How to build a digital sales enablement strategy

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According to a recent study by McKinsey, 70% of B2B decision-makers are open to fully self-serve or remote purchases in excess of $50,000 – and 27% would spend more than $500,000. Over three-quarters of sales reps surveyed by Salesforce report that they have adapted to new ways of selling due to changes in buyer behavior. 

In this ever-changing environment, digital sales enablement is all about providing tools for your sales team, including the materials, content and resources that help them:


  • Engage with buyers throughout the sales process
  • Sell effectively
  • Build relationships with prospects and customers
  • Close more deals
  • Drive revenue for your business

In this article, we’ll discuss why digital sales enablement is important, how to create a sales enablement strategy, how to choose the right technology solutions and how to measure the success of your program.


How to structure your digital sales enablement strategy

Digital sales enablement is a critical part of scaling sales organizations beyond just a select few overachievers into a team of high-performing salespeople who have the resources and knowledge to succeed.

Here are four recommendations for structuring your organization’s digital sales enablement strategy:


1. Get alignment internally

Gartner predicts that by 2025, 75% of the world’s highest growth companies will deploy a RevOps model that supports revenue enablement activities across all customer-facing roles.

You can improve communication and drive revenue by aligning your sales and marketing teams as you’re creating your digital sales enablement strategy. 

Here are a few tips for aligning sales and marketing to boost revenue:

  • Get agreement on terminology so that it means the same thing to everyone. This includes things like key performance indicators (KPIs), where data will be collected and where it will come from and what the overall business rationale is for making a particular decision.
  • Define your personas. What kinds of customers are you selling to, what are their biggest pain points and what motivates them to buy? Also consider who you are not selling to, and include that in your strategy. (An example is excluding gmail addresses from your email nurturing flows or not accepting these on your forms). 
  • Define your most important metrics so sales teams know what success looks like. Also agree on objectives based on industry benchmarks. 
  • Agree on a tagging strategy for digital sales enablement assets. Having a clear strategy for tagging and metadata that everyone implements will help you determine the effectiveness of the assets you develop.

2. Understand the customer journey

The key to creating an effective sales enablement strategy is understanding the customer journey. To give your sales team the right tools, they must be able to pinpoint the customer’s needs and shape their message accordingly. 

For example, according to the aforementioned McKinsey study, 70-80% of B2B decision-makers now prefer digital self-service or remote human interactions to in-person communications, and 67% of B2B buyers report that they prefer not to interact with a salesperson as their primary source of research during the purchase process.

Consider doing a sales process audit – a detailed, data-driven analysis of your company’s sales process to map out the customer journey and discover areas where you could improve sales performance. Consider: 


  • How many pieces of content does a prospect usually consume before buying? 
  • What kinds of questions do they ask? 
  • Do people typically use a messaging service to talk to the sales team, or would they rather schedule a phone call? 
  • Does your sales team book a lot of demos each month? 
  • What pieces of content or resources are missing from the current sales playbook? 

You could also interview or survey current customers to find out if there were any barriers or bottlenecks in their sales process. 

This analysis will help you understand the needs and wants of your prospects and whether your sales strategy is meeting those needs.

Question everything – each touchpoint can be improved! 


3. Create sales content for every scenario

Gartner reported that B2B buyers only spend 17% of their time meeting with potential suppliers when considering a purchase, compared to 27% of their time researching independently online. 

With so many buyers looking for information about your product or service, you must meet their expectations. 

Once you’ve researched the customer journey and set expectations for your teams, create high-quality content that maps to the buying process and allows a large number of salespeople to deliver value to their prospects. 

Types of sales enablement content that will help your sales team meet targets include:

  • Competitor research and comparisons
  • Pre-call sales checklist
  • Sales call scripts
  • Email/messaging templates
  • Demos and videos of products
  • Ebooks and white papers
  • Case studies
  • Testimonials from customers
  • Informative articles and blogs

This is where guided selling becomes a key tool to provide meaningful, relevant and timely content and information to sales reps during the sales process to keep buyers moving toward a purchase decision. An advanced sales enablement tool can use predictive analysis to enable sales reps to focus on what matters most to buyers when they are selling. 


4. Continuously train your team

The goal of your training program is to teach your salespeople how to use the resources you provide them. The most effective digital sales enablement efforts incorporate traditional training programs with virtual collaboration tools. 

For the best results, make sales training a continuous effort instead of providing just one annual event. Training sessions spaced too far apart lead to forgotten content, lower adoption rates and unused digital sales enablement tools. 

If you want reps to maximize their time and be able to improve their skills, e.g., during their lunch break, you can try training formats such as micro learning and just-in-time (JIT) training to enable just that. 

For example, micro learning has been shown to improve long-term knowledge retention, and an effective sales enablement strategy takes the latest findings into account.


Since JIT training is short, it’s easier for reps to learn on the go and in a mobile format so that they can make the most of their time.

With JIT training, the knowledge is available precisely when it’s needed; employees are able to use their learnings to improve their performance right then and there.

Instead of long workshops, content for JIT training is short and highly relevant to specific tasks – a maximum of one to five minutes long.


Choose the right digital sales enablement tools

A recent Gartner report found that:

  • Buyers want a seller-free experience and to steer their own unique buying journeys
  • When buyers run into a situation in which they need assistance, sellers and buyers need the means to collaborate digitally during the buying process
  • Better customer experience means that buyers should be able to choose if, when and how much they interact with sellers
  • Sellers need to be able to understand and track buyer engagement through the process

Your sales enablement platform doesn’t just make sales collateral more accessible – it gives your sales reps the tools they need to seamlessly engage with target buyers at any stage in the customer journey. 

One system can provide visibility into the entire content lifecycle, tracking which items are touched by each customer and when, as well as the effectiveness of each piece of content.

Your sales enablement tool helps you align your content with your sales team and makes content accessible from wherever your sales reps are working, including in-person, online, offline or on mobile devices.

When choosing your digital sales enablement technology platform, consider these recommendations:

  • Look for omni-channel platforms so that you can connect planning, marketing and execution within one solution.
  • Be clear on your use cases when communicating with proposed vendors, and seek out solutions that have client references of similar size and vertical to your company.
  • Prioritize vendors that have built-in, real-time analytics and reporting.
  • Assess vendors’ artificial intelligence and machine learning capabilities, so your sales team can get on-the-spot prompts based on prior customer interaction data.
  • Evaluate the strength of each vendor’s integrations and partnerships to support additional opportunities for your organization.
  • Assess a vendor’s ability to grow with your organization as your sales team grows.


Why use a Digital Sales Room? 

Consider using a digital sales room (DSR) to solve these issues and make your content as accessible as possible. A digital sales room is a secure, centralized location that provides buyers and sellers access to all the content, communications and stakeholders related to a deal cycle. 

DSRs drive more effective buyer engagement because they can be used to continue conversations and collaborate with all decision-makers as they navigate the buying process. 

Giving all stakeholders a single location they can return to throughout the deal cycle makes it easier for them to find the content they need, when they need it – so they can take the next step and make a purchase.

These dedicated online environments also provide a tailored, differentiated experience for every buyer without using extensive resources and management. 


Measuring the results of your digital sales enablement strategy

Regardless of the size or scale of your digital sales enablement solution, measuring the results of your efforts is critical. Your goal is to identify the information leading to the most closed deals so that you can optimize your knowledge creation. 

Here are a few metrics and KPIs you can measure to help improve sales enablement within your organization:


  • Average sales cycle length: Sales cycle length is the average number of days or months it takes to close a deal. This is a measure of sales efficiency and can be used to create sales forecasts. Better sales enablement strategies and tools can shorten sales cycles as reps close deals faster.
  • Number of leads converted to opportunities: According to Salesforce, the average lead-to-opportunity conversion rate is approximately 13%. A lead converts into an opportunity when they take an action like downloading a white paper or booking a demo. You can determine the lead-to-opportunity ratio by dividing the number of leads you convert to opportunities by the total number of possible leads. This conversion measurement indicates the quality of your leads. 
  • Opportunities converted to sales: Calculate your conversion rate (or “win rate”) by dividing the number of conversions by the total number of sales interactions your team had in that month. The average conversion rate by industry, according to Ruler Analytics, is 3.2% for B2B e-commerce, 3.5% for B2B services, and 1.7% for B2B Tech.
  • Net Promoter Scores (NPS): Net Promoter Score is a customer experience metric that measures customer loyalty. Net Promoter Scores are measured with a single-question survey, asking respondents to rate the likelihood that they would recommend a company, product or service to a friend or colleague. Customers report their satisfaction using a number from 0 – 10.
  • Sales representative productivity: When they have the most relevant tools and data at their fingertips – and when manual tasks are automated as much as possible – salespeople can work quickly and effectively, achieving quotas more frequently.

You can gain a deeper understanding of buyer and seller behavior using your own customer insights, which you can gather and analyze using the analytics capabilities of sales enablement platforms. 

Modern sales enablement platforms include robust reporting functionalities that enable sales management to get real-time data-driven insights and monitor the performance of sales teams all in one place. 


Digital sales enablement in a changing world

Given its potential impact on your company’s revenue numbers, sales enablement is no longer a “nice to have” – it’s a critical piece of the puzzle for gaining a competitive edge in the post-pandemic world.

A smart and innovative digital sales enablement strategy – in conjunction with top-quality sales enablement tech solutions – can give your reps the tools they need to successfully engage with the buyer throughout the sales process and provide better experiences every step of the way.

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