Nicholas Gregory, Steve Hamilton, and Jennifer Leary gave this presentation at the Sales Enablement Festival in October 2021.

In this article, we’re going to talk about how to progress up the sales enablement ladder, and build a long-lasting, fulfilling enablement career.

So many of us just fall into sales enablement, and there’s so many different paths you can take.

Before we dive in to this really deep topic, let’s look at our main talking points:

  • The type of experience you need to make it into enablement
  • What you should expect from the role once you make it into enablement
  • The key skills that we look for when hiring in enablement
  • How to earn that elusive enablement promotion
  • Reaching the top level of enablement and staying on top of your game

First thing’s first - what is sales enablement?

Before building out a career in enablement, the first question you have to ask yourself is ‘what is sales enablement?’ because if you ask 100 people, you’ll probably get 100 different answers!

So how do we define sales enablement?

Sales enablement is a strategic initiative that enables anyone touching the customer to be fully prepared, engaged, and able to execute against the roles and responsibilities outlined in their job function - which ultimately leads to revenue, whether you're supporting the customer or selling to the customer.

There's three components, which are: people, processes, and content.

So, who are the people? What are the processes they need in order to be enabled, and what content do they need to know to go out there and be successful? Obviously, all of that has to align with the overarching goals that the organization has established in terms of scale.

A critical part of this is the skill set and mindset. If you as a sales rep have got the skill and you've got the competence to do your job, then you're going to perform at a high level, and that's going to drive the business outcomes, and you're going to have great customer interactions.

So sales enablement starts with providing all those necessary elements to the team so they can perform. It's the tools, the coaching, and data is a big piece of it which is growing in importance.

With data, it’s in terms of understanding what's happening in the marketplace, synthesizing that information, and then turning into a coaching opportunity with the team.

They’ll understand what's happening in the marketplace and what's happening with their customers as a result.

This goes back to the skill set and mindset that they need to have to perform at their absolute best.

Do you need enablement experience to get into enablement?

No, you don’t. It's really important to understand that those who are very successful in sales enablement have a diverse portfolio of skills and background.

It's not just a straight line, or a “Hey, I've only done this, therefore I'm not going to be good at enablement”.

Whether it's marketing, sales or something else, to start that career path, having that background in sales just to have an understanding of the mechanics of how sales works can help.

But to be able to branch out, and to learn different facets of the business? That just makes you a stronger collaborator, it makes you a better influencer, it helps you align better within the organization, and helps you communicate better.

There really is no definitive “Yes, you have to start here”.

It's more about: do you have a passion for helping sales teams perform at their highest level? Do you have a passion for helping leaders coach and lead at the highest level?

If you have that passion, then a lot of those skills will come naturally and you can always supplement by learning additional skills as well.

Something that you'll find across a majority of us that are in enablement is that we have that mentality of helping people in general, because it's not going to be very formal all the time.

There's going to be informal moments, people calling you on the phone or sending you an email where you’ll need to help on something very tactical.

You need to help them and have that mindset, just as much as you help the masses across your region, your company and other parts of the organization.

The skills needed to move into enablement

Especially coming from sales, you’ll see individual sellers that are really, really strong in terms of hitting quota. But the person exceeding quota isn't always necessarily the same person who wants to ‘teach a person to fish’.

There's a bit of a mindset difference there - one's not better or worse than the other, but their enablement mindset has to be: “Yeah, I want to teach others what I know”.

It's such a unique time for anyone who wants to get into enablement.

For instance, if we're talking about entry level, and you love technology? There's loads of sales, sales and marketing, and enablement platforms out there and we need really strong, curious smart people to run, support, manage, evolve, work with the vendor to figure out what's next with those.

That's one entry point, loving technology, and loving figuring out how to get people to consume information. That's a really interesting place for people who are just starting to break into.

Through that, you're exposed to lots of content, lots of presenters, lots of different ways of learning all the foundational pieces of enablement.

The other place is if you are a writer, or you enjoy content such as interviewing in-house experts, or consultants from outside the organization to encapsulate content, and put that into something that's consumable for learners. That's another interesting place.

Then certainly from the sales angle - if you've been an SDR or a BDR, or you're a senior seller, and you've decided that you want to teach other people how to do this. That's another great entry point.

It’s exciting news that there's so many different ways to get your feet wet and get into the sales enablement world.

Natural curiosity

We all know that to be successful in sales, you've got to have that natural curiosity, and always be willing to learn. Learning about your customers, what you learn away from the customer, what you learn from the customer directly, and that goes with sales enablement as well.

Just going into sales enablement doesn't mean: “I have arrived, I know everything related to engaging with customers and what it takes to be a successful sales rep, sales leader, customer success manager, and so on.

You’ve got to keep learning by yourself, and that goes with what you learn internally as well as what you learn externally.

Always be learning in general, investing in yourself even when maybe your company may not invest in you from a formal training perspective.

Look at different perspectives and insights about the world of sales, from many different facets outside of your company as well.

Just be that lifelong curious learner, you’ve got to have that if you’re an enabler.

What should you expect from the role on a day-to-day basis?

What should you expect to do? Expect to do a lot!

The cool part about it is that there's so many different areas to pursue. One thing you should definitely expect is to be constantly learning and understanding the business rhythms, the operating rhythms and how sales is operating.

Understanding what the customers are looking for, understanding the marketplace, leveraging data and analytics to understand those points and to be able to produce that key content in those tools, that the sales teams need to be successful.

That will be an important part of your role.

The great part is the fact that every day is a great new opportunity to make an impact and no two days are the same.

There's a different question that comes up, there's a different scenario that comes up, there's different conversations with different stakeholders within the business. If you’re up for a high level of diversity within your day, and if you're up for really stretching your brain to learn, enablement is a great place to get into right now.

Another important note is that there's a lot of opportunities across all industries right now in enablement and no two are the same.

If you're pursuing an opportunity in enablement, you really do have a lot of options. It boils down to this: what part of that opportunity do you see yourself thriving in, and making an impact in, being successful in, and helping other people be successful too?

Enablement is wide open, and as an individual looking to get into enablement, it's really about that self reflection: “What do I want to get out of enablement, and how can I help?”

It’s people-centric

It's not absolute, but you have to like people to be in enablement. You spend a lot of time with a lot of people, both the people that you're enabling as well as content providers and vendors.

It's a highly people-oriented role.

Obviously there’s crossover into the Operations space and data-driven metrics, which certainly plays a part there but if you're wanting to get into enablement, know that there's a lot of there's a lot of face time.

There's a lot of people, and there's a lot of empathy required. People are learning, and that’s hard. It's hard to learn new content, it's hard to fail certifications. It's hard. People on enablement teams ask to take classes in HR, coaching, and walking people through difficult moments, because there's a lot of that.

The “people” side of enablement is incredibly rewarding, however.

What’s looked for in an enablement hire?

There’s so many things to look at, especially during an interview:

  • Engagement during the conversation. It’s not your regular interview, it’s a conversation and you want to see how the individual interacts with you and members of your team.
  • Can they think strategically, and what’s their thought process? Can you ask them about a certain topic and have a conversation where you can see that they think differently, and bring new opinions and options to the table?
  • Passion for learning, which was mentioned earlier. Are they curious about the role and about sales enablement? Do they have a real interest? Because you can always upskill someone if they have that passion to learn.
  • Are they a fit culturally? This is a big deal, as you have to make sure that any individual fits within the teams you support and alongside the stakeholders in your organization.
  • Be solution-oriented. Don’t come with a problem without at least three options to solve it.
  • Ability to pivot, adapt, and be flexible. You can’t get caught off guard if something changes dramatically, or if the budget gets cut, or whatever. You have to be able to adapt and continue on. Are you comfortable to sit behind a screen for several days, in the weeds of a project, then have to also be able to be in front of a room full of people?
  • Have a degree of authority and be able to influence and command a room. It’s not relevant to tenure, it’s in your DNA or personality to be able to have a conversation where someone listens to you and you add value. Things can go south if that’s not present.

Obviously a lot depends on what role you’re recruiting for, the maturity of your organization, how big your organization is, where you all operate, and so on.

Enablement promotions and moving up the ladder

When you’re looking at promotions, it;s a little bit cliché but you’re looking for that person that could replace you.

You can start by examining what success they've had in general. Look at the KPIs in general, where do they move the needle on whatever the organization is measuring across the business?

Look to the other leaders that this individual might have supported during that time too, what's their perspective on what they've done? It's not a check-the-box exercise, but getting some real feedback on whether they’re ready to make that move.

Because maybe they're going to be supporting at a different level in the organization, or even be more involved within your team and sphere of influence themselves.

It’s important to note that it is a journey and you own a part of that person's preparation to make it to that next level as well.

That means ensuring from day one that they have this aspiration of moving forward - that way we don't have to look back and say: “Oh, I wish I could have helped Jane or Joe be better in these sorts of capabilities.”

You need to start that from day one. Look for people that could step into the promoted role a year from now, or two years from now, and start liaising with them practically rather than ending up saying: “Wish I could have or would have done that”.

Additionally, always look for people that have taken on more than their current role - whether it's volunteering for something outside of the sales enablement function, or always raising their hand to take on additional projects, or something outside their comfort zone, because that tells me that they can.

It tells me they're capable, they're interested, and they're curious - all the things that have been mentioned earlier.

Other things to keep an eye out for any demonstrated ability to be managing, coaching, or leading within their own role. Whether that's managing up, managing down, managing outside.

If you’re seeing that they're leading other teams, other initiatives, other people, those are big things to look for when someone's aiming to move to the next step.

Try to have the right amount of conversation too. Understand what they're looking for and give them opportunities to show you that they're willing, ready, and able to do that well before they're asking. Then, when the ask is there, it's an easy transition.

Connecting with leadership outside of the enablement team

Speaking directly to those who are looking to rise up in an organization in enablement, ensure that you are having consistent conversation not just with the individual that you report to, but also with other leaders of the business.

That way, when they’re in meetings and a certain project comes up, they know your name, and they know you're interested in doing a different, higher-profile role.

It really helps to have those conversations outside of the sales enablement team.

It's great when the person you report to knows your intentions, and that you want bigger projects but it’s very helpful to make sure that others - especially in leadership positions - who are making decisions on products, and even putting together a project team, know that you want a bigger role, and that you're willing to do a bigger role.

You know you've got the passion, the knowledge, the know-how, but it helps for others within the organization to know your intentions as well, so that you can get put in those positions where you can rise up in the organization within the enablement function.

Reaching the top level and staying on top of your game

Cultivating those relationships, as discussed earlier, is key. Always ensure that you’re conducting yourself in a way that’s still providing value back to the business, in a way that’s keeping my relationships intact, and keeping the communication open.

Then make sure that you’re carving out time in the day to do that on a daily basis, so you don't lose track of it.

Seeking out and talking to others who are an enablement function is critical to understanding what they're doing. There's so much to scale and learn from when talking with others that are really just walking in your shoes, just with a different company.

They're a leader in the business, they've got teams, and it's great to reach across and find out: “Hey, what are you doing when it comes to this or that challenge?”.

When it comes to upskilling, try to keep ahead of books that are published.

Sales enablement is having its moment right now, and there's so much content out there.

With so much changing, try to stay abreast of the technology as well and the opportunities and evolution in that space.

Mentoring is another thing to try, to get perspectives from fresh talent, new organizations, especially on things like virtual selling. Apply what you know within these new macro trends and that’ll keep you searching for answers and events, because you need people who've done things that you haven't done.

It's good to follow up with your peers, and just brainstorm and share ideas.

Changing company or industry - what to look for in the transition?

Remember the points about the definition of sales enablement at the beginning? Pressure test that in interviews.

Ask them the questions to figure out how invested they are in sales enablement:

  • What does sales enablement mean to them?
  • What has sales enablement done for the organization?
  • Where does sales enablement sit within the organization?
  • What are some of the current initiatives?
  • What’s the three-year plan for enablement?

Do a big amount of discovery on all things: current state, previous, and the future of what enablement means for the business. These things are very revealing.

If it's a role that might be buried in the organization, you’ve got to ask yourself: “How much influence can I really have within the organization in the short term or even long-term?”.

There’s a lot of questions you can ask but ultimately at the heart of what you need to find out is that vision of sales enablement.

How do they see sales enablement evolving over the next 2, 3, or 4 years, what's important to the company, and what are the expected business outcomes?

The last thing to always ask when you have these conversations is how sales enablement is measured within that company.

That's critically important to understand. If you’re going to take a role at a new company, you need to understand how your position and how your team is going to be measured.

That also provides a lot of insight in terms of how that company views sales enablement as a function, and as a contributor to the business outcomes that are being driven.

Those are some real key questions, and the conversations go from there.