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The 7 Cs of Contextual Sales Enablement

January 17, 2018 / by David Bloom

As we've seen with the exciting and massive growth of the Sales Enablement Society, sales enablement as a function is red-hot right now. Many practitioners and industry leaders continue to evolve and work on its 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 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 given how little time reps have and how important it is for reps to bring a relevant and valuable point of view to the conversation.

In sales enablement, 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 case? Where are they in their buyer’s journey (hopefully mapped to your sales stages!)? What product are they interested? What competitors are they considering? And what have your successful colleagues done in these situations?

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

The Other 6 Cs of Sales Enablement

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?


coaching your sales reps in context


1. Coaching - Provide best practice tips and tricks 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 bootcamp, and get their reminders in front of the sales team at just the right time.


sharing sales win stories peer-to-peer video


2. Colleagues - Sales people learn best from each other. Have your reps capture their win stories and best practices and serve up the relevant ones in 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 coaching tips for reps working on similar deals.


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3. Conversations - 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 can truly give sales teams an idea of what “great calls” sound like. Imagine having the best of your top BDRs’ attention grabber, AEs’ objection handling or SEs’ discovery call served up in context of the ramping reps.


sales customer testimonial video training coaching


4. Customer testimonials - 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 a contextual customer testimonial where their story was for a similar use case or in a compete-against similar competitor?


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5. Competitive Intel - Have the product team providing a quick 3-min video on how to crush a competitor, or create a quick battlecard. No more searching through other systems and file storage or having to go ask the product team directly. The product team can now be 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 served up based on a specific deal size for a net new or add-on customer could provide great insights.


Now, what would this look like in context?


Building an Onboarding Program with the Sales Enablement Cs

Imagine you’re onboarding a new Account Executive. How do you leverage the Cs of Sales Enablement in an onboarding program? Here’s an example on 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 (Gong.io) 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 (Gong.io) (Conversations)
  9. Get feedback and coaching on your initial calls (Gong.io) (Coaching)
  10. Listen to other winning examples (Gong.io) 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 It All Together

Having a repository of 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 a number of great sales enablement tools out there that can bring contextual 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.


How do you apply content and coaching in context at your organization? What tools are you using to make it easy for reps? I’d love to hear from you in the comments below.



Topics: Sales Enablement, Sales Training & Coaching, Sales Onboarding, Sales Enablement Best Practices

David Bloom

Written by David Bloom

David Bloom is the CEO & Founder of LevelJump, a sales onboarding and enablement solution built on the Salesforce platform. Prior to founding LevelJump David built and sold a corporate training company and held a variety of sales and marketing leadership roles at Fortune 500 life sciences and technology companies including Salesforce.com, GSK and Pfizer.

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