I’ve had this conversation about 6 times in the last year – how can you scale from selling to small businesses (SMBs), up to Enterprise organisations? What are the marketing challenges? What’s necessary, what’s nice-to-have, and what’s a red herring? This is something we’ve done incredibly well at Redgate over the last five years (from almost nothing, to now being more than half of our business), so, “just for the record”, I wanted to note down the things that I believe are important for success, and so that, when this conversation comes up again, I can just refer back to my notes!

It’s important to note, this is what worked for us. We have a particular product set, in a particular market. We already had certain advantages and certain disadvantages. And I haven’t put much here about the ordering of implementation – this would depend on what you already have, and where you really are short. For example, if you already have a senior sales team in place, that’s great, you can jump past item #1 on the list. But if you don’t, that would be your first port of call.

Additionally, there are some pre-requisites here. The most obvious is that you have some sort of product-market fit. You must have this if you’ve already been successful with SMBs! But if you’re still pre-PMF, none of this will work. This is a plan for building an Enterprise go-to-market on top of a successful SMB business.

Anyway, here is what I believe to be a check-list for growing your business from SMBs to larger enterprises. This is a multi-year strategy – you’ll need faith in this all working: don’t expect results in month 3. But it will work, if all the pieces fall in to place.

1. Hire a salesforce capable of the Committee or Consensus Sale. The first thing isn’t marketing! But any work you do understand customers, generating interest, changing positioning etc etc, will be a waste if you don’t have a great team in sales who can manage the deals, understand the needs of a complex group of buyers, take a sale through a standardised sales model and, eventually, close the deal. There are many different models for sales organisations and of course, if you have a smaller org, you don’t need anything complicated. But I’d suggest it’s necessary to have at least 1-2 people who can pick up some of those early Glenngarry leads, and really prove out your model.
2. Build your Ideal Customer Profiles. Selling to SMBs you might have had a very simple ICP – perhaps you just needed to convince an end-user, possibly a team-leader. Very simple, and singular. But to sell to the Enterprise, you’ll inevitably be marketing yourselves to a wider group of more senior folk. NB: You can’t and mustn’t forget about the end-users: most enterprise sales follow the pincer model – you need to appeal to both end-users and the more senior people. But you can’t ignore the latter anymore. So who is your key senior decision maker? Heads of IT? Head of Finance? C-level execs? VP of Operations? Figure this and then make sure you know everything about their world – their concerns, their pain, their pressures. And then, in the next stage, you need to make the link between their world, and your offering…
3. Figure out why and how your offering is uniquely positioned to solve the problems of your ICP. This is one of the hardest bits. As I say, you’ve had success selling your product to a more junior buyer at an SMB. But that doesn’t mean that the “VP of Operations” (or whoever this persona is) understands what you offer and why she should care. That VP has a world of problems that she’s trying to resolve right now and unless (a) you’ve figured out which of those problems your offering addresses, and (b) why your offering is the best solution to that problem – you’ll never get her interested enough to talk to you, however many marketing dollars you throw at your campaigns. This takes research, talking to those people, a deep, deep understanding of the true value offered by your product, and the skill to the link the two. Never underestimate the difficulty of this challenge.
4. Figure out your target accounts. I.e. the organisations most likely to buy. Depending on the size/scale of your org, this might be 10 accounts, 100 accounts, 1,000 accounts or more. But you need data about (a) technographics, (b) firmographics, (c) ideally, history of interest in your market, to build out a set of target accounts. A “Quick win” here – if you’ve already had some success selling to larger orgs, just not nearly enough then target these warm accounts first. If “Bank of America” have bought $1,000 of software from you, then that’s an “in”, that should increase the likelihood of them appearing in your account list.
5. Build an Account-Based Marketing capability. Specifically, you need field marketers working in partnership with your sales teams, who understand how to run 1:1, 1:few and programmatic campaigns to targeted accounts. Unfortunately, this isn’t a cheap skillset. But there are an enormous number of resources on what you’re looking for (e.g. SiriusDecisions), so you can start there.
6. Hire the BDRs and SDRs in sales to work in partnership with the field marketers. I can’t emphasise enough how important the partnership is between sales and marketing. If there’s mis-alignment, disagreement, if you’re going after different accounts, don’t agree on strategy and so on – then you’ll fail. The core of great collaboration is working together on the same goals – hiring BDRs and SDRs in sales or marketing to work directly with your field marketers is key.
7. Build the tech stack. You need a decent CRM (likely Salesforce…), a world-class marketing automation platform (we use Marketo) as a starting point. On top of that, there are two essential ingredients to a successful Enterprise GTM – a great sales prospecting tool (we use Salesloft – very highly recommended) and a “buyer intent” platform. We use 6Sense for the latter and love it, though Bombora is another contender here. Both of these are necessary for success – the first because, when you’re prospecting into larger orgs (with orchestrated plays, worked out in conjunction with marketing), there will be a very complex set of interactions between you and an array of people at the target org. You can’t manage all this by hand with multiple accounts, you need some level of orchestration. For the latter – “Buyer intent” (specifically – finding companies that are looking for solutions like yours before they’ve come to you) is a key tactic for targeting your effort. When you know that a given company is looking for solutions like yours, you can use the platform to spend on advertising targeted directly at them (rather than mass advertising which misses the target in 99% of cases).
8. Pricing and Packaging. You need a pricing and packaging structure that matches how enterprise orgs want to buy. Too cheap, they won’t even look at you. Too expensive – well, unless you’re already the market leader, again, why would they look at you? But there’s more to do than this – the model for P&P is also crucial. Annual contracts? Monthly? Per-user, pre-transaction, or some other model? The primary goal here is to not make your pricing model a talking point for sales. If a customer is questioning your model and finding it confusing, you’ve created a barrier. There are some great third party companies that can help with this work, we’ve had great success with ProfitWell for example.
9. Content, Case Studies and Thought Leadership. More on this below, but companies like to choose the winner in a given market, particularly if they’re new to that market. What can you do if you’re not the de facto market leader right now? Write incredible content about the market, the problems (your customers have), and how they should solve them. This insight comes from deep understanding of the market, but needs to be translated into great articles (there’s no point knowing things and not telling everyone!). You also need case studies from existing customers. Of course there’s an issue here – if you’ve never sold to an Enterprise, how can you write a case study for one!? You need to bootstrap this process – start with a well respected medium size org on your books, perhaps a well known name. Start there, then build up as you get more and more clients.
10. PR, analysts, article placement. How do prospects know that you, specifically, are the winning vendor in the market? They read press, they read articles, they go to their analyst. You need to be in front of all of these, and that’s all based on the thought leadership work you’ve done previously.

In a sense this is an over-simplified plan – how do these all work together? What do I do first? Are they all necessary? How do I know it’s working in the early days, when I don’t have all this yet? All very good questions. Here, I think it’s really important to show early wins, hence why getting senior sales reps as a first step. Those first reps won’t have all of the support and help outlined above – they’ll have to do a lot themselves, beg and steal to get what help they can. But if they can get a couple of deals over the line, this is incredibly valuable – for insights, for case studies, for analysis of “What worked here? Why did they actually buy?” and so on. Those early signs will also help getting buy-in across the org for this new strategy, something that will then fuel future growth and success.