BJREES

B2B marketing and AI

Tag: scaling-mid-market-to-enterprise

  • A Checklist for Scaling from SMBs to the Enterprise

    A Checklist for Scaling from SMBs to the Enterprise

    If you’re growing a SaaS company, there often comes a moment when success with SMBs isn’t enough. You’re ready to move upmarket. But selling to larger organisations requires more than just a bigger sales target – it means changing how you think about customers, teams, tools, and messaging.

    Here’s a straightforward checklist, based on what I’ve seen work, to help you scale from SMBs to enterprise.

    1. Hire a Sales Team That Can Sell to Committees

    You can’t grow into the enterprise if your sales team isn’t ready for it. Selling to one or two decision-makers in a small company is very different from selling into a team of senior stakeholders with complex buying processes. Even if your organisation is small, make sure you have at least one or two people who can manage enterprise deals properly – structured sales approach, strong qualification, and an ability to drive deals forward across a buying group.

    2. Redefine Your Ideal Customer Profile (ICP)

    In the early days, your ICP might’ve been simple: one end-user, one pain point. That changes when you move into larger organisations. Now you need to understand who your senior decision-makers are – IT, Finance, Operations—and what matters to them. And you still need to win over the end-users. Most enterprise deals depend on both.

    3. Understand Why Your Product Solves Their Problems (What is the “Job to be Done”)

    Enterprise buyers won’t connect the dots for you. It’s not enough that your product worked well for a team lead at an SMB. You need to be clear about which problems your target stakeholders are trying to solve, and why your product is the right solution. This takes more than just positioning work – it takes real insight from customer conversations and a solid understanding of the world they operate in.

    4. Build a Target Account List

    You need a focused list of the right organisations to go after. Use data — firmographics, technographics, and any buying signals you can get hold of. If you’ve already got larger organisations using your product, even in a limited way, start there. Prioritise warm accounts.

    5. Set Up Account-Based Marketing (ABM)

    You’ll need marketers who can work alongside sales and run targeted campaigns for specific accounts. Whether it’s one-to-one or one-to-few, the key is relevance and coordination. This isn’t cheap or quick to build – but it’s essential.

    6. Align Sales and Marketing at the Frontline

    If sales and marketing aren’t working from the same account list, or aren’t aligned on messaging and strategy, things break down. Bring in BDRs and SDRs who can work directly with field marketers. Shared goals, shared plans.

    7. Build the Right Tech Stack

    You’ll need the basics: a good CRM (usually Salesforce) and a solid marketing automation platform (like HubSpot). On top of that, I recommend:

    These help you run coordinated outreach and target the right accounts at the right time.

    8. Revisit Pricing and Packaging

    Your pricing needs to match how enterprises buy. That’s not just about the number—it’s about the model. Whether you go per-user, per-transaction, annual or monthly—make sure your pricing is clear and credible. If pricing becomes a point of confusion, you’ll lose momentum. Tools like ProfitWell can help here.

    9. Build Out Case Studies and Thought Leadership

    If you’re not already the market leader, your content needs to show that you understand the market better than anyone else. That means writing clearly about customer problems and how to solve them. Get case studies from the best-known companies you’ve already worked with – even if the deals were small.

    10. Don’t Forget PR and Analyst Relations

    Enterprise buyers do their research. That includes the press, analyst reports, and third-party content. Make sure your message shows up in the places they look.

    If you’re moving from SMB to enterprise, I’ve created a detailed checklist in the Resources section.

    📩 ben@bjrees.com
    🌐 www.bjrees.com

  • Scaling up marketing

    Scaling up marketing

    Scaling up marketing is tough. You’ve missed the fun of the early days where you can try a new thing each week and you’ve not yet reached the safety of a well established brand. The board will be on your back, expecting enormous growth yesterday when you know in your heart that building a brand takes time.

    Assuming you don’t have infinite budget, infinite resource and a super-experienced team sitting there waiting for their next job, you need to prioritise. And to prioritise you need a strategy. Part of choosing a strategy is looking at your starting point. What are your unfair advantages? Where are you weak? Trying to start from scratch where you don’t have the expertise or traction in the market can be very tough, particularly if the board want results ASAP.

    I use the diagram below as a way of focusing efforts where it’s needed:

    Marketing pyramid v3

    Click here to download a copy.

    To help navigate this diagram a little:

    • There are five strategies listed from top to bottom. The further down the list you go, the less targeted the strategy becomes, though of course you are casting a wider net.
    • From left to right, the diagram provides a summary of what the strategy actually is, a grid showing where the strategy is most effective (is it better for large or small companies? And is it better for companies who already know what they want?), then most importantly, the cost of the strategy both in terms of budget but also in terms of the number of people you need to implement it effectively.
    • Crucially, when looking at costs you have to look both at the financial cost but also the number of people you need. To take a simple example, Google ads don’t need a large team to implement and maintain. However they cost a lot, whether you believe they are effective or not. In contrast, high quality content is cheap if not free to create. But you need a team of very talented people for this to be effective.
    • Finally I’ve put in a column of “how to scale”. Not everything can be scaled by pouring more money in. More money won’t give you higher quality content. More money won’t fix your hiring process. More money won’t fix your culture (in fact it does the opposite). When looking at how to scale it’s crucial to do the strategic diagnosis first of what you are capable of doing as an organisation, where the real problems are and so on. Without this you’ll burn everybody out, but also it will take far too long to hit the targets that you have.

    This is where the real skill comes in, in senior marketing roles. How do I make an impact soon? What numbers can I show that actually show progress for a long term objective? Where are the quick wins to keep the board onside? What can I do if I’ve got pots of money? What can I do if I haven’t?

    I’ve provided various resources which will hopefully help scaling up marketing. Otherwise get in touch to see if I can help.

  • Scaling from SMBs to the Enterprise – a 10-Point Plan

    Scaling from SMBs to the Enterprise – a 10-Point Plan

    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.

  • Join a Scaleup to Scale Your Career

    Join a Scaleup to Scale Your Career

    It’s hard getting ahead in Marketing. It’s a discipline changing every year (certainly true of 2020), it covers an enormous breadth of disciplines which need a great variety of skills and it’s notoriously difficult to prove the impact of your work. So what can you do to give yourself the best chance of success? Of growth and moving to the next level?

    I’ve always believed that a significant part of your career success is dependent on the organisations you work for. You can be the smartest marketer around, but if you’re working at a deadbeat company in decline, you’ll struggle to grow and show success. Equally, for better-or-worse, if you’re only an average marketer working at a place growing 100% year-on-year, you may get away with perhaps more than you should!

    So obviously we all try to work for exciting growing companies. But the other big factor is the size of the company you work for. I’ve worked at companies of 50,000 employees and of 2 employees (one of which was me!) and it makes an enormous difference, not only to the sort of work you do, but also your chances of learning and growing. A growth mindset is crucial for your future success. I’ve personally found that Scaleups – organisations that sit between early stage startups and the big corporates, focused on scaling up to the next level – have provided the best opportunities for growth.

    My first job out of college was at British Airways, as a developer. I had no idea what to expect, but it started well. The first month was a formal training program (on their systems), and it felt very structured, almost a continuation of college. I was getting training and everyone seemed to know what they were doing.

    So a great start. But 6-12 months later, something didn’t feel quite right. I soon realised that every problem (at my level), every process, every significant decision had already been figured out by someone, likely years before. A simple example – the precise naming, file location, structure, font and format of every doc I had to write had all been worked out approximately 10 years before. I suggested “Perhaps for a small change, we can just write a short note (a ‘Minimal viable document’!), something really useful to the reader, rather than writing 25 pages, taking more time than the actual code change”. That didn’t go anywhere. I soon found that my ability to grow on-the-job was very limited – it’s a cliche, but you quickly become a cog in the machine.

    So many years later I tried a startup. A very small startup in fact, just two of us. There was not a formal training program when I joined here! And it was really exciting – I did really enjoy this time. Certainly, a little hairy at times – there wasn’t the backup of a large corporate with deep pockets. But the rollercoaster ride was part of the fun. And I definitely felt like I had an enormous influence over the strategy for the company – this is one of the key attractions for smaller orgs.

    But this comes at a price – I was there for over 3 years in a Product Manager role. But my growth in the disciplines of product management and marketing was pretty close to zero. I learnt a lot about the hustle of working at a startup. I learnt a lot about closing deals, about getting 25 things done all at once. But my understanding of the emerging disciplines of product management, product marketing, brand, digital marketing, marketing operations etc etc didn’t advance in three years.

    So where’s the Goldilocks zone? Where can you get this sort of support for growth without just becoming part of the machine?

    I now work at a company of 400 people, in a strong growth phase with a laser-focus on learning and development of its employees. A Scaleup like this – somewhere moving from the stage of “Everyone doing everything, just get the release out!” in to a more disciplined stage of “Okay, how do we scale all this? We have success already, how do we make this 10x bigger?” is the sort of environment where you can really become a master of your discipline.

    When I worked at the startup, I did all of the product management, a lot of marketing, some development work, and a lot more besides. I did what needed to be done to survive, as we did everything we could to find some sort of product-market fit. I didn’t have the time to work out “What would be a better way of running that digital marketing program? How would I do that better next time?” – the rollercoaster was moving too fast for this sort of introspection.

    At Redgate, we have a marketing department around 45 people strong. We have product marketing, digital marketing, brand, ABM and customer marketing functions (all with disciplines within each of these) as well as a nascent marketing operations function. We pride ourselves on being world-class in all of these areas. Of course we’re not there yet – part of a growth mindset is accepting that you’ll always be striving to do better – but I feel we improve at everything we do year after year. However great, say, our digital marketing team was a year ago, they’re better this year (through growth and learning activities), and will be even better this time next year.

    We even run an internal conference devoted to the goal of growing our capability. Called “Level Up”, this year will be a week long event covering an enormous range of topics across the whole business. Previous years have been a single-day offsite, but with everyone working remotely this year, we’re trying something new. I’m really excited about this as, yet again it reinforces the crucial role that learning and development plays when a company is scaling up. It’s just not good enough to still be working in the same way this year as we did a year ago – as the business grows, we need to grow as well.

  • Focus on Marketing Effectiveness to Scale Up

    Focus on Marketing Effectiveness to Scale Up

    Here’s a very non-theoretical problem – you’ve got two ways of spending some digital marketing budget, either a) LinkedIn advertising, or b) Facebook advertising. The former works pretty well, you manage to calculate a return of $1.50 for every dollar you spend. The Facebook adverts are more effective though – a return of $1.80 for every dollar spent. Question is – which do you do? Obvious isn’t it, it’s Facebook?

    No, the answer is both. I’d argue that, for most orgs, particularly those in a mid-stage, scaleup phase, the more you can spend on things that work, the better. Why? Because the only reason you’d choose one over the other is from a desire to improve Efficiency – to get more bang for your buck. But for many orgs that isn’t your job, your objective is to improve Effectiveness – to improve your outcomes, to grow, to maximise your revenues and profits as soon as possible. It doesn’t matter if some activities are less efficient – do them all!

    Les Binet and Peter Field explain the difference very clearly here, around 5:58:

    I think there’s an additional subtlety here for growing businesses – that the relative importance of these two approaches varies depending on the stage of growth for your company, and the objectives handed down by your boss or board. For some very early start-ups, you’re not worried about metrics like “Marketing ROI”, “Marketing generated pipeline” and so on – you’re just trying to find product-market fit, and finding any way of reaching your audience. Marketing effort is far more likely to be focused on early strategy – what is the market we’re after? Who are these people? What would they use instead of our product? Who are we competing with? How would we reach these people anyway? You’re not yet at a point where you know how to spend marketing dollars!

    For many large orgs, particularly those with investors, efficiency does become much more important – growth is relatively flat and the strategies might focus more on reducing the customer acquisition costs. I’ve spoken to a couple of people at this sort of company in recent years – not a role I envy perhaps, but at least it’s clear what you’re being asked to do. Your job is to optimise, find efficiencies, cut costs, track the Marketing ROI ruthlessly, and cut waste.

    The middle stage is interesting though. You’ve got product-market fit, you know your market, why customers buy from you and you’ve figured out a few channels and activities that seem to work. But now everyone just wants more. More leads, more growth, more $$ – there’s never enough! This is a great time for marketing – as noted in Rise of the Revenue Marketer, there’s a clear link between the activities of the marketing department and company success – it’s exciting, but it can also be a little daunting. Here’s a poorly sketched illustration, of the phase I’m referring to:

    Phases of growth

    The trick is to remember that efficiency is not your goal here. In the example at the top of this page, both tactics give profitable return – so you just need to do both. Accept that you’re picking both low-hanging fruit and high-hanging fruit. Some of your leads will be easily won – great customers, right in the middle of your Ideal Customer Profile. Sales pick them up, work the order in a matter of weeks, and hey presto – easy money. Others will be much harder to convince – the customer is a long way from a sure bet (maybe wrong industry, wrong org size, wrong technology stack). They’re very early stage – sort of interested, but they’re not sure what they want, or if they want it from you (tip – this is where great lead nurturing becomes invaluable). It’s going to take a lot of effort to win those deals – but you still need to do it. You’re not being measured on how efficiently you ran your campaigns (as mentioned in the video above, the most efficient way of running a campaign is to not run it at all!). You’re being measured on the maximisation of outcomes of leads, opportunities and revenue.

    There’s an obvious chink in this armour – a well run business has to be profitable. Is it really okay just to spend wildly? I believe strongly in tight budgetary constraints – total freedom on spend leads to laziness, and a lack of focus. In the example at the top, we’re still trying to measure what’s working and what isn’t. We’re not doing things that are unprofitable. And if the return on something was $1.01 for every dollar spent, I’d be far less interested. It’s important to still work very hard measuring what does work. You should be constantly looking for more impactful ways of spending money, and also discarding tactics that aren’t working (easier said than done!).

    But you need to be careful on cutting spend on the long-term brand building activities – the money you spend on non-activation activities that can’t be measured in the short term. These are the things that make you more effective in the long term. In a marketing department you have to weigh up your investments in short-term activation activities (“Click on this link to download our report!”), with those for long-term awareness of what you do – warming up customers for future activation. If you get this right, then you will be considerably more profitable – we all know it’s infinitely easy to get a customer interested when he/she is already aware of you, and has a positive inclination towards your offering or brand.

    So a strong mix of long-term brand building (or “Investment in propensity to buy” – far more palatable to many 😉) and a wide range of activation activities, focused on how you can be most effective – winning both low and high-hanging fruits – is, for me, the strongest strategy when your goal is growth. And if you want to scale up as quickly as you can – stop worrying about efficiencies – that’s a problem for the future!