Guides and reflections on scaling marketing from startup to enterprise. How to adapt processes, messaging, and teams when moving upmarket and tackling more complex customers.
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.
I started doing some manual research into the security risks with different AI tools. But then I thought, why not get the AI to do it for me? So that’s what I did. Once again I am very impressed…
1. Data Privacy and Confidentiality
ChatGPT: Users may inadvertently share sensitive information, potentially leading to data leaks. ChatGPT conversations may not always have the same enterprise-level data security controls, depending on deployment.
Gemini: Google advises against sharing confidential information with Gemini, as conversations may be reviewed to improve quality, raising privacy concerns for sensitive data. (searchenginejournal.com)
Apple Intelligence: Apple prioritizes on-device processing and privacy, with Private Cloud Compute to protect user data. However, the effectiveness depends on consistent use of these privacy features by users. (security.apple.com)
Microsoft Copilot: Integrated within Microsoft 365, Copilot has enterprise-grade security and compliance features built-in, including support for GDPR, HIPAA, and other regulatory standards. However, the risk of users accidentally sharing confidential data through Copilot remains, especially if the model is trained on organization-specific data without strict data policies in place.
2. Phishing and Social Engineering
ChatGPT: Can be exploited to craft convincing phishing emails or social engineering scripts by generating content that mimics corporate communication styles.
Gemini: Google Gemini has been found to have vulnerabilities that could be exploited for phishing, potentially enabling attackers to take over chatbots or impersonate users. (securityweek.com)
Apple Intelligence: While Apple Intelligence AI hasn’t been specifically linked to phishing exploits, any AI with language generation capabilities could potentially be leveraged for social engineering if misused.
Microsoft Copilot: As it interacts with Microsoft 365 tools, Copilot has the potential to automate and personalize phishing messages within Microsoft’s suite, particularly within Outlook or Teams. Enhanced by organizational knowledge, phishing attacks crafted by Copilot could mimic familiar internal communication patterns, making them harder to detect.
3. Malicious Prompt Injections
ChatGPT: Susceptible to prompt injection attacks that could manipulate the AI’s behavior to provide unintended or sensitive information.
Gemini: Vulnerable to indirect prompt injection, which could enable phishing or chatbot takeovers. (securityweek.com)
Apple Intelligence: Apple has measures to guard against vulnerabilities and offers rewards for identifying AI security flaws. However, the risk of prompt injection remains if used in complex workflows without safeguards.
Microsoft Copilot: As Copilot becomes embedded across Microsoft 365 applications, prompt injections could potentially allow malicious users to exploit workflows or access sensitive data by manipulating Copilot’s responses. This is particularly concerning in applications where sensitive data is routinely processed, like Excel or SharePoint.
4. Data Exfiltration and Unauthorized Access
ChatGPT: Without proper security configurations, there is a risk of data exfiltration if ChatGPT is misused or linked to sensitive applications.
Gemini: Accused of unauthorized data scanning on Google Drive, Gemini has raised concerns over potential data exfiltration or access without user consent. (techradar.com)
Apple Intelligence: Apple’s approach emphasizes on-device data handling to mitigate unauthorized data access, though secure implementation and user adherence are necessary to minimize risk.
Microsoft Copilot: As an AI system integrated with Microsoft 365, Copilot has extensive data access, which could be exploited if permissions are misconfigured or if attackers find ways to bypass controls. Because Copilot can access files, emails, and other stored information, this could expose sensitive data if not closely monitored.
5. Compliance and Regulatory Risks
ChatGPT: Compliance risks may arise if sensitive or regulated data is inputted, especially if stored outside organizational control, potentially violating GDPR, CCPA, or other regulations.
Gemini: Google’s Gemini AI practices could pose regulatory challenges, particularly around user consent, data retention, and control over how user data is handled.
Apple Intelligence: Apple’s privacy focus and on-device data processing align well with regulatory standards, but enterprises must ensure their specific use cases remain compliant with industry standards.
Microsoft Copilot: Copilot aligns closely with Microsoft’s regulatory and compliance frameworks, making it a safer choice for organizations bound by strict regulations. However, organizations still need to ensure data governance policies are enforced to avoid regulatory risks related to AI-driven data processing.
Conclusion
While ChatGPT, Gemini, Apple Intelligence, and Microsoft Copilot each bring distinct features and security controls, core security risks are common across all platforms. These include data privacy, phishing, prompt injection vulnerabilities, data exfiltration risks, and compliance challenges. Microsoft Copilot offers the advantage of built-in enterprise security and compliance support, but also presents risks, especially around data handling, unauthorized access, and phishing automation.
For all platforms, implementing clear data-sharing policies, monitoring AI interactions, user training, and regular security audits will help organizations mitigate these risks effectively.
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:
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 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.
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.
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…
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.
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.
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.
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.
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).
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.
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.
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.
We’re about to go into our quarterly review period at Redgate. We don’t just run QBRs, we also run reviews across all parts of the business. These are a chance to examine the last three months – what worked? What’s going well? What’s not going well and needs fixing? All part of a strong agile process for keeping an eye on what’s really happening, and making adjustments through the year.
But there’s a flaw in these meetings when it comes to marketing. The implication of this process is that the things we did in Q1 have a direct and measurable impact on the outcomes from Q1. I.e. when I’m talking about our Q1 outcomes, the activities that occurred in-quarter are the most relevant for discussion.
But that’s a very partial view of the truth. As all marketers know, marketing is a mix of long, medium and short term activities which, if played right, add up to the outcomes we all seek, such as pipeline for the sales teams.
We’ve just had one of our best quarters for marketing-sourced pipeline in a long time. I can’t say “forever” because we’ve changed how we measure things over the years, but a quarter-to-quarter growth of 20% is something I’m very happy with. I’m not giving absolutes in this chart, for obvious reasons, nor a key to what the colours mean!, but the chart below shows how COVID-19 hit Redgate for marketing sourced pipeline through 2020, then how we’re coming out of the pandemic stronger than ever:
So, great, and I couldn’t be more proud of the incredible marketing team at Redgate for making this happen.
But we’re trying to build a scalable, predictable revenue engine here. It’s not enough to know “What”, we need to know “Why?” – what did we do to achieve this? What can we re-produce? What activities had no impact, that we can cut? This is a Sisyphean task, full of estimates, best guesses, rules of thumb. And I thought back to a poster that used to be on the wall of our HR department (back when we all worked in offices!) stating “Not everything that can be measured is valuable, and not all valuable things can be measured” – which is particularly appropriate here. But we should at least have a stab at trying to know what influences these numbers.
Here’s my go, some based on data, some not. And I’ve given these in reverse “timescale” order – from things we did actually do in-quarter, ranging down to activities that have been in-play for years. And of course it’s almost impossible to weight these things – what was most important? What only made a small difference? Very hard to know..
Project to “Leave no lead unturned”. A slightly clunky phrase, but we made an operational change in Feb to hire a couple of great temps who are responsible for passing the right marketing generated leads to the right people in Sales. Like every single B2B company in the world, our internal systems for lead flow are less-than-perfect, so, while we fix those issues over the year, we have two people passing leads over by hand, ensuring leads don’t get lost in various buckets, or in the wrong hands. By doing this we at least know we’re maximising the revenue for each lead we do generate. Timescale: 1-2 months
Fast, agile response to a competitor mistake. Without going into details, one of our competitors made an error, and within days we’d made it clear to our customers that we were there to help them with an alternative if their bosses were asking them to “look around”. We explicitly didn’t “exploit” this error – we never mentioned the competitor’s mistake in any of our comms – but we did make sure that when people were looking for alternatives, that path was easy for them (for example, through comms and campaigns, through sales training – what should people say when these customers make enquiries? – that sort of thing). Timescale: 1-2 months
A launch. We launched a new offering in February. Of course you can’t do a launch every month, or even every quarter (it can call your credibility into question, if you’re constantly doing grand launches for point releases!). We try to do 1-2 “big” launches each year – incredibly well researched, meticulously planned, focused on real customer needs, and when we get this right (like we did this time), these launches resonate really well with customers. Timescale: 2-4 months to plan the launch, but the research goes back much further..
Experiments with digital spend. It’s so easy to just keep spending $$ on the same ads, the same channels (“If it ain’t broke, don’t fix it”). But end of 2020, we decided to do some bold experiments moving budget from A to B, and this has really paid off. What we found was the the efficacy of, say $1,000 is enormously different for different products at different lifecycle stages. Specifically, if a brand is well-established, then digital advertising is much less effective than for a new product or brand. This makes theoretical sense of course, but it’s great for the reality to match the theory. Timescale: 3-6 months
Internal marketing re-org. This is way harder to measure. But, we made some changes in marketing end of 2020, to reduce the friction between different areas and to make the partnership with Sales simpler. Primarily this was about changing the responsibilities for our field marketing teams in different offices, making it easier for them to collaborate with their local sales teams. It’s hard to say “That change made us $500k in pipeline”, but what I can say is that it’s made it much easier to collaborate on various projects (e.g. some of the things above), which I think would have been far less successful without the change. Sometimes your job is to remove barriers and hurdles, rather than add new activities. Timescale: last 6 months
Treating our customers with respect and empathy during COVID-19. Really? That led to marketing ROI!? We made a conscious decision in April 2020 that, during the pandemic, we wouldn’t exploit the situation for our advantage. We could have gone to customers and turned the screw on various deals, trying to take advantage of their difficulties. Instead we decided “How can we help our customers this year? How can we support our customers through this difficult time?”. We started things like the Redgate Community Circle, with a focus on educating customers (so that at least, through the year, our customers could spend time on self-learning). We made sure that, if a customer was struggling to get a deal or an approval renewed, we gave them that time and space, extending trial periods for example. We actively listened to the struggles they were having (e.g. healthcare orgs struggling to keep up with demand) and made sure adjusted our interactions to give them the support they needed – for example, providing additional free support to healthcare companies, no questions asked. Can I directly measure the return on this effort? No. Do I think it was valuable? Definitely. Customers like working with vendors who understand them and their pain. Timescale: 1 year
Moving out of the pandemic. Obviously this isn’t something you can “do” – we as vendors have had zero control over the course of the pandemic. However I think it’s crucial to recognise where your success is a mixture of internal and external forces. In marketing, we have a symbiotic relationship with our customers – we’re always trying to understand their concerns, at the same time as representing what our company has to offer. It’s obviously been beneficial to Redgate that our customers are feeling more confident, perhaps a little more willing to think ahead and getting back to solving some of their long-standing problems. Timescale: 1 year
Long term brand work. We’ve made a number of changes over the years to clearly associate the value customers get from us with the Redgate brand. Specifically, it should be trivially easy to remember “I learnt a lot this year about how to do my job better. It was Redgate that helped me out there”. Or, “I read a great article about what I need to do about problem X at my company – it was Redgate that wrote that”. We’ve done a lot over the last few years to simplify, simplify and simplify again our brands and the associations with that brand, which I think has at least partly led to current success. Timescale – many years!
Obviously I’ve missed a lot of things here – so many great projects over the last 12 months, small and large. And, as I mention, it’s really hard to to figure out “Okay, but which of these were really important?”. Problem with that of course – successful marketing is a complex combination of lots of activities, hopefully orchestrated together to give the result you need. No single activity is sufficient or even necessary for success, but I think you do need most of these things working together for growth.
But to go back to the original problem – how do we present a successful quarter as a set of repeatable, scalable activities? Should we just repeat all these things!? The skill is to choose between either stopping, maintaining or increasing these activities. There are a number of areas which are certainly in the maintain mode – the brand work, experiments with digital spend being just two examples. We’ll keep doing these, but not more. And a couple of things you can’t or shouldn’t “continue” – marketing re-orgs are very expensive, and I certainly hope that we need to do less and less work supporting customers during the pandemic – an option I’d be very happy to lose! But the trick is knowing what to double-down on – something I’ll be working on over the coming weeks.
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.
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:
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!
Surely not!? Surely it’s the Marketing department (I am a marketer after all)? Or maybe Sales, maybe Engineering, maybe Customer Support. But no, I want to argue that getting HR right is one of the step changes you can make to a business, with far broader impact than any of the areas listed above.
There are a lot of well known beliefs, often cliches about the people in your business. A famous quote from Richard Branson is that “People are our greatest asset” (because if you look after them, they will look after your customers). But that isn’t what this piece is about. We all know that looking after employees is vital, and that your HR department is key to that. But I wanted to talk about something more – specifically, the implementation of good management practice and discipline, and how that underlies the success or otherwise of your company.
We’re very lucky at Redgate. We have, by far, the best HR department (or “People Team” as we know them) that I’ve ever worked with. But this isn’t because they’re just great people (they are) – it’s because of the principles and management practices that they encourage, enforce and monitor in the company. I’ve listed these below. But the reason it’s so important to have a great HR department, is to make sure the company understands and sticks to these principles, even if it causes difficulty in the short term – to make sure the reality matches the theory. A lot of these principles have come from that group, but they also work closely with us to make sure we stick to them.
NB: My experience of the last few years has been that every time you “fudge” these principles (for example, ignoring them to keep a talented individual happy) it leads to disruption, mis-alignment and bigger problems down the road.
Here are some of the principles we try and stick to at Redgate, where our People Team have come up with these, then been instrumental in making sure they happen, regardless of department. A lot might seem obvious, but Redgate is the first place I’ve worked where these are actually implemented!:
Provide proper feedback. Everyone, in every role, gets a quarterly meeting where feedback is gathered from colleagues and peers. This is then discussed with the individual concerned, written up and uploaded to record. More than this, we don’t shy away from difficult feedback – better to mention issues early and often than wait until they’ve grown in to a “big deal”. It’s tempting when busy, to ignore this process, particularly where “You don’t think there’s anything that needs discussing – that person is great!”. But our People Team have made sure we stick to this principle, and it has pre-empted so many problems down the road, I’m thankful for this “enforcement”!
Simple management structures. There are different opinions and ideas here. But after many years we’ve come to the conclusion that “Simple is best” (“Ingeniously Simplicity” is part of the DNA of Redgate). Specifically:
A manager manages approximately 4-8 people. You can strain this in the short-term (“I’m just managing 10 people for 3 months, to help a colleague out”), but long-term, if someone is a manager this is the correct number of people. And sometimes, for new managers, you might let them manage 2-3 people for a period, but that’s with a view towards growth.
No dotted lines. No double managers. No “I’m half managing this person, also responsible for a bit of this other function, and still looking after bits of my old job. That’s okay isn’t it!?”. Make the hard calls on who’s doing what. Without this, you’ll never get true accountability, period.
A manager is accountable for the people, function and performance that they manage. If you’re managing, for example, the digital marketing team, then you as the manager do far more than just handle the teams’ holiday requests – you understand digital marketing better than anyone else in the business (including your manager), you set the objectives for the team and are accountable for making them a great team, doing the best work they could be doing.
A function is split in to simple, logical sub-units that everyone else can understand. For example, your Sales function might be split first by geography, then in to “Strategic Accounts”, “Mid-market”, “Inside Sales”, “Renewals”, then other functions like Sales Enablement, Sales Ops and so on. The details don’t matter, what matters is that people know that “The Mid-market team is responsible for revenue from that tier, if I’ve got a question I know who to ask, and if I want to hold someone accountable, I know the manager to talk to”. Again, Keep It Simple.
Professional Managers. You don’t get to be a manager at Redgate until you’ve been through a rigorous “Transition to Management” process, run by the People Team. So many problems occur when you “Give someone a chance at management” but either a) that person isn’t ready or b) doesn’t really want to do that role! The real problem with this is that it’s not just the new manager that struggles. It’s his/her team that really suffer, often in silence. So it’s vital that someone is ready for management (for everyone’s sake), and also really wants to do it – are they really happy giving difficult performance feedback as part of their job? If not, don’t take the role! As a manager of mine said many years ago:
Everyone thinks they can do their manager’s job. The question is whether they want to
Do Performance Management. This is the most difficult area to write about; and I wouldn’t want to go in to details. But perhaps the most important part of the structure that the People Team provide us (and support us with) is performance management. Everyone has a Job Description and this is what people should be doing day-to-day in their roles. It seems obvious, but losing focus on these things is where many problems arise. And handling those mis-alignments early and often is the key to good performance management. If someone’s JD states that they should be “Creating a strong social media strategy, executing that strategy, and collaborating well with the rest of the business on social media plans” – then this is what they should be doing! If not, then the sooner you have a quick word (“I’m fine with you spending time on project X, but I still expect you to do these things in your JD”), the better. Of course there’s an art in being flexible, and giving people opportunities to grow – which we strongly encourage. But helping people grow in the role they’re doing is a key part of your job as a good manager. And of course, not being afraid to tackle difficult issues when they do arise.
Build a great team. If you are lucky enough to be managing a team, it’s your responsibility to make that group of individuals a team. I won’t wax lyrical here about what makes a great team – only perhaps that you know when you’re in one. But the job of helping those people work together, providing vision and common purpose, multiplying their efforts ten-fold to make them more effective – that, at its core, is a central part of your role. NB: It’s not the team’s job to make sure they work well together – it’s yours! Again, our People Team make sure that happens.
These principles of management are to me, the under-pinning of any department – sales, marketing, engineering, finance, ops, research, IT, customer success, whatever you have at your org. And as I say, though they seem so obvious, they are rarely implemented.
But why? Why do they matter so much? If you work in marketing, you should be spending the vast majority of your time thinking about great marketing. How can we reach more people? What do our customers really value? What market should we actually be working in? Is our brand still right? How can we run the best conference in the world? How can we help land that six-figure deal? And so on. My experience is that when you short-cut the management principles above, you find your time taken up with work which isn’t great marketing. Sitting in rooms figuring out “Who owns what?”, “Why these two people have clashing objectives”, “Why this person doesn’t know what he’s doing”, “Who’s really running that team, Jo or Colin?”, “Why team X just can’t seem to work together”. Firefighting people issues that just shouldn’t come up in the first place. Good management practice is how you pre-empt this stuff, so that you can spend your time on the great positive work you could be doing.
To make sure these things are implemented you need an amazing HR department to frame the work, develop a programme and support it going forward. Of course, I’ve missed off 100 other things a strong HR team manages, and I apologize for that. But for me, these management principles are one of the key “value-adds” this group can provide to make your company and teams really thrive.
I love the book Rise of the Revenue Marketer. In it Debbie Qaqish describes the need for a change program to move your marketing department from being a cost centre (“We’re not sure what marketing do, but we need them to do the brochures”), to a revenue centre (“They’re responsible for generating a significant proportion of our company’s revenue”). Though the journey is easy to describe, it’s a long and arduous path to take.
We at Redgate have been on this path for a while now, and we’ve made enormous progress, particularly in the last 12 months. But one of the things that slowed us down was holding on to certain beliefs about how to measure marketing performance, how to measure the impact of marketing work – and holding on to those beliefs for too long, when perhaps they just weren’t true. Lots of these ideas came from conferences, blogs, books and make a lot of sense on paper. But when you get to the real world of implementing something, the reality is not always as expected.
Here I’ll go through five “myths” that I found to be unfounded. Of course, these come with big caveats – we’re one specific org, with a specific market, with particular advantages and disadvantages – so all should be taken with a pinch of salt. Still, with that caveat in mind here are my five, starting with the most controversial:
Myth 1: Attribution Models are Useful
The idea of a marketing attribution model is that you can take every lead, opportunity or sale and somehow work out “What were all of the things we did in marketing that contributed to that outcome, and what value would we give to each of these things?”. For example, I just generated a lead, I could go back and look through the path history of that individual, find that she clicked on a PPC ad, attended an event, did a Google search, interacted with us on Facebook, and so on. I then have some smart “multi-touch” model that assigns value to each of these (maybe the first or last get higher scores? There are lots of alternatives). If you then know the value of a lead (let’s say, $10), you can work out the Return on Marketing Investment (ROMI) for each activity by comparing the “value” (e.g. maybe $3 for the PPC click), against the spend.
But, I think this is baloney. This is a classic example where – just because you can do the maths, doesn’t mean to say the results are accurate or useful. The model is flawed for at least the following two reasons:
Data. It’s impossible to get all of the data about an individual’s path history – everything they’ve done, interacting with your brand over the last few years. Not difficult, but impossible. You don’t know about the offline activity they’ve done, you don’t know about the browsing they’ve done on their mobile, on their home laptop at the weekend, you’re very unlikely to have a link to their activity from three years ago (when they actually discovered the brand) and so on. NB: some MarTech orgs promise they can deliver on all these things, but I don’t believe them!
Over-simplistic view of how customers learn about a brand. The reality is that an individual will have 100s of different interactions with your brand all of which build up to a given perspective. They’ll attend an event, they’ll speak to a specific person on your stand who may or may not be great, they’ll read 100s of different pages on your site, they’ll talk to their colleagues about you, they’ll read third party review sites, they’ll kick the tyres of the software, they’ll see an ad on a news site (without clicking on it!), they’ll remember a comment from their boss two years ago (“Oh, you should check out Redgate, see what they’ve got”), and so on. All of these things somehow add up to a favourable view of your org (or otherwise!) and to try and model that with a simple sequential attribution model isn’t, I think, valid. The best you can hope to do is make sure every interaction with your brand is awesome and have faith that will lead to positive results.
Okay, maybe it’s not all baloney – but the approach is, I believe, significantly flawed. Nevertheless, there are some things that can be measured – which brings me to myth 2…
Myth 2: Everything should be Measured
Not sure this is controversial actually. To quote Seth Godin:
The approach here is as simple as it is difficult: If you’re buying direct marketing ads, measure everything. Compute how much it costs you to earn attention, to get a click, to turn that attention into an order. Direct marketing is action marketing, and if you’re not able to measure it, it doesn’t count.
If you’re buying brand marketing ads, be patient. Refuse to measure. Engage with the culture. Focus, by all means, but mostly, be consistent and patient. If you can’t afford to be consistent and patient, don’t pay for brand marketing ads.
The danger is that, in an effort to measure everything and show the return on everything, you stop activities because they’re fundamentally un-measurable. The myth is that “Because you need to show a repeatable, predictable and scalable revenue engine, you need to understand and measure the impact of everything you do”. But that’s taking the argument to an extreme view – the reality is that there will always be spend in your budget where you won’t be able to tie revenue to that spend. Ever.
Myth 3: You Need a Funnel
Perhaps controversial again. A traditional funnel implies a sequential path for a customer from something like “Awareness of problem” to “Discovered our solution [to that problem]”, “Evaluated our solution” finally “Becomes customers [then perhaps evangelist etc]”.
Again, we’ve never found this to represent reality. Of course all models are exactly that – models. They’re not perfect, but if they’re useful, that’s okay.
But I feel the funnel fundamentally misrepresents how real people actually interact with a brand. From talking to customers what you find is that there are just an enormous number of holes in this approach. For example:
The “Awareness of problem” is just too crude. The chances are that your content was very unlikely to be the way people became aware of the problem; that actually their knowledge has built up in a fragmented way over time; that they’re still learning all through the sale, even post-sale.
The idea of “stages” like this just doesn’t make sense generally. Often people are already customers of yours – and they’re finding new things you offer. Their understanding of your offering is forever a slow build up (from a theoretical “nothing” many years ago, to some partial understanding now), that it goes back and forth.
A funnel implies a single direction of travel, a path to enlightenment, ending with purchasing your tool. But, from talking to customers I find a much messier reality – people go back and forth, there are interrupts and so on. We’ve found it almost impossible to actually classify people in to different stages – it’s too over-simplistic to be useful (we’ve found).
Myth 4: Conversion Rates Matter
Again, controversial. But our experience is that conversion rates are the lever you are least able to pull. Why? Because for most orgs, they have a pretty well optimised process for converting leads at different stages. At Redgate, there are certain lead types that convert at a 70% conversion rate, within a 2 week period – and that has been consistent for about 10 years, almost regardless of what we do! We’ve spent a lot of time and effort on this stuff – its value is in “Can we improve/optimise this?” – and generally we find we can’t. Of course you monitor it, to make sure it’s not dropping (e.g. because some leads got lost), but otherwise – stop worrying.
Finally, myth 5…
Myth 5: This is an Impossible Task
I wanted to end on a positive. 2-3 years ago, I thought the task of building out a “revenue engine” that was vaguely water-tight, believable and actionable was never going to happen. There were so many holes in the data, it was so hard linking activities to outcomes, that it wouldn’t actually happen.
I pleased to say that isn’t what has happened. It’s been pretty arduous, but we are now on the brink of a model that allows us to:
See the impact of many (but not all!) of our activities
Track the resultant leads through to opportunity then revenue
Match the activities with budgets to pull out ROMI
Use this insight to stop certain activities (already cut a few things), start a few more, and adjust how we do other things.
A simple example of the last point – in 2018 we ran a number of webinars of different sorts. We tracked through the leads, opportunities and revenue from each of these and found that the impact of having a “star” presenting the webinar (someone big in our community) had a far bigger upside than expected – at little or no additional cost to us, other than the trouble of finding and convincing these stars. I.e. one webinar with a star involved would generate more high quality leads than 2-3 webinars without such a person on the event. So this year, we’re changing our program a little – fewer webinars, but each more impactful with more big names presenting.
Just a small example, but there are countless more – we’re building out a model where we know how and which levers we can pull (and which we can’t), and at what cost. It took a long time to get there, but it’s finally becoming real. Feel free to get in touch if you want to know more!
