6 Questions to Answer Before Investing in Sales Enablement Content

At a high level, sales enablement content is fairly self-explanatory. It’s content (blogs, videos, webinars, white papers, etc.) that enables your salespeople to sell. How? By shortening the sales cycle or by empowering sellers to close leads they otherwise wouldn't.

It's also particularly valuable for B2B SaaS startups with long sales cycles – 40 or 50 unique touches with a prospect before a deal closes. Sales enablement content helps these teams by giving them something valuable to share every time they follow up.

But how do you create the right sales enablement content for your startup? To answer that question, I spoke to someone who crafted a stellar sales enablement strategy that made me a better salesperson when we worked together: Rheaply’s new Senior Director of Marketing & Demand Generation, Jenn Kloc.

jenn_kloc_photo2Thanks again for speaking with me, Jenn 👋

Note: Jenn's background is in demand gen, so this piece speaks to sales enablement with a demand-gen bent. (This tends to work best for startups and smaller organizations that have to squeeze the most utility from every content piece.)

So without further ado, here are the six questions Jenn uses to guide sales enablement content strategy.

1. What Is Sales Enablement Content?

Great question. Here are four examples of what sales enablement content can be and how it benefits prospects and salespeople:

  • Webinars. Have a recurring topic that customers and leads keep bringing up? Educate them (and your salespeople) with a webinar. Every attendee or registrant becomes a lead that your sellers can engage.

  • Blog posts. If your salespeople frequently encounter the same questions, write blog posts that answer them. Sure, your sales team can relay information on calls, but blog posts are resources that prospects can visit at their leisure or that your salespeople can send to revive a conversation.

  • FAQ videos. The content may be similar to the blog series but the medium gives prospects a new way to engage with your business.

  • Thought leadership pieces. By highlighting relevant topics and trends, thought leadership can position your company as the logical, credible place for prospects to go. (And, hey, you don’t have to keep all that great content on just your site – there are lots of media outlets on the hunt for your insights.)

As you can see, there are tons of different mediums for sales enablement content. (And I limited these examples to formats that address both demand gen and sales enablement!) There are plenty more “typical” sales enablement content types to choose from, like testimonials, sales scripts, and product one-sheeters.

The takeaway: embrace the assortment of content. In Jenn’s words: “Once you’ve found the biggest pain points your product solves, highlight them in a wide variety of formats.”

2. Which Sales Enablement Content Is Right for Us?

Your salespeople are key stakeholders for your sales enablement content. But don’t just confer with your sales team.

“Find people across different functions at your startup whose opinions you trust,” Jenn said. “Share your thoughts on the sales enablement initiative. Let those stakeholders poke holes in it. That’ll ultimately make the content stronger.”

As you share plans with stakeholders, consider:

  • How are we using content to support our sales function today?
  • What does our sales team need from us today? Are there any content gaps to fill?
  • What content will our salespeople need tomorrow?

Be sure to ask these questions whenever you brainstorm new pieces for the program. The answers will change over time.

3. How Will This Content Help Us Reach Our Business Goals?

“You may have a really cool marketing idea,” Jenn said. “But if it doesn't ladder up to your business goal, like furthering revenue growth, it won’t get buy-in from leadership.”

However, this doesn't mean all sales enablement content should be exclusively about your products. “Product marketing is table stakes,” Jenn noted. “You need to have one-sheeters and product overviews.” But overviews alone do not a sales enablement strategy make.

“Your sales team is prospecting, building the pipeline, and talking about your company and product(s) all the time, " Jenn said. “If they only have product one-sheeters to share, their emails are, quite frankly, going straight to the trash.”

For context on how hard it is to break through: recent research from marketers we admire found that there are 16x more digital solutions on the market than there were a decade ago.

4. How Do We Measure Success?

“There's always going to be content that’s hard to measure,” Jenn said. Whereas SEO content’s performance is pretty easy to evaluate, the performance of sales enablement content is a bit more opaque.

But you can measure it. Maybe by viewing how many people download an asset. Or by tracking whether a prospect opens an email with the asset attached. Or by, if that same prospect booked a meeting with your sales rep, checking whether that meeting led to closed-won revenue.

When quantitative measurement isn’t possible, Jenn suggested other ways to gauge impact. Ask your salespeople…

  • What did your prospect think of that content?
  • Did the content help prospects better understand our offering or industry?
  • Was the prospect interested in learning more about the content topic?

If your sales team doesn’t offer thoughts, that can be valuable, too. “Lack of feedback is probably a sign your sales team isn’t using the content,” Jenn pointed out. “For marketers, that forces you to think ‘Did I need to write that in the first place? Is there something else that would meet our customers’ and sales team’s needs?’”

5. How Can We Improve the Content?

When marketing and sales are on the same page, sales enablement content flourishes. That’s why ongoing meetings (keyword: ongoing) between marketing and sales are integral to improving content. As Jenn put it: “It’s essential for someone in a demand gen or revenue marketing role to have regular meetings with the sales team.”

Those recurring meetings are important because, as any salesperson will tell you, the best sales enablement content changes over time. Case in point: I started working with Jenn at BenchPrep, an L&D startup, in August 2020, when COVID-19 was the driving factor behind people reassessing their L&D needs. Cut to today and ChatGPT is dominating headlines.

There’s always something new.

Sales enablement content should stay in conversation with those trends. It’s easier to write that content when you meet with your salespeople on an ongoing basis.

Once you’ve set that meeting time, you can outline recurring topics, like…

  • What's next. You’ve done the work of brainstorming with your sales team. Now’s the time to share what made it into your editorial calendar – and when you’ll publish the pieces.
  • How to deploy content. Make it easy for your sales team to share content. Jenn’s done this by putting together “marketing packages.” For example, every time you write a blog post, include email copy that your sales team can copy / paste into their outreach. Bonus points if you can make it even easier for them to use by writing email templates to share your marketing content in their engagement tools, like Salesloft or Outreach.
  • Feedback. Before finalizing new content, check in with your sellers about what you’ve already created. See if there are any new concerns that prospects are bringing up in calls. Use this meeting as another opportunity to brainstorm.

This could be your marketing & sales teams. High-fiving. Looking like Kevin Bacon.

6. How Can We Get the Most Out of Our Content?

Guess what? You don’t need to craft blogs, webinars, or case studies on new topics every week to improve the quality of your sales enablement content. As Jenn put it: “Your existing content can have different lives.”

Double down on topics you’ve previously emphasized. For example, let’s say you host a webinar. You can use that webinar to fuel a series of blog posts. Maybe you summarize those blog posts in a newsletter. And maybe you reuse those summaries for the email copy you supply to the sales team.

This repurposing and remixing makes life easier for you and it gives your prospects new ways of accessing a broader message you want them to hear.

The X-Factor for Effective Sales Enablement Content: Unified Marketing & Sales Teams

The success of your sales enablement content is determined by the partnership between your salespeople and marketing team. The more collaborative, the better.

In many cases, sellers move through the business world with a “how does this help me?” mindset. (I sure did.) And that’s necessary. Sales reps and AEs are the gears that power a startup’s revenue engine. They must focus on work that builds the pipeline.

This is why it’s so important to highlight the benefits of sales enablement content to your sales team. Without understanding how sales enablement works, it’s tough for salespeople to see the value. But trust me, I never felt more confident selling than when I had content to share that perfectly explained a solution to my prospects.

Interested in hearing more about how a content marketing plan can move the needle for your sales function? Grab some time.