The insider guide to sales enablement best practice

If you don't have a sales enablement person at your company, and you're the only product marketing manager at your company, or even if you're not the only one but you don't have sales enablement, this article is going to cover what to do when you don't have sales enablement.

For those of you reading that do have sales enablement in your organization, I still use a lot of these practices in my role today in which I'm very fortunate to have a sales enablement person and a whole team to help me out.

In this guide, I'll be discussing topics such as:

• The importance of sales enablement
• The tie between sales enablement and product marketing
• How to build a content depository

Plus much more.

Why is sales enablement important?

Buyers are more informed

Seismic published a study that found about 60% of buyers, before they talk to a salesperson, have already made a decision. They already know what they want, they've looked through your product sheets, and they understand the product intimately.

Customer-centric selling

That means for a seller, the customer sale becomes a bit more customer-centric. We have sellers who now have to have a conversation one level above, "Do you need this, oh, here's what you need." It's less of a seller being a consultant and telling them what they need, the buyer already knows what they need, and they need to know how your products are going to solve that problem.

That can be a difficult thing for a salesperson to do if they're not properly enabled, and things go awry. The reality is, sales enablement is a hot potato.

What happens when you have no one doing sales enablement is it gets passed around. The problem is when no one's holding the hot potato, no one gets the results of what hot potatoes make.

Hot potatoes make amazing french fries and the french fries are things that everyone across the organization benefits from, not just sales. That is:

• A stronger marketing message,
• A scalable sales process - for those of you in startups, as you're adding people to your sales team, how do you make that process repeatable?
• Competitive intelligence,
• Consistent marketing messages, and
• Staying away from the behavior that sometimes happens where salespeople don't have anything from you so they start making their own things. Then they start making their own products for some reason because apparently, that's the next stage with no sales enablement.
  

Where does sales enablement fit into product marketing’s role?

My feeling is that as a product marketing manager, I am the steward of three things.

1. I am the steward of the insight and strategy for my organization, understanding the market drivers, the personas, use case development, and the target market.
2. I am the keeper of the messaging, and
3. Go-to-market strategy.
   

Of course, we collaborate with a lot of people to do all of these things well, but these are things we really own.

The thing is we also own enablement sometimes too. That's why it's at the end.

• This could be training and development - in my product marketing life, I have trained salespeople, it wasn't the product managers who were doing that.
  
• I've had to support sales content and build presentations.
  

It's all of these different things we're doing and not just those three core tenents of our jobs.

Phased approach to building up sales enablement program

When we look at a phased approach and building up a phased approach of sales enablement, when you're starting from nothing, I came up with these five phases.

These are things I'll do no matter where I am or when I started. In an organization, I try and look at where I can fit these phases into my daily work to help sales.

When we look at these phases, no matter what you're doing, or how you choose to do these, whether you're doing them in parallel or one after another, make sure you're always having alignment with your sales and marketing leadership.

Don't take this on unless you have alignment with those folks because then you're ending up doing a job that maybe is distracting from other core things you need to be doing or a different focus for the organization. You also don't want to build sales enablement materials that the CRO disagrees with, because then they'll never use them.

Phase 1: Interview, interview, interview

Sales is your customer, so talk to them

The first phase is really about interviewing. Just like we do customer interviews all the time, in this case, for sales enablement, sales is our customer. It's important to talk to them.

Expand interviews beyond sales

But I say sales in a general sense, you have to look at sales as not just the account executives, but people who go beyond that. Anyone who touches the sales cycle. That could be a sales engineer, business development, or even someone in demand generation who is maybe getting requests from a salesperson on certain content they need to be able to do their job better.

Keep a record of those core themes as you're doing these interviews. I try to record them but most of the time I'll do shorthand notes. I'll put all of my information in an Excel sheet, and then I'll start to group the interviews, in the Excel sheet, by themes.

Then I know that if 15 times someone's saying we don't have good competitive intelligence, I probably should work on competitive intelligence first.

Win/loss interview questions (template) | Download

Our win/loss interview questions template gives you all the prompts you need to understand why a sales opportunity resulted in a win or loss.

Product Marketing AllianceJames Shaw

Consider teams outside of your immediate geography

Sales teams in EMEA and in the United States are going to be totally different. For example, in Germany, they are very centric in their region, it has to be very German-specific, and use cases have to be according to that country.

It's important to understand those needs when you're starting to build up a program.

Leave the building if possible & keep the interview short

My advice is leaving the building is the best thing to do. I have had the best conversations over a cup of coffee or a drink, of course always on me, but also on the company, because I'm expensing it afterward - super sneaky.

It's just good to get out of the office because then people start to break down their walls a little bit and they don't feel like they're being listened to that much.

Keep questions focused on their concerns, what they need

As far as interview questions go, you should make sure they're open-ended. Don't ask something somebody can say yes or no to, really give them some time to answer.

I've also found that pauses can be useful, there have been times when I'm interviewing someone or talking to a salesperson and I'm just pausing because I'm writing something down. But that pause signals to them I'm still waiting for them to say something so the real juice comes out and I get the real information on what they need and I start to understand more.

Best practice: interview questions

When looking at best practices for questions, the first thing I start every conversation with is:

• How can I help you?
• How can I help your sales cycle?
• How can I improve your sales cycle?
• Tell me about your process, what was the biggest loss that you had and why?
  

Sometimes it doesn't have to do with sales enablement, sometimes it really is just a competitive situation, things happen. But it's good to understand the why of someone losing a deal competitively.

Also, I say if you had a magic wand, if I could do anything for you, what do you wish? What were the resources that you wished that I could give you? Then usually I'll get a list and I try within reason to answer some of those.

It's a good way of getting them to open up and nail down exactly what they need.

Phase 2: Key use cases and competitive market

Determine if use cases and competitive information are formalized

The reason I bundled these two together is sometimes depending on the use case your competitive market changes.

For example, at an organization I was at, we had the same product that we sold into insurance and financial services.

• If I was in insurance, my competitor was an insurance-centric claims software.
• If I sold into financial services, my competitor was a fintech startup.
  

Those are two totally different use cases, vertical markets, and now my competitive market has changed. I had to enable those vertical markets as well as the use case so just keep that in mind - sometimes these things are tied together.

Resources

If you're not sure about building resources for these things, I spend a lot of time in CRM, I use my sales interviews as ways to dig into this a little bit, and then, of course, there's market research out there like Forrester and Gartner.

I tend to bother the analysts quite a bit, I'm a former analyst, so I tend to get on their annoying side by asking weird questions, but they're okay.

What content is needed to support current sales goals?

Also, looking at what content is needed to support these use cases and this competitive analysis.

• Is it simply a SWOT?
• Is it something more detailed?
• Do you need a quick guide?
• What are those things that you need?

Look for partners in your company to help you create these resources

You shouldn't be doing this alone, you should be doing this in practice with product managers. A lot of times I have found sales engineers to be very helpful on some of this stuff, too, because they're getting to the demo stage, or maybe a Bake Off with a competitor.

Living document

Make sure you're keeping these as living documents. Don't do a SWOT and be like, 'Man, I'm done with this SWOT and this battlecard and I don't have to think about this competitor ever again.'

No, you still have to think about them. Keep a cadence in which you're going to update this information.

Best practice: privately-owned competitors

As far as competitors that are privately owned, this was a big challenge when I was working at a startup because all my co-competitors were also private.

What I did was I started to look at their VC firms because a lot of them have to issue annual reports. In their annual reports, they talk about their investments. Then I could dig in a little bit into the strategy of my competitors that were private.

I also went on a lot of developer and user sites, websites, looked at LinkedIn user groups, and tried to listen for complaints, looked at release notes with my product manager, and measured some more qualitative things like the sentiment on Glassdoor, looked at their hiring pages.

If you see they're hiring a lot of developers, for example, with a certain type of skill, it might be a hint that they're trying to build something a certain way. If somebody is hiring for a tonne of cloud-centric developers, and they're on-premise competitors, you know the direction they're going to be going.

Phase 3: Content inventory

As you're building all of this stuff out, it's important to keep a content inventory to understand what you have in existence and what you need to build.

Content needs to cover every step of the buyer’s journey

A major mistake I see a lot of organizations make is they don't have content that spans the entire buyer’s journey.

What I mean by this is, that we have a product sheet that's great for demand Gen, to fill out a form and get that information down off the website, we capture somebody as a lead. But as that person becomes closer to being a customer, we don't have a technical brochure or something that gives a bit more of a deep dive into that content, and what that product actually does.

Those are things you would work with, with your product manager, or someone technical in the organization to build. It's not that you should own all of this content but it's one of those things about understanding where in the buyer’s journey you need to fill in the gaps and determine those gaps.

Plan out content

You should plan out content. In the case of building out something, I used to do this guide for every product release, it was me, development, and our PMs. It was what was new in the release and it was like a 20-page white paper document thing that went into the features and the market benefits and all of this stuff.

Before we even started writing this we treated it like a campaign. We wrote a campaign brief around it:

• What was the goal?
• Who was going to do what?
• How are we going to handle it?
• What was the layout?
• What was the content structure?
  

That way, when we started to actually execute it, we had a clear idea of how to handle such a large document.

Also looking at keywords, if you are going to put these things into a repository, think about the keywords you want to associate with those files. Keep that in mind. Or if there are keywords in there already are those the right keywords for your salespeople to find the content they need?

Measure the success of current content

You also have to measure the success of the content. To be honest, the quota attainment and the sales time decrease is a project in itself to understand to measure.

What I do today, because, as a product marketing manager, I'm not necessarily responsible for sales enablement, but I just want to understand what sales decks people are actually using that I'm making, or am I wasting my time making this brochure for you?
the

Things like that we have our sales enablement content in SharePoint and in SharePoint, I can export a report and see the download usage. Once a month I'll export this report and then look at what the downloads were for different things.

That way I can start to understand which assets are not very popular, then I can talk to my sales leadership and say, "Look, I noticed no one is using this, can you tell me why?"

Best practice: keep a DAM mindset

As you're moving down these phases the end goal - phase five - is you're creating something, an enablement center, or some sort of repository, it's important to keep a DAM mindset.

Remember content needs to be found

Remember that no matter what you build, the content needs to be found. You can't just build this stuff and dump it in one place.

Clear folder structure & naming convention

You need to have a folder structure, you need to have a naming convention, this is particularly important when you have things you're going to give to sales that are internal facing versus external.

You do not want them to send something that's like a buyer persona and you have your pains and your gains, and then they send that off to a customer. That is my worst nightmare ever that somebody sends an internal label document to a customer.

Make sure that you have a file naming convention that reflects what the intent of the content is.

Version control rules

Also, have version control rules. If there is version two out and people are still using version one, they are no longer allowed to use version one. You have to be a stickler about that, especially if you're dealing with products or a rebrand or things that are moving super-fast, you want to make sure you're giving your sales team the most up-to-date information possible.

Keep file sizes low

Only because I know that we love PowerPoint and with PowerPoint comes giant file sizes. If somebody is doing a pitch, and they're just scrolling through it on their iPad, they don't want to spend 20 minutes waiting for something to upload.

Phase 4: Formalize resource repository

All the great stuff you are doing needs to live somewhere

You've built all of this stuff, the great stuff that you're building, you've gone through all the phases, good for you. You also didn't sleep for three months while you were building a sales enablement resource center. Welcome.

All the great work you're doing needs to live someplace.

It doesn’t have to be fancy

It doesn't have to be fancy, if you can't afford something like a CRAN, Seismic, or Sabo that's okay. There are free things you can do, you can create a Dropbox that people can access.

In my previous organization, and I'll go through this in the case study, we had JIRA and we just so happened to also have Confluence because JIRA and Confluence shipped together. I used Confluence, everybody had Confluence, so why not use what we had?

Think through structure of content

Also, make sure that you're thinking through the structure of this before you get into it.

Make sure to align structure with sales leadership

With this resource repository, you want to make sure that you're aligning with sales leadership on the actual structure of it because that will determine how people find the content.

Best practice: organizing the repository

This is just a rough outline of how I've organized things in the past.

Customer type

I apologize if it's a little bit of an eye chart, but usually, what we'll do is start with, what's the customer type? Are you B2B/B2C? I've worked in organizations that have sold both types of software.

Use case (by vertical market)

Then the vertical market, maybe the use case - it depends on how you want to organize that. At one company I worked for we launched a sales enablement Resource Centre and we did it by the product first, which lasted all of five months, we had to switch it to the use case and vertical market.

Competitors, use case content, general product content

Then competitive information, use cases, and general product content.

All of these places can be interconnected with each other, but it's just keeping in mind that first structure when somebody goes to the page, what they're going to see first.

Phase 5: Enable on resource repository

The fifth thing is really to enable that resource repository.

All this hard work you're doing and all of these sleepless nights are worth nothing if no one uses it. You need to make sure you're getting your salespeople on board and using this repository you're creating.

Ideally, you want to align it with something that's already going on in their lives like a boot camp or Sales kickoff.

Best practice: play into what sales does best

To really get them into it, my best practice here is just to play into what they do best, which is to make it a competition.

I had a co-worker who launched one of these and what she did was create a karate theme sales enablement Resource Centre. The more resources you use, the higher your belt is. Whoever got the black belt first got an Apple Watch.

She said the usage was ridiculous and still is today. It's really funny to watch the dynamic going on, and it encourages them initially to start to go in to use this resource center.

Case study: starting from scratch

As far as the case study, this is starting from scratch.

Background and goals

In January 2019, I was working at a financial services startup, and we hired seven new salespeople. When I say new, they were babies straight out of college, not really financial services experts - great dressers though.

We had about eight existing sales representatives. All of them attended this January kickoff, I helped with the boot camp, did the marketing messages, did my presentations, and at the end of it, they had to deliver what's called a value pitch.

The VC wants this value pitch and if the salespeople don't score a certain number, they're let go. Of the new people, everyone scored lower than desired.

They turned to me and said, "Hey, you do marketing, you can build a sales enablement Resource Centre". I ended up getting tasked with this.

Sales population overview

• We had 60% of the sales force had less than five years of experience, professionally, sales experience, everything, they were very, very new.
• Three had a financial services background - these were people who already existed in the organization, or had majored in finance.
• I had two geographies I was dealing with - the UK and the United States.

Phases in action

Interview, interview, interview

The first thing I did was interview about 15 people. We went out for coffee, we went out for drinks, I talked to people that were sales engineers, salespeople, the SEs, the new guys, everyone, and gathered information.

Key use cases and competitive market

What I found was that a lot of the resources that we had, while we did have them, they were very scattered. This is why I started to think about building a resource repository for them because it was one of those things where we just didn't have a good place where we had everything in one place.

They also were going into a lot of sales engagements blind because they didn't have a lot of competitive information. A lot of our competitors were private, information was all that they had. I knew there was going to be a competitive swing to the sales enablement Resource Centre.

Content inventory

When I looked at the use cases, what I did find was most of the sold use cases also had the least amount of content. This financial services company dealt with FINRA and SEC regulations, we didn't have a lot of information in the background on what FINRA means for that buyer, what SEC means for that buyer.

Sending someone who's brand new out of school to talk to a compliance officer who's like, 'well, how does this affect FINRA for me?' is just such an unfair thing to put a person through. None of us would be successful if we didn't have that information.

We decided, working with my leadership team, that we would target three competitors because we knew these were the top three. Also, competitive things like SWOTs and battle cards take a long time to make. Me and the product manager decided we would cover three competitors and also build some product-specific content for the regulations as well.

We had a content inventory, we spent two days working across all of these different departments and gathering the information, we realized again we were missing all of these things.

Formalize resource repository

I built the Resource Centre in Confluence. The structure was decided and designed in lockstep with the VP of Marketing, but also the CRO. At the time, I had a little bit of an advantage to this so when I show you the success numbers don't get excited, I'm not that amazing. I just happened to have the CRO as my boss at the time.

It's a little bit of a different story when the sales guy is telling his subordinates, 'hey, you better work on this and do this'.

Enable formalized resources

Because the boot camp had passed but we knew we wanted to retest these guys in a couple of months, what we did was created an event.

I created a spy game and these guys loved it, they were obsessed with it. Every single spy mission had something they had to do that had to do with Confluence, the sales enablement Resource Centre, and getting them more towards a value pitch.

Again, weekly progress meetings across so always aligning with our sales and marketing leadership.

Closer look at the game

Looking at the game a little bit closer. Every week I would go to their cubes, print out their mission, and leave it. We had the experienced sales guys in on it, they were fake prospects for me.

• The first mission was they had to cold call the prospect and tease out what competitor that prospect had.
  
• The second mission was they had to use Confluence to look up the competitor and recall the prospect. That meant that they were looking up battle cards, quick guides, and all of this information on Confluence.
  
• The third mission was to build a value pitch using the persona that they were assigned, that prospect they were assigned, and also using Confluence. In Confluence, we had built out a persona section so using that as a guide to build out to their prospect.
  
• Their final mission was to do the value pitch in the group, and redo it in the group, which was great because they didn't realize they were getting retested. They were younger, I think there was a lot of anxiety around that first pitch because they knew how important it was. The second one was fun.
  

The other thing was whoever won got a gift card and that was like the real goal here in addition to really getting into the spy stuff, they were also very into the gift card.

Results

As far as the results, all of the new employees adopted the Resource Centre and we actually had a lot of the established salespeople adopt the Resource Centre, as well.

Probably the best part of this is that there was a roughly 20% increase in the average score.

While some of them didn't score out of the park, from what I know, they're all still working there. I think that's a great thing.

Thank you.