July 25, 2017

4 Tips for Creating a Top-Notch Sales Enablement Strategy

Ensuring reps have the tools and collateral they need to be successful is hard — especially for leaders in high-growth companies, where scaling creates a constantly evolving environment. Creating a strategic sales enablement plan will make your team more productive and help you reach your goals each quarter.

Sales teams can close more deals and create lifelong customer relationships with time-saving hacks that put training and evaluation first, and content delivery that is easy to consume, memorable and effective. Here are four of the best ways to build out your sales enablement strategy.

Build a sales enablement strategy early in the life of your business to establish a strong foundation that you can continuously build on as you grow

As soon as possible, pinpoint the bright spots in your team’s process, as well as the areas that need improvement. Assess which reps are most productive and successful, and answer questions like:

  • What tools are they using that help them work most efficiently?
  • What are they saying on calls that’s effectively resonating with prospects?
  • Have they found a way to structure demos in a benefits-driven approach that the rest of the team could learn from?
  • How are they positioning your product against competitors?
  • Is there a particular customer segment they’re seeing the greatest success with?
  • What content are they following up with that helps prospects move forward in the sales cycle?

And finally, what of all this can be standardized across the rest of the team? Compile these answers in a central location and develop a playbook and technology roadmap using what you learn directly from your reps.

Look for sales tools and content that can become part of your reps’ workflows to save time and improve efficiency

Focus on tools that reduce rather than add steps in the workflow. The key here is finding tools that are simple, seamless and integrated.  For example, browser extensions that can pull information while reps prospect on LinkedIn. Or a link they can pop directly into an email to minimize the back and forth of scheduling, like Calendly.

Tools that live in workflows reduce the amount of the non-selling work reps must focus on, while also increasing their chances of actually adopting the tools and seeing success.

When it comes to content, video is an innovative sales enablement piece that, when used in tandem with other digital and traditional marketing content, can reach prospects most effectively.

Sales and marketing should work closely together to develop and leverage video content to craft demos that focus on the benefits of their product, making it more clear and easy to digest for the prospect in a few quick bites. If reps are using video in their prospecting emails, they can use a CTA button with a Calendly link embedded at the end of the video to capture new leads and quickly convert them.

Video can also be used as an educational piece to nurture prospects that are in earlier stages of the marketing funnel. Transition your written blog content to videos featuring top thought leaders in your company and leverage across email campaigns and on social.

Quantitatively measure sales enablement success and make improvements along the way to maximize ROI

To improve sales within your organization, identify areas in the sales cycle where reps are struggling, and find a way to establish a quantitative baseline. For example, if video content is a focal point in your strategy, you can pull analytics from your video-hosting platform. Vidyard accomplishes this by offering a view of who’s watching the videos your individual reps are sending out, how long they’re watching before they drop-off, and whether they are re-watching portions of the videos. Use these metrics to determine what’s driving the most engagement—and what’s not—and make tweaks to constantly evolve and optimize your strategy.

You can also use gamification to measure sales reps’ competency and develop skills further. Use an app integrator like Zapier to setup automated rewards based on your workflow. When a sales rep contacts X number of leads or reaches X number of sales, they can earn a token. Those tokens can be cashed in for a reward that makes sense in your team and company culture and all these metrics can be automatically tracked through your CRM. Maybe the top three sales reps in a quarter get to have an in office video game tournament and winner gets a sweet gift card to Dave and Buster’s.

Gradually and smoothly transition to a better sales enablement process as needed to align with business priorities

Use metrics and feedback to determine when to implement a new step. Look at results; analyze, then make adjustments accordingly.

Keep sales reps engaged with quick email videos highlighting new training tools or giving shout-outs to top performers.

The key to improvement is to start small: pilot a new solution with your most senior reps, get them accustomed to using that new solution in a particular workflow, and gradually expand to the rest of the team.


Sales enablement isn’t easy, and it’s never finished. The most successful sales teams  collaborate with their marketing team on an ongoing basis to provide the insights they need to develop meaningful, innovative content to engage, and ultimately convert, the right leads.

By choosing tools that complement your reps’ workflows, tying in your marketing team to build a strategy, rolling out changes slowly and finding a way to quantify each aspect, you’ll close more deals than competitors who still rely on email threads and clunky spreadsheets.

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Rachel Hobbs

Rachel Hobbs is senior marketing manager at Calendly, the fastest growing company in scheduling automation offering a powerful software that makes it possible for business professionals to easily meet with customers, prospects, partners and candidates. In her day-to-day role, Rachel develops and executes marketing strategy to help generate acquisition, activation and retention.

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