Ashton Williams: [00:00:00] This ended up being Slack’s first ever in person kickoff. Morale, retention, feeling connected to the team, attrition, all of those things. Like we saw impact there. The sentiment was just one of absolute inspiration and we made a bet and it really paid off in both what we call overall AEs hitting quota.
Ashton Williams: It’s a great time to be in enablement when everyone is at quota, but also to see like that new product that we focused on. Be our absolute darling. It has continued to be the feature of our QBRs. It’s continued to be the thing we double down on. It has been the thing we’re putting more investment on the roadmap in because we’re moving it.
Ashton Williams: And also, you know, that’s always lovely to see that customers love the things we build.
Steve Watt: Welcome to The Enablement Edge, the go to resource for enablement. And go to market pros. We’re bringing you the secrets, strategies, and tactics that drive meaningful impact. You’ll get valuable insights and expertise from enablement leaders, so you can [00:01:00] become an effective change agent, turn strategy into reality, And transform your organization for the better.
Steve Watt: On today’s episode of The Enablement Edge. First of all, I’m joined by my friend and colleague, Amber Mellano, co host. Great to have you here as always, Amber. And we’re joined by today’s special guest, Ashton Williams. She’s director of Slack Enablement. At Salesforce. And she has some stories to share and some amazing insights for our listeners and guests, Amber, having just come out of this conversation with that, what, what jumped out at you?
Steve Watt: What, what is one of your real highlight?
Amber Mellano: You know, I think one of the things that really struck me as an enablement professional myself was she said that enablements, I was trying to do [00:02:00] more. Without always focusing on the most important thing, and that you’ll find when you do focus on the most important thing, the rest of the things either fall into place or their prioritization becomes clear and they kind of fall off the platter.
Amber Mellano: I thought that was really powerful for enablement folks that are typically, you know, in fire department mode, just trying to put fires out everywhere. That really resonated with me. How about you?
Steve Watt: I agree completely. She and her team did an amazing job of focus and rallying the wagons around that focus and you know, another thing that they did really well is they executed with a degree of commitment that aligned with the importance of this product release.
Steve Watt: I mean, we’re talking about. A really mission critical product release. And every aspect of what they did was aligned with that from the executive commitment to it, to the financial commitment to it, to. You know, flying [00:03:00] all of their sales people to three different locations around the world and doing it face to face because they knew this was too important to do in conventional ways.
Steve Watt: They really aligned the execution with the importance of the mission and that came through loud and clear. And I think that’s a big reason as we’re going to hear from Ashton, why it’s so successful.
Amber Mellano: Really powerful. And what a success story she has.
Steve Watt: Ashton is fantastic. This episode is fantastic. I hope everyone enjoys it as much as I did.
Steve Watt: Let’s jump in. Welcome to today’s episode and Ashton, thank you so much for joining us today on the show. I’m really excited for today’s topic.
Amber Mellano: Thanks for having me. Hey Ashton, we’re so excited to talk with you today. Before we really dive into the meat of our conversation, we’d just like to talk a little bit about how you envision enablement.
Amber Mellano: So, every organization at all different levels of maturity defines enablement a little bit differently. I’d love to hear from you before we really [00:04:00] dig in about what do you think is the most important part of enablement function and how you can ensure success in building an effective enablement strategy.
Amber Mellano: I love
Ashton Williams: this question. So I actually would say I’ve, I’ve done enablement at a few different scale companies, and ultimately our job is to help keep performance consistent through change and through scale. And depending on the size of your company, that can look like different things. You know, I’m at a tech company, product launches are big changes, but I’ve been at smaller companies where it’s really, we’re en masse hiring or we’re changing our go to market.
Ashton Williams: I think the most important thing you can do in an enablement function is How do you keep performance up while we make changes, figure out the business scale, and navigate, you know, the economy and the business we’re trying to provide for? Um, and ultimately, be focused on data. The only way to be able to do that is to always know what are we trying to impact, who are we trying to impact, by when, and know your numbers.
Ashton Williams: So, if I can give any tips on what that means to me, enablement is unlocking impact [00:05:00] regardless of your scale and change.
Steve Watt: I love it. Great guidance. Great guidance. You mentioned product launch, and that’s exactly why we were so excited to have you on the show, because you’ve just come off a big one. And just to set the stage here, and, you know, Ashton is going to really take us into it, but, you know, product launch enablement is nothing new.
Steve Watt: Enablers have been doing it for a long time. But what if it’s a really big, absolutely mission critical product launch? What if it’s global in scale? What if it’s gotta happen super fast? And what if it gets moved up so it has to happen even sooner than you were planning for? Oh, and let’s throw in some executive turnover and all kinds of crazy stuff going on.
Steve Watt: Somehow, this is What you got through and came out in a tremendous place. And I think our listeners and our viewers are going to really enjoy having you unpack that for us. Ashton, take us back a little bit, [00:06:00] set the stage of what you faced. As you moved into this?
Ashton Williams: Yes. Well, once upon a time, there was a Q1 at a little company called Slack, where we were moving into the AI space.
Ashton Williams: And at that time we had really brought on all new executives. I believe it was a new executive every 30 days for about a year. Um, we had moved up our AI product launch to really start the year off with a new SKU and something that we felt was going to be really high impact in the market. And at the same time, you know, we were undergoing the restructures that one does with the merger and acquisition.
Ashton Williams: We were a year or two into the acquisition with Salesforce. So our teams were still getting settled in their new go to market. We did a go to market change, we did a new product, and we got a new executive team. And so, all of this is accumulating while my team is moving. We’re merging into the Salesforce enablement team.
Ashton Williams: We’re getting our executives settled on the Slack side, and we’re trying to think about how are we bringing this big product, which is our big [00:07:00] bet, this year, um, to market. I also would be, um, Remiss to not acknowledge that, like, at our scale, my product marketers and my sales strategy and rev ops people are our best friends.
Ashton Williams: This launch was certainly not done in a silo and certainly not just held by enablement. It takes a strong product marketing team to give you product market fit and all that messaging to be able to go into high impact learning. And that was really where we started from, which was great.
Steve Watt: And we’re talking about thousands of sellers around the world, and you are on a short timeline.
Steve Watt: You are enabling them on something that was going to make or break their year.
Ashton Williams: Well, what made this extra special is, um, you know, we have sellers at Slack that sell Slack product, but we actually felt, what if all of Salesforce could just benefit from it? If you’re a Salesforce customer. Why wouldn’t you want to buy the other products that they have?
Ashton Williams: And so not only were we teaching our own Slack sellers to be specialists and experts in our product, [00:08:00] we were also opening up that selling motion to every seller at Salesforce. So we had a dual initiative. Teach our folks to be the best there is and have them help, you know, the new folks that are onboarding to selling Slack for the first time in the midst of a launch of our AI product, which is new to everyone in the market.
Ashton Williams: You know, it’s been around for a little while, but still needs to be demystified. Customers still have lots of questions and AI is kind of our future right now. So in Q1, it felt huge.
Steve Watt: And you went all in, right? This wasn’t just the number one priority. This was it, right?
Ashton Williams: I would say. We went all in in so many ways on this product, uh, from how we built it, from how it got moved up, from what it got integrated into to really trying to understand who could sell it, making sure the whole world could have it as close together as possible.
Ashton Williams: And We doubled down on technical enablement for this. So our solutions team went through a certification. Then we went through our sellers and we brought our [00:09:00] CSMs into that. And so everyone had to be an AI expert as being part of Salesforce anyway. That’s part of our strategy, which, you know, we’re looking to be the number one AI company.
Ashton Williams: Um, but with this new SKU launch in February. We all had to be ready to go, um, alongside the wider company motion. How we did that is we were also doing a kickoff. And so the way Salesforce works, which is important for everyone to know, we do something called go for growth every year. Everyone knows your books are going to change.
Ashton Williams: We’re going to have a kickoff. February is your time where you get settled in your accounts and you get your new book and you go through all your kickoff motions. There’s the company kickoff because we have a number of products and launches that are happening. We double down on messaging and what you need to know.
Ashton Williams: And then we have your region and industry kickoffs. And that’s where you’re really sitting in your teams, going through your account plans, and really getting a head start to the year. And we call this fast start. All of this must be done by February, usually. And as you can imagine, you know, as big as we are with many products, we are getting airtime [00:10:00] can be quite challenging.
Ashton Williams: And so we actually did a dual motion, one where we ran sessions for our Salesforce core sellers. So the folks that sell Salesforce product, we were in Vegas, we were in person, we had training for all of our leaders. And then in those regional sessions, We delivered there and our product marketers really were the stars of that delivery as long as our solutions folks.
Ashton Williams: And then we actually led Slack’s own kickoff, which we did in person, three regions. So all of America’s flew to one place, all of APAC flew to Sydney and everyone in Europe flew to Dublin. So we ran three simultaneous in person live kickoffs right after coming back from our February of kicking off in Vegas.
Ashton Williams: And kicking off around our offices. Uh, to say that I traveled a lot would be an understatement during that time. But what was really special about that is, is it was a virtual experience because we had to connect three regions in one time zone and make it work. But it was also a local experience of [00:11:00] my industry, my country, my language to unlock learning.
Ashton Williams: And I think that. It was just a behemoth of a project and it, it paid off.
Amber Mellano: One of the things we talked about on our pre interview was the fact that you went all in on this new SKU. As we’ve just heard, all of the effort that got put into doing that. How did you do that? How did you figure out, how are we going to pull this off?
Amber Mellano: I think one of the things that you said is enablement teams are used to trying to focus on all the things and what’s more important and you got to, got to focus on what’s most important and all the other things will fall into place. Tell us more about that mindset.
Ashton Williams: I’ve always been of the mind that you cannot do everything very well and even if people ask for everything, they probably need one or two things.
Ashton Williams: So, you know, as a leader to really support my team, it’s my job to narrow down those priorities and get us focused on what we can actually have impact on. And we had another new SKU that had just come out like six months earlier, and we were doubling down on major innovations for that. We had nine other [00:12:00] releases happening during that time.
Ashton Williams: Salesforce was releasing AI product at the same time. In addition to, you know, in every country, there’s a little bit of nuance of what we’re releasing within a feature set. And so. There were a number of things we could have done, and we could have spent time on skills. We could have spent time on, you know, the thing we thought was going to move enterprise business, but we actually narrowed it down with our sales strategy teams to go, what’s the addressable market?
Ashton Williams: Where’s the big bet? What’s going to start in Q1 and close in Q1? And what’s going to give us the best opportunity? The most bang for our buck at this time. It’s got to be just easy enough to understand, easy enough to move. Do we have the runway to really train people to be experts at this? Do we have the runway to get our technical experts up to speed?
Ashton Williams: Because an AE and an SE are absolute best friends or solutions engineers, what we call them. And so we really had to think about where can we have the most impact and the wave of AI was happening. So that was in our favor, but also, uh, we It wasn’t a super complicated product, which [00:13:00] meant you could go deep on it and you could move it forward and you could explain it to customers.
Ashton Williams: Our FEPs could actually learn that and master that in a quarter. And we decided to double down on that being, yes, we’re doing other things, but if you walk away with one thing, it’s going to be Slack AI.
Steve Watt: How did you manage the tension, the competing demands from different product owners, different part of the business?
Steve Watt: Was it like, Hey, what about our products? What, what about our focus? We’re important, too. This is important, too. I think you’re over rotating on one thing. As important as it is, you know, you need to support our stuff, too. Surely you face that. We all do. How did you, kind of, not only first gain that focus on one thing, but how did you maintain it?
Ashton Williams: So I will say this is a testament to a really strong executive team. I love this role because I love the executives that I work with. They came in and were very aligned and committed to what they were going to align on. So we were [00:14:00] fortunate that this conversation wasn’t as painful because And they also saw the need to, you know, they’re new here, so they also have to focus on the what they can do right now.
Ashton Williams: And that worked out. I think in the wider company, the tension we have, which any acquired company or brand under a brand is going to feel, is there’s the corporate tax of what’s happening en masse, and there’s what’s going to move this business unit forward. And I think we were really fortunate that we were In that February time, we were focused on being a part of what’s going to move the business forward.
Ashton Williams: And then in March, when we did our own kickoff, we got to focus on what’s going to move our business unit forward. And we made the trade off of spending the money to bring people together after kickoff, um, and doing our own. Uh, and that was a decision made with our CEO, CRO and CSO and, and CMOs. And so I would say we had a really aligned team.
Ashton Williams: Leadership team that felt like we needed to have the time carved out. We needed to come together, but we also needed to participate and we just extended [00:15:00] our time a little. And the trade off could have been that we learned too late in Q1. We didn’t make pipeline, but that actually didn’t end up being the case, which was great.
Ashton Williams: So it was a risk, but the rewards were great.
Steve Watt: You were mindful that there may have been some necessary pivots along the way. Were you able to kind of. Maintain focus and clarity, but also a little bit of flexibility.
Ashton Williams: Yeah. I think the, one of the reasons I’m forever proud of this project, I think is it’s an enablement.
Ashton Williams: We often try to avoid the pivot. We want to get on the track and we want to have no more changes. And we’re really frustrated when our leaders change their minds. Right. But if you are keeping your eye on the business, anyone, I’ve, I’ve been in sales. I’ve been a sales leader, you know, week to week, you get new information.
Ashton Williams: It’s like, when you’re talking to a customer every week, you’re asking them, is this still a priority? Has anything changed? What’s going on? And we actually managed our working groups and executives in the same way. Hey, it’s a new week. Here’s where we left off. Has something changed? We need to consider something else to something to add or drop.
Ashton Williams: Are these still the priorities? And it was my [00:16:00] role to really make sure that every week we were checking in, is this still it? Are we still betting here? And so instead of trying to shield and protect from a pivot, I really prepared my team that like, Hey, this week we’re going to ask some questions. You need to be clear on how far along we are, what the risks are for a change.
Ashton Williams: I need to know that because I’m going to ask, okay, is there new information? And every meeting there was, every meeting we got proposed a pivot. I’m not going to pretend that did not happen, but I was prepared to go, okay, let’s say you pivot this today. We are now 60 days out from the event. People are flying in, speakers are aligned.
Ashton Williams: So you have two weeks. To sort it out and fly someone new in, and I don’t know that that risk is worth it, right? But I often say, you know, you hear someone say like, but the executive said. That is my most hated statement of like, why are we doing something? If you provide executives with visibility into the risks and what’s happening, they’re gonna make an informed decision.
Ashton Williams: But if you’re like, hey, what about this? They’re gonna be like, great idea! Sure, of course you’re going to get a guess, it doesn’t [00:17:00] sound bad, but when I present the risks or what the trade offs are, then we’re really having a united conversation. I think at Enablement we forget that our job is also to showcase risk.
Ashton Williams: If you change here, we lose momentum, we’re pivoting the field, our focus might look different, we’re cutting that timeline on getting the pipeline and getting people doing the thing. And we forget to say that sometimes in the meeting where we’re like, we just don’t agree. And I’m like, well, but why? And so I think You know, and, and I hope, hopefully my executives feel this way that I wasn’t super annoying asking that every single week, but it really helped us all Get back to like, why are we doing this?
Ashton Williams: Are we clear? And by the time we got around, like everyone’s just on the bus. And most enablement initiatives, it doesn’t even have to be the best initiative you ever run. But if your sales leadership, your executives, and your teams are on the bus, It’s always going to be great because that’s what we always strive for, right?
Ashton Williams: Is everyone engaged and going in the same direction.
Amber Mellano: That’s amazing. We talk a lot about, um, enablement [00:18:00] having a seat at the table on this podcast. And I love that what you’ve just described is enablement helping the entire business stay aligned. And keeping in mind, based on data, to tie back to what you told us in your initial statement, you had the data of this is the cost of pivoting now, this is where we’ve already gotten to, this is what we’ll have to do if we do pivot, and helped everybody remain on task, on goal, and, uh, and that’s a powerful, powerful motion to be able to keep that going.
Ashton Williams: Yeah, I, I always want to add here, because I think when we say data, it can be so scary. I didn’t have the sales data. I didn’t have the total addressable market data. I certainly didn’t have the product data, but I had to have my data. And so my ask was always, what data do you have that, that might inform this?
Ashton Williams: I can tell you. The logistics that are going to shift, the costs that are going to move, and the impact of the learning, because that’s my job. But, I didn’t need to know or stay on top of every single sales deal that might have pivoted while we’re talking about something, right? That, that is questions to [00:19:00] ask, and I think we also, and anyone can get really scared about having to have the same level of data that our sales leaders have, as opposed to knowing what questions to ask, knowing they hold.
Ashton Williams: Quite a great deal of it. And that’s actually where I say my PMMs, my sales programs and strategy folks, like I know what data they have and are responsible for, and I know what data I have to have and being able to have that gives me freedom to go. I know, you know, something here’s where I’m at. Where are we going?
Ashton Williams: Yeah, that’s amazing.
Steve Watt: Let’s talk tactics. Let’s talk specifics. What did this enablement look like?
Ashton Williams: Yeah. Let me tell you about the program. Cause I think this was. This was such a fun one to put together and it came across so many teams to think through how to make this great. So basically if I talk about the learning journey here, the first stop was our leaders flew to Vegas in person and had a live session where we actually provided something called an EDO.
Ashton Williams: Basically, it is a demo org made for our AEs to be able to demo our product. It’s a demo [00:20:00] that allows them to show their Slack instance, right? Without necessarily showing their personal Slack instance. But getting everybody hands on in the product and really learning about the innovations as they’re going through that demo became really powerful.
Ashton Williams: So all our sales leaders went through that. Then they went into their kind of regions and kicked off with their respective industries and they got sessions on, This product for this industry. So they could really make product make sense in the context of the industry or country with which they sell.
Ashton Williams: And those were, you know, webinars that we ran globally that moved through different teams. Then we went into a certification and so they had about six sessions on AI where we did Q and A. We brought AI scientists, we brought our solutions in and everyone had to really double down on like, what does this mean?
Ashton Williams: As overall business trend, but also what does this mean in this product and how does it work and how does it impact our customer’s business? And they went through a whole series and then completed a formal certification, which was competitive positioning, [00:21:00] nailing that demo, AI, our other SKUs. And then we ran a separate certification for our solutions engineers to also be able to nail all those things.
Ashton Williams: And we broke the product out by basically line of business. So like, who are you talking to? And what is the story for that person? Is it a CRO? Is it a CMO? Is it a CSO? And so we were really able to create the container that makes product knowledge land. I think when we just talk about product, you’re asking sellers to do a lot of work to make sense of product on its own, and we forget that the containers they live in is Who am I talking to and what industry?
Ashton Williams: If you tell product without those containers, it takes so much longer to learn. And I think what we did really well in this was either this thing doesn’t need a container because it’s actually that big. Or here is how you would say this to this executive in the room. And this is what you would show, say, do.
Ashton Williams: And for the one layer down, what would that look like? And instead of spending so much time on how does this work or this new [00:22:00] cool thing, we really went, what’s the conversation you’re going to have and how do I prepare you for that so that you can answer the questions the customer’s going to have? And I think that that really lended itself well to people feeling confident.
Ashton Williams: We also had live pitches and we made people do it in person. We love a show, you know, but I think it was a combination of, you know, The learning container, the hands on practice, and then leaders, because they went first, were equipped to actually reinforce and coach, and they could run that exercise any time they needed.
Ashton Williams: And I think that’s really what made it special, is it engaged every section that an AE has a touchpoint with to learn.
Steve Watt: You were very quick to celebrate your partners in product marketing. You made it very clear that this was a joint venture and a strong partnership. Tell us how that comes together and works well.
Steve Watt: Because in some firms, there can be There can be tension there. There can be tension over who owns what, there can be tension over priorities and, and a whole lot more. How do [00:23:00] you, uh, work with them such that that really is a powerful partnership?
Ashton Williams: Yeah, you know, I’ll say it took us time to get that right and tension between PMM and enablement is like tension between sales and marketing.
Ashton Williams: It’ll always be there and it’s a healthy one. Right. We’re both trying to do our best work and we’re going to step on each other’s toes sometimes. And that’s actually good for the business. Um, I think my attitude towards that also makes for a little less tension, but I would say we were able to get to kind of freedom within a framework.
Ashton Williams: And so we set out early on to say, you know, we own X, Y, Z. And these are the things you can trust us to deliver. You do not need to figure out where people are going. You don’t have to be able to logistics of the event. You don’t need to figure out how long a session should be. You do not need to rally the sales leaders and get them all involved.
Ashton Williams: Like we got you, but what we do need from you is solid vetted content. So you need to make sure. That all the leaders are bought into the messaging that you’re presenting. You need to preview that [00:24:00] with them. You need to be sure that how we’re going to market is staying and not changing. We need the demos.
Ashton Williams: We need the decks. We need the customer stories. If you have that bill of materials, Our job is to make you look wonderful and make it hit the field in a way that resonates that lands and that has impact. And we share those wins. But what we’re not asking you to do is run training and figure out the best way to deliver that.
Ashton Williams: Sometimes we’re asking you to be the speakers in the SMEs, right? And I think, you know, Because of just how condensed this event was, it forced us into like, I actually can’t do more than this thing. And that became freedom for everyone to go, I own this, I know what I own, I know the person to go to, I know whose name I go to for this.
Ashton Williams: Um, I also within my team gave them So they had like one person owned content. Their job was like sales leaders and PMM, like dry runs, making sure the content is vetted, checking in on it, pushing deadlines. One person did that and another person had logistics. Do we need to move buildings? Are invites [00:25:00] going crazy?
Ashton Williams: Because now that we have a kickoff, everyone’s inviting everyone and we don’t have time. You know, how are we moving people left to right? How are we getting things virtually connected to the other regions? How are we organizing the other region’s schedules to overlap with us? And those swim lanes really helped.
Ashton Williams: I think they’re challenging and my team will tell you they were challenging, but having a single point of contact also meant full visibility to be able to unblock red tape. Right? That person sees all the content. They can tell you if that deadline is real or not, if that matters or not, who’s, how many people are going to be in that room or not.
Ashton Williams: So they could also unlock things like when other folks get stuck. Um, and vice versa, our PMMs were really focused on that event that went outward to kind of our internal Salesforce partners while we were focused on the event that was inward to our own Slack sellers. So we also even divided and conquered in who owned what part of those events.
Ashton Williams: They took the lead there, we took the lead here, and you know, sales programs underneath was like, we got your numbers, we got your headcount, we’re going to tell you [00:26:00] if something’s changing. Um, and that informed what became kind of a smaller workshop versus an overarching theme of the event or launch.
Amber Mellano: Tell us a little bit more about the outcomes that you got to. This is such a great story. We want to give you a chance to really bask in the glory of all of the things that you accomplished. Can you share some, some of that data with us about
Ashton Williams: your, your accomplishments here? Yes. So I can’t share everything, but I think what I can share are there, there were three main things that we set out to do.
Ashton Williams: So one, we had an entirely new executive team and a new go to market model. People’s jobs changed and we really wanted people to feel connected to their teams. Like that this change was exciting and to see the path forward to success. This ended up being Slack’s first ever in person kickoff. Some people had not met despite being at the company for years.
Ashton Williams: Um, and we didn’t do it in San Francisco, our headquarters in San Francisco. So everyone was like super happy to fly somewhere. So it felt extra special, but I would say just overall, like morale, [00:27:00] retention. Feeling connected to the team, attrition, all of those things, like we saw, we saw impact there. The sentiment was just one of absolute inspiration, and I know we all feel rah rah after a kickoff, but it has shown through.
Ashton Williams: We’re, we’re well into Q3, and people still feel like that was the best. We still get compliments on like, that was the best event I’ve had, and I feel like I love working here. So, that’s always great. The second is, the SKU we focused on ended up being an A. Absolutely impressive motion. It became one we could move quickly on.
Ashton Williams: We were hitting insane targets. Uh, most people at a hundred percent, if not more year over year, we saw things like for this one forecast up 60, 30, 40 percent in different regions. Um, we also were accounting for a pretty huge chunk of Salesforce’s overall AI business and for how small our cloud is, that’s really impressive.
Ashton Williams: So it was an unlock, I think, of. We made a bet and it really paid off in both what [00:28:00] we call overall AEs hitting quota. It’s a great time to be in enablement when everyone is at quota. That is the best feeling. People are happy, they’re making money and we love that. But also to see like that new product that we focused on.
Ashton Williams: Be our absolute darling. It has continued to be the feature of our QBRs. It’s continued to be the thing we double down on. It has been the thing we’re putting more investment on the roadmap in because we’re moving it. And, and also, you know, that’s always lovely to see that customers love the things we build.
Ashton Williams: And then the third was really, we were pulling together a global team. So our teams were actually segmented by country before. They didn’t all ladder into one leader. And this time we actually pulled everyone back. under one leader. So they were a unified global team after having been disparate for a year.
Ashton Williams: And the scale and, and logistics and translation and learning and nuances of really orienting three mega regions across different countries and languages. And we still had some [00:29:00] folks who like dotted line reported out, but we invited them to really figure out all those audiences. And making it make sense for them.
Ashton Williams: That was also something that I would say we still, people still go back and are like, can I just have like the kickoff document that has all the videos? I want to see that again. Like, that’s what people are still coming back to. But also that people felt unified even when they didn’t report into us. And I think that that tells me that we did a great job.
Ashton Williams: People are proud to be in their seat. They’re proud to sell the thing they’re selling and we sold it like hotcakes and we still are.
Amber Mellano: What a success story from start to finish. Everybody involved. That’s exciting. What about any things you would, you would do differently or looking back, you would maybe have changed your approach?
Ashton Williams: Yeah. Um, I would say in this specific, specific instance, the runway, like more time. I don’t think any answer other than more time would have been like, everyone will say that. I think we had about a 60 day, maybe 75 day runway from like we decided to do [00:30:00] this to like we had it. So, um, that’s a really short runway to move that many people around the world.
Ashton Williams: Uh, it cost us a lot more because of that runway. Uh, so I would have loved to have more economies of scale there. Um, but honestly, with a new executive team coming in, I don’t think we could have. I think the only thing I would have done differently is, um, based on this timing, we had half of our go to market.
Ashton Williams: So we had sales and solutions in person with kind of leadership from our post sale orgs because we just couldn’t move that many people around. And I think if I were to do it differently, the only feedback we got was, it was just such a mess. To not have everyone there, but with 60 days out and no event space booked, we just couldn’t fit everyone.
Ashton Williams: Um, but I think figuring out just a better way to include them because realistically, if we sell something like hot stakes, our post sale team has got to make, help customers see value from that. And I think there was a bit of a [00:31:00] lag on like getting them what they needed because we focused so much on the pre sale motion during kickoff.
Steve Watt: Sounds like the old adage, don’t let perfect be the enemy of great or enemy of good. What you did was great. Was it perfect? Well, no, but whatever it is. And you could have spent two years planning perfect. And by then it would have been too late. So it sounds like a tremendous triumph and something that you and your team.
Steve Watt: And I mean, not only your enablement team, but the broader team should be very proud of. Uh, Really glad that you shared those stories with us. Let’s close out with just a few, uh, interesting, thought provoking questions that we’ve been asking a lot of people. The first one is what do you think is going to really change in enablement over the next 18 to 24 months?
Ashton Williams: Oh, that’s such a good question. I do really think that AI is changing. or modernizing [00:32:00] enablement. I think there’s like a part of our role that is strategy and aligning our leaders. And then there’s like the tactical things that we all do that are the stuff we love, you know, the instructional design, the building of a great session, the designing of a program.
Ashton Williams: But then there’s those things that really complement that. Your comms plans, how are you moving things through programming, data. And I think AI actually lifts a ton of that admin work that used to be insurmountable in order to get to clear data or just like finishing a program’s launch, you know, I think, I think that will really force people to Who lean heavily on the administrative and tactical.
Ashton Williams: And I think a lot of sales leaders who don’t understand enablement lean on their folks for that. Hence we get event planning or, you know, please write all my comms. Um, but I think AI really changes how much weight those hold. And I hope that that frees us up to be strategic partners and consultants and make it easier for us to grab the data and the things we [00:33:00] need to show the value.
Ashton Williams: But I do think it changes our jobs a bit. Like AI can coach someone today. Um, AI can be a one on one assistant to a rep. And so we used to have to think about how to get to those things en masse. So I think we’re going to have to modernize our approach to. Learning for impact. And I think AI is going to be our friend in that.
Steve Watt: What is never going to change?
Ashton Williams: I think what will never change is the need for internal education to keep sellers sharp. I don’t see a world where you can launch a product, make a big change, put a new tool in place, change your hiring profile. And not have a dedicated team to support that and be successful as you scale.
Ashton Williams: So whether it becomes, and I actually joke around this, like, enablement is born of the original HR functions of a factory, right? We are the, the, how do you not get hurt on the assembly line team? And then, oh, how do you learn to be more efficient on the assembly line team? Okay, [00:34:00] we’re no longer an assembly line, so there’s more to learn.
Ashton Williams: Um, whether we fall in an education arm under people or we report directly in the sales, I just, I don’t think any company can safely scale and protect their investment without investing in their people. Uh, and I think sales specifically requires a unique investment that is not the same as company productivity, and I feel like that will never change.
Steve Watt: Final question, Ashton, what’s the best piece of advice you’ve ever been given?
Ashton Williams: So I once had a mentor, a boss, I was a bit earlier in my career and, um, I was just freaking out. We had, we had like a hundred things happening and I didn’t know what to do and I was asking him like every two seconds, like, what do you think of this and what do you think of this?
Ashton Williams: Um, and you know, it’s, it was similar to the kind of enablement CRO relationship and he sat me down and he was like, you know, I hired you because I think you are the best person [00:35:00] to decide our way forward. I don’t know how to do your job. I need you to know how to do your job. And if you don’t know, I trust that you’re going to go learn and network and bring back things that I personally cannot do.
Ashton Williams: And I think at Enablement, when we’re seeking alignment, sometimes we’re seeking validation for our choices as opposed to going, no, I I’m the expert in how people are going to learn this best. I’m the expert in how I know you want to shout 30 things at people, but like, you want them to do X. And really taking ownership of like, that is our wheelhouse.
Ashton Williams: That is the place our toes should not be stepped on. Um, it’s so easy to forget when we’re seeking kind of alignment or if we’re in an uncertain climate. And I think that advice is one I come back to all the time. There’s sometimes where I’m doing something out of scope and I’m like, How should I do this?
Ashton Williams: And then I’m like, you know what? It’s being handed to me because nobody knows how to do it. And so I got to figure it out. And that’s just business. Um, but I’m so much more peaceful about that. [00:36:00] And it was funny, like it was a real conversation where I was like, Are you going to fire me? And he was like, No, no, what?
Ashton Williams: He’s like, I just want you to like, trust yourself and like, whatever call you make, like, If it’s bad, we’ll figure it out. But like, I don’t know a better call than you do. And I think sometimes we underestimate ourselves and the, the, we have a wide angle lens on the business. I always want my sales leaders input.
Ashton Williams: They know my customer better than anybody, but they don’t know all the things that are moving. They don’t sit with finance and CHR chats. And like, we just have this wide angle lens on the business. We really need to remember that that is a superpower to be a consultant here.
Steve Watt: Excellent advice. Sounds like an excellent boss too.
Steve Watt: Really appreciate you sharing that and sharing everything that you brought today, Ashton. I find The stories you tell, the insights you bring, and the way you bring them with just so much passion and so heart, so much heart. I find it not only a real education, but a real inspiration as well. Thank you so much for joining us today.
Ashton Williams: Thank you so much for [00:37:00] having me. It was a pleasure.
Steve Watt: Thanks for joining us on The Enablement Edge. We’re on YouTube, And all your favorite podcast providers. See you next time.
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