One of the best things about our sales enablement events is you can put your questions to our guest speakers in real time, whether you’ve prepared them in advance, or a light bulb appears over your head while you’re listening to them talk and you just have to know more.

And why wouldn’t you take advantage of the opportunity to mine the experience and expertize of enablers at the top of their game and get practical, personalized advice?

With that in mind, we thought we’d share with you some of the questions posed by our virtual audience to the ‘Deploying a Sales Strategy that Works’ panel at the Sales Enablement Festival in May 2021.

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: We're just getting started with sales enablement, what are the key tools we should get first in our tech stack beyond CRM?

Q: How do you get executives to buy into the value of your sales enablement department?

Q: I've just moved from a large multinational company to a start-up. Any tips for setting up sales enablement from scratch and how to create a flexible strategy that can adapt as we scale?


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Q: We're just getting started with sales enablement, what are the key tools we should get first in our tech stack beyond CRM?

Steve: I think there's a few real key components of a tech stack.

Number one is no surprise: you've got to have a rock solid CRM; you’ve got to be on Salesforce. I'm not saying that to promote Salesforce, but it's been my experience using multiple CRM platforms, that Salesforce is going to get you to where you need to be.

I also think you need to have a sales enablement platform where you can do some microlearning, some coaching, and that your sales enablement team, but more importantly, the field sales teams, are actually using.

Things where you can record sales pitches, and go through learning “huddles” for product content.

And I think based on what your sales environment looks like, there's a lot of data analytics that can be gathered from sales conversations, and there are companies out there that provide those analytics too, so you can understand what the seller and customer conversation is like. But you’ve got to have that foundational component [a CRM] in place first.

Tom: The first important thing as part of our tech stack at OwnBackup was having a proper LMS (learning management system) tool in place to deliver learning at scale to the masses.

Learning is only half the battle: you can present as much content as you want in any format as you want to the end-user or learner. But they need to show you that they've actually learned it.

So that ended up with us selecting Brainshark as our LMS, not just because it could distribute the content we want, but because of their coaching activities.

For example, the rep could be doing product training but, as well as doing a knowledge exam showing us that the rep has learned the product, they actually now have to role-play the product, where they're delivering the pitch for the product.

Or, we build scenarios where they have to address a specific objection as it relates to the value of the product, then the manager has to grade and give him or her feedback. And last year alone, we documented over 2 or 3,000 pieces of unique feedback given by managers to their direct reports.

Everyone, including leadership, strongly believes that this absolutely had an impact on the bottom line, because the way people grow, the way people get better, is not just by giving them better content, but it's by giving them coaching and feedback.

We have one great type of report that I can share with leadership and say, “hey, here's how many pieces of documented feedback we were able to deliver or create”. As part of our sales enablement strategy, we ask, “what kind of feedback loops can we create with technology, so that we're helping to create this feedback and coaching culture in our company?”.

Now when we're looking at new pieces of technology that we want to implement, we ask if there’s a coaching element to it. And if there's not, should we be looking at another vendor in that category that does have it?

Rachel: The only other tool that I would add to this is a listening software, a call tracking or a data aggregation tool like Clari or Gong. Especially in a remote world, if we have companies or people that aren't yet back in the office, it's imperative to measure the effectiveness of your content and your training by looking at the indicators of the conversations that they're having.

So are they using resources that you provided and trained them on in conversations with customers in real time? Can you provide feedback in a scalable way across many different demos, discoveries, etc, technical validation calls that are happening?

As you grow and scale your enablement team, in addition to the LMS could be a content management solution like Guru or a Highspot.



Q: How do you get executives to buy into the value of your sales enablement department?

Rachel: The first thing I would say is: it's not the enablement show - it's the company show. The first step is to meet with the executive team and understand what the business goals are, to get a really good handle on how enablement strategy is going to play into that.

The next thing is to look for a quick win, like building a really great onboarding program, and start to measure leading indicators like their productivity metrics. These onboarding metrics will really give you the wind in your sails that you need to prove that enablement can be very impactful.

New hires are always in high growth mode, so you can prove your value directly to a business objective. Presenting that information to the sales leadership team or the executive team is going to help plead your case for more headcount, hopefully.

Steve: The one thing that I always look back to in terms of getting that executive sponsorship is really establishing the ROI back to the business. There's obviously a cost to set up or to maintain a sales enablement function, so those outcomes are needed, whether it's through what you're going to get from customer NPS, or what you're going to get from higher annual contract value, annual revenue, whatever the case may be: it's that return on investment that if we do x, then the company will get y in return.

Getting that sponsorship is key.

Tom: I've personally found that being proactive in approaching leadership to be one of the key ways of getting buy-in because you're coming to them and inviting them to help them co-create and co-own the sales enablement solution.

If leadership, especially the frontline managers, are bought into the solution, from an enablement standpoint, it's 1000 times easier. Because otherwise it's an uphill battle to enable both the reps and the frontline managers and that can be painful.

Q: I've just moved from a large multinational company to a start-up. Any tips for setting up sales enablement from scratch and how to create a flexible strategy that can adapt as we scale?

Tom: Every start-up is different. An obvious pain point is “how do we set up every new hire for success?” Or maybe it's taking a particular product to market.

I think it's about understanding the key goals and objectives that everyone's focused on, and what you can do from an enablement perspective to support that.

Step back and take time to understand the current state of enablement, and what kind of infrastructure you need to build. For example, if you’re going to need an LMS, it takes months to build it up and set it up for success, so you have to be forward-looking as well. So you'd have the right solutions at the right time for everyone.

Steve: If I were to be leading sales enablement for a start-up, number one would be to make sure that you've got a very solid onboarding program in place. That’s going to be critical, not just to get them educated, but also from a retention standpoint. When a seller leaves an organization, it is typically due to a poor onboarding experience.

Another piece is establishing what that sequence is going to be in relation to technology and tools. Since you're starting from a blank sheet of paper, there's no preconceived notions about any other tools or technology, it's basically about sourcing what's going to work best for the organization.

But there's a sequencing involved. And I think that that requires some strategic thought process and collaboration with those who are on board, so you get those shared goals in place and everybody's aligned with what you're trying to accomplish.

Rachel: Step one: become very comfortable with being uncomfortable at the level that you're at. It's really tempting to roll up your sleeves and say, “I'm going to build the best program ever”, and then you realize it isn't working, and you have to do something else.

So you're going to graduate from moments of random acts of enablement, to level two of program execution and thoughtful strategy and being able to zoom out to the satellite view of the business and zoom in to the street level view of what you need to do for the teams.

Then, hopefully, one day graduate to more of a a synchronous go-to-market motion, where you're measuring, you're scaling, and you're integrating on a regular cadence.

Then there’s manager enablement: making sure that you don't forget to coach the coach or train the trainer and building out a program for manager enablement.

The third would be operational effectiveness: your tools and systems, the way you manage your sales enablement team - are you set up for success? Do you have what you need in order to scale the business?

After that, you'd hopefully take on a sales process and methodology launch where you focus on the way that you close revenue, the way that the business grows, how you get there will be iterative, but it will also be very important.

There are three different levels to everything that you do: where you are today, where you're going and where you'll be eventually. And that really just comes down to assessing, planning and building trust, which it sounds like you're doing right now, and moving into producing, training and eventually mobilizing. But good luck, because that's a lot more hiring.

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Read part 2  and part 3 of our selection of the best Q&As from the event.