Are You Ready for Enterprise? When to Go After the Big Fish

Automated Transcript

Alastair Cole 0:06

Hello, good afternoon and welcome to The Sales Scoop. This is a weekly live show for tech business founders who want to improve how they sell. Every episode, we tackle the hottest topics in tech sales and bring you the shiniest pearls of wisdom from experienced sellers. I'm your host for today. Alastair Cole. I'm a computer scientist and ex software engineer. When I think about closing enterprise deals, I think about heading to Canary Wharf and working with one of the big four accountancy firms and magic circle law firms, some of the most discerning enterprise clients out there. Today, I'm delighted to say that I'm joined by my good friend and B2B sales expert, Kiran Gill. Hi Kiran.

Kiran Gill 0:58

Good afternoon. Alastair, hi everybody. My name is Kiran. I'm a co-founder at The Uplift Partnership, and I've been selling enterprise for over 10 years now. And what enterprise means to me is about the long, extreme sales cycles that you have in there, and being a part of the team that was successfully sold into a client, but it took us two years to close that big fish.

Alastair Cole 1:23

Well, wow, yeah. I mean, that's one of the classic challenges which we'll get into enterprise deals. So together with the pair of us, our co-founder Douglas, we are The Uplift Partnership - we accelerate sales for tech businesses, and we're different because we build and sell our own SaaS so we know your world. We'll be taking questions as we always are during these live shows. You can dive in on LinkedIn and ask a question. We'll pull that out in real time and get to it if we have time. So feel free to dive in with comments and questions on the LinkedIn chat now. And so today's topic, my friend, you know it's, it's, are you ready to go for enterprise? When is the right time to get into going for those bigger fish? And you know, let's just start by how, what your definition of enterprise is when we were talking about enterprise deals as a term that's used a lot, what do you think of? What should people be thinking of when we think about enterprise?

Kiran Gill 2:29

Okay, so enterprise, for me, quick definition is a company that has multiple headquarters around the globe. That's probably one thing that you need to look at. They might have a main headquarter somewhere, but they'll probably have multiple offices, probably in each region, and each of those regions will probably work autonomously compared to everybody else. And you're looking at 10s of 1000s of people who are working in that organisation, and so that is pretty much what an enterprise kind of outfit is, and they will be either majority. There are some enterprises out there that aren't listed, but you're probably talking at these companies are probably listed on the 250 if not the 500 if not the 100 foot C or NASDAQ, depending on which stock market you're looking at, yes,

Alastair Cole 3:21

and you know, the benefits, obviously, of landing those bigger fish are, you know, quite obviously, you know, higher revenue potential per client, bigger deals. You know, obviously that, as well as it being a larger deal size, that the contracts can be longer term, much more lucrative. And, you know, market credibility as well, I think, is a really, really, really big deal. Your ability to set yourself apart and demonstrate that you can land and deliver those really big deals, what else comes to mind for you in terms of, like, benefits that the good things about going forward and lending. If you can enterprise clients,

Kiran Gill 4:05

If you can get enterprise clients into your company, it can be life changing in the sense of reputation, selling into other organisations of the same, similar kind of size. It can also be totally changing for the whole organisation, in the sense of how you see yourself. So I've been a part of a small company that was able to land a very, very large client, and suddenly, you know that there's a stature inside of the company that you can do this and you are successful. And so it comes with many, many benefits, and also the injection of cash, and because once you're in, you have opportunities to sell to other departments within that same organisation that gives you more opportunities globally. So suddenly you become a global outfit for a small company is the best thing in the world. Yeah,

Alastair Cole 4:56

yeah, you talked about global, you know, off. On those enterprise deals you get access to new markets, new teams, all through that kind of strategic partnership, it becomes an alliance. And, you know, from my time working with Google, right when my days are essence, that they became a, you know, a huge part of the income. And sometimes that can get a bit scary when you know you need to dilute. But actually, those big clients can just generate, you know, they can. They can run whole businesses. They're so powerful, so loads of opportunities. You know, we've talked a little bit about some of the challenges, the right kind of long sales cycle. What's the toughest thing in your eyes? My friend about going for enterprise,

Kiran Gill 5:43

It's the changing landscape, because within Enterprise, there's a lot of politics, and a lot of the companies have a lot of things going on internally. Oh, that you don't care, you're never a parent that you can really see. So as a salesperson, selling into enterprise, you need to be very close to the client and be able to multitask, and even after the sale, you're continuously selling within the client to make sure that everyone's seeing the value of your product. Because come the next cycle of when the money is getting churned out and everybody's signing off for the next year's worth of cuts, your name might be on there because you haven't done enough work internally to promote your product or service.

Alastair Cole 6:26

Yeah. I mean, the challenges are obviously getting them, you know, in the door, right? That's, that's big, that's tough enough, right? Longer sales cycle, you've got a complex buying group to get into, and then once you've landed, not only you've got to deliver, you know, often a much larger deal than you've ever delivered before. But as you said, it doesn't end there. You know, you've got, you've got to, you know, manage the client. You've got to continuously deliver the right kind of level of resourcing, demonstrating value for money. So there are a lot of challenges there. What we've done for today is to think about five areas in which we would ask founders to challenge themselves. Are they ready? And the first of these is, is their product maturity and scalability, right? And having sold and delivered enterprise level technology products into, you know, top tier enterprises, you've got to have a robust product, right? Because there's no you can't be selling vaporware, whether it's technology or whether it's services. You've got to be able to walk the walk. What would be your watch outs in terms of you know what things to look for in terms of product maturity here and before people, before businesses go after enterprise, yep.

Kiran Gill 7:48

So there's two, two aspects to look at it. From this point of view, if the lead is coming inbound, the chances are the due diligence has already been done and they're comfortable with the size of your company and your product to have that conversation with you, and that's a great thing about an inbound lead. Getting an inbound enterprise lead is difficult at the best of times for smaller companies. If it's outreach, that means you're approaching, that means you need to think to yourself, Is this really what we want to do now, at that point, realistically, have you been selling into mid market and larger clients. And these might not be clients of 10s of 1000s of people, but they might have 1000s of, you know, potential users, or hundreds at least, have the come to be able to have those kind of customer assets and customer success stories that you can go to your clients and show this Enterprise Client. Look, we're successfully doing this in many other places, and we're ready to go to the next level. If you haven't got that kind of resource behind you and got those kinds of testimonials to support your claim, you might not be ready for enterprise.

Alastair Cole 8:56

Yeah, that your product, certainly, if it's a technology product, and even if it isn't, you know, it's got to be able to deliver at scale to service those enterprises with multiple offices, 10,000 staff. So it's got to be scalable. It's got to be robust. There's got to be solid. You know, security in place, certainly with digital tools. We're talking about cyber security, we're talking about resilience, all of which is kind of like top tier, you know, major products. So your product maturity and scalability has got to be, you know, really high. You've got to have a proven track record and some very, some very slick onboarding as more customers than ever will be coming onto the product once you've landed that enterprise deal. So, yeah, but that's, you know, the question is, is your product mature enough and scalable enough for enterprise? The second one, really big one here, does your sales team have the necessary experience? What should I be thinking about now? Kiran,

Kiran Gill 9:58

right. So selling in. Enterprise. It's a team game. You're not going to be selling into enterprise with probably one or two salespeople involved. You're probably going to be selling into enterprise with probably a team of sellers. Now I've been fortunate to be part of a team that is a lot wider. There were seven of us selling into one Enterprise Client. And also I've trained teams to sell into, into enterprise and again, technology tends to be that you have pre sales account managers, global account managers. You will have SDRs. You will have marketing people, Junior marketers. You'll have a lot of people trying to get in there, not involving your CEO, your CFO. It depends on how complex it gets. So your team needs experience. At the helm of this team, you're going to have a sales person who's going to be driving this and who's going to orchestrate this. Now these sales people tend to come with quite a lot of experience and have done this before, and because this is a marathon and not a sprint, they also understand while everybody else is panicking around them and saying, oh, no, we need to close it this week. They know that this takes time and effort, so that is the big thing about your sales team experience. Have you got the right people in the place? Have you got the right people with the right experience? If you have, and I have seen this so many times, the wrong sales person who doesn't have the right kind of skill set, suddenly all your effort could be just lost in the last few miles of the race, towards the end of the closing period of that deal.

Alastair Cole 11:32

Yes, and so, so critical. Those individuals, you know we're talking about, you know, I think the one of the most interesting is you said there was about the experience of the leadership of that team. You've got to have someone you know, who's done it before, knows how to hire the right people for that. So is that, is it possible for you know, kind of founder, seller, selling into medium sized businesses? Is it, is it, is it possible for them to assume that role, or should somebody external be brought in to kind of head up that enterprise team?

Kiran Gill 12:11

It depends on the complexity of what you're selling. I think the thing is, we're talking multiple meetings over multiple months, potentially with stakeholders coming in and out of the buying group, and you need somebody who understands how to orchestrate this. And what message do you give to a CFO? What message do you send to a CEO? What message? And you might not even be speaking at that level. You might be talking at a regional but even at regional level, at a global organisation, these people are pretty hefty in the sense of VPS, and people who are running MDS of a market unit, these still could be in one country alone. I can remember selling into an organisation where they had 5000 employees just in one country. This is bigger than most companies looking at, so you're selling it to each one of these new customers and then a salesperson who doesn't understand this goes in there and thinks, Oh, it's only a regional person. Suddenly, you're out of the waters. Right away. You can't even get back into the deal. The great thing is, most of the time at enterprise, you're looking at RFPs, and if you're looking at a request for a proposal, and that's what an RFP is, if that comes in, the chances are they've already done their due diligence about you, and that's you just preparing your team to get ready to sell into the client, and preparing yourselves. If it's outreach, that means you've done your homework. That means somebody in your organisation probably knows what they're doing, and that's why you've gone there, because if you have, if you don't know what you're doing, your outreach probably wouldn't get there anyway in the first place. Yeah,

Alastair Cole 13:46

Yeah, that's fair. Some good tips. Thank you. So in number two, the enterprise sales team experience is absolutely critical. We have to have done it before. Understanding the landscape is a patient game. The third area is financial and time resources. Do you have the money and the capacity in order to go after these bigger fish? And I think, you know, a lot of the time are kind of going for the enterprise deal for a lot of us, or the first one that we land, you know, you're given an opportunity, and you feel like you just want to go for it, right? It kind of happens organically, and I think that's the case for a lot of businesses, and sometimes you might win it by chance. When you're thinking about it from a more strategic level, should we continue doing this? You've got to think about the time and money, you know, and be prepared for extended sales cycles and slow payment terms, potentially with larger businesses at enterprises. So what else should, should founders be thinking about occurring in terms of, you know, the resources that they're going to have to pour into going after enterprise deals.

Kiran Gill 14:58

So it's cost of sale. As a part of a global selling team, I used to fly around, back in the good old days, and we would travel from European city to European city, across to Africa to sell, you know, basically to a large corporation. And that's how it was done. So the cost of sale was massive. There was no guarantee that this was going to be able to be landed. And there was a lot of relationship building going on at the same time. And sometimes it was very, very slow and painful, and money was being spent now, and that's also for resources around me, of me getting people to build slide decks and getting ROI calculators and all those things you need to help convince all these people that you're the right person, because every individual stakeholder in every different market unit had their own way of looking at the deal, and all of them had to come together to say yes. So the cost of sale was massive. And sometimes, like I said, sometimes these deals could take 18 months to two years to close. Now everybody around me might be going crazy and thinking, oh my god, this is never going to close. And there were good days and bad days, and you never really knew until the contract was sent. And even when the contract was sent, whether it was going to be signed, and all those things that come along with selling into enterprise, and this is part and parcel. So the cost of sales is massive. Be prepared a good salesperson who's selling into enterprise probably will have four or five enterprise deals going along. That person probably is very expensive, and you probably won't see a lot from them in the first 12 to 18 months. And then suddenly the deals start landing. And once they do, now, if you've got a founder seller who understands this and is us, has the skills and the capability to do this. That's the best thing in the world, because now you've suddenly got somebody in the team on the company who's able to do this for you.

Alastair Cole 16:52

Yes, I mean that, those curveballs that you talked about that's happened to me. I mean working into enterprise 10 years ago, we were literally signing on the paperwork when the kind of global crash happened, 2008 and and and before the signature went on, of course, that enterprise clients looking at all the deals that they're trying to, they're going to be signing, you know, that month, in that moment, and, and they, they, they chopped a huge amount of value out the deal, like a kind of overnight. And, you know, we'd worked so hard for so long that that was another curveball. It's like, well, you know, you had to be invested in the long term, because just what you were going to close that quarter or that year, isn't the full picture. There's the following year and stuff. So you, you know, you could have, could have pulled out then, but, um, really, really critical area, right? The time, the effort, you know, it often feels like its success is just around the corner, because they're so big, but just around the corner can be, you know, months away. So let's move on from number three to the fourth area you should be having a think about and be absolutely crystal clear, and that is the value proposition, specifically the compelling enterprise level value proposition you've put together. It's got to speak to, you know, them, their pain points. How does that differ in your experience, the kind of value proposition that you would use to get into enterprise, versus smaller businesses? What's the difference there?

Kiran Gill 18:32

The difference is it tends to be slightly more generic when it comes into enterprise initially, and then you tailor it to get more and more bespoke as it gets to the person you want to speak to. And also you won't have one value proposition. You're probably going to have multiple value propositions to different people in different departments. And also culturally. You might have different value propositions if you're selling regionally, and you're selling to somebody in Africa and then also selling to somebody in Scandinavia, your terminology might be slightly different in your value proposition. So again, you need to think about who you're selling to. So initially generic that will get you through the door, maybe, but then tailoring it down to certainly speak to the people you're speaking to in their departments and their pain points and their challenges and their wants and their needs and all those things you have to do in a value proposition. And then probably what you need to start thinking about, actually, does your value proposition resonate outside of that group? Because what happens if that stakeholder leaves, and the next person who comes into that department, will they be able to read that value proposition say, actually, you wrote that for Derek, and Derek's gone, and I'm not Derek, and guess what? I'm bringing in my own vendor to do this, and that's happened as well to me. So the value propositions are so important when you're talking to an enterprise, I think the bigger difference is when you're spending into selling into smaller organisations. You. You don't have to worry about change of ownership or change of department so much, and that same person probably is going to be there in six months, or in 12 months, or 24 months, where, in enterprise, honestly, you're selling into somebody for six months. You think it's all great, and suddenly, overnight, they've gone and now you have to start all over again.

Alastair Cole 20:20

Yeah. I mean, it might, that might sound a long way off, but it's it that is the case, you know, and it's part of the reason that, you know, one of the key areas of NPS internet promoter scores is test getting feedback out of 10 from a really broad range of clients. So I've seen it happen in the B2B world, where we've just naturally fallen into making sure that we're pleasing the most senior person on their own, not giving everybody else enough love. And when that senior person announces they're going, we're left, you know, kind of trying to make up the difference. So you've got to keep everybody in the buying group happy. You've got to be in it for the long haul. You have to keep them happy for a long length of time. And my mind naturally goes to the kind of self service and supporting outbound that your digital presence, your website, has to do. And as you move up to enterprise deals, it's no longer good enough to just have, say, a landing page that is per ideal customer profile. You're talking about, probably more of a section on your website that speaks to your ICP, that speaks to their industry, more resources, more tailored pages and content for that business and those, those buyer personas you have to look after everybody in a much more professional way. So, yeah, I mean that that's really big, crystal clear value proposition is, is absolutely, is absolutely key, right? And then the last of the five areas that we would advise you to look into in detail is implementation and support readiness, you know, having closed the deal and got to that magical moment where, you know, procurement and legal have managed to, you know, get into bed together and make a success of it, and now you've actually got to deliver. You know, it's about implementation, which requires, you know, high quality team and technology on the ground, and it's about preparing for a new level of customer support, which is much harder keeping, you know, keeping your customer success scores high is even harder against enterprise. So what? What are you, what's your experience? Kiran, of that, that part the deal signed now you have to implement and support was it like with

Kiran Gill 22:43

enterprise? Well, at a smaller company can be hectic, so selling into a larger company and then suddenly realising that you have to now deliver what you've promised, and your reputation, and, like you said, customer success is all on the part of that that can be absolutely, you know, manic, scary, exciting, all those things, but you must have an understanding when you're going into something, do you have the resources? The chances are you're going to have a lead up time before you have to deliver everything. There's an understanding and a part of the RFP, and especially the procurement and the implementation process, there will be conversations with you to understand, and they will want to make sure that they are comfortable with you and your technology coming into their company, and that you have the support and the readiness to actually bring that in. Because remember, reputations could be burned if you make a mistake, and your company makes a mistake, and it could be game over. So that is also a massive critical point to think about. Are you ready for enterprise? Because you might think you want to get that big whale. You want to be Captain Abe. You're chasing it down. You're out on the open seas, and you're running after it. Sorry, sailing after it, but, but the problem there becomes is, what happens if you catch it and you can't handle it because reputations, and I've seen this happen where, you know, I worked with a client who did catch a big fish and then wasn't able to implement it, and then had to run around help getting everybody else involved to help them implement the strategy or the the technology in house. Now, luckily, they were a part of a bigger group, and they were able to do that, but, yeah, sometimes you can't do that.

Alastair Cole 24:24

No, totally, and that's why you know that that last one, you know it might come last chronologically. But actually you need to be thinking about implementation, sport readiness right at the start. You need to be able to, you know, you need to be able to talk to your enterprise buyer about how you're able to do that. Because it's true. You know, I've seen it too with new platforms and new systems being brought in that, you know, for individuals at Enterprise who are kind of taking a gamble on a new supplier, their reputation is on the line, and, and, and, you know, you. If, if it all goes swimmingly, then you know that sometimes they get a little bit of kudos, but not necessarily enormous, but obviously, if it goes badly, then you know, I've heard from clients that that's their kind of reputation burned for their their tenure at that company until they go somewhere else, they're so that they're less likely to take on new products. So convincing them that you can implement and that you can deliver the right level of support is critical, you know. And having worked with them, SLAs with enterprise clients, you know, are tough, and you know they want their pound of flesh, they're prepared to pay for it. But it's playing in a different league. And, you know, if you haven't got the 24/7 support, or it's not as robustly delivered as you promised, it's gonna wake up in the middle of the night. I've been there, you know, two, three o'clock in the morning. You know, you're playing with, you know, playing with the real, the real big boys and girls. And you've got to have the infrastructure in place. So those are our five areas you should be considering if you're thinking about going for enterprise. Certainly, it's possible. Certainly there is a right time to do it. For me, it's as much of a kind of mindset shift of you changing up and moving into into new gear, everything you know, talked about delivery, but right at the start, the fact that it's, you know, someone saying they're interested means, you know, they're going to need another six months. You know, it's a different kind of ball game. If you're thinking about it, are you ready for enterprise or the next step of your sales growth? One way you can answer that question is by taking our 360 degree sales diagnostic product. There are seven areas we score you on, and 52 metrics that sit underneath those seven sections. And all of that is delivered in a 25 page personalised report with full score and breakdown bespoke recommendations and revenue roadmap of how much additional income you could make by going for enterprise deals in your market. You can get more information about that at TheUpliftPartnership.com. To see other shows of ours that come out weekly, live on LinkedIn, you can head over to TheSalesScoop.com - check in on the high touch versus low touch. SaaS selling became a confident founder seller, where the last two up next for us seven days and today we've got the fantastic Winnie Akadjo on the show. Winnie is a live streaming specialist, so we're going to have to up our game. She's the founder of LVS hub, which is a live streaming B2B sales platform. So really looking forward to having Winnie on the show a week today and a week after that, two weeks today, Kiran and I will be reprising our strategic thinking for next year. We'll be diving into what we see are the five sales foundations you'll need for 2025: the building blocks of revenue growth for technology businesses. That's us 1229, we've managed to bring the ship back to Port Kiran with an enormous enterprise fish on the end of our ocean reel. Thank you for your time today, my friend, it's been a pleasure.

Kiran Gill 28:39

Thanks. Alastair,

Alastair Cole 28:41

Great — that's it! Thank you. Everybody see you again next time, bye, bye, bye for now, bye for now, bye.