Sales Enablement Best Practices

One of the exciting aspects of working in an emerging area like sales enablement is that, today, nobody knows or indeed, has all the right answers. In many respects we’re “building the plane while flying it”, as we collectively figure out what good looks like.

As a result there’s a refreshingly high level of collaboration, modesty and openness among industry colleagues - in my experience fellow sales enablement professionals are generous with their time, humble and willing to help each other out.

Admittedly, I’m also fortunate to work at a company like HubSpot - it opens a lot of doors and people are always interested to hear how we approach sales enablement. Candidly, setting up meetings with sales enablement leaders at interesting companies is rarely difficult. That’s why twice a year I take a couple of days out of the office to visit other sales enablement professionals at their place of work - it genuinely is the best time I invest each year. As an aside, there’s little formal sales enablement training available, so this opportunity for peer learning, ideation, feedback and discussion is incredibly valuable.

Indeed, over the past 18 months I’ve met with talented people (several times) at Google, Facebook, LinkedIn, Stripe, AdRoll, Dropbox, Zendesk, Intercom, LogMeIn, Procore, DocuSign and Xerox to chew the fat over all things sales enablement. During these meetings I’ve shared my point of view on sales enablement, gained critical feedback and developed some of my ideas - all of which has helped sharpen what I consider to be my sales enablement best practices and guiding principles. They’re by no means definitive, but they act as a starting point for how I approach my work at HubSpot.

Let’s get down to it - here are my sales enablement best practices:

1. Consider sales reps your customers and get close to them
I wholeheartedly believe that those companies which get closest to the customer will win. The same is true of sales enablement - by considering sales reps your clients and trying to remain in close proximity to them, you’ll become more understanding and empathetic to the needs, wants and challenges of the sales organisation.

At HubSpot I very deliberately go and sit by sales reps for a part of each day. Being physically close to the sales team means I have a closer relationship with them, I’m more attuned with the mood on the sales floor, and can use this insight to provide a more valuable service to the sales organisation. But physical proximity is only half the battle - you need to consider and treat sales reps as cherished clients - ultimately, this means ensuring they’re successful, rather than happy (happy clients often leave, whereas successful ones seldom do).

2. Be a strategic consultant, not a tactical order taker
The most effective sales enablement teams are akin to consultants, rather than order takers. The key point to understand is that what a sales team says it wants may not necessarily be what it needs. This may sound like a minor semantic difference, but once I realised the difference between wants and needs, it had an immeasurable impact on how I work.

For instance, a sales manager may say they want more case studies for their region, but once you truly uncover the challenge, you may find out that buyers are more conservative in their market, so what they actually need is more evidence of social proof (this could be third party review websites like TrustRadius and G2 Crowd, customer testimonials, videos and of course, case studies).

In the same way that a doctor listens to a patient before making a diagnosis and then suggesting a remedy, sales enablement works best when it is free to analyse a problem, suggest recommendations and then build a programme to make those recommendations a reality. In short, if you focus on uncovering true needs you’ll elevate yourself to the position of a strategic consultant, but if you solely focus on wants, you’ll be stuck as a tactical order taker.

3. Understand the importance of revenue responsibility
Let’s be honest. When it comes to winning an argument, revenue trumps everything else. The best sales enablement teams are focussed on revenue - whether that be quota attainment, influenced revenue, productivity per rep (PPR) or another sales related metric.

What the best teams have figured out is that by focussing on revenue you will have the biggest impact. Or put another way, if you’re not influencing revenue, then you’re on the way to becoming an overhead and expense. And teams which fall into this category are often “nice to haves”, rather than “must haves”.

Ultimately, teams which lose their focus on the bottomline often see their budget reduced, sphere of influence diminished and impact minimised. In contrast, the best sales enablement leaders are rightly fixated on revenue and how they can increase it. I literally can’t overstate the importance of a sales enablement function having some form of revenue responsibility. Make it your focus and keep it front and centre for your team.

4. Define your service offering to the business
Generally, sales enablement is poorly defined within businesses and subsequently misunderstood. This means that it’s crucial you clearly communicate to the business what areas your sales enablement function will own.

It’s not hard to see how misunderstandings happen. When I think about the scope of a sales enablement team it can legitimately cover content, training, technology, deal support, the company’s customer relation management (CRM) tool, sales playbooks, sales methodology and more. Clearly, that’s a big list of important initiatives, and in reality, any team from sales enablement, sales operations, sales strategy, training and learning and development (L&D) could rightly claim it as part of their remit.  

Subsequently, one of the first and most important jobs when building a sales enablement team is defining what areas you will cover, but of equal importance communicating what work sales enablement will not do. Both defining what you will own and omit will bring a lot of clarity and focus to your organisation.

5. Shared goals are the one true way to drive alignment
One of the most impactful, but simplest changes I ever made was to share the same goals as the sales organisation. In my mind, sharing goals are the one true way to drive alignment and more teams should do this. Yet the reality is much different - shared goals between different teams are often the exception, rather than the rule.

Having the same goals as the sales leadership makes sense on a number of levels. It brings much needed clarity, simplicity and intellectual honesty - ultimately, it means everyone is pulling in the right direction - we’re both winning, and by definition losing together. However, the opposite is unfortunately all too common. Oftentimes, a sales enablement (or marketing) team will be hitting their goals (which are different to the sales organisation), yet the sales organisation is failing to hit their goals.

My point is that, can a sales enablement team ever truly consider itself a success if the sales organisation is failing to hit quota? My gut feeling is that it can’t, but my recommendation is that you can avoid much of the finger pointing, by having everyone share the same goal.

6. Base decisions on revenue and number of sales reps impacted
As I’ve already mentioned, when leading a sales enablement team it can be easy to get caught up and slowed down in what sales reps say they want, rather than what they need - or worse still, supporting those with the loudest voice, most seniority or highest salary.

I’ve found that the best way to navigate this challenge is by making decisions based on estimated revenue and number of sales reps impacted. If you’re having a tough or heated discussion, I suggest bringing it back to this. In my experience this approach typically creates an understanding and acceptance of a decision, if not wholehearted support.

At HubSpot I use a simple 2X2 grid to rank projects based on estimated revenue and impact on sales reps - put simply, I always focus on activity that will most likely influence revenue. I often share (in jest) that working in sales enablement has taught me to say “no” a 1,000 different ways - quite simply we’ll never have the resources to implement all the ideas, suggestions and projects (even the good ones) that sales managers and sales reps champion, so having a process to categorise and rank work, which is shared with your stakeholders is crucial.

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7. Take a blended approach to measurement
Some sales enablement activities are easy to measure and attribute, while others are not. That’s the cold, hard truth of the matter, and it’s for that reason I recommend teams take a blended approach to sales enablement measurement.

Although, sales enablement plays and tactics, such as content, training and technology are easy to understand, measuring the impact, success and effectiveness of a sales enablement team is less straightforward. On the one hand it can be simple to identify a metric that has high business impact, such as quota attainment, but often it is challenging to attribute precisely how much influence sales enablement actually had on said metric.

And on the other hand, you can have metrics that are easily attributable like net promoter score (NPS) of a training session or tool adoption, but often these have less impact on the business. It’s for these reasons I believe a blended approach to sales enablement measurement is needed.

If you’re interested, the metrics I’m measured by at HubSpot are monthly quota attainment of the EMEA sales organisation and I personally carry an influenced revenue goal from deal support. Thirdly, I run an NPS survey at the beginning of each month, to understand how sales reps felt I performed the previous month. This trifecta of goals keeps me focussed on important business metrics (quota attainment), ensures I am personally influencing revenue, and that I provide a good service to the sales organisation.

8. Be comfortable with some hand to hand combat
Working at a fast-growing software as a service (SaaS) company like HubSpot has taught me to deeply appreciate and value scale. While scale is important we should not seek it all costs - we need to also recognise and be comfortable with the fact that some enablement activity doesn’t scale, and frankly, never will.

The key takeaway here is to find the right blend between one-to-many, lower value and one-to-one, higher value activities. Most importantly, we should always seek to optimise for impact and revenue, not scale. Occasionally, it feels like scale is the very first question that sales enablement professionals ask, when really we should figure out if something will work first, and then tackle scale later.

Or put another way, would you rather run a programme that helps a cohort of 10 sales reps at your company improve their quota attainment by 20%, or one that helps all 100 people on of your sales organisation improve by 1%? Sometimes a higher impact programme for a smaller number of sales reps can be the right approach.

9. Be honest about your level of sales enablement maturity
Sales enablement is a rapidly emerging, but immature function. Many companies are investing in the creation of sales enablement teams, but as they’re so new, there’s a distinct lack of thought leadership, standardised measurement and best practices available.

To try and bridge this gap I often meet with sales enablement professionals at other SaaS companies. While the discussions are often uniquely insightful, some patterns typically emerge based on how long the respective sales enablement teams have been operational. Their teams can nearly always be categorised as being in one of the following stages: set up, tactical, reset, strategic and best-in-class (you can read more about the five stages of sales enablement maturity here).

By truly understanding your level of maturity you can understand where you are today, but more importantly where you want to be tomorrow.

10. Recognise that you’re in the business of influence
Strategic communication is an integral part of successful sales enablement. And the success (or failure) of a sales enablement function is intertwined with its ability to influence a sales organisation and change behaviour.

While it may not be immediately apparent, communicating well with and managing stakeholders is a prerequisite for successful sales enablement. Therefore, you need to be thoughtful about communication, as getting it right helps a sales enablement team earn trust and build credibility, which over time expands its scope of influence. This is important as ultimately, there’s just two states that a sales enablement team can ever be in. Either the sales leadership rates the sales enablement team and think they add value - or they don’t.

Sales enablement is a unique function, with its own opportunities, challenges and pressures, however, I think it shares many parallels with the role of a management consultant. Just like consultants, we sales enablement professionals are in the business of problem solving by providing counsel and guidance, but ultimately, we are reliant on other teams to execute.

But merely problem solving and managing stakeholders is not enough - to be successful, sales enablement leaders must influence via persuasion, coaching and cajoling, so people take action and change their behaviour. Ultimately, that’s what drives results.

These are my sales enablement best practices - what are yours?
So there you have it. These are the sales enablement best practices that I operate by at HubSpot. It’s my operating system if you will, and I’d love to discover how other sales enablement professionals are thinking about this too. Admittedly, these best practices are by no means definitive, nor are they applicable to every business, but they’ve given me a solid foundation to build a high-performing function. They will likely evolve over time, but today, they give me the framework to make the right decisions to help our sales organisation succeed.

I hope that you find these best practises valuable, but more importantly, I hope they spark discussion at your organisation around the role sales enablement can, should and will play. Critically evaluating and talking about sales enablement is how we’ll elevate the role to where it truly belongs. I’m proud to play a small part in what is a big moment for those of us working in and around sales enablement.