Top 5 questions to ask while evaluating sales enablement tools

In 2020, Gartner estimates that global organizations spent $1.7 billion on sales enablement tools. Moreover, sales enablement tool adoption will continue to grow faster than the overall sales technology category.

Interestingly, even companies that have already purchased an enablement tool continue to look for new solutions. Gartner reports that 68% of organizations are looking to switch enablement tools every year.

Whether you’re buying an enablement tool for the first time or upgrading an existing one, you should ask yourself these 5 questions:

#1 – Do you have the right sales enablement content?

Sales enablement tools do not magically create content for your reps.

With a sales enablement tool, your reps can find the right content at the right time during the buyer’s journey.

Audit your sales content assets before investing in a tool. Be sure to review:

  1. Sales Collaterals. Do you have a good mix of content assets such as product datasheets, pitch decks, competitive battlecards, case studies, training courses, and ROI reports?
  2. Online Content. Don’t forget to include content hosted on your website as well as external sites. Take note of your web pages, blog posts, infographics, ebooks, reports, and videos. Make sure to also include customer testimonials and bylines on external websites.
  3. Custom Content. There is probably a lot of content that account executives and sales engineers create for specific opportunities. Consider repurposing this content to support your broader sales team.

A content inventory audit will give you a better understanding of the state of your sales content. Additionally, you will learn if you need to update or retire some of your existing assets.

#2 – Will it play well with your existing sales technology stack?

With the shift to virtual selling, more sales reps are using technologies that can help them deliver engaging customer experiences. Gartner estimates that reps use 13 different sales technologies to support their virtual selling efforts.

Make sure your sales enablement tool integrates with your existing sales technologies. Here are some things to consider:

  1. CRM. Your CRM system is the heart of your revenue operations. Check how well the sales enablement tool integrates with your CRM. The enablement solution should use opportunity insights from your CRM to deliver the most appropriate content at each sales stage.
  2. Email. Account executives use email to schedule meetings, share information with prospects, and handle customer objections. The sales enablement tool should allow reps to search for and access content in their email. It would be better if your sales enablement tool could analyze an email thread in a rep’s inbox and provide relevant content tailored to a prospect’s query.
  3. Sales Engagement. With sales engagement tools, business development teams can create multi-touch outreach sequences that help turn prospects into customers. Ask the sales enablement vendor if they can deliver content recommendations in your sales engagement tool.
  4. Calendar. Your sellers are always checking their calendars. They use their calendar to schedule prospecting time, research participants, and attend meetings. Check whether your sales enablement software can help reps prepare better for meetings by presenting relevant content in their calendar.
  5. Messaging. Reps can collaborate with internal teams using tools such as Slack and Teams. Make sure your sales enablement tool lets reps search for content in Slack and Teams. Your reps should be able to track buyer engagement metrics in your messaging tool, such as views and shares.

#3 – Will it be easy to implement and manage the tool?

It isn’t a simple matter to set up and maintain a sales enablement platform.

Before choosing a sales enablement solution, keep these factors in mind:

  1. Migration. Does the tool integrate with your existing content management system (CMS)? Is it easy to export documents from Google Drive, SharePoint, Dropbox, or Box? If your sales enablement tool does not co-exist with your existing CMS, you’ll spend a lot of time on content migration.
  2. Tagging. Tags can help organize your content. However, too many tags can lead to complicated and overlapping taxonomies. For accurate search results, you must constantly build and update tags. Check if your sales enablement provider uses AI/ML to index and scan your content. By automatically classifying and indexing data, you can improve accuracy, reduce redundant work, and speed up the implementation process.
  3. Recommendation Rules. Will you need to create ‘If-Then-Else’ scenario-based rules to surface the right content? Building and updating recommendation rules is a full-time administration task. Find out whether your sales enablement tool uses AI to recommend content.

#4 – Will your reps use the sales enablement tool?

Your team will spend weeks creating folder structures, tag hierarchies, and manual rules. You will also need to train your reps how to find and share content from the sales library.

However, after your sales content library goes live, you discover that sellers still use outdated sales collateral. To make matters worse, reps only visit your sales library to download content to their local machines.

Seller adoption is where the rubber meets the road. Here are five tips to ensure adoption:

  1. Flow of Work. Can the sales enablement tool deliver the content reps need in the tools they use? Sellers should be able to find and share content in their email, calendar, CRM, or messaging software.
  2. Content Usage. You should be able to see what content your reps are sharing across deals. Additionally, you should know what content your reps are looking for, but cannot find.
  3. Buyer Engagement. Sellers should understand how prospects engage with their content. Sales reps can tailor their buyer interactions when they can see how their content is viewed, shared, and downloaded.
  4. Feedback. Reps should be able to share their opinions on the effectiveness of sales collateral. Reps should be able to comment on and rate different content assets using the enablement tool.
  5. Custom Content. You should be able to track the custom content that your reps create for different deals. You can then create new content so that reps don’t have to keep re-creating content.

#5 – Will it make inter-departmental coordination easier?

As your organization grows, it is challenging to maintain alignment and collaboration across functions. Your sales enablement tool should help bridge the gap between sales, revenue enablement, and product marketing teams.

Assess the sales enablement tool’s ability to help with:

  1. Content Prioritization. Enablement tools should allow sellers to request new content or updates to existing content. Marketers should be able to communicate their current priorities and turnaround times. This can help align and prioritize content requests across the sales team.
  2. Content Performance. Marketers should understand how their content is being used by reps across the buyer’s journey. They should be able to access insights into how prospects engage with their content. Using these insights, marketers can create engaging and effective content.


It is critical to define business goals, ensure alignment, secure executive sponsorship, and manage change when deploying a sales enablement tool.

To achieve the desired outcomes with an enablement tool, you must audit your sales content, develop an integration strategy, realize the administrative burden, understand how reps will use the tool, and build organizational support.

It’s easy to get started with GTM Buddy’s sales enablement solution. Your reps will spend less time digging through folders and more time closing deals with just-in-time content recommendations.

Curious about GTM Buddy’s just-in-time approach to sales enablement? Schedule a demo and see how you can sell better and faster with GTM Buddy.

About the author


Deepak Jannu

Deepak Jannu is the head of product marketing at GTM Buddy. Before GTM Buddy, he was the VP of product marketing at OpsRamp.

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