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Sales enablement is a critical function to organizations - it can drive success, sell, engage, and retain, customers, offer more to employees, and much more.

Yet startups are often resource-strapped and left questioning whether sales enablement is something they should invest in. In this article, I’ll put a case forward for sales enablement in any and all organizations, explain why, and how you can start and grow a sales enablement function from the bottom up.

I'm going to come at this from a slightly different perspective from what you've likely seen before - big companies with quite big teams, quite established, quite mature businesses talking about sales enablement.

I don't really come from that world. I've done a bit in the sort of enterprise space but primarily, I focus on the startup world and that's my comfort zone. I'm currently heading up both sales operations and sales enablement.

I think differently to those with dedicated sales enablement teams, I don't have that. I've got a team of six people and we run sales operations and sales enablement globally. I'm going to talk a little bit about why a startup should invest in sales enablement.


For those of you that don't know to GoCardless, to give some context, we are a small but fast-growing London based company. We sell a recurring payments platform.

We're the first company out there to enable customers to take recurring payments, completely borderless, so it doesn't matter what country you're in, you can collect that currency in a single bank account.

We're taking the pain away from our customers in terms of how they collect their payments.

Who am I?

I'll briefly go over this to set the scene a little bit about who I am, what I do, where I've come from, and to give you context for the rest of the article.

I'm a salesperson, I would always describe myself as a salesperson, I spent 10 years selling. I've done everything from cold calling on a commission only job from Yellow Pages, making around 300 calls a day and I didn't even have a CRM system - I got a ream of paper every day to work from through to managing big strategic accounts generating 10s of millions of pounds of revenue per year.

For the last eight years, probably the most exciting for me, and that's been working with sales operations and sales enablement. I did a stint of two years in product marketing, running a team across Europe.

At that stage, I didn't even really know what sales ops or enablement was. I soon learned pretty quickly when all of a sudden my managing director said do you want to come and work in sales ops and enablement?  I had to go onto the internet and research and find out what it was before I accepted the job.

What I'm going to talk about today is designing, deploying, and what I've done from a sales ops and enablement perspective, in two hyper-growth startups, slightly different sizes, but fast pace, fast-growing companies.

I currently work at GoCardless. I worked at Zero - I was employee 80 in the UK. I'll talk a little bit about what we had there.

I worked at Sage, and prior to that spent seven years at RS Components, so a big corporate company, but left there and moved into the SaaS space.

Sales cures all

Before I start, I want to talk about a quote, it's not from anyone like Mandela, or anyone like that at all. Someone called Mark Cuban, he's really successful businessmen from the US, you may recognize him from Shark Tank, he's done pretty well for himself, he's got a reported net worth of 4.1 billion.

He says sales cures all - there's never been a business that succeeded without sales. For me, that's massively important.  

I've worked with sales led companies, product-led, marketing-led, and even finance-led companies. The number of conversations I have with our VP of product who says 'it's the best product, it's just going to sell itself' and it doesn't. It's a great product, but you still need salespeople.

If a company is not going to succeed without sales, why wouldn't you invest in a function that is going to support and make sales better?

The agenda

A bit about sales ops and enablement: to me, what are the challenges that a startup faces from a sales perspective, I'm going to cover a couple, there's a lot more I could talk about, how do sales enablement address these?

And then moving on to sales enablement within a start-up - what is the difference in a startup compared to an enterprise?

Finishing with is sales enablement an option?

What are sales operations and enablement to me?

Have you ever heard of a V2MOM? It's something Salesforce came up with, it's your vision, values, method, obstacles, and your measurement.

We stole that and we use that internally.

That top sentence there is my sales operations and enablement vision, that's what we want to do. We want to proactively create the conditions where more deals that are more profitable with better customers are the natural result. Everything we try to do should hopefully take us in that direction.

To split out what I view as sales ops and sales enablement, this is how we carve it up in GoCardless.

Sales operations

Sales ops by the nature of the title is more tactical, it's the function that is there to help sales run smoothly.

  • We manage the tech stack.
  • We report the overall efforts to the business.
  • Quota is obviously a big part of it.
  • Planning and process. What is our planning process? How do we manage our headcount? What does our orb design look like?

Obviously, I've got commission there - commission should absolutely be a sales enablement task, and sales enablement are heavily involved in this and actually are responsible for designing the strategy for commission, but they're not responsible for the management and the ongoing data of that.

Sales enablement

Sales enablement, for me, is very much an overarching strategy. It's about how do we drive sales marketing, and in our world, we have a customer organization, which is our onboarding, customer success, renewals, account management.

It's about how do we bring all of those together and have one strategy? We own the content strategy from a sales perspective. That doesn't mean we tell marketing what to do. But it does mean that the content the salesperson would use throughout a customer buying journey is owned, the strategy is owned within sales enablement.

They do sales development and readiness.

Everyone reading knows what sales enablement is but when I talk to a lot of people, the first thing I have to do is explain it. Because when I talk about sales enablement they think of sales, development, sales readiness, they think sales enablement is "You've come here, you've started, you've done your two weeks onboarding, off you go, you're enabled".

But it's so much more than that. It's about that development and readiness, but it's that ongoing journey. It's then about creating content and so much more. That's certainly how we see it and how we run it at GoCardless.

Definition of sales enablement

When I first got asked to do sales enablement I did my research and found this document from Forrester, I read this definition (I've got to admit I didn't read all of the document, it was quite tough reading), and even that was really quite wordy and confusing.

What does this mean?

For me, I broke it into three things.

Strategic and ongoing process

It was about being strategic and ongoing and this comes back to my point earlier - sales enablement isn't just two weeks onboarding, it isn't 'I've done a one-day training session', it's so much more than that.

So it cannot be tactical, it has to be strategic, it has to be ongoing, it never stops.

Equips all client-facing employees

The second point is it's about all client-facing employees. For me, when I talk about all client-facing, even though marketing isn't necessarily picking up the phone or visiting someone face to face, I bring them into that camp as well.

Because anyone that's engaging with a customer should go through the sales enablement program, anyone that's engaging whether it's through an email, whether it's through an event, a conference, right the way through to post-sales, and we've done onboarding, we've spoken about their renewal, how we're going to unlock and take more share of wallet, absolutely everyone that talks to a customer is covered by sales enablement.

Continuously and systematically have a valuable conversation

Then it's about consistently and systematically having a valuable conversation. This is where sales enablement leverages technology.

We talk about the CRM, we talk about the process, we talk about automation, we talk about serving up the right content at the right time to take the conversation to the outcome where we want it to be.

How do we continue to add value and take a customer through a journey where they want to go but where we want them to be as well?

Simply put...

Simply put, and this is how we talk to everyone at GoCardless about what sales enablement it, it's a set of tools, knowledge, and processes that enables a sales force to continuously succeed.

Because if I talk to them about the Forrester definition, they're all going to be confused as well.

Whenever we talk to anyone, we get a new start to join (and we get a lot of new starters, we've doubled the size of our company this year from 200 to 400 employees, we hire between four and 12 people a week and do an induction every single Tuesday), we have to tell people really quickly what we do, and this is what we explain and this lands with everyone and they understand it.

What challenges does a start-up face in Sales?

There are a lot of challenges I could talk about from a startup world, a lot of challenges in how we sell, but actually, I'm just going to pick on a couple.

No process

For big companies there's a lot of legacy that needs to change, I've worked for companies where we've grown through acquisition, and then we've got this process that we had already and then we bought another company with a different process, then another one and another one. In that world, it's about how do we bring all of those processes together?

We're in a different world at a startup, we don't have a process, sometimes we don't even have a CRM system. Coming from a SaaS world and working with companies with lots of developers, we don't always even buy a CRM system.

Unfortunately, we had a developer that thought it was a hobby and he built us a CRM system and it lasted about six months, built another one - that lasted about three months. At that point, thankfully, we were able to talk him out of it, and we bought Salesforce. It was painful, but we didn't have that process and it was a real issue.

But not only sale stages because our two sale stages were paying and non-paying that was it - were they a customer or weren't they? But also if you look at the top of the image, it was about:

  • What is the journey through the business?
  • How do we engage with sales?
  • How do we engage with marketing?

Nobody knew, stuff just happened. That's because we had 10 - 20 people focusing on something. We had a lot of software guys and girls upstairs developing, but we didn't have anyone thinking about:

  • How do we go to market?
  • What is that journey?
  • How do we engage with a customer? And,
  • How do we sell?

Little or no forward planning

One of the other challenges that we see a lot is little or no forward planning. Unless you're really, really fortunate, unless you're an organization, unless you're a startup, that's almost got unlimited money, you've got some investors that are just happy to keep chucking money at you, without really worrying about it, you have to sell today and you have to bring in the money today.

What are you doing today? What are you doing this week? What are you doing this month? Because without that, we're not going to be here next year.

Without hitting our milestones, without hitting our gates, we're not going to get that next round of investment. We did some funding earlier this year, we sort of did our series E, which is amazing, but we've got gates here, too. And unless we hit those gates, we're not going to survive, we're not going to be around.

We focus on today, and we don't really think about tomorrow. That's the expansion part there, we sell to a customer, but it's much easier normally to then take more money:

  • How do we sell a new product?
  • How do we expand to a different market?
  • How do we renew them?
  • How do we retain them?

We don't think about that, we think about today. That's because we don't do the middle bit, don't really have a strategy, we don't have a tactic. We just sell, we hire great salespeople, and they sell, which works to a certain extent, it works for today, but it doesn't work for the future.

You don't always want to be a startup, you can't be a startup forever. There's a point where you need to transition to a scale-up and then to mid-market, enterprise, whatever you want to define it as, but this little or no forward planning is a real issue that we face commonly.

It's something that's a real challenge because the CEO wants to talk about it in five years’ time, but the salespeople in the sales manager have got really tough targets to hit. How do we transition them from thinking about today to thinking about tomorrow? How do we address some of these challenges?

I'm going to talk about a couple of the sort of startups I've worked at and how we've done this.

How does sales enablement address these challenges?

A macro view of the GTM functions

We look at this macro view, we take a holistic view of the business.

We've all worked for companies where you have a sales plan, and sales go off-site and they work out what their strategy is, what are they going to do that year? How are they going to go to market?

The marketing team go off and do theirs. The product team go off and do theirs. The customer will go off and do theirs. But actually what we need to do is bring them together.

I'm not saying sales enablement are the only people that are responsible for this but they need to be an absolute driving force behind this. They need to be bringing that together and looking at this as a sales - marketing - customer process and turning it into a go-to-market process.

But consistently thinking about the customer, keeping the customer at the heart of this, thinking about:

  • What journey do they want to go?
  • How do we engage?
  • How do we sell?
  • How do we retain them?

Think about the future - where do we want to be in five years’ time?

A macro view of the tech stack too

That goes right for our tech stack as well. We're out there and we're always evaluating what technology we need. It would be really easy to select suppliers and vendors on what can they do for us now?

Because they've got a simple approach, they're really simple to install, their adoption is great, but will it scale with ours? Will it turn into the corporate platform, the enterprise solution that I need in five years’ time?

Because if we continue to grow as we are - we've gone from 200 to 400 in 12 months, are we going to be 800, 1500, when do we hit that number? And will that vendor work with us then?

That's what we have to think about with our process - how do we sell, how do we market, how do we engage with that customer?

Integrated contact strategy

This comes back to alignment and that comes back to sales enablement working cross-functionally across the business to bring everything together.

It starts with planning. As I already said, sales go off-site and do their planning, so do marketing, but what we need to do is bring that together as one plan, thinking about the company, thinking about marketing, sales, onboarding, customer success, thinking about absolutely everyone.

So that we know what our plan is, we know what we're going to do, and then:

  • How do we communicate that?
  • What is the content we deliver?
  • What is our communication, and content strategy?

We look at this a lot internally. We have a long-term integrated plan, we know where we're going to be, we know where we want to be in five years’ time. Through sales enablement, product marketing, through other functions within the business, we have an aligned go to market strategy.

We then have a go-to-market content strategy. That's the output of the integrated planning.

That's about us knowing how do we want to talk to somebody? That then gives us this right content, the right message, the right customer at the right time.

A story

Years ago in my days as a salesman, I remember setting a target of doing four visits a day and driving up and down to see these customers. It was before we had all of these SaaS platforms and everything spoken.

We didn't have that, we had a perpetual license CRM system that was really clunky, we would just implement in a marketing automation system, we didn't talk to our CRM. Most of our marketing was post, we sent out flyer after flyer and it would depend on where we were in the month or the quarter.

I remember turning up to customers and thinking 'I'm gonna do a really great job with this new value proposition, this new product, I'm going to talk about the value it adds to their business'.

I'd phone them the next day to follow up and find out they've just had a flyer through the post offering them a 20% discount, offering a promotion, offering a buy one get one free, whatever it may be, and it completely undermines what I'm talking about delivers a really confusing message or vice versa.

Marketing sent us some great thought leadership but it was the last day of the quarter, I was just short of my number, so I'd pick up the phone and do almost anything I could to get a deal over the line.

Because I was focused on today, I wanted to hit my number, I didn't think about what message or picture I was painting for that customer. What were they going to view us as, as a company, not me as a salesperson? What was that perception of us as a company?

The importance of sales enablement

This is where sales enablement comes in. This is where sales enablement brings it together, this is so important in a startup. Because when you're a small company, you don't have hordes of people coming to you, we get a fair amount of inbound traffic but nowhere near the volume we want, nor need to hit our numbers.

We can't afford to waste any opportunity. We can't afford to deliver the wrong message. We can't afford for a customer to be confused about who we are and why they should partner with us, especially in a SaaS world.

We deal with 50,000 customers at the moment at GoCardless - 47,500 of those are on a Netflix model. They love one-month contracts, they can cancel with 30 days notice, we have to work on:

  • How do we retain them?
  • How do we engage? And,
  • How do we ensure that they know who we are, where we are going, and why they should partner with us?

That's where the salesperson, marketing, the product, and everything has to be aligned and deliver one message. That's a really, really important function for us at GoCardless.

How does sales enablement grow within a startup?

It would be amazing to say that every startup invested in sales enablement but they don't. If you've got two salespeople, three salespeople, you probably can't afford to hire a sales enablement manager, you can't afford to hire someone to focus on your technology.

But I think as long as you've got someone that focuses on it, it's a part of their job, it's on their agenda, they know about it, they understand it. That's exactly where we've come from.

Growing with a start-up

Thankfully, our CRO when we hired him, sales enablement was something that he was really passionate about. He'd been around, he'd worked at Salesforce and lots of other big companies previously where sales enablement was really important.

He joined us, and he was building out a sales team but every step of the way, he was considering enablement, he was considering content, he was considering the process, considering the journey. He was considering what we needed for the future.

Unfortunately, he didn't have the budget to hire anyone at that point. But a little bit later we got some budget. Did he hire a sales enablement manager? No. What he hired was someone that was a bit of a generalist, someone that could do a bit of onboarding, someone that could bring some content to life, someone that could do some Salesforce admin work, someone that could work a spreadsheet and do a bit of analysis for him.

But the important thing was that the sales enablement thread kept going, and we continued to invest in it. That continues to grow until you have a team.

We've got the blue person at the top, that's our sales enablement manager, we've got the green people that sit in sales ops and enablement, and they're not dedicated to sales enablement, some of them have a split role between sales ops, sales enablement, and other functions.

But I think the really important thing for me, is these people in grey here because they're not sat in sales enablement, they're product marketing, L&D, HR, product, finance, wherever they are. It's about pulling everybody together behind that strategy.

As long as you start with a strategy, as long as you then keep the focus and continue that focus to grow, if you build a team and it scales with the business, you're starting well. It's just important that everyone in a startup understands what sales enablement is, and why it's important.

Does sales enablement differ in a start-up vs. an enterprise?

Does it differ in an enterprise? I've thought about this long and hard and having worked at both startups and enterprises, I can't really think about any difference in what they're trying to achieve.

The outputs should be the same

The outputs the same, right? It's content. It's about marketers that can act on performance data, salespeople that can act on performance data, it's the ability to leverage technology, it's that cross-functional go to market alignment, and that doesn't matter whether you're in a 10-20 person company, or a 13-14,000 person company, that is the same.

However the approach will be different

But I think what the difference is here is the approach, it's the agility, it's the fact that we don't have a lot of the legacy, we don't have some of the issues that potentially exist in an enterprise. We need to hire different people because we're not focusing on evolution.

We're not taking a sales process that's there. We're not taking something that's been in existence, everyone understands it, and work out, how do we improve it? How do we make it more efficient?

We're looking for a different type of person that's prepared to put their hand up and say, 'this is how we're going to do it'. We're looking for someone that's going to design it from the outset, someone that is bold enough to go up against the product team, go up against the marketing team and say, "This is what we're gonna do", and actually create it from little or nothing.

It's about being agile versus legacy.

Agility: an example

This year, we rebuilt Salesforce from absolute scratch. We did it in 12 weeks, deployed it globally, and we've got over a 95% adoption rate. We were able to do that because we didn't have a lot of the legacy.

We didn't have hordes and hordes of stakeholders globally so there are some real benefits to having sales enablement in a startup. It's tough, but there are some real benefits to being able to do this at pace and add value.

But as long as it's understood why sales enablement should exist.

We do have issues. Being in a start-up and not having any money at the start, we had no technology, we bought every bit of technology we could afford as soon as we got a bit of funding. But Salesforce being not the cheapest tool out there, our developer says 'fine, we'll install it'.

They basically wrote code for everything, they customized it to high hill, to the point I had literally 12 salespeople and on the opportunity record, I had 386 fields.

275 of them were custom and we have 19 administrators in a company that employed 50 people at the time. Not one of them had ever use Salesforce before, or even heard of trailhead, or done an ADM 201.

Any man and a dog that wanted to be an admin got it to the point one of our customer success managers, she was an admin. Over the weekend, she was thinking of what does customer success need? She came in and created 60 mandatory fields on the opportunity because she needed that to enable customer success to be really successful.

We have our issues and that's why I say it's different.

The output is the same but the challenges you go through are really different.

I remember when I joined Zero, on the first day I had a meeting with the managing director and I said "What advice have you got?" He said, "Zero runs really, really fast, if you want to be successful, you've got to run fast".
I'm thinking 'shit I've only been here one day, and I've already got to think about how do I run faster than a hyper-growth company?"

But that's something that's actually stuck with me as really, really important - startups do move fast, but sales enablement has to stay one step ahead.

Is sales enablement an option for a start-up?

I suppose it depends if any of these sound familiar.

  • Are you in a high growth phase?
  • Do you want to be?
  • Are your new sales reps taking longer to ramp?

For us, we have different ramp times, whether it's SB, mid-market enterprise, I've got my enterprise reps that are not fully productive and hitting a fully ramped quota until nine months, quite frankly, that's not acceptable. We need to bring that down.

  • How much of their time are they spending on nonvalue add tasks?
  • How much of their time are they not closing deals or progressing a deal to the next level?
  • Do you need to increase a rep’s quota?

This comes back to the productivity I spoke about earlier and in the SaaS world, there's this magical number everyone talks about where quota should be four to six X your OTE, well, unfortunately, we were at two X. It was like, how do we get to six X?

How do we be best in class? But how do I do that without just chucking their quota up and pissing everyone off and they quit? Because then I've got a different problem to deal with.

If any of these sound familiar, I suppose the question is, is sales enablement an option? No, it's not, not if you want to succeed - sales enablement is a must-have.

If you want to ramp your reps faster, if you want to reduce that time for them to become productive, start to add value, start to recoup your investment in that person back to the business, if you want to increase the selling time.

If you want to increase the quota but still make it fair and make it achievable, and drive the business in the right direction against whatever your benchmark is but without increasing churn.

Startups have pretty high churn, but as a company, we're at about 25% churn rates at the moment, it's coming down, but about 25%. I got a 6% churn rate in sales, and not one of those that have churned this year has been regrettable.

So actually, we're in a pretty strong position and that's because we focused on this. That's because we bought sales enablement in early, we were able to take people on a journey about what are we going to do? And how are we going to support them, and invest in them?

All of this should drive an increased return on investment. Knowing if I hire an SDI, if I hire an AE, what do I get back? If I spend a pound in marketing, what do I get back? Driving and predictability and scalability, which is absolutely critical for a startup, it's absolutely critical for our investors to know what are they getting for what they've given us.


So in summary, sales enablement shouldn't be an option if you want to succeed, it shouldn't be an option if you want to sell, engage, and retain customers. It's absolutely crucial.

We've really turned around our retention rates, most of our customers can quit on one month’s notice yet from net revenue retention we’re at 103% at the moment, so we're actually driving more from all of our customers and retaining them.

We're offering our employees more, we're focusing on them, we're thinking about the people, we're thinking about what do they want to do and investing in their future to help us but to help them as well.

We're helping them over the long haul and we're aligning our functions. For me, I think the only question should be, how much do I invest in sales enablement? Or if you want to flip it on its head and talk to the business and those that are not a believer in sales enablement, it should be how much can you afford not to invest in sales enablement?

And what are the issues? What's going to happen? And what damage will there be if you don't invest in sales enablement?

That's it for me. Thank you.

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