Episode 164: Ashton Williams on Building an Enablement Function From Scratch

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Shawnna Sumaoang: Hi, and welcome to the Sales Enablement PRO podcast. I’m Shawnna Sumaoang. Sales enablement is a constantly evolving space, and we’re here to help professionals stay up to date on the latest trends and best practices so that they can be more effective in their jobs.

Today, I’m excited to have Ashton Williams join us. Ashton, I would love for you to introduce yourself, your role, and your organization to our audience.

Ashton Williams: Thanks, Shawnna, I’m so happy to be here. My name is Ashton Williams, I’m currently the Revenue Enablement Manager at Ada. Ada helps companies scale their CX using AI-powered automation. I was their first enablement hire, so I’ve been building from the ground up.

SS: Extremely excited to have you joining us, and that sounds like a really exciting initiative over there at ADA. As you said, you were the first enablement hire and have been responsible for building the function from the ground up. I would love to get your perspective on your experience, what are some of the key building blocks of enablement that are needed in order to create a really successful enablement function within an organization?

AW: Oh, such a good question. I think I always start by saying you really need to fail fast. I know that’s not a building block of enablement, but so much of what we do comes from learning a company, learning a culture, learning how that team needs to grow in the strategy. First, I say try things.

One of the things that I started with was really putting together what I call an MVP, or the minimum viable product. What’s that one thing I can get out the door really quick and iterate on? If I think about something like onboarding, which was always the first thing at a fast-growth company that you build, we built something really bare-bones and quick. Then we’re able to get data on that, track that, and continue to optimize that as we grew.

I’d also say, be prepared for having a team one day. When you get hired, you’re usually a team of one and you’re not ready when the time comes and you need headcount. You weren’t thinking about them ahead of time, so maybe you didn’t build things accordingly to bring people on board easily, or you’re making that ask a little late in the game when there’s too much going on. I always say future-proof yourself and be ready for a team and assume you’re going to get it.

Then, of course, that partnership with your managers. Your frontline managers especially are going to be your best allies in building anything. In any enablement function, whether you’re taking organization from good to great or starting from nothing, those have to be the cross-functional collaborators you spend time with as well as your product marketing team, if you have one.

SS: Absolutely. I think that’s fantastic. I imagine it’s not all easygoing, especially in the earlier days, so what were some of the biggest challenges that you faced in your journey as you were building out the sales enablement function? Do you have any advice on how you overcame some of them?

AW: Yeah, I’d say for me personally, I came from a large and established company, and I think I really took for granted some of the building blocks that were already there. They had a culture of coaching, they had wide staff, they had programs that were already built, and you didn’t have to spend a ton of time getting buy-in to make change, if that makes sense. The things you were changing were already part of this large ecosystem. For me, I was new to tech, I was new to startup, and being the first enablement hire, I spent a lot of time just educating on what enablement is.

I think the biggest challenge that I faced was really the Sales Ops partnership. At a fast-growth company, especially a new startup, you don’t have a ton of data or historical models to build off of, you’re learning as you go. While you can look at trends, sometimes they’re short-term, depending on where you are in your growth. I was so used to having the dashboard, the historical metrics, all the activity metrics, all the things to really quantify enablement. I realized that before I could build out a truly optimal function, I had to spend some time understanding our operations situation.

We actually had to get the team on Salesforce. That was the first thing I did when I got there, getting everyone on Salesforce so we could have data, and then implementing some tools so we can actually track the enablement that’s happening. Getting a CRM was not something I expected to be part of in my enablement journey or to be super important for my enablement journey, but just being able to really track activity, what the reps are doing, successful conversations, and find the places we could make those incremental lifts that enablement is usually known for, ended up being my first start.

I’d say advice to those being the first hire or even looking for a job right now is just really understanding where that company is at in their tech stack, their growth, their operations, so that you’re prepared for the challenge ahead of you. I wouldn’t take it back, it was a great learning experience, but I definitely didn’t envision that that’d be the first thing I would do there.

SS: No, I imagine that’s quite a lift right out of the gate. Now, you also talked about one of your key initiatives being implementing the first sales onboarding program, and in a recent interview that I watched of yours, you stressed the importance of onboarding in cohorts to really immerse reps in the culture of the organization. How can that help set reps up for success and improve the impact of onboarding?

AW: Oh yeah, such a good question. I’d say that there are a couple things. Onboarding is probably the one program where how someone feels about your organization is critical to the success of that program in addition to them completing certifications and leading onto ramp. It’s your second chance to make a first impression, especially in a virtual world where we’re starting in our living rooms and bedrooms.

What I’ve seen is when you ramp people together, they tend to move faster. They have a colleague, they have someone at the same stage as them, they can ask those questions. That organic learning even virtually happens because they’re starting at the same place. Also, from a scalability perspective, just being able to run your programs in little batches definitely takes the lift-off of quite a few people and allows you to run that white-glove onboarding that still has your live session, your coaching, and certifications that aren’t all asynchronous at a scale that makes sense for the pace of growth.

I also would say that most, especially in sales, reps are competitive. If the bar is set high by someone in the class, or if you have a bunch of people who are competing, they will finish so much faster. We actually saw that firsthand. We had two people start on their own and not that they moved slowly, they were moving at their own pace, and we had two people join together, and those two people finished the program before the last two who started individually even finished. Those last two caught up. It was crazy to see ramp equalize even though they all have different start dates just based on the pair having started together.

SS: I think that’s fantastic. Now, how do you go about driving adoption and really building excitement amongst reps for a lot of the new enablement programs that you implement, similar to the onboarding program?

AW: Yeah, that’s a good question. I’d say that you want to start with why. I have a sales background myself and I remember being put through training and not really knowing how it was going to help me make quota or why I needed it. Or sometimes, your enablement team gets it wrong on timing and timing matters. In enablement, that’s going to take teams off the floor or it’s going to take time from their day. It has to show a payoff. The same way you would communicate to a customer about ROI, I think you need to do that for your reps.

There’s excitement that you want to build that I’m solving a problem you’ve asked for. Or I understand your world and you’re struggling with this and I’m going to help you get to your goal. Or here’s how much time we’re going to dedicate, but here’s the impact of that that we hope to see. I don’t even think you need to drive excitement necessarily, but you do need to gather buy-in and commitment. We don’t all have to be aligned, but we need to commit. And I’d say for that, my reps have been pretty wonderful, and I’ve had my sales managers really be beacons there.

People care about promotable work, so if enablement’s running training, but managers are like, don’t worry you don’t really have to do it, it’s not really going to help, they’re not going to do it. I think we always forget that we have to go through managers to get things done properly, and to ensure that managers are your vehicles to scale some of those programs.

We always do a pre-launch to our managers, get them to anticipate any questions the rest might have, share what timing works best, what space we should be in. We try to run our programs in collaboration with them.

SS: I think that’s fantastic. Now you mentioned your sales background yourself. How does that help you with sales empathy as you are informing your approach to building new enablement programs?

AW: Yeah, I worked for a sales training company, so I had a pretty unique sales background where I was also selling training, being trained, and acquiring partnerships. I’d say having done the job and actually done the job of a sales manager, it helps me remember what it’s like to carry quota. The stress, the peaks and valleys that come with that. How prioritization of things like enablement or training can be difficult because I don’t have all day to do trainings, I have customers calling me. Or the impact of small things.

I think in enablement, when you get far removed from your team or you lose that empathy for them, you want to build something big and grand and beefy and on paper it looks great, but we’re not thinking about the learner who has to go through that or the person who on the other end has to take that and implement it. That’s when programs often are really a ton of certifications and not a lot of practical application, or they’re long and cumbersome and they don’t make sense and people are working overtime to finish training and do their jobs, or they’re pulling them away from activities that have priority. I think that helps me remember the seasonality of the role as well as how important time and prioritization is when you’re managing customer demands.

SS: Absolutely. Now, I have one final question for you. I had heard you say in a recent interview, you talked about your experience moving from sales into an enablement role. I would just love your tips for our audience, what are some of your tips on how professionals can make that transition themselves into enablement and find the role that really best suits them?

AW: Yeah, of course. I’d say that my search was very much like selling. When I wanted to break into a new industry and a new field, I went on LinkedIn and sent a bunch of messages to ask people who were already in the role, already in the field, for advice of this community, and this community is so wonderful. So many people responded and helped me understand terms of the job I didn’t quite get or things that were unique to that field. I’d say start off by growing your network.

I did that through visiting a ton of open houses for roles and just meeting with people. Enablement is not something that, I’m sure you know, those roles back then didn’t open up very often. People who were in training or enablement didn’t leave. I remember going to startups and going, have you thought about enablement? How’s your team scaling? Have you thought about it? Are you growing? I remember consulting with companies on, do you need this role? Trying to make a home for myself.

I’d say if you’re trying to break in for the first time, do your research on the trade and what that role can look like because it can look very different at a company that’s scaling quickly versus a company that’s in a turnaround for example. Interview as much as possible, get familiar with interviews, even if the job isn’t your favorite job. Sometimes you just learn so much in those interactions or the job description doesn’t describe what you actually see when you get there. Those were some of the best learnings that I had as well.

Then three, oftentimes we get really caught up on not having done the role before or coming from a different industry or not having the experience. Oftentimes sales enablement’s job is to have a different viewpoint. It’s to be between the silos and live in that gray area and see things from the customer lens to help empower your sellers. Sometimes the people who come from completely different places have the best experience and to not be afraid of making that switch based on your past.

SS: I love that. I think that’s such a powerful statement to close this podcast on. Ashton, thank you so much for your time today, I enjoyed the conversation.

AW: Oh, it was wonderful. Thanks for having me.

SS: To our audience, thanks for listening. For more insights, tips, and expertise from sales enablement leaders, visit salesenablement.pro. If there’s something you’d like to share or a topic you’d like to learn more about, please let us know. We’d love to hear from you.

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