The Ultimate Guide to


Sales 

Enablement

The Complete Guide To Building A Successful 


Sales Enablement Program
 The Ultimate Guide to Sales Enablement

About Crayon:

Crayon provides software-driven market intelligence to deliver real-time, actionable insights for

businesses. Check out Crayon’s competitive intelligence platform to track 100+ different signals about
your competitors to get a complete picture of their movements.
Request a Demo of Crayon

About Highspot:

Highspot gives businesses a powerful competitive advantage to have more effective buyer 

conversations and achieve revenue goals. Highspot's AI-powered search, analytics, in-context training,
guided selling, and 50+ technology integrations deliver modern sales enablement that sales reps and
marketers love.

www.highspot.com

Questions?
Call (857) 990-4800
Email sales@crayon.co

© 2019 Crayon

www.crayon.co

i
1
Getting Started
Building and growing a business successfully involves many moving parts. Having a strong
and effective sales team is the key to achieving that success. You can build an incredible
product, have the best customer service, and attract a wide audience, but if you don’t have
an effective sales team, you won’t be able to capture new business. How do you ensure
your sales team is successful? Enter Sales Enablement.

Sales Enablement is an integral part of every successful sales team. Sales Enablement sets
your sales team up for success with the help of tools, resources, and up-to-date competitive
intelligence information to help them be more productive.

So, how can you set your sales team up for success with a sales enablement strategy? That’s
what this guide will cover. We’re going to walk you through the Sales Enablement basics, all
of the essential trainings and materials you’ll need, and finally, the analyses that will help you
measure success, help your team iterate on their processes, and bring in more revenue for
your organization.

Let’s get started!

3
 Table of Contents

Getting Started 2

What Exactly is Sales Enablement? 5

Sales Content for Your Reps and Your Audience 8

Great Content Starts with Sales and Marketing Alignment 14

How to Create Content Sellers Will Love 19

Best Practices for Content that Fuels Revenue 22

Training Your Team for Success 
 25

Teaching Your Team to Talk the Talk 28

Putting Your Knowledge to the Test 32

Measuring Your Sales Enablement Efforts 35

Tying it All Together 40

4
2
What Exactly is
Sales Enablement?
Sales enablement is the process of arming your sales team with the right tools, resources,
and up-to-date intelligence so that they can do their job more efficiently, and win more deals.
Sales enablement is a critical role within any organization with a sales team. Ensuring that
your sales team has the skills and materials they need to win more competitive deals is 

invaluable. Sales enablement materials can include tools, training resources, collateral, and
follow-up materials.

There are three subjects of sales enablement that your sales team should know inside and
out: Sales Skills, Product and Company, and Market and Competitors. Sales skills include 

capabilities such as managing a discovery call and facilitating a demo.

Having an understanding of your product and company means that your sales team would
know every detail about product functionality and use cases. Having market and competitive
knowledge means your sales reps knowing how you stack up against the competition, so
that they can effectively battle competitive conversations.

Having a strong sales enablement strategy in place is extremely powerful. By arming your
sales team with the proper resources and training, your sales team will be stronger than
ever.

Your Sales Team Will Be Ready to Tackle The

Tough Questions

When anyone is buying a product, they more than likely are weighing a couple
of options. With the help of sales enablement, your sales team will be ready to
go head-to-head with competitors, answer the tough questions, and position
your product or solution as the best.

6
Your Sales Team Will Build Trusting 

Relationships with Prospects

The foundation of a strong relationship is trust. Prospects will make the decision
to buy from the person who earned their trust, so when salespeople are able to
answer all questions openly and honestly, without trash-talking the competition, 

and put the customers’ needs first, they will build a strong rapport with 

prospects. 


Your Sales Team Will Win More Deals

Trainings, certifications, scripts, and utilizing sales enablement materials are all
small pieces of the bigger sales enablement picture. But, with the help of these
many pieces of sales enablement, your team will be able to win more deals.

Now that you know the basics of sales enablement, let’s dive in!

7
3
Sales Content for
Your Reps and Your
Audience
An integral component of effective sales enablement material is strong content. Your sales
enablement materials can be influenced from all roles on your marketing team. Content 

marketing, which can generate three times as many leads as traditional marketing, is a 

powerful tool in a marketer’s arsenal, and pairing content marketing with sales takes it to the
next level. Results improve, leads convert, your data is supercharged — and your business
grows.

One thing that will help your sales team become experts on not only your product, but your
competitive landscape, and in turn close more deals, is sales content. Sales content can be
valuable pieces of collateral that can assist your sales representatives every step of the way,
from prospecting, to giving a demo, to tackling a competitor, and finally closing the deal.

Not only is it important to provide your sales team with this valuable content, but it’s 

important to know how to align the content with your target market, and create content that
your sales team actually enjoys using. Let’s break down the different types of sales content
and strategies for successful sales content. 




Internal Sales Content

Internal sales content is content that will come in handy when your sales team is 

communicating with prospects, but will not actually be shared with those potential buyers.
These can help your team facilitate successful conversations that reflect your brand, position
your company as the best solution, and tackle competitive deals. 


Battlecards
Competitor battlecards are one of the more popular sales enablement materials businesses
create today. Competitor battlecards provide an overview of a specific competitor’s 

company, products, and services and provide guidelines on how to win a deal against that
competitor. The most effective battlecards are easy to consume, up-to-date with the latest
competitive intelligence, and tailored to the sales process.

9
Make sure that all data in your battlecards is up-to-date and validated beyond sales rumors
because misinformation about competitors is worse than a lack of information. It’s also 

extremely valuable if you store your battlecards in one centralized location, such as within
your CRM or sales enablement tool.



Pricing Calculator / Comparisons
Providing a quick reference or deep dive tool around pricing can help your sales team feel
comfortable addressing pricing conversations when they arise. If your pricing is simple, offer
a quick reference guide with best practices on how to talk about pricing and which 

packages are best for which types of customers. If your pricing is complicated, consider 

offering an interactive spreadsheet where they can reliably calculate correct pricing for each
sales situation.

Decide if this is truly an internal-only tool or if it can be shared externally, and make this very
clear with the sales team. You wouldn’t want the wrong pricing information to get into the
wrong hands and ruin a sale - or worse, many sales.



Win / Loss Data
Win / loss analysis can be incredibly helpful at a high level - how the business overall is 

winning and losing deals - but also on an individual level. Sharing back win / loss data, both
quantitative and qualitative, can help a sales rep get more perspective and awareness about
areas where they excel and those where they struggle. Quantitative win / loss data can be
drawn from a CRM system, and qualitative win / loss data can be drawn from prospect 

interviews and surveys. In either case, look for the trends and use those takeaways to inform
coaching plans.

Consider sharing win / loss trends in small group sessions to encourage discussion and 

sharing of ideas between sales reps. You will likely find that each person has their own
strengths and weaknesses, and they can be best equipped to provide effective ideas or
coaching to their peers. We’ll dive deeper into how to conduct a win / loss analysis in 

Chapter 9.

10
 External Sales Content

External sales content is content such as thought leadership, case studies, post-sales 

materials, and third-party research. These pieces of content may be used to assist a sales
rep, or it may be content that lives on your website, that helps your prospects through the
buyer’s journey. Let’s dive deeper into different types of external sales content. 



Presentations
An overview presentation is something that your sales team can use to introduce your 

company and solution to a prospect. This is likely to be one of the most used pieces of sales
enablement content you can create, since it would be used with every single sales 

opportunity. Beyond the initial overview deck, consider other steps in the sales process or
other detailed questions that can come up, and create presentations that address each 

common situation.

Modularize your sales presentations to make it easy for sales to find and customize the
slides they need. A master sales deck can do the trick here, or create separate 

presentations for each topic to make it easier to update and distribute.



Case Studies & Customer-Centric Content
Case studies, customer interviews, testimonials, and even online reviews are an incredible
asset to help sales win more deals. Whether written or video, feedback from your customers
goes a long way in telling the story of how and why your solution is the best.

Reuse and repurpose customer-centric content! One case study can turn into multiple
quotes to be used across your website, fodder for multiple social media posts, and can be
integrated into the many other types of assets mentioned here.

Thought Leadership Content

Thought leadership content in the form of blog posts, ebooks, videos, and more, are great
for sales to engage with customers both pre- and post-sale. Content about challenges your
prospects face, trends in the industry, and the company’s approach to innovation and solving

11
for the customer’s pain, are helpful at every stage of the buying process. First, this content
helps attract buyers to your company, then it can tee up an open and productive sales 

conversation, it can re-engage prospects who have become unresponsive, and finally, it can
build loyalty among your customer base.

Encourage your sales team to subscribe to your own blog. That way they’ll get all of the

latest content automatically, and it can serve as a reminder to share out the new articles
with relevant prospects and customers.


Product Deep-Dive Content

One-pagers on features and benefits, spec sheets, or even product pages on the website
can help fill the need for deep-dive product content. Particularly if you have a technical 

product or a large product suite or if you are in a commoditized industry, deep-dive product
content can be a key sales need. Help documentation may support this effort as well -
whether accessed just by the sales team to address questions or to expose to prospects 

before a sale.

Streamline the updating of this content as much as possible, since details are likely to
change frequently. Webpages are easier to keep updated than PDFs, and if the content is 

already being updated by a technical support team, piggyback on their efforts whenever 

possible.


Post-Sales Materials
Customers want to know that, after the sale, they will have a positive experience that 

delivers on the sales rep’s promises. It can be helpful, then, to offer visibility into the 

post-sales process in your sales enablement materials. You can detail the onboarding 

process, share worksheets or timelines that customers typically use, or even introduce 

prospects to their future account manager. Post-sales materials can help assure and excite
prospects while also helping set proper expectations.

12
Leverage your customer success team to figure out what details should be covered in these
materials - what questions often come up from new customers? What surprises them? What
gets them most excited? Those are great areas to highlight.



Third-Party Industry Research
Third-party content - industry research but also third-party blog content, news articles, etc. -
can fill a similar role to your own thought leadership and case studies. Specifically look for
content that validates your approach, your leadership, or the problem you’re solving in the
industry. Materials like this are great to leverage in follow up emails to prospects, initial 

prospecting emails to capture attention, or even sales conversations.

In addition to sharing the articles themselves, look for industry statistics that sales reps can
mention on the phone to provide third-party validation about industry trends.

13
4
Great Content Starts
with Sales and
Marketing Alignment
Marketing and sales teams may have different goals day-to-day, but they both work toward
the same overarching objective: grow the business. When marketers and sellers focus on
working toward that goal together, great things happen. Content marketing is one area
where marketers stand to benefit from sellers.

Here are a couple of ways sales and marketing, which includes product, customer, and
demand generation, among others, can align to create the best content possible.



Create More Precise Buyer Personas
Buyer personas are an essential part of defining a target market and deciding how best to
approach the said market. 74% of B2B marketers have said that they use sales team
feedback for target audience research.

Because the sales team is on the front line, they’re in the best possible position to assist in
nailing down your buyer personas. The sales team will be talking to prospects on the phone
every day and will, therefore, be in a position to take note of their objections and challenges,
as well as their greatest needs and problems. This puts them in a strong position to answer
key questions, such as:

• What are my buyers’ biggest problems?

• What would prevent my buyers from purchasing my product or service?

• What media do my buyers consume the most?

• What sources provide my buyers with information?

If you already have buyer personas, revisit them with the sales team. They may have key
information that your content marketing team has so far overlooked.






15
Provide Content Insights
The easiest way to increase buyer engagement with content is to create stronger content. It
sounds simple — and it’s even simpler when you invite the sales team to help you create it.
Because sellers are handling buyer objections every day, they’re in a very good position to
come up with content ideas and key messaging.

This proves especially useful if responding to the same objection over and over again. For
example, you could leverage their insights to create an informative section on your website
that addresses common objections. After all, who knows more about your buyers than your
sales team, who are engaging with them every day?



Align Sales and Marketing with the Buyer’s
Journey
The best sellers use tailored sales content — materials developed by marketing to support
the sales process — to engage buyers at the right time with the right information to close
deals faster. Today’s most effective content bears little resemblance to the jargon-heavy
brochures of years past. In fact, modern sales collateral pivots away from the vendor’s
perspective and instead incorporates insight from credible third parties. According to
Gartner, “content that features a third party telling or validating a story is inherently more
credible and trustworthy than the same story told by a vendor.”





Answer These Four Questions to Develop
Effective Sales Content
None of this is news for top-performing sales and marketing teams. But as buyers’
expectations evolve alongside rapid technology disruption in every industry, it may be
increasingly difficult for sales and marketing to consistently develop content that influences
revenue. The key to successful sales collateral is to map the content to your buyer’s needs
by asking these simple questions:

1. Who are we selling to?

16
 2. What questions do they need answered and when?

3. Who do they trust to answer these questions?

4. What content will most effectively answer their questions?



Build the Foundation for Sales Collateral
that Connects
Answering these questions will define the basics of your buyer personas. Let’s say your
company sells a modern application development automation platform, so software
developers and their managers are both target buyers. Here are the questions that matter::

1. What is their motivation?

2. What does their purchase process look like?

3. Who do they consider influencers?

4. What is their preferred communication style?

These insights are a critical part of developing sales content that connects with your buyers
and differentiates you from your competition.



Develop Sales Collateral that Maps to Your
Buyer’s Journey
Once you have a strong foundation of anecdotal and data-based intelligence, you can
confidently develop content that aligns to the buyer’s journey so your sales team can answer
your prospects’ questions with credible information that matches their current 

decision-making stage.

Regardless of the stage, it’s critical to map sales collateral to your prospects’ motivations at
any given time. SiriusDecisions found that 71% of sales leaders say that their sellers fail to
connect their solution to prospects’ needs. So, just as best practices and credible third-party

17
advice are influential early in the buyer’s journey, detailed case studies that align with the
prospect’s use case and demonstrate a clear return on investment will be critical in the
decision-making stage.

18
5
How to Create
Content Sellers
Will Love
Despite all of the effort that goes into creating content, an eye-opening 60 to 70% of 

marketing content sits unused. This means that a significant portion of the time and 

resources going into content creation is really just going to waste.



How can you ensure that sellers will use marketing content?


Know What Your Sales Team Needs
Reps need to be able to anticipate and overcome obstacles that buyers will inevitably 

present — and marketing content is a key part of achieving that. In fact, 95% of B2B deals
are influenced by content.

But how does the marketing team ensure that they’re creating the right content for sellers?
The answer is simple: ask the reps! With their experience interacting with buyers, sellers will
have a clear idea of what works. Use their feedback to map existing assets to the buyer’s
journey and identify content gaps you may need to fill.

Working collaboratively with sales to strategically plan content ensures that marketing is
meeting defined needs, not blindly creating new assets that will go unused.



Build Content That Can Be Personalized
Business buyers are 65% more likely to switch brands if a vendor doesn’t personalize 

communications. That’s because no matter how much your product can optimize processes
or eliminate bottlenecks, ultimately a human will make the purchasing decision — not a 

machine. Content should not just focus on what the product can do, but how it’s going to
make buyers’ lives better and easier.



Because every buyer is going to be different, it’s important for reps to be able to customize
content. One way of achieving this is by creating modular content that’s easy to remix and
customize. This will help your sales team stay on-brand and, more importantly, enables reps
to provide personalized value and subject matter expertise that will truly make an impactful

20
impression. A whopping 74% of buyers choose the sales rep that was first to add value and
insight, which can only be provided when content is tailored to their needs.


Make Sure Sellers Know Where to Find Content
and How to Use it
You may be producing fantastic content, but it will all be for naught if your sales team doesn’t
know how to find it and maximize its potential.

There are many ways to approach content management, but one of the most robust 

solutions is implementing a powerful sales enablement tool. Companies have seen huge 

success by empowering their sales teams with an enablement platform. Sales Enablement
PRO found that organizations who have utilized an enablement tool for more than two years
have 13% higher win rates than other companies and 11% higher quota attainment.

Sales enablement tools save sales reps time by providing one content repository for all their
content needs, cutting down on the amount of time they spend searching for and creating
content. Reps can find what they need, when they need it. Sales enablement tools also 

improve the quality of content by providing marketing teams with analytics into content 

performance, answering questions such as:


• What content is being used—and where?

• Are sales teams getting what they need?
• Is my content resonating with customers?


Using what they’ve learned from the data, marketing can adjust content investments to 

better align with what is resonating with sellers and buyers, resulting in higher quality 

content. With more impactful content and more time they can dedicate to selling, sales 

enablement tools help reps reach quota attainment. A study conducted by Aberdeen Group
found that best-in-class companies employing sales enablement practices were 50% more
likely to have sales reps who achieved quota. We’ll dive deeper into sales content analysis in
Chapter 9.

21
6
Best Practices
for Content that
Fuels Revenue
Regardless of what line of business you are in, content-based marketing provides
organizations with an effective way to engage audiences while also generating new leads
that translate to revenue growth.

The prerequisite to driving high-quality leads into the hands of sellers who can capitalize on
them is to discover what content your target audience actually wants to see. Creating
content that provides value follows a methodical process with a few key steps. Here’s how
to get started.


Step 1: Know Your Customer

The first rule of creating great sales content is understanding your ideal customer. As Oracle
CEO Mark Hurd advised, “When you’re dealing with customer relationships, you have a
limited number of times to make a true impact.” So make your content count.

Building out your ideal buyer persona provides a close look at who you need to be creating
content for. Answering basic questions can help you start this process:

• Demographics: What is their age, gender, income, location, profession?

• Interests: What do they value and enjoy?

• Challenges: What are their pain points? What needs do they have?

Having a firm grasp on these qualifiers will help you create content that attracts your
preferred persona.


Step 2: Develop Your Content Strategy

Your content strategy will ensure you are reaching the right people, with the right content, at
the right time. Various channels, formats, and design should all play a part in your strategy as
well as mapping your content to find any gaps. By mapping content to the buyer’s journey,
you have a clear understanding of what content is intended for which persona, during what

23
stage, and if there are any holes to fill. This high-level view of your content landscape draws
a very clear picture of what content sellers have in their arsenal. Depending on buyer
preferences, you need to leverage multiple ways to present the content. Whether you
choose a case study, webinar, or video, your best approach is to reach your audience on the
channels they’re already using and entice them with a benefit they can realize right away.
New and insightful content helps sellers have more impactful buyer engagements.



Step 3: Optimize Your Content

Once you’ve created content with clearly defined buyer personas in mind, created a content
strategy and mapped content to check for gaps, it’s time to optimize. Analyze your content
performance to see what content is resonating with sellers and what content is successfully
engaging buyers. Sellers will continue to use content that works for them. Using this insight
you can create similar content or make it a priority to update an existing favorite. With
visibility into what content buyers are opening, reading, and downloading, you can gather
insights into what topics or products buyers are eager about. Fine tuning top performing
content arms sellers with assets that will compel buyers to move to the next stage of their
buying journey.

Now that we’ve covered how to create winning content, let’s dive into the different types of
sales enablement trainings for your team.

24
7
Training Your
Team for Success
Not all sales enablement can be delivered in downloadable content. Interactive sales 

training can be a great avenue for instilling the knowledge behind each of the other sales 

resources - whether about the product, competitors, customers, or even sales skills 

themselves.

Let’s take a look at four valuable types of interactive sales training that will take your sales
team education to the next level.

Workshops and Skills Training

Workshops are interactive activities that both analyze your team’s current strategy, and work
toward improving your team’s skills. Workshops can help your sales team with a wide range
of skills such as writing emails, business acumen, sales call planning, how to gain buy-in
from prospects, and negotiation skills. 


Competitive Intelligence Training

With a better understanding of what your competitors are doing, Sales will be able to speak
knowledgeably about the market and build trust with prospects. While on a phone call, if a
prospect asks a competitive question, your sales team will be able to answer questions with
ease, thanks to competitive intelligence data. Doing a live training on your competitive 

landscape is a great way to engage your sales team in a conversation about how you differ,
why you win, and landmines to avoid.

Product Training
Your sales team should be experts on your product. How else are they going to effectively
sell your product to prospects if they’re not well-versed in your solutions? Product training
should be done as part of the onboarding process, as well as whenever you have a new
product update or feature release. Product trainings will help keep your sales reps sharp,
and they will be able to answer any question that comes up on sales calls.

Presentation Skills
Most likely, your reps are spending a lot of time on the phone each day and are strong 

communicators. But, how many of your reps have experience giving business proposal 


26
presentations? It’s important to host presentation skill trainings that dive deeper than general
public speaking abilities.

Partner with the best teacher in each area for the best trainings: perhaps a sales manager for
sales skills, a product manager for product details, a competitive intelligence professional for
competitor details, a user experience or marketing researcher on customer details.

You’ll also want to provide your sales team with sales scripts and email templates that will
set them up for success. Keep reading to learn best practices for scripts and templates.

27
8
Teaching Your Team
to Talk the Talk
When a sales rep gets on the phone with a new prospect, or when they’re sending off
emails, ideally, you want them to book a meeting every time. But, how do you know what
they’re saying on the phone or what they’re including in their emails? While you don’t have
total control over what’s said or typed, you can help set the stage, and set them up for 

success with sales scripts and email templates. Let’s take a look at best practices for both
scripts and templates.

Sales Scripts

Scripts for the sales team to use on calls are

helpful for getting them up to speed, whether for
new messaging, new products, new audiences,
or all of the above. New sales team members, in
particular, can benefit from sales scripts, since
they will not yet have the context or experience
delivering your specific pitch or sales process.
Be sure to incorporate what questions to ask -
not just what to say - to set up each rep for an 

interactive conversation.

When you’re creating sales scripts, set a high standard across the board by following these
best practices.

Align to Personas
Make sure that you’re not giving prospects a generic sales pitch. Create sales scripts that
align to each persona, in a personal way, that will speak directly to their pain points and how
you can help them solve it.

Get the Best Soundbites from Your Best Reps

When building your sales scripts, listen in to the sales calls of the best reps. What are they
doing that has proven to be successful? Take those best pieces of information and insert
them into your sales scripts for all reps. Share recorded videos of your top sales executives

29
delivering these scripts on calls. Video and audio recordings are great for getting the right
soundbites ingrained in their vocabulary, and can be consumed over and over on an em-
ployee’s commute.

Role Play and Practice

Just designing sales scripts and passing them to the sales team to learn won’t be effective.
What you need to do is have your sales team practice with one another, such as, one rep is
the prospect and the other is trying to sell to them. Practicing the script will allow them to
learn it, and become more comfortable with it.

Share Recorded Videos

Share recorded videos of your top sales executives delivering these scripts on calls. Much
like audio recordings, video are great for sales reps to see how the top performing reps 

conduct discovery calls and demos. Plus, these can be referenced whenever needed.

Email Templates

Sales email templates allow you to streamline,

standardize, and support every step of the sales
process. Preparing emails that sales executives
can customize and send in different situations
makes their process easier but also ensures
that they’re taking advantage of all of the other
materials you create. If you are crafting the
emails, you can incorporate the most effective
messaging as well as relevant content assets.

Regularly review metrics on your email template usage and success rates - seeing which
templates are sent most, which ones have the highest response rates, and which ones are
correlated to increased win rates. This can help you optimize the templates and encourage
sales teams to use the most effective emails.

30
To ensure that your sales team is sending out emails that don’t miss the mark, follow these
best practices when making your email templates.

Make it Personal
Rather than having a generic intro, “Dear Steve,” build a connection right away. Tell sales
reps to choose a common quality. Maybe they went to the same college as a prospect, that’s
a great starting point! Try, “Hey Steve - It’s nice to see a fellow Wildcat in the Boston area! I’m
reaching out to talk about X, Y, Z.”

Remind Them About Your Content

Even if someone has downloaded your content, they may not recognize a sales rep’s name
right away. Or, if the content was downloaded from a partner, they will need a gentle 

reminder of who your company is. Use a generic content email template for sales reps to 

reference. Such as, “Hey Mary - thanks for downloading our Product Marketing 101 Ebook.
How are you liking the content so far?”

Tell Them How You Can Help

Rather than cold emailing someone to try and set up a demo, have a template that allows
sales reps to customize your persona’s pain points. If you have multiple personas, this allows
sales reps to have a standard email, where they can fill in name, company, and pain points.
This allows your reps to show the prospect that they are there to help.

31
9
Putting Your CI
Knowledge to the
Test
Once you’ve conducted your trainings and workshops, a great way to test your sales reps’
understanding of the topic is through quizzes. While you are training your sales reps about
your platform and solution, you want to ensure they are able to pick out the golden pieces of
information that align with each ideal buyer.

Whether you’re doing your sales trainings on a weekly, monthly, or quarterly basis, it’s
essential that your reps are really absorbing the key concepts you’re providing and are able
to confidently leverage those concepts on sales calls. If your reps don’t understand the
fundamentals, they just won’t be able to sell the product successfully. So, quizzing your reps
is a great way to ensure they’re ready to tackle the market.

If a rep doesn’t successfully pass a quiz following a sales training, you know that you need to
provide additional training or content on that topic or competitor to help reps level up their
knowledge.

Here are some quizzes you can implement for your sales team:

Demo Readiness Quizzes: Once your sales reps have ramped up and are ready
to start closing deals, help them sharpen their demo skills so that they’re able to
hook the prospect and will be able to walk through the capabilities of your
solution effortlessly. 


Competitive Intelligence Quizzes: Teach your sales team the ins and outs of
each of your competitors. It’s important for your sales team to be able to answer
tough questions about how you compare, without sounding biased or unsure.
Quiz your sales team on each competitor, and how you stack up to each.



Product Feature Quizzes: In tandem with your product trainings, your sales team
should test their knowledge about your product before getting on the phone
with prospects. Being quizzed on their product knowledge will better prepare
them to be able to speak confidently about everything your product has to offer.

33
 Messaging & Positioning Quizzes: Pick out key pieces of your messaging that 

align with your personas, and have your sales reps familiarize themselves with
the messaging. Once they know your messaging inside and out, they will be
able to speak confidently about your company and how your company 

positions itself in the market. Quiz your team by doing role playing exercises to

ensure that they’ve got the messaging down.

Now, your sales team is ready to hop on the phone, send out more emails, and close more
deals.

34
10
Measuring Your
Sales Enablement
How do you know if your efforts are helping your sales team? Analyze your efforts. Let’s take
a look at which analyses and metrics are critical for sales enablement professionals to be
tracking. By diving into these types of analyses, you can apply everything you now know
about sales enablement materials, sales training, and templates, to improve your strategy.
Let’s take a look at how to conduct each analysis, and how each can benefit your sales 

enablement strategy. 


Win / Loss Analysis

Your win / loss rate is the percentage of sales opportunities that are successfully won (or
lost). This is important for you to understand where your sales team is succeeding and
where they are struggling to close deals. To calculate your win / loss rate, divide the number
of won opportunities, by your total number of opportunities.

You may also want to look at your win / loss rate specifically for competitive deals. When
you’re going head-to-head with a competitor to win over a prospect, you’ve entered a 

competitive deal. You’re probably no stranger to your competition, so you know that 

prospects are likely evaluating both of your products or solutions, and need to be convinced
that your company is the best fit for their needs. Analyzing your competitive deals and your
competitive win / loss rate will shed light on who you come up against in the most 

competitive deals, but also give insight as to whether or not your sales enablement materials
are helping your sales team beat the competition. Much like calculating your overall 

win / loss rate, use the same formula ( # of Won Opportunities / # of Total Opportunities), but
only include deals where you went head-to-head with a competitor.

Knowing your win / loss rate and competitive win / loss rates are important, but it’s also 

critical to know what pushed a deal one way or another. If you understand your win / loss
rate as an organization, as well as at a per rep level, you can make overall strategy changes
but also individual plans for reps. You want to analyze why you lost, as well as why you won.
That way, you know where you need to invest more resources, which sales reps need 

specific trainings, and which sales enablement materials to refresh.

36
Funnel Leak Analysis
Having a clear understanding of your sales process and at which stage prospects are 

dropping off the funnel is crucial for sales enablement success. Depending on which parts of
your funnel prospects are dropping off and becoming lost opportunities, you can make
changes to your strategy.

If your prospects are falling off at the beginning of the sales process, and don’t even get to
see a demo of your product, this is an opportunity to improve upon your outreach strategy.
Train your reps by following a sales script, create email templates, and even have your reps
follow specific email nurture campaigns to build a strong rapport with prospects from the
very beginning.

If your prospects are receiving a demo from your sales team, but then choose to discontinue
the relationship, this gives you an opportunity to work with your whole team, or an individual
rep, to improve their demo strategy. Here, you can use talk tracks, visuals such as sales
decks, and internal resources such as battlecards to improve your team's demo 

performance.

If your prospects are dropping off after learning about your product in and out, this is an 

opportunity for you to sharpen your sales teams skills overall. Let’s say you lost the deal 

because it was highly competitive. Implementing competitive sales trainings and sales 

quizzes, as well as arming your sales team with battlecards that live within your CRM can 

ensure that they’re ready to tackle the hard questions.

By analyzing which parts of the funnel are experiencing the most drop off and why, you can
better arm your sales team with the resources they need to support prospects through the
entire buyer’s journey.  










37
Sales Content Analysis
As a part of your sales enablement strategy, you’re creating a handful of beneficial tools for
your sales team. Great! But, how do you know if they’re actually being used? This can be 

difficult, especially if your materials don’t live in one centralized location. To make it easier,
store your tools in one location such as a company wiki, or even better, right in your CRM or
centralized sales enablement platform.

Sales enablement tool usage rate is a measure of what percentage of your sales team is 

using each resource and how deeply. To do this, track your sales team activity or even 

survey your sales team about which employees use which resources or which resources
they don’t. For example, if you’re using a platform such as Salesforce to house your 

battlecards, monitor the number of views each battlecard receives, as well as how many
sales reps are using them. Based on what you find, you can improve upon specific sections
of your battlecards, or give your intel a refresh.

If you’re creating materials that don’t seem to be getting used often, open up a dialogue with
your sales team about what they need, what would be the most beneficial to their 

day-to-day, and how you can revamp current materials to meet those needs.

Understanding the why’s and why not’s of your sales content usage is critical to ensuring
you are producing the most impactful sales content for your team.



Sales Cycle Analysis
The sales cycle length is the amount of time between when a potential buyer first engages
with you to when the deal is closed. Many variables contribute to the length of your sales 

cycle, such as selling to multiple people from one company, their budget and approval 

process, and their projected timeline for investing in your product. Your sales cycle is 

probably something you wish you could simplify and shorten. To calculate how long your
sales cycle is, analyze the time between the first contact between a prospect and your 

company, to the day that a deal is closed. Then, average all your deals together to figure out
how long your average sales cycle lasts. To get started, you should explore the following
questions:

38
 • How long is your typical sales cycle? Does this differ depending on the deal size?

• Why do some deals have shorter sales cycles? What about those with longer sales 

cycles?

• What is moving leads through the funnel?

• What are the conversion rates between each stage of the funnel?

• What can you provide to your sales team to help them shorten the sales cycle, and in
turn, close more deals and make more money?

Understanding the average length of your sales cycle and the key variables that play a role
can help you figure out how you can help your sales team win more deals, faster. You can 

figure out which nurturing campaigns can help move along the sales process, which types of
content help influence buying decisions, and which sales tactics result in shorter and more
successful sales cycles.

Now that you have a strong understanding of these fundamental analyses, you’ll be able to
analyze your own sales performance and figure out how to best enable your sales team to
win more deals.

39
11
Tying it All
Together
Sales Enablement is critical to the success of every organization. It’s important to have a
sales team that is thoroughly trained, armed with effective resources, and able to employ the
skills, templates, and content they need to bring in revenue.

Enabling your sales team on subjects such as competitive intelligence, product, and basic
sales skills, is key to helping new sales reps get up to speed but also existing sellers 

continue to improve. Whether sales enablement is tackled by a dedicated sales enablement
team, comes out of a collaboration between content and product marketing, or simply is a
shared responsibility across the organization, everyone can contribute to this all-important
task. Once your team is armed and starts working their deals, as the sales enablement 

professional, you’ll be able to analyze what’s working, what’s not, and where you need to 

invest more of your efforts to better enable your sales team.

By enabling your sales team with the right tools, resources, content, and training, your team
will be ready to tackle any deal that comes their way, and bring in more revenue for your
business.

41
 Ready to arm your sales team with actionable competitive intelligence?

Crayon's competitive intelligence platform captures 100+ different types of insights about
your competitors automatically in a single platform and gives you the tools and insights to
enable your sales team to win competitive deals. Keep tabs on everything from the latest
customer reviews to key executive departures to pricing changes and promotions.

Create and distribute dynamic battlecards that allow your sales team to have up-to-date
competitive insights at their fingertips. To learn more about how your team can increase
sales win rates and beat the competition, request a free demo of Crayon.

Request a Demo of Crayon

Crayon is a competitive intelligence platform that enables businesses to capture, analyze,

and act on market movements from competitors, partners, and customers. Tens of
thousands of teams use Crayon's software to capture and analyze a 360 degree view of
competitors' activities and enable Sales, Marketing, Product, and Executive Leadership to
win in competitive markets. To learn more about Crayon, visit www.crayon.co.

Highspot gives businesses a powerful competitive advantage to have more effective buyer 

conversations and achieve revenue goals. Highspot's AI-powered search, analytics, in-
context training, guided selling, and 50+ technology integrations deliver modern sales en-
ablement that sales reps and marketers love.

www.highspot.com

42