Building a Sales Enablement Practice: An Interview with Allego’s Mary Charles

Selling today is harder than ever. Buyers have unlimited access to information and compare vendors and solutions without ever interacting with sellers. At the same time, more teams are working remotely. Managing a dispersed sales team is a unique challenge.

Why are some companies thriving in the current environment while others are falling behind?

The secret is modern sales enablement. Today’s winners are mastering virtual selling with an up-to-date approach to content, tools, and knowledge to help their sales teams succeed. But knowing how to pivot to a modern approach isn’t obvious.

To find out more, I sat down with Allego’s Sales Enablement Director Mary Charles. Mary specializes in leveraging modern learning techniques and tools to enable and train global software sales teams to achieve revenue objectives in a fast-paced, competitive environment.

She’s a sales enablement leader with over twenty years of experience in the software industry, who began her career in sales at AT&T. See how Mary describes her journey and get practical advice for building a sales enablement practice.

Q: How did you get into sales enablement?

Mary: “Before I got into sales, my field was going to be teaching, but I ended up getting a sales job. I had a series of roles in outside selling. Then there were opportunities for me to do training, before it was called sales enablement. I taught other people what I knew from my sales role and then went back in the field again. I did that through a series of jobs at AT&T and at the next company, I did the same thing. I did outside sales, then came in and taught other people. So that’s kind of how it started.

“When I moved to UNICA my role was sales ops. Part of my job was training and enablement. When that role ended up being too big for one person, I had a choice and I decided to focus on sales enablement.”

Q: What is sales enablement? How does it differ from sales management and sales training?

Mary: “Sales enablement is like being the conductor of the orchestra. You bring together all these different parts. The way that you do it is by collaborating with subject matter experts. You coordinate with others to bring skills training, product training, and any kind knowledge that people need to do their roles in sales, as well as the tools and how to use those tools.

“Sales enablement is helping salespeople maneuver through all of those things so that they can be the most successful, which typically equates to selling more business? Salespeople need the right skills, the most up-to-date knowledge, and to be able to leverage whatever tools they have.

“As a sales enablement person, part of my role is not just to deliver formal training, but also to facilitate peer-to-peer collaboration, collect win stories and share them with the rest of the field, get feedback on what’s working and what’s not working, to help translate that to product marketing, for example.

“Product marketing is my closest partner in enablement. In all my different roles, I’ve always been very linked to the product marketing team and I’ve always reported into sales, which is where I think it should be.

“We don’t have sales trainers at Allego. If there’s formal training to be delivered, it’s by the subject matter expert. So it could be the product marketing person, a product manager, or the sales operations person.

“I work with each subject matter expert to help develop something into sales enablement. I show them how to do a blueprint. We map out the areas they need to cover and the benefits, with the key points for each topic so that the session goes smoothly.

“We have a prep meeting and a dry run meeting. I work with them on the communications plan. I help them think about the perspective of the sales rep and what questions they might have and what might be confusing.”

Q: What are your top priorities for sales enablement at Allego?

Mary: “We have three priorities: customer adoption, demand generation, and pipeline progression, so those are what my sales enablement revolves around. Our goal is to have a regular calendar of ongoing sales enablement for the team.

“My priority is always working with sales leadership to identify the needs of the team and constructing enablement around that. For example, we did a formal session on a particular skill around discovery and pain funnels related to our sales training methodology. George Donovan, our CRO, is a subject matter expert, so he delivered that in conjunction with me and the manager of our enterprise team.

“Now people are going out and practicing that in the real world with their prospects. We record those calls, listen to the recordings, and debrief and collaborate on what sounded good and what didn’t work. Then we have a formal assessment process to look at how people have progressed.

“My role was to create the structure for that. I created a formal scorecard—what are we evaluating? What does a 1 to 5 rating mean?—so that as we go through it, we’re all using the same criteria and the rep knows this is what’s expected of me and this is how I’m going to execute around these skills related to this particular item.

“The top priorities for sales this year are demand generation and pipeline progression. For demand generation, one of the challenges is making sure that the seller is identifying surface level pain, business pain and personal pain. We defined the issue, investigated why we’re having that problem, and decided how to address it. Then we use scorecards and measure the improvement of the skill.”

Q: What are some of the biggest challenges for sales enablement managers today?

Mary: “One general challenge is prioritization—working with sales leadership to identify what the priorities are. Depending on the size of organization, it could be a long list and you need to narrow it down. Another is aligning and making sure that you’re focused on what the head of sales is focused on in order to achieve the overall results.

“A third challenge is getting management buy-in to sales enablement and participation. Some of our prospects say “We don’t have a coaching culture” or “We have a lot of sales reps we’ve promoted to be managers, and they don’t know how to do effective coaching.” Having a strong leadership team who is well enabled themselves to be good coaches and getting them to participate is important.

“If you have a good sales leader and a sales management team who believes in enablement, then your chance of success is much higher. The challenge is if you’re only doing formal training using an LMS and it feels like a punishment, then people don’t want to do it.”

Q: What advice do you have for someone building their sales enablement practice?

Mary: “Number one is alignment with your sales leader and buy in. You want it to come from the top. Find a good ally in marketing, whether it’s the CMO, VP, or director of product marketing. Plan what’s coming out with that team, what will you have to teach people, and how will you work with them.

“Number two is to show people that what you’re doing will have a direct impact on their sales results. There’s got to be some “give to get.” If I’m asking someone to do a new certification, I better be giving them something like some great recorded customer stories or top tips from our number one sales rep. If you’re giving them value, then when you have to do something that’s more formal and they need to practice, they’re more likely to do it.

“There’s always a lot going on and you have to prioritize. For example, if you’re doing a product launch, you’ve got to be at least four weeks to six weeks ahead of it. That’s what you have to focus on. There might be other skills training that you can schedule around that.

“I’m part of sales leadership, so I attend leadership meetings. If you’re not part of that, it’s a lot more challenging. You want that team to think of you as someone who understands what the goals are and who’s helping come up with solutions that positively impact results.”

Learn More

To learn more about modern sales enablement, download your copy of Forrester Playbook: Build a Business Case For Modern Sales Enablement.