Our events provide an opportunity to not only listen to the professionals share their stories and tips for success, but to get actively involved by asking the questions that matter to your business - and getting real-time answers.

Here are some more probing questions posed by our virtual audience to the ‘Deploying a Sales Strategy that Works’ panel at the Sales Enablement Festival in May 2021 (missed Part 1? - it’s right here).

The expert panel providing all the answers included:

  • Thomas Cheriyan, Director of Sales Enablement, OwnBackup
  • Steve Hamilton, Director of Sales Enablement, Sage
  • Rachel Ha'o, Global Sales Enablement, Iterable

Here are the questions you put to them:

Q. Is sales enablement content overrated?

Q. How do you initiate sales coaching opportunities?

Q. How do you measure whether AEs (account executives) are translating product value to the customer effectively?


Psst, if you're an SEC member, you can catch the replay of this panel discussion in the OnDemand section of your dashboard.

Not a member yet? Want access to ALL the presentations from our sales enablement events, to keep and refer back to forever (as well as discounts on our in-person events, more exclusive content, a library of make-your-life-easier templates, and more)? Check out SEC’s membership plans...


Q. Is sales enablement content overrated?

Tom: Is content overrated? I guess it depends on the content. It's really easy to spend the next year just creating and publishing content. But, “What content are we trying to publish and create - and for whom - and is it going to move the needle?” Like [an] infosec presentation for our prospects to help us close the gap and expedite the approval process - that's not overrated. It actually has a direct correlation to helping us close deals faster. So, from a sales enablement standpoint, we absolutely should be running with that.

There may be other types of sales enablement content [that you shouldn’t run with]. I don't know what's a good example right now, because I'm afraid whatever I say, I think I'm gonna get like somebody from the crowd, like throwing a rock at me or something!

But you would have to ask yourself, “Is this the type of content that is needed? Or am I doing it just because somebody asked me to do it? Ask why five times: what is the critical issue we're solving? And is it measurable in some form? Are we measuring the usefulness of the content based on views?

Or is there a better way to measure the usefulness of the content as it relates to larger deal cycles, or larger deal sizes, or faster deal cycles, or being able to move from the discovery stage to the demo stage faster, or more thoughtfully? Or maybe making it longer, because you’re spending more time in the disco stage, and that’s actually what needs to happen in order to get more deals done, or better deals done.

There's a million ways to tear at it. But I think you'll know how good or bad the content is based on which types of data you're using to measure the effectiveness of that content.

Q. How do you initiate sales coaching opportunities?

Steve: It's a really important topic because I have seen, and I think we've all seen, that if sales coaching's a miss, it is very impactful to the results that you get. If it's a hit, it can change things dramatically. Unfortunately, a lot of situations occur where conversations about sales coaching only happen at that senior level of salesperson, and there is a gap between that level and the frontline manager.

If you really want to understand what is truly needed from a sales coaching methodology or process, engagement with the frontline leaders has to take place too, as they are the ones who are doing this every day. There are a couple of things that I also believe to be true in terms of driving success from a sales coaching standpoint.

Number one, it's got to be a daily rhythm, it's a priority, you need to want to do the sales coaching piece of it, not because you have to but because you want to try to make your team better.

The other point is to ensure that the coaching is to the behavior and not to the result. I think a lot of sales leaders coach to the number, when what I would advocate is the behavior that is driving that result. So coaching to the behavior is really critical as well.

Then it really becomes part of your operating rhythm in a sales organization whereby you are establishing a culture as to what it means to be a sales leader - because that sales coaching methodology is in place, it's supported across the organization. And you get to see the results from effective coaching as well.

So it's a very big, important topic that I think is sometimes missed in the whole sales enablement conversation. But it's important, and it's very meaningful to the business and results that that one gets.

Tom: For every type of course or content that we're actually making in Brainshark, we make it a specific point to create a coaching activity on top of the knowledge exam, because they need to actually role play and managers need to give feedback to that person trying to show mastery of that content. So we absolutely do incorporate it into our content creation process within OwnBackup.

Rachel: I'm glad this is being recorded because I'm going to watch that piece of advice back for myself! Both of you touched on some really important points. One is: make it relevant. Two: is to care.

If it's relevant, and it's timely, and you care, it may not be the most attractive content or subject matter, but if you know your team really well, and their personalities, you can make something that otherwise would be kind of boring into something that's really fun.

If you have something like infosec coming up, and it's a [business priority], you absolutely have to ship that content. There's no way around that. Infosec might be hard for some people to grasp generally so making it entertaining, and understanding the team's culture [is key]: are they a video team or a reading team?



You also have to think about ADA compliance, the accessibility of your content. So what might work for some learners is not going to work for others and video might not be the way to go for everyone on your team - a live session might be more relevant for people that have learning disabilities, and that's something that you have to think about as well.

On a human note, I'm hypersensitive to my content being boring and yesterday gave a prospecting training dressed as baby Yoda because it was May the 4th, and we have this whole thing on “may the salesforce be with you” and they love seeing sales leaders have that level of humility and then translating that into the content you build. Hopefully that will combat hearing that salespeople don't like what you're shipping out.


Q. How do you measure whether AEs (account executives) are translating product value to the customer effectively?

Rachel: This is a great question, especially if you have a multi-dimensional product, meaning there are different elements to the product that you sell in tiers, you sell the different elements of, especially on the post-sales team and customer success; they often end up holding a bag or upselling elements of the product.

I would say the first thing to do as an enablement expert, in partnership with the product marketing team, is to zoom out and determine, “What is the value that we want to articulate to the customer?”

And whether that's creating value drivers, or working with the marketing team to determine what that value proposition is, and how to articulate it for the person that you're speaking with, that would be step one.

Step two is training everybody on it, and making sure you have a live training, or training recording workroom where people can record themselves, or you can watch them, take that value driver or point of view, or whatever resources that you've created for them, then use that as a template, swapping out certain drivers or vocabulary based on the person they're speaking with - so measuring your ability to think critically about the product value.

The third is watching when they use it in the wild. I highly recommend getting a listening software like Gong or Clary that will help you measure [AE conversations with customers] and start to put in different trackers for the words or the vocabulary that you've given them to articulate product value, and measure:

  • The percentage of calls that people are using those value markers.
  • How many conversations had a decision-maker in the room when the salesperson or the customer success person was speaking to the prospective company?
  • Whether they actually articulate the value statement that you gave them to use.
  • Did they customize it to the business that they were speaking to?

Then you'll see that translate to more lagging indicators down the line in Salesforce opportunities or whatever your CRM is, where you have certain deal qualification markers filled in. You'll be able to see if they are getting this information about how the product can be of value for this particular business? Are they documenting it? And then are they able to redeliver that information and some type of executive summary maybe later down the line?

Pretty useful stuff, right? SEC members have got access to tons more actionable content like this - why not sign up and level up? Here’s what you could be missing...

(... get more top tips and tricks from Tom, Rachel & Steve in Deploying a sales enablement strategy that works: Part 3).