The 6 Cs of Contextual Sales Enablement Content

Sales enablement is a red-hot function right now. The growth of the Sales Enablement Society, the development of titles with sales enablement in them, and the rise of “sales enablement” as a search term all point to a function on the rise.

Sales enablement over time

It’s also an industry that’s rapidly evolving, with many practitioners and industry leaders continuing to fine-tune their structure, definition, job description and responsibilities. Should it report to sales, marketing or perhaps neither? Is it marketing and sales content? Is it training? Is it people? Process? A combination of it all?


I don’t plan to answer those questions but will share an opinion that organizations spend far too much time focusing on just sales enablement content without the context.


According to Gary Vaynerchuk, he would argue that if content is king, then context is God, which in sales today is extremely important. Reps have precious little time to consume and repurpose sales enablement content and bring a relevant and valuable point of view to the conversation.


In the world of sales enablement content, it is essential to provide sales teams what they need based on the context of what they’re working on.


  • Who are they talking too (persona)?
  • What are their priorities and use cases?
  • Where are they in their buyer’s journey (mapped to your sales stages)?
  • What product are they interested in?
  • What competitors are they considering?
  • What’s worked before in this situation?


Jill Konrath, has a great youtube video on showing up to an initial meeting “naked.”



Basically, she’s saying to not show up with any content on an initial meeting because it should be all about the buyer, their pain points, and providing them with an insightful buying experience.

When showing up with sales enablement content, you’re showing up promoting your own agenda, not theirs, therefore start the conversation with a less-than-optimal buyer experience.


So what else can we bring to reps in context other than just marketing content (case studies, white papers, pitch decks, etc.), before getting on to their next meeting? That’s where the 6 Cs come in.

1. Coaching 


Provide best practice sales enablement content from subject matter experts. There are so many great sales thought leaders providing insights for a more effective sales cycle. Take your top sales leaders and mentors, or the thought leader who recently ran your sales kickoff or training boot camp, and get their reminders in front of the sales team at just the right time.

2. Colleagues 

sharing sales win stories peer-to-peer video

Salespeople learn best from each other. Have your reps capture their win stories and best practices and serve up the relevant sales enablement content in the context of the deal. Imagine a culture of peer-to-peer learning at scale where your top rep is simultaneously running a deal and providing just-in-time, contextual, bite-sized tips for reps, from reps working on similar deals.

3. Conversations

Converational intelligence

Conversation intelligence is such an exciting space in sales right now. Emerging companies like Gong, ExecVision, and Chorus are all on a mission to turn sales conversations into assets by transcribing and analyzing them. Not only does this provide insights for call coaching, but it can truly give sales teams an idea of what “great calls” sound like. Imagine having sales enablement content that captures the best of your top BDRs’ attention grabber, AEs’ objection handling or SEs’ discovery call served up in context to ramping reps.

4. Customer testimonials

sales customer testimonial video training coaching

The best of these are most often found on a company website and for lead gen purposes. These customer stories are critical in today’s sales environment. And who are we kidding? Our reps don’t have time to go sifting through customer sections of the website. Imagine a rep working on an opportunity and having sales enablement content in the form of a contextual customer testimonial, relevant to their size, pain, and industry.

5. Competitive intel 

Competitive intel

Have the product team providing a quick 3-min video on how to crush a competitor, or create a quick battle card. No more searching through other systems and file storage or having to go ask the product team directly. The product team can now create sales enablement content that’s placed in context.

6. Contracts


Success leaves clues, and sometimes when it comes to negotiating a contract, your team may need to think outside of the box. Now, this use case is not for everyone, but in more complex sales, having some different contract types as sales enablement content, served up based on a specific deal size for a net new or add-on customer could provide great insights.


So what does all this look like? Here’s how you build an onboarding program full of sales enablement content designed with the 6 Cs in mind.

Build an onboarding program fit for the 6 Cs

Imagine you’re onboarding a new Account Executive. How do you leverage the 6 Cs of sales enablement content in an onboarding program? Here’s an example of how you could do it:


  1. Watch a video of the CEO explaining the company vision (Colleagues)
  2. Watch videos of customer testimonials to understand why they bought and how the solution helps them (Customer)
  3. Listen to customer calls ( to understand how they bought your product (Conversations)
  4. Watch/Listen to expert training on deal cycle best practices (Coaching)
  5. Watch a win story from one of the top reps explaining what they did, what they learned, and how others can benefit from their learning (Colleagues)
  6. Practice and publish your attention grabber, value proposition messaging, or story (Colleagues)
  7. Get certified on your pitch by peers or managers (Colleagues, Coaching)
  8. Start your sales activities (dials, meetings, demos, etc) and record them ( (Conversations)
  9. Get feedback and coaching on your initial calls ( (Coaching)
  10. Listen to other winning examples ( of conversations with prospects (Conversations)
  11. Hit your meetings or pipeline milestones
  12. Listen to and practice your objection handling (Conversations)
  13. Get feedback on your objection handling and listen to your recordings again (Coaching)
  14. Become familiar with competitor battle cards (Competitors)
  15. Close a deal (Contracts)
  16. Share your win story with the rest of the team (Colleagues)
  17. Reinforce content and coaching with just-in-time contextual sales enablement on opportunity stages in your CRM

Tying your sales enablement content together

Having a repository of sales enablement content for sales (LMS/CMS), or doing a dump-and-run-style onboarding/kickoff won’t help sales organizations close deals faster. It will just overwhelm teams with too much information, too soon.


There are several great sales enablement tools out there that can bring contextual sales enablement content and coaching to life. Some of them even integrate with CRMs (Salesforce) and can really help a rep save time by suggesting and prescribing content and coaching instead of reps seeking out information.


So as you’re planning your sales enablement content strategy, keep in mind that there are many more “Cs” to bring into context to help your reps provide your prospects and customers the most meaningful experience with your organization.