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16 min read

Best practices for how to start (or fix!) your sales enablement

Sales Enablement | Tips

If you were to ask 50 different people who are involved in sales what sales enablement is, you would likely get 50 different answers. Much like product marketing, there’s no one standard definition. What complicates the one true definition is that every business is unique, and therefore, sales enablement will look different in every company.

To provide some clarity and context, Product Marketing Alliance defines sales enablement as:

"A strategic, cross-functional discipline designed to increase sales results and productivity by providing integrated content, training and coaching services for salespeople and front-line sales managers along the entire customer’s buying journey, powered by technology.”

Sales enablement helps ensure that all sellers have strong selling practices without relying on a select set of sales stars. It’s about driving repeatability, predictability, and scalability of the best-selling tactics.

In this article, I’ll be focusing on the best practices for how to start or fix your sales enablement approach. I’ll look at topics like:

What’s required for sales enablement programs?

A strong sales enablement program includes….


Content is the area people are most familiar with when they think about sales enablement. In fact, according to the State of Product Marketing Report 2021, it’s a core responsibility for 78% of product marketers.

Content should be about traditional sales collateral that provides sales with the means to communicate the value of your company’s offering in order to drive leads, increase conversations, capture additional spending, and boost retention.

Additional spending and retention as your enablement efforts may also be directed towards your customer success/support teams.

This content includes both:

  • Internal content: Intended to give sales reps guidance and isn’t meant to be seen by prospects or customers. These include competitive battle cards, sales scripts, product information sheets, and so on.
  • External content: Intended to be provided to prospects and customers by sales like case studies, pitch decks, product demos, pricing overviews, blogs, webinars, and so on.

It’s critical to note that this content needs to be aligned to the customer journey (and as a result, the marketing and sales funnel) in order to drive success. Without that, reps may struggle to properly engage and convince prospects and customers.


When we talk about sales tools, there are many rabbit holes we can go down. In fact, according to the 2021 Sales Tech Landscape by Smart Selling Tools, there are over 1,078 sales tools in over 45 unique categories.

There are many sales tools you won’t be responsible for in your role as an enabler, but it’s a priority for you to understand what the sales tool tech stack looks like for your organization so your tools can integrate into the sellers’ daily workflow.

From an enablement perspective, sales tools are any technology that helps sellers be more efficient and effective. They’re generally designed to help salespeople save time throughout the sales cycle, and understand:

  • Who prospects are,
  • When they should engage with those prospects, and
  • What they should talk about in that conversation.

Ultimately, they help sellers drive the right conversation with the right buyer at the right time. And that means making sure that reps are continuously learning more about what you're offering and how to do their job better.

Examples of this include sales asset management tools, learning, training or coaching tools, and conversation intelligence tools.


Sales enablement best practices require standardization, simplification, and ways to track progress. That’s why it’s so important to build out your sales enablement processes in a way that drives efficiency and productivity for everyone involved.

With a function that is so focused on cross-functional collaboration, sales enablement processes make sure you know who’s accountable for what at whatever stage you’re at.

Like any business process, a process for the sake of process isn’t the goal. There’s a whole slew of these you’ll need to build out over time as your sales enablement function matures and needs to scale. It’s important for you as an enabler to know when a process is needed, and drive alignment around that process.

Building sales enablement processes will start with driving alignment between the buying journey, marketing funnel, and sales processes. From there, you can expect to build out things like:

  • A content development, pipeline, and auditing process.
  • Ways to drive ongoing process efficiencies.
  • A process to onboard, train, and continually reinforce learning for sellers.
  • Ways to build repeatable sales plays so you can scale effective selling motions.
  • A process to get feedback from sellers on what is working with prospects and customers, transfer insights from customers to sellers, and so on.
  • Communication governance to sellers so, internally, they’re presented with the right info at the right time.


If you can’t track the success of your sales enablement work, how do you know how effective your activities are? You have to be able to define and measure metrics that not only prove the value of your work to the business but ensure that you can drive continual improvement. What you track depends on what you need to measure and if you have the ability to track it - and both will likely change over time.

It’s important to note that while you’ll need to rely on quantitative metrics that can be measured in numbers, you’ll also want to enhance that data with qualitative feedback through methods, like interviewing sales reps.

Product Marketing Alliance’s Sales Enablement Landscape 2020 report highlighted many of the metrics product marketers track. You’ll be thinking about KPIs that answer questions like:

  • What percentage of reps are using the content and tools you’ve provided?
  • Which are used the most?
  • How many deals are you closing and what is the size of those deals over time?
  • What percent of deals are won or lost and why are they won or lost?
  • How long is the sales cycle?
  • Which territories or segments are bringing in the most revenue? How much revenue is from new or existing customers?
  • Are your customers buying add-ons and driving up attach rates?
  • How long does it take to onboard new sellers?
  • Are sales reps hitting quota?
  • How confident are your sellers?

How to build and scale sales enablement programs

It can be a daunting task to start or correct a course on sales enablement activities and programs. How do you know where to start or when you need to fix something? How do you ensure you get buy-in on whatever you’re building before you release it?

That’s why it’s critical to create a framework for how you’ll develop, iterate, and scale your sales enablement activities. So, everything from launching a full program to launching a specific piece of sales content. You need something that isn’t specific and can be applied to any project or task as needs change over time. A framework can help you get quick wins and build trust while also planning and providing for the long term.

Luckily, there’s much inspiration to be drawn from our product counterparts with product development processes. Product teams are hyper-focused on building the best solution for their customer’s needs - if you think of your sales teams as your customers, you may find you have the foundation of skills you already need. Especially if you’re a product marketer - you flex those muscles every day in creating strong business cases, go-to-market strategies, and so much more.

Enter the framework: Discover, Development, Launch, Iterate…


The discovery stage is all about information and data collection, analysis, and synthesis. This is where you’ll uncover the current situation and core problems you need to solve - and articulate back to the business how you’ll solve those problems and what impact you expect them to bring.


As it sounds, the development stage is when you’ll design and validate the program or activity you’re building. Validation means that you test out the artifact or program before you put all your eggs into the launch basket.


Just as we’d launch a product to customers, we have to put the same effort into launching sales enablement for sellers. It’s more than just releasing the program or pointing them to a new piece of content, this stage also involves all the efforts to drive adoption across your sales organization.


Developing and launching sales enablement isn’t one and done—needs will change, your organization will evolve, and you need a way to analyze what’s worked well, and what hasn’t worked, and then make adjustments and recommendations on what needs to come next.

Think of this framework as a cycle—everything you recommend in the iteration then feeds into the discovery of the next version. Next up, we’ll start talking about how you can do proper discovery and communicate what you learn, how you’ll solve problems for the organization, and what it’ll impact in order to get buy-in.

How to do discovery

What is discovery, and why is it important?

If we bring it back to thinking of sales reps as our customers, discovery is your initial requirements gathering stage. This is where you benchmark where your organization’s at, pinpoint the primary pain points and prioritize your focus accordingly.

Discovery can make or break your attempts at sales enablement, because, without proper discovery, you’re unlikely to be able to articulate what you’re solving and why it matters; critical components for getting buy-in from your organization. Discovery helps you set clear objectives, strategies, and tactics to make the right impact.

Discovery should be done whether you’re:

  • Starting fresh with your sales enablement to understand what content, tools, and processes, and need to be built to impact which metrics.
  • Course correcting an existing program that’s not getting the adoption or having the impact you expected - you should go back and see what’s changed since you initially created your program.

Now, how do you go about getting the data and information you need? You’ll want to look at both quantitative (meaning numerical, quantified data) and qualitative (non-numerical information gathered firsthand from observation) sources. We’ll talk about these sources as we examine the main areas we’re looking for information: business, sales organization, and prospect/customer context and data.

So, what are you specifically looking for in those areas? Well…

Business context and data

A good sales enablement strategy is aligned to the business goals and objectives, and that’s why your discovery starts there. You should expand this discovery to think beyond the scope of specific sales - understand the entire organization’s goals and focus.

You should be asking yourself and the rest of the organization:

  • What is the mission and vision for your company?
  • What are the highest level objectives across the company?
  • What is the past, current, and expected future performance of your company?
  • What value does marketing bring to your sales organization? How aligned are marketing efforts to sales needs?
  • Is everyone internally aligned around the type of go-to-market efforts needed to drive revenue (e.g. go-to-market strategies focused on acquiring new customers, retaining existing customers, etc.)?

How do you go about getting this data?

Much of this data will be readily available from company intranets, strategy documents, and department-level goals. You’ll need to rely heavily on cross-functional partners to help you pull together this information.

To give you an example, when we undertook this effort at my organization, we found the following:

When I joined my company in 2017, Product Marketing was brought into the organization during a period of rapid growth - we were there to help with our B2B enterprise motion in order to help the company eventually go public. We had aggressive targets around new enterprise customer acquisition with our “land and expand” motion, and all of our go-to-market efforts were centered around that.

  • Mission: Democratize technology skills for individuals and organizations
  • Vision: Be the go-to-technology learning partner for tech leaders across the globe
  • Current performance: 40% overall growth
  • Future goals: Targeting an IPO, requires enterprise expansion using land and expanding customer acquisition strategy

Sales organization context and data

Next, and probably most obvious during discovery, is digging into the sales organization itself. Like the macro-level business context, you need to understand what performance targets sellers are looking to hit in the future, current performance today, and historical performance.

You also need to understand how that performance is throughout the sales funnel and how it's broken down by the segments - that means understanding what sales process they use, different segments your sales team supports, the different roles they play in supporting those segments, and what process they use to sell to prospects and engage customers.

  • What sales process do your sellers follow?
  • What is your sales team’s performance against targets? Are sellers underperforming, meeting, or overperforming to targets and quotas? Are there significant differences for different segments (e.g. territories, size of an organization, etc)?
  • What are the different roles that exist within your sales organization, how do they engage in the sales process, and how do they support sales goals?

When I say processes, I’m talking about the repeatable steps your reps take to move someone from a lead to closing the deal. A sales process helps provide predictability for reps and is most effective when it’s aligned to the customer journey.

Let’s look at an example of a B2B sales process—Your sales process likely won’t look exactly like this and is highly dependent on your specific business but is a baseline to give context. It starts with:

Prospecting: Where your organization is finding or sourcing leads for potential customers. At this point, customers are aware of their problem and looking for a solution.

Approach and contact: Where a rep reaches out to a potential customer and the potential buyer engages in initial conversations to understand if you may be able to solve their problem.

Discovery and qualification: Where reps are further qualifying the prospect and getting more information to inform later stages, while the potential buyer evaluates the feasibility of the solution for their specific problem.

Presenting and prospecting: Where reps outline how the solution will solve that specific product with demos, as the potential buyer pares down their list of potential vendors and validates that their needs are met.

Negotiation and objection handling: Where reps engage in pricing conversations and negotiation, while the potential buyer works through their own internal purchase process.

Closing: Where reps get contracts in place and your potential buyer is now an actual buyer.

Follow-up: Where there’s likely a hand-off from the rep who closed the deal to someone who’ll manage and maintain the relationship as the buyer looks to get started and have success with your product.

Common pitfalls for sales enablement teams

A common pitfall for sales enablement teams isn’t spending enough time getting buy-in from or enabling the sales leaders themselves. Sales leaders want their organization to repeatedly deliver revenue—and that’s why they can be your enablement function’s best advocate.

Along with Sales Managers, these folks are responsible for coaching and training reps while making sure they drive the right behaviors and adherence to the sales process. Their success is based on their team’s ability to hit their quotas, so they’ll support your efforts and enforce best practices—making use of the tools your enablement function provides for reps. Sales reps listen best to those within their organization - and therefore, sales leader buy-in will do wonders for the adoption of your programs.

Beyond the behaviors they can enforce, they’re also critical input sources for your enablement work. Any time you ask reps to engage in enablement activities (like a new product training), you’re taking away valuable selling time. By getting sales leaders on board with what you’re producing, you’ll see less friction in getting seller time. Additionally, they can inform what metrics they track and what metrics you should look to impact.

The rigor your sales team has around following the defined sales process and all the steps within it; where reps are spending most of their time; what best practices have reps had the most success with; what their top challenges are; why deals are getting caught up, won, or lost; the length of the sales cycle; how informed reps are about your target buyers and product value prop; how they are updated on all that buyer and product information; and who else is engaging with sales, why, and what their pain points are.

  • How disciplined are sales reps throughout that process (e.g. entering data into Salesforce, forecasting, etc)?
  • What activities take up most of your reps’ time (e.g. looking for information, admin tasks, etc)?
  • What are some existing sales best practices that need to be scaled across the entire revenue organization?
  • Do you know what the biggest challenges your sales team currently faces (e.g. closing deals, lack of qualified leads, prospecting skills, ineffective sales methodology, etc)?
  • Why are you winning and losing most deals?
  • How long is the sales cycle?
  • Are all your sellers able to consistently speak about the value of your products to different buyers at every interaction?  Can you confidently say that all your reps are using consistent messaging?
  • What kind of training and communication exists to keep sellers on new sales tools and product updates?
  • How often are existing sales-facing initiatives updated?
  • Do you know how sales reps are using the tools provided to them and if they are leading to a positive impact?
  • Who are the various functions across the business that interact with or support sales? Why are they interacting with sales and what are their major pain points when it comes to those interactions?

Now you may be wondering, what quantitative and qualitative sources are available to help you figure all this out?

From a quantitative perspective:

Start with your Sales Operations team if you have one. They can tell you how segments and territories are split out, where most leads are being sourced from to sales, what performance looks like across those segments and across your sales reps, which reps are performing well vs. needing some help, and how long the sales cycle is. They likely will also have data from your sales organization’s CRM on the sales process steps.

Another way to add some mathematical rigor to your discovery work is through a sales confidence survey. Product Marketing Alliance has created a sales confidence survey you can use as a baseline to uncover:

  • How helpful and impactful sales enablement and assets are.
  • What selling situations do they need more support in.
  • How well they understand the product and its value.
  • How competent and confident they are in their role.
  • And how equipped they are to talk about the competition.

Sign up for our pro membership plan and discover plenty of templates and frameworks just like the sales confidence survey to help you completely streamline your product marketing approach.

Where the rubber really hits the road is in the qualitative work that you’ll engage in. I cannot emphasize enough how important qualitative discovery is. Not only will it help you create relationships with the people you’re trying to create programs for, but you’ll see and feel those intangible moments that data cannot effectively translate as well as help you dig deeper into pain points or opportunities for improvement.

A great tactic here is to conduct interviews with sales reps and sales leaders to dig into what’s really going on. Just as you would interview a customer to understand their pain points, do the same for sales.

You can use the sales confidence survey questions we discussed—a more effective angle to really understand how you can help is interviewing through the lens of what they do every day. For example, you can interview them through the lens of a specific deal and ask:

  • How did the lead come to you?
  • Who in the sales organization did you work with and how?
  • How did you prepare for meetings with the prospect? How much time did you spend?
  • What did you do to conduct discovery?
  • Are they any tools or assets you used that were helpful? Not helpful? Why?
  • If the prospect asked you questions about the product, where did you go for information?
  • How did you track the deal throughout its lifecycle?

…and so on. If you’ve already got data on your reps’ performance, then you can source reps who serve various segments (or your most important segments) as well as high, medium, and low performers to know what is and isn’t leading to success.

Again, there’s quite a lot of sales-specific context and information you’ll need to collect - and this is likely where you’ll spend most of your time.

Prospect/customer context and data

As we all know by now, sales enablement means serving customer-facing teams which require a deep understanding of the customer. You’ll want to understand some sales-specific aspects like:

  • Who are your primary buyers and are there influencing personas involved in the decision-making process?
  • What does the buying and customer journey look like and how does your brand, company, employees, and product support through every step of that journey?
  • What are the stages of the customer’s buying journey and how does the content you create support moving buyers through that journey?

To give you an example, when we undertook this effort at my organization, we found the following:

We were shifting to selling to a new audience (from Human Resources and Learning/Development teams to Tech Leaders) which introduced new pain points to uncover, products to sell, prices to promote, messaging to use, and value to discuss. It also changed who influenced the deal.

If you’re a product marketer, you should have this data readily available. If you’re not a product marketer, I recommend reaching out to a Product Marketer or Marketing Manager at your organization or looking at the resources available via Product Marketing Alliance, like:

  • B2B persona questions, examples, and templates
  • Buyers funnel stages template

Regardless of if you have this data or not, an effective approach to build on your existing knowledge is to shadow sales calls.

First and foremost, you’ll build trust with your sales team by being “in the trenches” with them. To get buy-in, it’s critical that you explain the intent isn’t to grade their performance but get context on how you can help them better with the resources and training you’ll provide. A best practice is to work with sales leaders to make it mandatory that you can sit in at least a few calls from their team.

Second, you’ll see the sales process through the customer’s eyes without the bias that’s inherent when you interview reps who have skin in the game.

You should go into this call with a setlist of questions you want to uncover and can build on the surveys and interviews you’re conducting internally.

We’ve covered a lot and discovery doesn’t happen overnight - it’s important you put a plan in place to help you conduct efficient and effective discovery across the business, sales, and prospect/customer context.

Remember that it’s also important to make sure everyone understands why you’re doing that discovery so they feel motivated to take part.

Want to learn more?

No matter where you’re at in the journey; whether you’re partnering with a sales enablement team or owning it yourself, our Sales Enablement Certified: Masters course is packed with the real-life examples, case studies, expert tuition, templates, and activities you need to build and scale killer sales enablement programs.

Delivered by Sapphire Reels, Director of Portfolio and Integrated Marketing at Pluralsight, this course is going to give you the skills you need to confidently:

👊 Articulate the importance of sales enablement and sell it internally.
🔥 Design a sales enablement program from scratch based on business objectives and sales needs.
🚀 Launch and iterate on sales enablement programs.
🤑 Demonstrate the impact of sales enablement on the business and revenue generation.

So, what are you waiting for?

Get Sales Enablement Certified

Written by:

Sapphire Reels

Sapphire Reels

Sapphire Reels is a Senior Product Marketing Manager at Pluralsight, the technology skills platform that helps enterprise organizations develop skills at scale.

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Best practices for how to start (or fix!) your sales enablement