Download the deck >

My name's Steve, I'm Head of Product marketing at Guru and I'm really excited about the topic of this article, it's something I have lived and breathed for a really long time.

Before I dive straight in though, I want to do a quick visualization exercise.

Picture the scene

Most people reading are probably either in sales enablement or product marketing - both really tough, dynamic jobs. I want to put you in a day in the life.

You wake up and head to work. The first thing you find out is that a competitor of yours has launched a competitive feature and the VP of sales is freaking out.

Next thing you know your rep that you've been working really closely with on a six-figure deal - close lost. You did a lot of one on one coaching with him, it's very difficult.

The next thing you know, your CEO is asking why win rates are slipping. I think all of these scenarios probably apply to most of you reading, it's a very challenging, dynamic role.

Now, let's say you need a breather, you go outside and get some coffee. You open the door and this is the first thing you see on the corner of the street.

someone handing out flyers

Somebody's handing out flyers. You're probably met with a whole bunch of different emotions, angst, anxiety, put your head down, don't make eye contact, right?

It's something that happens to us almost every day, especially for those of you who live in San Francisco. What's interesting about this is the other week, I observed this very thing happening. I sat back and watched it happen for a little while and was wondering, why are people even picking up these flyers?

Not to my surprise, about 30 feet behind was a garbage can overflowing with the one-sheets. I had this epiphany - this is how a lot of people treat modern sales enablement, content, content, content.

One-sheets, datasheets, product FAQs, you name it, just throwing them in people's faces. It dawned on me that where sales enablement was, where it is today, it's changed a lot.

Sales enablement is booming

I'm going to walk through the history of sales enablement a little bit and talk specifically about some of that change. I'll revisit this towards the end.

What's interesting about sales enablement is as a function it is booming. It's a great time to be in the role.

sales enablement is booming

CSO insights put out awesome data, I would definitely check out the work of the Miller Heiman group. They put out a survey in 2018 that said 59% of the respondents have a dedicated enablement function. In 2013, that number was only 19%.

On top of that,  HubSpot estimates $66 billion is spent annually on sales training and enablement technology. This is clearly a burgeoning field, there's a lot of great energy around sales enablement - an awesome time to be in the role.

But there's a giant disconnect

When you see this investment into the role and into the technology, and then you look at the numbers, it's quite a stark contrast.

why there's a sales enablement disconnect

Pulling some data here from the CSO insights 77% of the survey respondents said salespeople don't understand their company's value to their prospects.

TOPO also puts out awesome data - 71% of sales reps say they don't have enough knowledge to move deals forward. And only 58% of reps are making quota.

That's the killer. That's the big one. That's why we do what we do.

Sales training versus sales enablement

It's interesting a question I've overheard before is what's sales training versus sales enablement? There's a tonne of confusion and despite being formally defined for the first time, in 2008, people still ask me, how do you define sales enablement?

I'm sure everyone reading gets that from their peers. No one knows. The vendor landscape is a complicated mess of a bunch of different types of technology.

What's changed since 2008?

I don't know how many of you were working in sales enablement or something similar to sales enablement or sales in 2008, a lot's changed. It's crazy. We talk about the rise of the cloud but it happened so fast. Just 10 years ago, the desktop was king. You had your desktop, you had your email client, you had one or two portals, you had your phone, that was it.

As enablement professionals, all reps needed to adapt their behavior to fit these technologies. Do we ship code every quarter? At best. Things moved much, much slower.

There was a lot less information about your product out on the internet. Because of that sellers were really, really, really, really dependent on content to help educate their buyers.

Fast forward to today. Do you have over 10 tabs open on your computer right now? Yes, a lot's changed. The web browser is king. Everyone has SaaS applications. Everyone's living and working in so many different places.

That's a real challenge for us in enablement. It's a real challenge, because anytime we buy a tool, and we ask a rep, 'go there to find the thing' they're never going to do it. Because that's the 11th, or the 12th, or the 13th place they need to go.

They're prospecting on LinkedIn. They're in Gmail, they're in Salesloft or Outreach, they're in Slack. They're inundated with tools and information. To make matters worse, our dev teams are shipping code constantly.

Things are changing, product updates, process updates, things are moving faster than ever. I'm sure we're all familiar with this data point, but our buyers are more educated than ever. 60% of the buyer journey is complete before they even talked to their reps.

What does that all mean?

There are a lot of definitions of sales enablement. This one comes from Forrester, it is by far my favorite.

a definition of sales enablement

They define sales enablement as a strategic, ongoing process that equips all client-facing employees with the ability to consistently and systematically have a valuable conversation. Super interesting.

There are a couple of pieces of that that I'm going to dissect as I go through this.

All client-facing employees

The first is 'all client-facing employees'. Not sales reps, not a specific sales team, but anyone who can communicate with a customer.

A valuable conversation

The second centers around 'a valuable conversation', which I'll get into a lot more.

What's super interesting about this as buyers of technology as well, I'm sure we've all experienced this firsthand.

The power of conversations

I think back to five or six years ago, I was really hot on this one particular piece of technology. I'd done all my research, I was ready to roll, lined up the introduction call, went through 10 to 15 minutes of discovery, solid discovery, and stopped the rep and said, "Hey, I'm bought into a lot of this, I get you have to do your discovery. Before we jump into a demo, though, I've got three questions".

One, is your API going to work with our product? I work for a data product, I need to bring that data from that tool into our product.

Two was a specific security question.

The third was around predictive analytics and what they claimed, that was just what we called AI back then. He couldn't answer either of those questions. I had to stop him and say, "Hey, listen. Totally cool. These are nonstarters for me, I need to know before I waste any more of your time with a demo".

What ended up happening was we shook hands, we walked away, and I ended up buying a competitor. I had the demo the next day, that rep was ready to roll, had answers to all those questions, moved the conversation forward, kept me engaged, and I ended up buying that product.

We think about the conversation and the role of the conversation and we get so tied up in prospecting, or pipeline management. They actually spend a third of their day talking to prospects.

the power of conversations

There's also interesting data that says in this world of email and everything else, 41% still say the phone is the most effective sales tool as buyers. Yet 85% of prospects and customers are dissatisfied with their phone experience.

Content as a crutch

I'm fortunate enough to work with a great sales leadership team, and the other day, I had another epiphany when our Director of Sales at Guru said, "Content is a crutch". I said, "Yeah, you're right, that makes sense. Content is a crutch".

We invest so much time upfront in learning and development and training, how do we make sure that's sustained ongoing enablement? How do we make sure that our reps actually understand what they're talking about and aren't dependent on someone sheet that they then send to their prospect?

What was super interesting about this conversation was he actually stopped me and said, "No, no, no, no. It's not a crutch for our reps. It's a crutch for our buyers". A light went off. I've always thought of enablement as teaching our reps how to fish but now I'm sitting back thinking with six or seven people involved in every buying decision:

  • How many of those do we have direct access to?
  • How many of those do we actually have on the phone, where we can ensure that our narrative comes across really crisp and clear?
  • That our differentiators come across?
  • That we're hitting on all the things that we're wanting?
  • That we're injecting the customer stories we want?

It dawned on me, if you think about enablement, we should not only be equipping our reps to have valuable conversations but for our buyers to have conversations internally.

Ron Swanson meme

Speaking of crutches, like a Ron Swanson meme, I get the irony there because that's a cheap laugh.

This was a really interesting moment with sales leadership at our company, and it's gotten me thinking all sorts of new things about enablement that I'm super excited to write about.

Content is just a piece of the equation

This is one of my favorite images, we show it to our reps all the time. What it does is helps them unpack what it is that they need to be successful.

Again, you talk to any rep, 'give me the one-sheet, give me the datasheet, another case study', all well and good and it certainly has its place, but when you think about what is actually required to move a deal and a conversation forward, there's all sorts of knowledge that is often overlooked, that we don't think about in enablement roles.

Process knowledge - how do I prospect at this stage, I'm in Salesforce, I'm moving it from discovery into qualification, what do I do in Salesforce? How do I communicate that to our buyer?

Conversational knowledge - how do I handle this objection? How do I handle the competitive question? How do I handle that security question?

Product knowledge - shipping code every week, every two weeks, things are changing so fast. How do we make sure that our reps are up to date on all the things that are happening around our product?

The seller/buyer journey

When you actually extend this across a buyer journey, I'm sure this will look very different for everyone reading, but you can start to think about the internal and the external, across each stage of the buyer journey.

the seller - buyer journey

When you're an SDR and you're prospecting, you need your persona information, you need to understand the pain points and the objectives of that persona. You need qualification questions in case they answer your cold call.

Then you move into discovery, you need a different set of discovery questions, you need sales playbooks, you need to figure out what are the different demo plays if they want to jump into a demo? Here's where content comes in.

You've done your prospecting, you've had a great demo, you've had a great conversation, you need content to cement and reinforce that conversation. That is the role of content in sales enablement these days.

That's not to say there isn't a place, content is very important but we often over-index on the bottom of this line, and we don't equip and enable our people to handle the top.

Another interesting thing is, as you extend this across the buyer journey, you start to get into CS and support, which I'll talk about again, but I really think going back to that Forrester 'equipping all client-facing employees with the ability to systematically have a valuable conversation' still summarises the work we do in enablement better than anything.

Measuring conversational success

How do we start to measure conversational success? I'm sure all of us have data teams or work with data directly.

measuring conversational success
Cohort analysis

Who uses cohort analysis? If you take nothing else out of this article, understand the power of cohort analysis for your enablement reporting.

With cohort analysis, you're basically grouping people up into what we do as onboarding class. If you're onboarding 5-10-15-20 reps at a time, you're capturing those as different cohorts.

I joined a company five or six years ago and one of the first things that the VP of Sales told me is 'we're going to go from nine to 90 on the client-facing side, you're going to have to onboard all of them'. One of the mistakes I made early on was not taking into account the outliers, there are always going to be reps that just come in and just do really, really, really well.

At the same time, they're always going to be those that lag behind, those that don't work as hard, those that don't go through the training the same way.

What cohort analysis allowed us to do is start to measure our success as an enablement function on a more holistic level. We could actually see as we refined our onboarding process, as we refined all of our ongoing enablement, are we making a material difference from class to class to class?

Because again, there are always going to be those outliers.

Custom metrics

Another thing I'd consider is defining some custom metrics. One thing that we love to do is scorecard our rep conversations. We'll talk in a second about tools but conversational intelligence tools like Chorus and Gong are incredibly valuable for sales enablement.

What we're able to actually do is go through and scorecard conversations, we look back, we see those conversations, we can scorecard them, we can start to understand how well they're handling objections, how well they're actually communicating product value, how well they're injecting customer stories.

This is not only a great measurement of conversational success, but it's also great to inform further enablement activities. We can start to figure out where we're weak within the context of the conversation. A lot of great roleplaying inspiration out of that as well.

Time to second deal

Another way to measure is time to second deal,  a really strong and powerful indicator. A mistake I made was time to first deal, but some people get lucky, some get a deal handed to them on a silver platter time.

Time to second deal is a much better indicator of are we having good conversations? Are we engaging people? Are we actually closing those deals?

Deal velocity

I mentioned this earlier, but one of the biggest benefits to being good within the context of a conversation is we keep the deals moving. Going back to that conversation I had with that sales rep. If he had been able to address my security question, if he'd been able to address the API question, we would have moved on.

The best-case scenario there is we're slowing the deal down with another conversation. He came back he said, "Well, I need to talk to my sales engineer, need to talk to my security team. I'll go grab a data scientist, I'll figure out how the predictive analytics stuff works". He sent me a one-sheet on their predictive analytics. I don't even think I ever opened it, it didn't matter. You lost me, you had me, I was engaged with ready to roll.

Again, at best, all he's doing is slowing that deal down. We know how important sales velocity is.

Number of calls held per closed-won opportunity

Directly related to that is number of calls held per closed-won opportunity. If it's taking us eight, nine, or 10 calls to close a deal in a certain segment (I say segment because that's obviously very dependent on the size of the deal) we can start to assess whether or not those conversations are more valuable if we're moving people down our funnel faster.

The conversational toolkit for reps

We can talk about this stuff all we want but at the end of the day, we need to start figuring out how to actually implement some of these.

the conversational toolkit for reps

Some of it's just ideology but there is a core set of tools that really help think about enablement and measure enablement through this lens.

Live chat

We talk about all the different places reps work these days, live chat for sales was not a thing, even two or three years ago. Intercom and Drift pop up and now it's a real opportunity and companies that seem to do that really well put themselves at a huge competitive advantage.

But that opens yourself up to more conversations, it certainly requires enablement through that lens.

Conversational intelligence

The second I can't recommend highly enough - if you do not use a conversational intelligence tool, I would highly recommend checking them out. Chorus and Gong are the two that I would recommend.

The ability to scorecard, to run playlists, to look for certain keywords if you think your reps are struggling within a conversation on a specific objection, or when SOC 2 compliance came out that was a big whole thing for us in enablement.

We just set up trackers to go and ping us whenever that comes up in a deal, we can just quickly jump right to the point in the conversation where that comes up. Super, super, super valuable.

Real-time knowledge management

The third is real-time knowledge management, this is interesting, knowledge management is not something that enablement people think about very often. But whether you're using Atlassian Confluence or something along those lines, being able to get that just in time information in front of a rep during that conversation is critical.

Whether it be the competitive battle card or whether it be a quick product FAQ, or are we SOC 2 compliant? Yes, just having that at the fingertips of a rep in the moment is absolutely critical.

That's the distinction between knowledge and content.

What's actually next for enablement?

The rise of the customer-facing teams and enablement opportunity

Going back to the point I made earlier, that Forrester definition that I love so much, what we're starting to see is a huge trend, especially in smaller, faster-growing companies of enablement as a function, starting to enable more than just sales - CS, account management, customer support.

Forrester also talks about a customer continuity curve. The concept is, your buyers have questions. They don't care who answers them. Whether they're working with a sales rep on a deal, and they spin up a free trial, and they have a question, they're gonna reach out to the rep, not support.

And vice versa maybe they hear about a competitor and they write into support and say, "Hey, how are you different than them?". What you need to do is ensure that all of your customer-facing employees can have that conversation, going back to that Forrester quote.

Conversational tools to help drive rep productivity ‘in the moment’

Whether it be conversational intelligence tools, live chat, knowledge management, thinking about how I can make them their best versions of themselves in that moment, answer questions, handle objections, move deals forward.

They spend a third of their day doing that, why not invest from an enablement standpoint in making them successful in those scenarios?

The role of real-time knowledge for ‘just in time’ enablement

Again, the role of real-time knowledge management, sales enablement, as a category is very confused. Sometimes people will be like, why doesn't one tool do at all? There's a lot of answers to those questions, but these are complicated problems that all these different tools are trying to solve.

It's important to understand that sales enablement is not a specific product. Though it is addressed as a category, there are many different types of products within sales enablement.

I was at dinner with a colleague of mine, who's our growth marketer and he said, "When you talk about sales enablement it reminds me of account-based marketing". For those that don't know, account-based marketing is the same thing, it can mean paid ads, it can mean direct mail, and everything in between. Often people will say 'I need ABM software', what does that mean? Really starting to think about the nuances within the category is really critical.

Content is king for content marketers, but conversations are the lifeblood of sales.

Thank you.

Download Steve's deck >