Archives: Ebooks

Top Industry Blogs

Top Industry Blogs

At Highspot, we devote our full attention to helping sales and marketing teams outperform. This means taking into account a broad assortment of perspectives shaping the sales enablement space. From strategies and tactics to competitive insights, technology advances, and more, the following blogs have shaped our approach toward delivering the value that customers demand. We recommend bookmarking those most aligned with your business goals and sharing relevant content with your audience. It’s a great way to curate new ideas and become a trusted sales and marketing partner.

Directory of Analysts

Sales Enablement Analysts

In a market as dynamic as sales enablement, independent research and analysis can help companies formulate their long-term strategy. Independent firms can also be helpful when selecting and evaluating sales enablement tools. In addition to reports and consultations available exclusively to their clients, many analysts share insights publicly via LinkedIn, Twitter, and their blog.

Identifying the right analysts and finding their various online resources is not always easy, so we have compiled a list of analysts in alphabetical order by last name from leading firms that include sales enablement as an important part of their practice.

Summary and Additional Reading

Path to Optimising Your Sales Cycle

Path to Optimizing Your Sales Cycle

Additional Reading

  • Best Practices. This article provides pointers to whitepapers, blog posts, eBooks, and webinars covering a variety of sales enablement best practices.
  • Fix Your Sales Portal. A sales enablement platform should deliver on these six essentials to make sure that your sales team gets the maximum value from the content you work so hard to create.
  • Top 3 Sales Enablement Myths. These three myths fall in to the “tell customers what they want to hear” category but unfortunately will lead to failed projects.

Measuring Solution Health

Sales Enablement Solution Health

A modern business is deeply data-driven. Once you have your sales enablement solution in place, you are ready to analyse and optimise your sales process.

With respect to sales enablement, there are three main areas to apply data-driven methods:

Sales Enablement Data Driven Methods

In this chapter we focus on solution health.

Solution Health Overview

The solution that you have implemented is not going to do much good for the company if it isn’t being used. We have found that it is most useful to measure that in three ways:


How many people have ever used the solution. If the solution requires users to sign up for an account, the number of accounts that have been created is a simple way to measure adoption. If you are using single-sign on, where accounts are automatically created as needed, you can use the number of people who have visited the enablement platform at least once.

Breadth Usage

This is another fairly simple metric, showing how many people used the solution over a period of time. Our primary view is the previous 30 days, which is usually a good way to understand normal usage. Patterns of use will often vary quite a bit over a single day or week, and those numbers can be affected heavily by a short-term event like a holiday or the end of a financial quarter. But if the solution is a core part of their work, looking at a 30 day period gives a reasonable picture.

To broaden the view farther, we sometimes compare activity during the past 30 days to the current content cycle. At many companies, there is a cadence for updating content that is tied to some event such as a sales kick-off. It might happen once or twice per fiscal year, or coincide with an external conference for partners and customers. At such moments, there is often a major refresh of content. Looking at usage since the last such refresh shows activity for users who don’t visit as regularly but do come for new and updated information when it is released.

Depth Usage

This metric can take more thought to compute than the other two, which don’t vary too much from one company to another. The goal is to measure how many people have used the product to accomplish something of value. We use a standard set of depth metrics that work reasonably well across many different organisations, but you may find it worthwhile to develop your own custom depth metrics to measure the activity that you are most interested in encouraging on the platform.


To track these metrics, we rely on a scorecard. It shows the current state of each of the three key metrics, assigning each of them a green/yellow/red color based on the target value. We also show a historical view to help put the current health in context.

Sales Enablement Health Scorecard

Note that the scorecard shows each of the three metrics (adoption, breadth, and depth) and combines them into a single overall health value that is computed using a weighted sum. We use different weights depending on the maturity of the solution.

In the post-launch stage, when the solution is new to the organisation, the focus is generally on adoption and breadth usage. The goal is to make everyone aware that the solution is available, signed up and enabled for use, and for them to start experimenting with it. The sample scorecard shows a solution that has been recently launched and it emphasises those first two metrics.

In steady state, adoption and broad usage remain important, but the focus shifts to put more emphasis on depth usage. It’s not enough that people find and use the solution; the key is whether they are getting value.

How to measure that will depend on your environment, but some metrics we find useful are how many people took an action like viewing an item or downloading it, how many people pitched, and how many reps have completed a training course. In addition, it may be useful to measure the number of actions generating value—how many items were viewed and downloaded, how many pitches were made, and so forth. Best practice for depth is often to have a number of different metrics and combine them together in a weighted average.

Depth usage is important not only because it delivers the most value to individual users, but it also typically yields the best data for measuring the effectiveness of your content. For example, if the sellers are not using the platform to pitch content but are instead simply downloading it and sending it via email, you will miss a lot of customer engagement data that you could have used to do a better job of optimising your content.

In steady state, a healthy solution has been almost universally adopted, has strong regular breadth usage, and has a significant percentage of the sales team using it in depth to enhance their sales efforts.

Other Metrics

In addition to usage, there are other ways to gather useful metrics about the solution, such as sending out polls. We encourage using a variety of ways to gauge the effectiveness of the solution. However, we do recommend that you make usage your primary measure of health. There are pitfalls to be careful about—if a user wastes a lot of time hunting for something and never finds it, the metrics can show a lot of usage and that user is definitely not happy with their experience. But over time, users vote with their feet. If they don’t get value, they will gradually reduce their usage to the bare minimum. If people come to the solution frequently, spend a lot of time on it, and there is strong depth usage reflecting successful use, that’s a reliable indicator that you are providing value to them.

Look at Usage by Team

Companies often find that a solution has been broadly adopted across the organisation, but some teams have been left out. So in addition to looking at the health across the entire target population, you should also spot-check other teams. For example, if your company is international, look at usage health for the subsidiaries. If you segment the sales team by vertical, or by size of the target customer, look at usage in the different segments to spot any issues that you need to address.

Qualitative Health Tracking

The metrics described above will give you a good picture of how the solution is being adopted and used across the organisation. However, it won’t tell you why there are problems and how the system could be further improved. In addition to metrics-based scorecards, it is important to reach out and talk to representative members of the user community.

We recommend a series of brief outreach interviews with:

Power users from each key community

For example, your most prolific publishers, content consumers, and pitchers. The sales enablement platform should give you reports that make it easy to identify who these people are. These users tend to have the most experience with the system and give the most detailed and demanding feedback.

Regular users

These people will give you a sense of what the typical user’s experience is like. They may have different needs and expectations than the power users, so you don’t want to confine your discussions to the committed experts. Most people won’t become expert users — they will do what they need to in order to get their jobs done.

Non-users who should be using the system

If some of your target user community rarely or never logs on, find out why. They might not know about it, because they were missed in the rollout. Maybe they don’t know how to use it, because there wasn’t the right kind of training. There might be some other solution still in place that they are using instead. Or perhaps their team has particular needs that are being poorly served. You won’t know how to improve adoption if you don’t know what is holding it back.

These conversations can be relatively short — the key is to understand what is working well and the top things that are making life difficult for the users. A few questions you might want to ask:

  • What is your role in the organisation? What team are you part of?
  • What are the most difficult challenges you deal with?
  • How does content play a part in your job?
  • What do you use the sales enablement solution for? How is it working for you? Can you find what you need, quickly?
  • Did you get the right amount of training on the so that you know how to take advantage of the solution?
  • What is really working well? What is not working?
  • Is there content you need that isn’t available? Do you have to build content yourself that you think the company should already have available?
  • Are you aware of the job training that is available to you? Is anything missing that you think we should be offering?
  • Have you taken any training? Was it worth the time? How could it have been improved? What could we do to better prepare you for the challenges that you face in your role?

Measuring Seller Readiness

Sales Enablement Seller Readiness

A modern business is deeply data-driven. Once you have your sales enablement solution in place, you are ready to analyse and optimise your sales process.

With respect to sales enablement, there are three main areas to apply data-driven methods:

Sales Enablement Data Driven Methods

In this chapter we focus on seller readiness.

Sales Team Readiness Overview

There are ten reports that will allow you to analyse and optimise your training investments. Each one answers an important business question. Together, they paint a complete picture of the training that you have, how it is being used, whether it is effective, and how much business value you are getting from it.

Sales Team Readiness Reports

Whole Sales Lifecycle

If you can’t analyse the effect of training on the entire sales life cycle, you can’t answer crucial questions.

  • If you don’t know which deals the seller was involved in after training, you can’t measure revenue influenced and business impact.
  • If you don’t track performance after the training, you can’t measure impact on turnover and on how long it takes a seller to become effective in their role.

Activity and Business Impact

The ultimate goal is to measure the return on your training investments. Training is expensive — you need to develop the courses, deliver them, and pay the opportunity cost of putting your sellers in a training session instead of having them focused on selling your products. You’d like to be able to say, “I spent $X on having this seller trained and it generated $Y in additional revenue.” Your sales enablement system can answer that question, but it will also provide intermediate metrics that yield additional key insights.

Activity metrics help you diagnose why you aren’t getting the business impact you want. You might not have the training that your employees want. They might not know about the training that is available. It might not be effective, and everyone avoids it because it is a waste of time. Each of the ten reports gives you insight into one particular area of training performance, and together they let you understand the whole picture and dig down as needed to understand where the problems are.


Top-level reports will give you some important information about the effectiveness of your training. However, you’ll often need to go deeper into the data by segmenting it in various ways. Here are some common ways to segment readiness data:

Sales Enablement Anaytics Segmentation

The Purpose of Analysis is to Drive Action

The goal is to use training as a way to make your sales team more effective and engaging with customers and increasing revenue. Each of the ten reports answers an important business question, identifying key issues and opportunities so that you know how to act.

Sales Readiness Action Plan

Measuring Content Performance

Sales Enablement Content Performance

A modern business is deeply data-driven. Once you have your sales enablement solution in place, you are ready to analyse and optimise your sales process.

With respect to sales enablement, there are three main areas to apply data-driven methods:

Sales Enablement Data Driven Methods


To analyse and optimise content used during the sales cycle, there are eight reports you need to have. Each one answers an important business question. Together, they paint a complete picture of the content that you have, how it is being used, whether it is effective, and how much business value you are getting from it.

Content Performance Reports

Whole Sales Lifecycle

If you can’t analyse across each stage of the sales cycle, you can’t answer crucial questions.

  • If you don’t know which deals the content touched, you can’t measure revenue influenced and business impact.
  • If you don’t know the sales stage where content is used, you can’t tell whether you have good coverage for each step of the buyer’s journey.

Activity, Local Impact, Business Impact

Ultimately, you want to measure the business impact that your investments are having. “I spent $X building this case study; how much revenue did it generate?” But even so, intermediate metrics yield key insights by measuring the steps along the way.

Activity metrics help you diagnose why you aren’t getting the business impact you want. A particular piece of content might not drive value because nobody could find it, or because reps don’t think it is worthwhile, or because it is pitched to customers who ignore it. How you fix the problem is completely different, depending on what you find! So don’t dismiss activity metrics — they don’t tell the whole story, but they do tell an important part of it.

Measuring local impact is often more precise. Let’s say that during a five-month sales cycle, you send the customer a particular piece of content. How important was it in closing the deal? It depends — there are many factors that affect whether a deal closes and how long it takes. The impact of one piece of content is much higher, however, on the particular sales stage when it is sent. A great pitch deck won’t close a deal by itself, but it can have a clearly measurable effect on moving that deal to the next stage of the sales cycle. And a bad one, especially in the hands of an inexperienced rep, can torpedo the deal quickly. So it’s highly valuable to measure and optimise content within a sales stage as well as across the whole sales cycle.

Content Evolves

During the early stages of the buyer’s lifecycle, marketers connect with audiences directly using content over which they have complete control. But in the later stages, when the sales team enters the picture, that “perfect control” is lost. As content filters through the organisation, it moves from central marketing through field marketers and sellers, finally landing in the hands of customers. Along the way, the content changes and evolves as it is remixed, reordered, and recombined. In many organisations, as much as 80% of the content shown to customers has been modified — it is customised by the field for the needs of each selling situation. The analytics system must be able to track the content, regardless of how it has evolved. By detecting the relationships between pieces of content, the system reveals its true performance and business impact. Otherwise, most of the data can’t be associated with the original content and simply disappears from view.

Optimising Your Business Step-by-Step

After you have put a closed-loop sales enablement solution into place, you can begin to take advantage of its features to enhance your engagement with customers. We have found that companies typically start with the basics, and then over time move to applying data-driven techniques to their entire sales process in order to analyse and optimise it.

Here is a typical path that companies follow in applying the analytics capabilities of the system.

Sales Enablement Maturity Phase

The first step is to move to the Managed maturity phase, using the first two sets of reports. Manage Assets can be done immediately, even before any sellers have begun using the system. In the process of putting the sales content into the system, companies are able to see where they stand. Content Freshness shows which content is old and should be pruned or updated. Content Coverage reveals areas where content is missing or very limited.

As the sellers begin to use the solution and data is available for analysis, the next step is to Track Activity. These reports will show which content is actually being used by the sales team internally and what is being pitched to customers. Even after the sellers have been using the system for a relatively short time, the reports will begin to show interesting patterns. The results are often quite surprising—in most companies, a very small percentage of the content is used heavily and most of it is simply ignored.

Now the company has its content properly organised and has begun filling in its most serious content gaps, and the people who are creating content actually know what’s being used. So, it is time to move to the next maturity phase and begin turning the company into a data-driven organisation. The Content Engagement report will show how content actually performs when it is put in front of customers. That data drives recommendations to sellers on what content will help them get deals closed, and it is used by the marketing team to prioritise their content investments. Content Comparison will show how the sellers are modifying and repackaging the original content, revealing best practices and areas that need attention.

The last phase is to move to the Optimised maturity phase. The key reports here are all focused on Business Impact. Based on measuring the impact of content on business results, marketers can determine the ROI of their content investments and move to a model where that guides their investments.

The Purpose of Analysis is to Drive Action

Graphs and tables are a means to the end — the goal is to improve engagement with the customer as a way to drive increased revenue and shorten the deal cycle. Each of the eight key reports answers an important business question, identifying key issues and opportunities so that you know how to act.

Sales Enablement Analytics Action Plan

Engagement is the lifeblood of the sales conversation—an indifferent customer is a deal waiting to fail. And in our hyper-informed age, you can’t deeply engage your customer without content. Use these reports to analyse and optimise your engagement with customers throughout their buyer’s journey.

For a deeper exploration of Sales Enablement Content Performance, please refer to the Definitive Guide to Sales Content Performance.

Solution Design

Sales Enablement Solution Design

When you are developing your solution, the Design stage is particularly important—it lays the foundation for the project. We have found that these four steps reliably lead to a solid design:

Sales Enablement Solution Design Best Practices

1. Identify Stakeholders

We find it helpful to think about solution users in terms of their role:

Sales Enablement Stakeholders

Once you have identified the key users of the system, it is helpful to put that into a team map that lists the teams involved. We prioritise the teams, based on how much of a focus their needs will be for this deployment. We also choose a representative for each team who can speak on its behalf. These representatives are involved in the development of the solution, either as a core member of the team or as a resource to be consulted during planning, design, and validation.

Here is an example of a team map for a company that has global subsidiaries:

Sales Enablement Stakeholders

2. Map Your  Content

Next, think about the content that you want to capture.

As we mentioned in a previous section, it is important to focus initially on the content that is most important, rather than trying to capture every possible thing a seller might need. While you may use this opportunity to do some clean-up, we strongly recommend that you not try to make all the content perfect before you launch — it’s easy to get bogged down in multiple open-ended content initiatives. Anyone who has remodeled a house will be familiar with the dangerous phrase, “Well, as long as we’re doing that, we might as well…” Giving the sales team a well-organised way to find the content you already have is a typically a big step forward in making them more effective! You will keep improving it forever — that is a job that is never done.

We capture the result of this exercise in a content map. Here is a typical example, where the company has decided that it will divide the sales information into eight groups. For each type of content, we show who is responsible for publishing it. The publisher might be a team (for something like product marketing), or it might be a single person. Where the owner is a team, we’ve chosen one person who is on point to represent it. Choosing a single representative is best, if possible—then you can make sure that you have somebody available who deeply understands each key type of content, but keeps the number of people involved to a manageable number.

Sales Enablement Content Mapping

There are many ways to divide your content into top-level groups. Here are some rules of thumb that we have found very useful in finding the best solution:

For most companies, it’s reasonable to aim for something like 8-12 top level categories that apply to the mainstream user.

That’s enough to keep things organised, but not so many that reps and publishers have to waste time figuring out where to look. A user can quickly scan the whole list to find the right place to go.

Get it right for the mainline sellers, then take care of the more specialised teams.

Often, there will also be specialised areas of content for particular roles, or particular regions, or the like. First make sure that your design works well for the typical seller, then start addressing those more specific requirements.

It is often best to put specialised content in separate areas, especially if it might be confusing to the people who aren’t interested in it. The people who need it will know what they are looking for, and the mainline sellers won’t see it mixed in with everything else.

Groups should be intuitively obvious for reps and publishers to understand.

You don’t want people to guess where something should go—try to make it as obvious and unambiguous as possible.

At the top level, don’t pick things that change often. For example, the marketing themes for the current fiscal year are not a good choice. They change every year, and often it isn’t obvious at all which of them a particular piece of content goes in. Is this pitch deck more about “Ultimate Flexibility” or “Industry-Leading Performance”? Or neither? Or both? You might choose to assign items to themes within a particular group—that can be very useful—but don’t use groupings at the top level that aren’t as drop-dead obvious as you can possibly make them.

The great majority of your content should fit obviously into a single top-level category. As we will see in the next section, this is why using the stages of your sales cycle as the organisational model is usually a bad idea.

Ideally, there is a small set of publishers for each group.

It’s easy to have different people working on different groups of content, but if you have a lot of people all managing the same group, that can cause problems. A small group of people making the key decisions about a particular set of content will almost always yield a better result.

Consider breaking out content that has important and unique ways of being organised.

For example, take case studies. There are often a large number of them, and in many companies they are organised quite carefully and in different ways to most content. In particular, they might be organised by vertical industry, by region where the customer is located, by language, by product, by scenario, and so forth.

A rep who needs a case study knows exactly what they are looking for and wants to be able to browse quickly, using whichever dimension(s) are most applicable to their customer. An enterprise in Europe might insist on seeing a case study from one of a few countries they feel are similar to their own. A manufacturing company might want a case study from their own industry. Somebody who is looking at your Cloud PBX product doesn’t care about your success in deploying some other product.

3. Target the Buyer’s Journey

Once you have the key types of content figured out, we strongly recommend that you map them to the buyer’s journey. The term “buyer’s journey” is meant to capture the set of experiences that a buyer goes through. It begins when they first learn about your company and its products. Over time, they engage with you and become a customer. Then there is an ongoing relationship where they hopefully renew their contract/subscription and/or purchase additional products. This journey is often described using a model like the sales funnel, as discussed earlier.

Sales enablement focuses on the second half of the sales cycle, when the sales team is involved. Many companies have developed a formal description of the buyer’s journey during this phase by defining the stages of an opportunity in their CRM system. For example, here is a typical set of stages:

Sales Funnel

Note that these sales stages are an imperfect approximation of the buyer’s journey. In most cases, it would be more accurate to describe them as the seller’s journey. The focus in the CRM tool is typically on tracking the progress of each deal and forecasting the likelihood that it will close. It often doesn’t perfectly reflect the buyer’s point of view, but it’s a good starting point. It does show the stages through which deals typically go, and in many organisations it is well-defined and consistently tracked.

Use Stages for Targeting Content, Not Organising It

We cautioned earlier that the sales stages are typically not a good way to organise content at the top level because the mapping is too ambiguous. We can see that when we consider what items might used by a rep at each stage of a deal. For example, consider the set of case studies that the company has created. For the buyer, case studies serve a variety of different purposes — they provide credibility that you solve real problems for real companies, they showcase use cases that your product addresses, and they highlight the business value that buyers will receive.

Buyers may ask for case studies throughout the sales cycle. They might want to see one quite early in the conversation, to see whether you are a credible vendor they should bother with—it might even come up during the Lead or Qualify stages. During Discovery, where your goal is to figure out if your product is a good solution for their problems, they might want to see a case study to get ideas about what you can do for them. The Prove stage is the one where customers are “officially” supposed to want to see case studies. But it’s possible that they want one during Negotiate, to convince some higher up to spend the money on your product. And after you Close a deal, you might use one (if you won) to convince the customer to expand their use of your product and get more value, or (if you lost) to try to get things restarted.

So if you were trying to organise content by stage, you could make an argument that you should put case studies in every stage. That’s a bit of an extreme, but it is very common for content to be useful during multiple stages, making sales stage a poor way to divide up the content at the top level. Publishers would always be guessing which stage to put things into, and reps wouldn’t know where to look.

However, it is extremely useful to target content by sales stage. The goal is to recommend the content that is most likely to be useful for a particular deal. You will never be able to predict everything that might be useful, and shouldn’t try. That’s why the system needs to have great support for searching and browsing — customers ask about all sorts of different topics, and they don’t organise their requests neatly into an “appropriate” sales stage. But there is generally a small set of content that is very likely to be relevant to any particular deal, and the goal of targeting is to put those items at the seller’s fingertips.

The sales stage is often the best indicator as to which content the rep is most likely to need. If they are in the Prove stage, customer evidence from similar deals is going to be very likely to come up. But sales stage alone is not the only consideration. It might depend on which industry the customer is in — you might have a pitch deck that is customised for the industries you most commonly target. Or it might vary by region — the deck that the team in Spain uses to pitch your product is probably not the same one that is used in the US. The right content can also vary by role of the user. An account manager who is supporting and growing the account of an existing customer probably uses different content than the account executive pitching a new customer who has never heard of your company before.

Depending on your business, targeting might be based on a wide range of characteristics of the deal, the customer, or the seller. So how do you decide what to show the rep?

The “Rule of 7”

When companies first think about targeting content, they sometimes start out with very ambitious goals. They envision themselves as a star quarterback dropping the ball right into the outstretched hands of the receiver on the way to a touchdown, delivering exactly the right content with pinpoint accuracy. This may be possible if you have an extremely structured sales process that is highly repeatable and controlled, but in most cases it is better to start with the basics and refine it over time.

We like to use an exercise we call the “rule of 7”. To get started, choose a particular seller and a particular deal. For example, you might pick an account executive in the Western US region who is pitching a telecom company on your Cloud PBX product. The deal is currently in the Discovery stage. You are only allowed to know as much about the deal as will reliably be captured in your CRM system, since that is what the sales enablement solution is going to know. Now the exercise is to come up with the set of content that the seller should have right in front of them for this deal, and force yourself to have no more than seven items. An item can either be a specific document, or it can be a link to a collection of items that are filtered down to the ones most likely to be relevant.

For this example, we’ll be even more disciplined and restrict ourselves to just six:

Sales Enablement Content Targeting

Once you have done a few examples like this, you are ready to create your general targeting plan. It describes the content that will be targeted for any deal in the pipeline, based on various characteristics. Here is an example showing part of a targeting plan:

Sales Enablement Content Targeting

As discussed earlier, we recommend that you start with the basics. You can always refine and extend your targeting once you have it up and running, and you can use analytics to see which of your recommended items actually get used successfully by the field in practice.

Targeted content is much more likely to get used if it appears in your CRM system as part of the opportunity. The rep will always have instant access to the content they are most likely to need, customised for the deal they are working on. The platform can also use data science to score every piece of targeted content and suggest additional items, based on what has been working for the sales team in similar deals.

4. Catalogue Existing Resources

The last step is to make sure you understand the systems that your company already has in place and that are relevant to your sales enablement solution.

Here are some common examples:

Content storage

Companies often have a wide range of systems where content is currently stored. They might be using cloud file systems like Dropbox, Box, and the like. They may have custom web sites, or SharePoint sites. Content may also be stored in the CRM system (such as the Content tab in Salesforce) or it may be linked inside of various social networks, like Chatter or Yammer.

You might integrate these systems with your solution—cloud file systems and social networks are natural partners for your publishing platform. Some of the content stores may be retired after you deploy.


The company may use Active Directory internally and/or a federated identity provider like Okta to give their employees access to internal or external systems. Single sign-on is a convenient way to reduce the cost of managing the solution.

CRM systems

Most companies use a CRM system (like to track their sales opportunities. Your sales enablement system can integrate closely with it to enhance rep effectiveness and measure the business impact of content and readiness investments.

HR and Learning Management systems

Training and performance may be managed through specialised systems (like SuccessFactors and WorkDay). You may choose to integrate them with other parts of your solution.

Web conferencing

Systems like WebEx, GotoMeeting, or allow sellers to present material to customers remotely over the Internet. Your sales enablement solution may also have this technology built-in. Web conferencing allows your reps to reach out to customers for presentations and demos, wherever they are.

Deployment Guide

Sales Enablement Deployment Guide

There is a tremendous amount of value that you can unlock through sales enablement. But it is important to keep in mind that you don’t have to “boil the ocean” right away. The most successful deployment projects that we have seen deliver value quickly by starting with the most painful problems that hold back your sales efforts. Once the system is up and working successfully, it is much easier to extend it into new areas and to support additional roles in the company.

Deployment Lifecycle

We have found it useful to break up the deployment into three phases.

Sales Enablement Deployment Lifecycle


During the develop phase, the project is planned, designed, and implemented. There are two common temptations that often cause problems during development.

Scope creep

It is very tempting to keep expanding the project as you go. While you build out the solution, you almost always discover new content that you hadn’t originally thought about, and new roles in the organisation that you could address if you add “just a little bit more” content.

Waiting for content initiatives

Virtually every company we have worked with had some set of initiatives underway to improve their existing content or develop some great new material that the sales team needs. “Maybe we should just wait until <content initiative> is done…then the content will be so much better!”

We strongly encourage companies not to wait and not to let the scope grow much beyond the original focus. There will always be active or contemplated initiatives to improve content. Those efforts are easier and much more likely to be effective with a solid platform in place. It is far easier to add content to a working and successful solution that is already deployed. Choose the most important content to focus on and get started with what you have. Most companies will use the process of collecting and organising their content as a good opportunity to do some clean-up and purging, which is a positive side effect of pulling it together. But try not to wait until some new class of content is developed — in our experience, that frequently takes much longer than anticipated.


The launch phase makes the solution available to the user community. In the enthusiasm to roll out a solution, companies frequently want to skimp on validation and training. This makes the solution less effective than it should be, and it hurts adoption. Often, the way that people in corporate headquarters think about organising information isn’t exactly the way that people in the field really use it. Getting experts in the target community as trial users will find those problems so they can be fixed before launch. And if people don’t get any training, adoption will be slowed down and users will take longer to become adept and efficient.


After launch, the company moves into the operate phase. By using the analytics system built into the platform, they can manage the content that is available on the platform and begin to move the company into a data-driven approach to optimising their sales cycle. We find that companies are most successful when they first use the platform to manage their content more effectively. Next they begin to analyse different areas of usage and performance. Then they optimise their content and their investments, using the insights from the analysis.

Building on Initial Success

As we have said above, we strongly recommend that companies start by focusing on the most important problem with the biggest business impact. For example, it is common for growing organisations to have a major content problem — sellers can’t find the content they need, and there is redundant and out-of-date material scattered across many locations. So the focus for the initial deployment might be the content that is needed by mainstream sellers to pitch and close new customers.

Once the basic solution is deployed and successfully addressing that most urgent need, it can be expanded to enhance the solution’s value:

Project Length

The time required to launch a solution depends heavily on the scope and on the amount of time that companies can dedicate to it. A simple rollout with basic content and a single sales team can be done in a few weeks. Deploying a solution for a multi-national enterprise with thousands of items and a heavily matrixed sales organisation is more likely to take a few months to complete.

Maturity Model

Sales Enablement Maturity Model

The goal of sales enablement is to optimise your sales process, making your reps more effective and efficient. Companies won’t “fix” their sales with a one-time initiative—it happens through a series of stages, each of which yields tangible benefits. Every company will differ somewhat in the path that they follow, and the state of sales enablement can be uneven—perhaps a good on-boarding programme has been put in place, but content management is in disarray. However, we have found that there is a great deal of similarity in the stages that most companies pass through.

Below, we show the five stages that companies go through as they improve the effectiveness of their sales teams:

Sales Enablement Maturity Model

Stage 1: Ad-Hoc

This stage is common in young, high-growth companies. The organisation is struggling to provide sales reps with what they need, and only the most important content is available. There isn’t a detailed content plan—marketing is scrambling to produce the most badly needed information as soon as possible. Rep on-boarding is sink or swim.

Sales Enablement ToolsTools Measure Sales Enablement Business ImpactBusiness Impact Measure Sales Enablement EffectivenessMeasurement
Content is typically stored in a shared file system (like Box) or perhaps in a web site built on a technology like SharePoint. It may just be sent around in email. The focus is on booting up the go-to-market process. Key content is not available, hurting rep effectiveness and forcing them to spend a lot of time creating content to move deals forward. Nobody is paying attention to anything except “what’s on fire”. There aren’t any content metrics that measure usage or performance yet.

Stage 2: Reactive

This is the stage where many companies get stuck. The team is working hard to ensure that the right content is available, but poor tool support makes that difficult. There is often a lot of content, though there are important gaps. Content has piled up and is scattered across multiple locations, and much of it is redundant or out of date. Some training is available, but it isn’t well structured or tracked.

Sales Enablement ToolsTools Measure Sales Enablement Business ImpactBusiness Impact Measure Sales Enablement EffectivenessMeasurement
There are multiple content stores, often owned by different teams. These might be a set of files in a system like Box or a site that somebody built in SharePoint. There might be an “official” company sales portal that has been custom built, but nobody likes it so people try to avoid using it much. Reps reach out for help finding what they need through email or perhaps a social networking system like Yammer or Chatter. Reps often don’t have the right content for engaging with customers, so deals are lost or stalled. Customers are not getting accurate and up to date information, leading to the wrong expectations and future dissatisfaction. Reps waste time looking for what they need and recreating content that already exists. Most “customer- facing” marketing content never reaches a customer. While the CRM system accurately measures sales, the use of content is still largely invisible. There may be basic usage statistics from some of the content stores – for example, web sites that report how many times a particular item was viewed.

Stage 3: Managed

At this stage, an effective set of sales enablement tools is in place and the company has the basics covered. There is a well-defined location for content, and it has been mapped to the sales stages of the buyer’s journey so it is organised in a way that reps can understand. There is a content plan and the company is executing against it; older items are regularly updated or pruned. Reps go through a planned on-boarding and training process.

Sales Enablement ToolsTools Measure Sales Enablement Business ImpactBusiness Impact Measure Sales Enablement EffectivenessMeasurement
There is a sales enablement solution in place. It provides a well-known “place of truth” for key content. It has effective search functionality. Content is targeted per opportunity in the CRM system. Reps have the content they need to engage, leading to higher deal close rates and higher velocity of conversion between sales stages. Reps are more effective at engaging with customers and able to spend more of their time selling. The system measures solution adoption and health.

Stage 4: Data-Driven

Analytics are now available for usage and performance of content across the sales cycle, creating a closed loop from marketing to sales to the customer. Content teams are using the information to optimise the content that is being shared with the reps and to optimise their investments. Unused and poorly performing content is removed or improved.

Sales Enablement ToolsTools Measure Sales Enablement Business ImpactBusiness Impact Measure Sales Enablement EffectivenessMeasurement
The business has created reports to measure the core aspects of content performance and seller readiness. Targeted content in the CRM system is scored based on its performance. Proven content engages customers effectively, yielding higher close rates and faster stage conversion. Marketing investments are focused on content that performs. Content coverage, freshness, awareness, usage, and engagement are tracked. Seller readiness and training effectiveness is measured against attainment.

Stage 5: Optimised

Performance is evaluated at every stage of content lifecycle. Best practices from the field are identified and used to improve content quality. Content is recommended based on performance in related deals. Measurement of business impact guides investment and content refinement.

Sales Enablement ToolsTools Measure Sales Enablement Business ImpactBusiness Impact Measure Sales Enablement EffectivenessMeasurement
The business captures best practices from the field by identifying how content is being modified and repackaged. There are reports that measure the business impact of content. Reps use content optimised to be effective for each kind of deal, improving close rates. Marketing investments are ROI driven. Content comparison shows how content is modified and remixed. Business impact metrics identify influenced revenue, deal conversion and velocity uplift, and ROI.

Platform Capabilities

Sales Enablement Platform Capabilities

Closed loop sales enablement tools and software offer a variety of capabilities to optimise the way that your sales team engages with customers and closes deals. All of them are designed to arm your reps with the resources and knowledge they need, so they are prepared to make the most of every interaction with a potential buyer.

Sales Enablement Platform Capabilities

Content Publishing and Management

Manage all the content that the sales team needs in order to effectively engage with customers, organised in a way that is intuitive for sellers to find it.

Publish a wide range of content The system must support all the different kinds of information that reps need, including document, presentations, images, videos, links to web pages, and so forth.
Organise items into the most appropriate categories For example, a rep might want to look for case studies that are in a particular region (France), a particular language (Chinese), or a particular vertical (Telecommunication). If they are looking at analyst reports, they might want to look at items from a particular analyst (Gartner) or aimed at a particular audience (Finance). Every piece of content should be organised in the way that is most natural for it, so that reps can find it quickly when they need it.
Easily change how content is organised New products are always being released, new competitors come along, new types of content emerge—the publishing system can’t require a ticket to be filed against IT every time something changes. Publishers need to be able to instantly update the way that the system organises information, or it will quickly become stale and out of date.
Update items with new versions When content is updated, publishers can replace older versions. All references to the older content should be updated, so that users are always working with the latest version.
Curate relevant news items Automatically pull in items from the Web, based on the company’s business. For example, market news, competitor news, and customer news. The items that are pulled in should be based on the ones have proven to be of interest to users within the organisation.
Support multiple editors Content is often managed by different teams within the organisation. And even within a single area of content, like product marketing, managing it might be a responsibility that is shared by a number of people. The system should support different editing models, ensuring that the right set of people is able to control how each kind of information is published.

Connect with Sellers

Enable sales teams to find the most relevant content through searching, browsing, and recommendations. Allow field organisations to customise content so that it is tailored to the needs of their team.

Search that works At home, the first place that most people go to find something on the Internet is the search box—almost anything they type will yield something useful. At work, that is rarely the case today. This is one of the most crucial pieces of any sales enablement solution—sellers need to be able to find what they need, instantly. In addition to indexing all the text in an item, modern search algorithms apply data science to rank items based on usage and relevance to the user.
Let reps collect their most-used content Depending on their role, sellers will typically use a small set of content many times. They might send out a particular pitch deck dozens of times a day, for example. The system should make it easy for them to assemble that content and organise it in the way that makes the most sense to them, while still making sure that it is updated when new versions come out. Otherwise reps will just keep what they most need on a laptop, where its use is invisible and it will soon be out of date.
Allow field teams to manage custom content Specialised teams often have unique content, such as a deck on local industry conditions. They may translate standard marketing material into other languages. If they target a particular segment, like global partners, they might need content that only applies to those organisations. It must be easy for field teams to create their own collections, mixing together material from corporate headquarters with their own specialised and customised items.
Allow reps to customise content It is often necessary for reps to create unique content for a particular customer. It might be as simple as adding a customer’s name and logo to a deck. It could involve assembling a deck for a particular conversation by choosing from a library of pre-built slides. Or, the rep might create an entirely new piece of content just for that customer. It should be easy for them to add that content to the system so that it can be pitched and its use and performance is tracked.

CRM Targeting

Within the CRM system that they use, show sellers the content that is most likely to be effective. Customise the items that they see, based on the characteristics of the opportunity, account, or person they are viewing.

Recommendations inside CRM system In many companies, sellers live within their CRM system (like When they look at an opportunity, contact, or lead, the content they are most likely to need should be right in front of them, without their having to go hunt for it.
Contextual targeting The content that a rep needs to move a deal forward will vary based on the stage of the sales cycle and the characteristics of the opportunity. You should be able to choose content based on virtually any characteristic of the deal. For example, you might show demand gen content when you are at an early sales stage. Later, you might choose case studies based on the region and the vertical the customer is in. Throughout the cycle, you want to present the content that is most relevant to that buyer’s journey.
Content scoring Based on how often content has been used by other reps, and how it has performed with customers, provide a score to help reps identify the most effective content at that point in the deal.

Cloud and Device Integration

Integrate with the services that the company uses and the devices that users rely on.

Cloud-based storage Many companies use cloud-based storage systems (like Box) to support internal collaboration. It should be possible to publish items from those storage systems and then update them with a single operation when a new version is available.
Cloud-based identity If a company is using a single-sign on solution (like Okta), the content system should integrate with it to streamline account management for publishers and reps alike.
Online mobile Support phones and tablets that are connected to the Internet
Offline mobile Support phones and tablets that are not connected to the Internet

Email Pitching

Send content to customers via email, and know if, when, and how they engage with it.

Rich text email Reps can compose messages in the system using an email editor that supports the standard formatting tools (bullets, different fonts, web links, and so forth).
Email templates Most reps frequently send out variations on a few standard email messages they or the company have created. The system should support templates, so that these common messages and the associated content can be set up ahead of time. Reps can send them out, updating them as needed for a particular customer.
Email client integration The company or a rep may prefer to use an existing email system, rather than sending the mail through a separate system. They should be able to paste in links to pitched content or access the sales enablement solution directly from their email client.
Activity notifications When a customer opens the email, views an item, or downloads it, the rep should be notified immediately so they can follow up as appropriate.
CRM integration If the rep wishes, all pitch activity should be automatically attached to the appropriate record(s) in the CRM system, so that system contains all the information relevant to a particular deal.

Live Pitching

Present to customers in person or over the Internet.

Pitch content When reps only need to pitch a piece of content such as a deck or document, they should be able to do so by giving the prospect a URL—viewers should not need to download anything, to minimise sales friction.
Window and screen sharing If the rep needs to do a demo to the customer, either from the browser or from an application running on their machine, they need to be able to share that easily. It might be directly handled by the pitching system, or the company might prefer to integrate with a web conferencing solution (like
Pitch archive and recording The system should record the information that was presented during the pitch, so that reps can remind themselves in the future exactly what they presented. The archive should include a link to the exact content that was presented as well as optionally allowing the rep to record the session.

Creation and Discovery

Create training material and help reps find what they need.

Authoring tool support There are a variety of different tools available to help organisations build training material in a variety of forms and media. The system imports the training and allows users to find and use it.
Search The user can search for the training they need based on title, description, and content. The results are ranked by popularity and/or effectiveness.
Browse The user can look for relevant training material by browsing through what’s available, using a variety of criteria to find what they need.
Recommendations The system uses a variety of criteria (such as the user’s role, seniority, current activities, and previous training they have taken) to recommend training that they may find useful and that has proven to effectively improve results for users in similar roles.

Flexible Learning Environment

Make the training experience as effective and convenient as possible.

Instructor-led and self-paced courses Courses can be led by an instructor or the student can take them at their own time and pace. In either case, students can ask questions and have discussions with the instructor and with each other.
Communication tools and social learning The students and teachers can communicate through a variety of social tools that support instant messaging, virtual classrooms, and threaded discussion forums.
Multimedia support The courses can include images, audio, and video.
Mobile and offline learning To enable learning in any context, course material is available on devices. It can be accessed while connected to the network and also when offline.

Tracking and Administration

Ensure that people are getting the training that they need and that they are learning the material.

Testing and grading Provide online testing with a variety of grading models (pass/fail, A/B/C/D/F, other). Enable trainers and managers to add assessments from observation.
Certification management Support certification programmes for users who prove their expertise in an area. This may be focused on employees, or it may expand to include others in the community who work with the company’s products.
Compliance Allow the company to mandate that certain forms of training be required, and monitor completion/pass rates.


Connect with other systems that you use to support your employees and your sales process.

HR Performance systems Integrate with systems that are used by the company to manage their employees and track their performance and compensation.
Customer Relationship Management (CRM) systems Most companies use a system to track their sales activities and results. They often define the roles of each person and show the sales activities that they are engaged in, making them an important source of information for targeted training and for measuring the business impact of readiness investments.

Platform Capabilities 

Fundamental requirements for creating insightful reports.

Segmentation One of the key ways that companies need to analyse activity and performance is by segmenting the data. There are many kinds of segmentation that are important—by time period (previous quarter), by user community (enterprise/SMB, Americas/Europe/Asia), by content type (case studies/brochures) and so forth. The analytics system must allow data to be filtered and grouped as needed.
Content similarity analysis As content moves from central teams like corporate marketing through the field to the customer, it is often modified and repackaged. In some companies, up to 80% of the content that customers see has been customised. The analytics system will lose all that usage and performance data unless it is able to track how content is modified throughout the organisation.

Solution Health

Monitor how much usage your sales enablement platform is getting across the organisation.

Adoption Track how many people have signed up and used the solution at least once.
Breadth The number of people who used the system at least once during a particular time period.
Depth How many people have used the system at some level of depth. There are various ways to measure depth, such as how many reps have pitched to a customer through it, or how many pitches have generated customer engagement, or usage above a threshold of time, or more than a certain number of item views.
User activity Identify “power users” in each user persona, and who is not using the product. Know who has heavy influence in the organisation, who is your best source for feedback, and which communities need to be targeted for outreach and education. Also find out search terms that are being used and whether those searches are successfully yielding results.

Content Performance Reports

Measure the usage and effectiveness of your content.

Content coverage Assess whether all the key types of content that sellers need are available.
Content freshness Find out whether the content is up to date by looking at content age and turnover.
Content awareness Determine whether sellers have looked at different kinds of content, to make sure that they are aware that it exists.
Content usage Track how frequently reps have viewed, downloaded, and bookmarked content.
Pitch activity See the pitches that reps have made to customers and the content that they pitched.
Content comparison Look at all the content being used across the company to see how it is being modified and repackaged in the field.
Content engagement See the pitched content that has engaged customers, and which parts of the information were of most and least interest.
Business impact How has the content influenced revenue, affected deal and stage conversion and velocity, and generated ROI?

Sales Readiness Reports

Measure the usage and effectiveness of your training.

Training rates The number of people who took the training that is offered and how many completed each course.
Training coverage Assess whether all the key types of training that sellers need are available.
Training satisfaction Track how satisfied the sellers were with the training courses that they took.
Test performance Measure how well the sellers learned the material that was covered in the courses they took.
Certification tracking See how many people attempted and achieved certification in different competencies.
Completion tracking Track whether sellers are completing the mandatory training sessions.
Turnover impact Measure the effect of training on sales team turnover.
Ramp time Measure the effect of training on the time it takes a seller to ramp up and become effective.
Revenue Measure the effect of training on the revenue attainment of the sellers who take it.
Training ROI Measure the overall return on training investments, based on the cost of developing and delivering the course and the opportunity cost to attend it.