step, which is a final rule, the golden rule for today, which is to step up your game across the board, right? You know, we've, these first four are all in service of being a different kind of sales function. When we talk about just stepping up your game, generally, let's dive into a few sub points, where would you advise startups that they need to up their game to sell into enterprise?

Kiran Gill 21:47

Well, first of all, you need to have a very robust, and a sales process that is built for enterprise, if you have been selling or have been not selling or selling to smaller companies, selling to enterprise is a totally different game. You know, it's like playing football in the lower leagues, and then suddenly, we have been thrust into the Premiership. I'm not saying that, you know, it's better, it's just different. And that's what makes it harder. So not being prepared, not having a sales process of where all the things that we've been speaking about today and not being prepared. I've seen some disastrous mistakes happening from competent salespeople. Because what happens is, they feel like they have that one opportunity they've got in front of a stakeholder. And suddenly, with not being prepared, not doing their deal qualification, not having the process, not having the relevant material, they need to convince the client, they've already gone in and done some kind of demo or, or, and they think that this is it. And when what happens, the deal slips away. And suddenly, all that effort of trying to get to the right person at the right time, suddenly, it's all gone. So just having a sales process that is built for winning enterprise, and also all of the other things that we've talked about target of the candidate coaching process, having, you know, the multiple stakeholders, having different value propositions, making sure that you've got different ideal customer profiles, blah, blah, blah, all of these things come together to do this professional selling, because it's so much work involved and the cost of sale in in a in enterprise selling is so much more, that you can't afford to make a mistake if you have that opportunity.

Alastair Cole 23:33

I think that's a great point, that cost of sale being hired, right? Because you've got more people working on it, there's more time involved in the sales cycle, as long as he just naturally invested for a longer time, I think that's a really good point. And you made a great point for the show about you. It's a bit like you've got not one shot, but it feels like you know, these opportunities don't come around very often because enterprises by their very nature are larger, so there are fewer of them. So you know, you said you needed to get suited and booted right? And you can't afford to make a mistake, which you know doesn't tell you no, of course, we must allow ourselves but there are a few opportunities you've got to be you've got to be on your game. And what would you say were any kind of key assets or resources that a startup should have in place before they think about going and selling into enterprises?

Kiran Gill 24:21

Well, first of all your deal qualification has to be done correctly, if it's not done correctly. And if you don't use a deal qualification methodology, then already you're behind. So you need one of those. And the other thing that you really need to understand is the business case that you are going to be showing to either your champion or the people that you're selling to or the people and the remember that that piece of work is probably going to be passed around to people that you don't even know are going to see this to make sure that this consensus buying is happening. So if your piece of work doesn't have a return investment in there, or is light on your business case is actually light on numbers. The chances are that deals are probably going to be lost. So what I've seen in the past, and I've seen myself, I've made that mistake myself early on in my sales career, where, you know, I was light on the numbers. And I thought, you know, I could get away with it by masking it. But under, you know, a very nice looking slide or, you know, some other things that maybe the client, at the end of the day, somebody along the way in an enterprise will crunch the numbers to see whether the return on investment is worthwhile. And if those numbers don't make any sense, or if those numbers don't even exist, the chances are no, you will not make the sale, it's not the chances are it will be you'll you'll be walked out the door, and other companies will show those return on investments.

Alastair Cole 25:39

And so those details, getting those basics in place, you know, sales strategy, the playbook, they're really important and evidence. There's evidence for this right? HubSpot found that, you know, 68%, more accounts are one when organisations have a strong ideal customer profile. It doesn't sound like rocket science, you write it down, everybody gets around an ICP, you're more likely to close accounts. And at the end of November last year, the Apollo CEO, announced the numbers from their research that just three intense salespeople feel confident in hitting their quota this year. So you know, there's a lot of anxiety about delivering on these enterprise deals and closing them and that, that's highly stressful. So those are, those are our five golden rules for startups trying to sell into enterprise, do your homework, knock on many doors, share your point of view, map the route to success, and generally across the board, step up, step up your game. You know, it shouldn't be scary. I've been in two minds this week, you know, enterprise feels like it's really hard and tough. But you've reminded me my friend that actually it is possible to have some fun with it too, as well as it being a scary challenge. Any any final thoughts, Kiran, or a key takeaway that we've mentioned today that is particularly pressing or prescient, you think for, for startups,

Kiran Gill 27:10

From a startup point of view, look, don't be scared of selling into enterprises, just be prepared. And, you know, come and speak to us about this. Because we know how to do this. We know we've been successful selling into enterprises, we've made companies who have worked with us sell into enterprises, it just takes that you need to be prepared. And make sure that you're you know that most of your time that you're, you know what needs to happen, and you're prepared when the opportunity then opens up for you. Because the worst thing that can happen is that the opportunity is there, but you're not prepared, and you let it go by. So don't be scared of enterprise because the rewards are massive, you land one of those big deals, you know, it's winter dance all the way to the pub. So that's what I would say.

Alastair Cole 27:58

But I think you've nailed it there. Don't be scared, be prepared. Well, it's great. At the top of the show, I shared some stats that came from our work with over 50 startups through our 360 sales diagnostic, which is how we start with all of our clients. They get a full score and breakdown of their entire sales function across seven areas with bespoke recommendations, and an incremental revenue roadmap showing them how much additional income they could generate by following our recommendations. You can get that at the uplift partnership comm forward slash 360. And the last thing for me to do as we wrap up bang on time, it's talking about our next live show in two weeks. Very exciting. It's going to be to improve your deal closing Forex, your win rate that's going to be on Tuesday, the 19th of March, same time seems to be a time that works for us, works for our clients and our audience. So that's Tuesday the 19th of March midday in the UK. Improve your deal closing and forex your win rates and that's drawing on the experience and the evidence that we have from our work with startups over the last four years. While I loved it, great show today my friend gave some some top tips there. And just a reminder for everybody, those five golden rules, do your homework, knock on many doors, share your point of view, map the route to success and generally step up your game if you want to sell into enterprise. That's it. Wonderful. Thanks very much for your time. Kiran.

Kiran Gill 29:39

Thanks, Alastair. Thanks, everyone. Talk to you soon. Reach out. Let's have a chat.

Alastair Cole 29:45

Wonderful, thank you, everybody. Bye for now.

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