In today’s unpredictable, fast-paced sales environment, midsize organizations need a formal sales enablement initiative to ensure that sales reps are having quality conversations with prospects that lead to more wins.

Sales enablement affects the bottom line in a real way. Unfortunately, many midsize organizations struggle with sales enablement strategies. One of the largest inhibitors to sales enablement in midsize companies is taking a random approach to it. According to the CSO Insights 4th Annual Sales Enablement Study with over 500 sales teams, companies with committed sales enablement content, technology, and training had 15% higher win rates than companies without one.

If you want to make a significant impact on your sales enablement program, consider these five tips for driving results:

1. Make Sure Sales Reps Have Easy Access to Content

Do you have a flexible sales enablement content solution? Is your content on one platform or scattered around in multiple drives and repositories? If your sales content is disorganized and reps can’t find it, it will gather dust and go unused. The investment spent building that content will have been for nothing.

Taking the time to organize content in a meaningful way that organizes content the way salespeople need it organized can significantly speed up the sales process, accelerate opportunity conversions and keep conversations between reps and prospects valuable. Consider adopting a sales enablement platform that provides a one-step, easy-to-use repository for all your tools and content, which also integrates with your current CRM to streamline all selling processes. In the 4th Annual Sales Enablement Study, CSO Insights found that sales teams that had a central repository for content had a 53.7% win rate, while sales teams that did not have such organization had a 45.6% win rate. That difference is telling.

2. Stop Wasting Time on Activities that Don’t Involve Selling

On average, sales reps can spend between three to seven hours a week searching for marketing materials to showcase products to prospects. Sometimes it takes even longer. The content sales reps need is not always available or easy to locate.

According to the 4th Annual Sales Enablement Study by CSO Insights, when it comes to the content salespeople need to close a deal, marketing only generates 33.8%. The rest is sought after elsewhere from sources such as product management, legal, sales ops or created by reps themselves. When a rep spends his or her time building or searching for content instead of selling, it can lower sales performance significantly. But when organizations can effectively manage content through their enablement function, they free up reps’ selling time and on average achieve an 8.5% win rate improvement compared to the average win rate of 49.5%, according to the sales enablement study.

3. Make Sure Reps Share Best Practices with Each Other

As you know, sales can be extremely dynamic. Messaging and products can constantly be in flux depending on the prospects’ needs, the size of the company, the industry and what stage of the buying process they are in. The best sales teams are always talking with each other, constantly communicating on what is working well or flopping and regularly making plans and strategies for the future. Sales managers should develop a tight-knit feedback system around sales enablement training, the accessibility of sales content and all-around best practices for sales reps. Encouraging this kind of dialogue can significantly lift a sales team’s performance. It would also be extremely valuable to include the marketing team to share insights and strategies.

4. Plan for Frequent Onboarding Training

Successful midsize organizations are constantly implementing ongoing training sessions to improve performance. The 2018 CSO Insights Talent Study found that it’s not uncommon for more than 20% of an overall sales force to be new to the organization. When that happens, results at the end of the year will depend heavily on the quality of sales onboarding. Ongoing onboarding training can impact quota attainment by 6.7%, according to CSO Insights.

5. Invest in Sales Technology

Many midsize organization sales teams don’t have the resources, time or budget to be constantly evaluating and implementing new technology, but the right sales enablement technology solution can help them become more effective in reaching goals and winning deals. It’s crucial to make the time to get together and research, vet and implement technology that will not only improve your sales performance, but also keep your teams from getting behind the curve. If your competitors are investing in sales technology, that might be a good sign that you should as well.

As you’re looking into viable solutions, there’s one crucial thing to remember: “It’s equally important to have a rollout plan,” according to the CSO Insights Sales Enablement report, “that details how you will get the new technologies in the hands of your customer-facing professionals and, using enablement services like training, coaching and content, ensure they are using them effectively.”


Transforming your sales team’s performance by implementing and optimizing these five fabulous sales enablement program tips should be at the heart of every midsize organization’s sales growth strategy. This process starts with providing sales reps easy access to content, eliminating non-selling activities and making sure your teams are communicating on best practices with each other. Ongoing onboarding training is a must, and you need to make sure your sales team has the right sales technology for them to succeed.

To learn more about how to win at sales enablement, please check out Miller Heiman Group’s Guide to Sales Enablement.

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