A survey conducted by Gartner found that 84% of marketing leaders and cross-functional partners experience ‘collaboration drag’ – and those that do are 37% less likely to achieve revenue goals. So, how can you ensure your cross-collaboration efforts enable your initiatives to take flight?
Shawnna Sumaoang: Hi, and welcome to the Win-Win podcast. I am your host, Shawnna Sumaoang. Join us as we dive into changing trends in the workplace and how to navigate them successfully.
Here to discuss this topic is Keith Swafford, the Senior Manager of Enablement, and Allison Gillespie, the Vice President of Marketing at O’Reilly Media. Thanks for joining us, Keith and Allison. I’d love for each of you to tell us about yourself, your background, and your role. Keith, let’s start with you.
Keith Swafford: Yeah, thank you. Great to be here. As you mentioned, Senior Sales Enablement Manager here at O’Reilly. I’ve been in sales supporting roles probably for the last 10, maybe almost 15 years. Within the last 5 or 6 years, been a part of a formal sales enablement group that we have here at O’Reilly. I originally was always more on the conference sponsorship side. That’s where I started my experience within the sales world and supporting sales. And then it’s evolved over through content marketing with what we were doing here at O’Reilly and then eventually into sales enablement.
So it’s been a great journey, balancing between the marketing and sales side, and I love it.
SS: Wonderful. And Alison, how about you?
Allison Gillespie: Sure. So, and again, thanks for having us. Allison Gillespie. So I am the vice president of marketing in charge of kind of everything B2B related as it comes to sales support, everything from leads, trade shows, you know, demand gen thought leadership and then sales enablement. And I’ve been in B2B marketing my whole career, but sales enablement was actually a function that we started probably about five years ago at O’Reilly when we started growing. And so we built it from the ground up and we’ll probably talk about that later, but O’Reilly is an online learning platform that enterprises in any vertical subscribe to upskill and reskill their teams. And so our big focus is on tech teams, but we actually cover all areas of the organization with our product.
SS: Amazing. Well, we are excited to have both of you here today. So again, thank you so much for taking the time to join us and have this conversation. Now, Allison, as a marketing leader, what are some of the key initiatives you’re focused on driving for the business? And how does your sales enablement strategy help you to do so?
AG: Sure. I think like all marketing and sales functions, growth is the main goal, right? So whether that’s revenue growth, customer growth. Personal growth, that sort of thing. So our goals, what we’re measured on is very similar to what sales is measured on and that’s driving pipeline. So that’s true for the marketing team. It’s true for sales enablement team. And we have a couple of key initiatives this year that we focused on. So optimizing our tools is a big one. We have a really, what feels like a really large sales and marketing stack and a lot of different tools that do different things, some crossover between tools, but sometimes not.
And so we’ve really focused this year on getting the most out of each tool. We’ve taken someone from sales enablement to be the lead on the tool, make sure, you know, we’re meeting with the vendor regularly. We’re kind of maximizing our usage. We’re using all the features and functionality that we need. And if we aren’t, you know, find out why and kind of dig into that more, develop communications and training, and make sure our sales team is actually using it in the way they should, and that it’s actually helping them in their day-to-day. So that was one. Another big one for actually our whole sales and marketing team was earlier this year, we moved to challenger methodology, which is a pretty well-known sales methodology.
And that put our entire sales team through the training at the beginning of the year. And then sales enablement has really taken the lead in making sure that we’re continuing to reinforce that training, that we’re providing the content that they need, the courses, the exercises. And I think the big shift there is that. It’s shifting from feature-based selling to more teaching, right? Teaching them about what our product or our service solves. So that’s been a huge initiative and a huge undertaking. And then I’d say just the third one from a marketing perspective is optimizing our marketing channels. Figuring out, always looking at what works, what doesn’t, what creates the most pipeline, how many touches does it take, you know, all of those sorts of things that go into a B2B marketing strategy and then optimizing the ones that do and stopping the channels that don’t. And so part of that is just making sure the sales team understands like, what are these marketing channels? Where are these leads coming from? What do they need to do for outreach? And Sales enablement definitely helps in that aspect of it because they helped create the cadences and the invites and the training around it and things like that. So that’s been kind of our three big initiatives this year.
SS: Amazing. And I love how enablement is really at the crux of making sure that all three of those get landed successfully with your sales team. Keith, how do you bring the sales enablement strategy to life in execution with your programs?
KS: Yeah, I think there’s, I mean, three or four ways of execution, making these things come to life and kind of wanting to deliver on some of those same items that Allison just mentioned. And I always want to keep it, this is what’s worked for us. And so, the first thing that comes to my mind is, We talk about this concept of where we’re actually we are a marketing-run team Like the enablement group sits within the marketing side of the business, but we’re actually a really seller-filled Enablement team so a lot of us actually have a selling background. So either we were supporting sales We have people that come from like SDR roles that decided hey Selling directly wasn’t the best for us But like I want to do this over here and still support sales with people who come from trade show Experiences and doing the sales there. So we have found that’s been a huge win for us of being able to have, yes, marketing priorities, marketing goals. And we fit under that side of the business. But when you have individuals that are on this enablement team that has sold or have supported sales for a long time, it creates, I think, a really effective team to be able to deliver on the things that we need to kind of day in, day out the month, I might want to come to projects.
The second thing that kind of comes to mind is we’re always trying to have, kind of create what are the clear priorities and visions. Specifically from sales leadership in the organization. And I need more clarity and, you know, envisioning goals beyond. These are the revenue goals that we’re trying to accomplish. These are the quotas we more of like what’s going on in the next one to two years in the sales organization that we want to see different. Right? So is that something that’s happening with the product in the branding and positioning, right? That falls to, that can fall down to us. Is there something with the skill set of our team in the next year or two that we want to see shift? If there’s something happening in the company, you know, so whatever level you wanted to look at it, what are those priorities? A 12-month, 16-month vision is really helpful beyond we’re trying to meet revenue, right? We’re trying to grow revenue. I think that’s been helpful for us.
The third thing that comes to mind is making sure our sales teams and our reps actually understand the process and kind of the workflow of working with us. And enablement, you know, does a sales or a sales rep who has a specific request or a project that they would like to see delivered for themselves or for their team. Are they confident with like the process of working with us that they can step in, know when to contribute, and know when they don’t need to contribute any more to keep things streamlined? So I think having consistency or just clarity of this is how we get stuff done as sales enablement and sales or marketing and sales together, I think has been really huge. And then finally, just, we need a home base for sellers, and this is really where Highspot comes in. Do we have a spot where sellers can say, I have what I need, and I know where to find it? I think those four things have been really helpful for us in being able to execute on the things that we want to meet our goals.
SS: Amazing. Now to dig into what you touched on in a few of those components, Keith and Allison, I’d love your perspective on this as well, but what would you say are some of your best practices for effectively collaborating to deliver on your marketing and enablement priorities, Keith?
KS: Yeah, I think the first thing that comes to mind is actually. Knowing and partnering with specific aspirational and talented sellers within our organization, sales, and even teams need to be able to recognize that there are certain people within the sales organization that are really good at what they do. They’re great sellers. And oftentimes other sellers want to copy their work ethic. They’re going to copy their output, right? They’re going to want to take the best things from them. And so I think a big part for us is being able to recognize those individuals. Recognize that, okay, is the output that they’re putting, is it quality? Does it align with what we want to do in enablement and within marketing? And let’s not create from scratch. Actually partner with them in the things that they’re doing. I think of a recent process where we went through and redid our trial process, or we call them content evaluations. And we looked at the data and we had.
I think there was two or three reps and they were all kind of doing the same process because they learned it from one rep that it ended up being like 60 percent of deals were closed if they went through this certain type of content evaluation. And so we all looked at that. We’re like, why isn’t everyone doing this process? The data is so rich. So that’s a great example of like, we’re in enabling marketing. I’m not going to go away and feel like we’re going to magically come up with a great experience. It’s like, no, we’re going to partner with what’s working well and then scale it. And the scaling part sometimes is the tricky part, but being able to scale it in that way, I think has made it really helpful and effective for us.
SS: Amazing. I love that example too, by the way. Allison, how about from your perspective?
AG: I would say hands down, the key to our success is having a partnership with sales. And partnering really closely with them. So we regularly, have a rhythm of communication, right? It’s basically an open door. If you have a question, just ask, there’s a level of trust there. If leadership is behind the sales enablement team, then the wholesale organization will follow. I think each party. Sales enablement marketing and sales, all know their limits. Right. And so we lean on each other. We may say like, Hey, we want to do this thing, but we don’t exactly know how to do it. And so we’ll go to one of our sales leaders and ask them their opinion. And, and it’s very collaborative. And that to me is. What makes it all possible? Because if we were going to siloed and, and I’ve heard, and I’ve talked to colleagues who have very siloed sales and marketing teams, one hand is not talking to the other, and you just don’t have that communication and that collaboration. And to give you an example, I was on a call with a vendor one time that we were considering. Purchasing with our CRO. He was on the call and the vendor was talking about how, you know, one of the reasons we might not have good usage is because sales and marketing aren’t working in tandem and he just stopped the vendor and he said, no, no, actually we are attached at the hip with our marketing team. So that’s definitely not the issue. And it was like the biggest compliment to me and to the team because it was like, yeah, we are attached to the HIP. In many ways, we are one team working towards a common goal. So definitely that is the key to success for us, for sure.
SS: Absolutely. I’m glad to hear that things are Good in terms of collaboration between sales and marketing over at O’Reilly.But what are maybe some of the challenges that marketing and enablement teams can face when trying to bring the two worlds together to support key business initiatives? And how have you guys overcome some of these challenges? Allison, I’d love to send this one back to you.
AG: Sure. This is probably not unique to O’Reilly, but it’s focusing on the projects and determining what is a high priority and what’s not. And so oftentimes, you know, a sales leader will come to us and say, we need to do this thing, whatever it is. And so we immediately get working on it. It’s a high priority. We do all this work. And then it’s like something happens and the priority has shifted and the sales leader has gone quiet or, you know, we don’t hear anything about it anymore, but yet we’ve spent all this time on it. And so it’s really knowing your colleagues, right? And kind of understanding what’s happening in the business and why the attention may have moved off that project and then finding those ways to get it approved and finalized. So, you know, for example, maybe they just got busy and we know they’re busy because they’re working on a big deal or something like that. So instead of pestering them constantly, like what’s going on, what’s going on, giving them some space, coming back to them in a week or go to their counterpart and say like, you know, we’re working on this project. Is this still a priority or not? Here are the things we need. And again, like just giving them the space because we know everybody gets busy and we know for our business that priorities shift and that’s okay. And so just finding those little ways to collaborate and kind of keep the project moving as much as we can. And then if it’s not a priority anymore. And everybody agrees on that, then let’s just stop working on it and we’ll move on to the next thing.
SS: Absolutely. Keith, what about from your perspective?
KS: Yeah, I mean, it’s closely related, right? This idea of you want to get departments that we’re working with, and I think most enablement organizations, they’re involved with so many different teams and so many different departments within their organizations. Everyone has their own priorities, right? So, let’s Take it outside of even just sales, right? We work closely with the editorial group because the publishing background that we have, uh, we have a product group, we have a product marketing group, you have legal and finance, all that stuff like ties back to a lot of the work that we’re doing. And so the prioritization of like all those projects, and I think specifically Clear communication.
Sometimes it’s been hard of being like, Hey, when you make this change over here in finance, it actually affects us over here in sales and what we’re doing in sales enablement or, Hey, in product, when you actually adjust this small item, Here within our learning platform that actually just shifted maybe about 50 conversations in the next two weeks with our sales organization. So I think that’s always been a challenge for us is like, how do we make sure there’s clear enough communication across all the teams that our sales people are the people who are actually, and it’s not even us in the enablement, our sales people are the ones who are actually having these conversations with customers and with prospects. And so when we make changes internally, How do we make sure that that gets communicated all the way down to the sales rep who is really the face of the company and being able to, you know, give reason to give explanation and really to still provide insight to our customers and prospect. Navigating that communication has always been a challenge. And it will be as the organization just grows.
SS: Love that. Alright, so one thing that I really love about O’Reilly Media’s mission is that you guys really have it centered around solving challenging problems and being able to inspire what’s possible. Allison, I’d love to hear from you. What is a challenging problem that you’ve been able to solve for the business through your enablement strategy?
AG: Sure. Yeah. It’s been about five years that we’ve had a sales enablement team. The one that comes to mind is onboarding. So about three to four years ago, the company started rapidly growing, which meant the sales team was rapidly hiring. At the time we just had one person on our team that was doing ad hoc onboarding, the manager would ping them and say, Oh, I have this new SDR starting. Can you do some sessions with them? Talk about this and this, but there was no, nothing was consistent. There was no formal. Plan, anything like that. And so we came together as a team as we started growing, cause we realized this was not going to scale. And we really streamlined the onboarding process. We templated it, and worked with sales leadership to say like, okay, what does sales enablement cover? What do you want to cover as their individual manager? And we took this huge chunk of work off the sales manager’s plate because, you know, at the time they were responsible for onboarding. Now it’s more of a joint effort, like sales enablement starts it. And then once we’re done, you know, we hand it back to the manager and it’s very much a collaborative process. So with that, we were able to reduce the ramp time for new reps. So what used to be, you know, six months ramp time to get them actually out there selling is now down to 60 days or less, depending on the role within 30 days, they’re already hitting the ground running and sometimes actually closing deals within that time. So we’ve seen a really good response from that. And we’ve continued to have growth. We continue to have turnover. We continue to refine the onboarding process as the business evolves. And kind of one of the biggest things that’s come out of that besides the ramp time is actually our HR team has emulated some of what we’ve done. So they’ve seen sort of like, oh, we have a process and a timeline that everybody goes through and they’ve emulated that for just the hiring process in general at O’Reilly. So that was a high compliment, I feel like for the sales enablement team in our work.
SS: I love that. And being able to shave it from six months to 60 days or less to get reps to build revenue for the business. That’s amazing, Liv. So kudos and congratulations on that accomplishment. Keith, how have you leveraged your enablement platform to help solve a challenging problem for the business and inspire what’s possible for your reps?
KS: I think of two ways that our enablement platform, Highspot, has been a huge help since we’ve implemented it. Highspot and its ability to really fine-tune, I think, our sales messaging and positioning have been really strategic. You know, we used to have branding messaging that I think would resonate really well with our prospects and our customers. But previously the messaging was really, you know, It was written and shared for everyone, so it could be for customer success, it could be for customer support, it could be for our frontline sales reps, right? So, we have the ability now with Highspot to really fine-tune that. So if we want to create sales plays, if we want specific courses, specific languages, if we have certain materials that need to be around, we can organize it and like distribute it in a very specific way across our groups. With way more precision and way more accuracy than we ever have.
And sometimes we still needed to hit all of those groups within the same messaging and branding. But for us to have that flexibility in the ease, since there’s such a, the tooling and the, the organization of things is there, it just allows us to kind of do what we need to do from branding and positioning and messaging, and then just deliver those things. So that’s been, it’s been huge to be able to get that specific and be that organized with it. I think it’s been a huge help. And then secondly, using Highspot specifically for the analytics to see which items are critical and which are just like nice to have. That, hey, this hasn’t been touched in three months. Do we need to update this? Do we need to make a revision of this and have those conversations of is this a good resource? If it is, yes. Why isn’t it being used? Just begin to ask a lot of those really good questions. Without the report, you can’t ask good questions on specific documentation that we’ve created. So we’re always trying to ask like, what’s going to stay? What needs to grow? And like, what needs to go? Those are the areas that we want to, Always be thinking about when we’re thinking about asset creation. And I think it’s even, even coursing and training, but that was been really critical with the analysts.
SS: I love hearing that. And you guys have actually seen some incredible progress recently with training and coaching. Our stats are saying that you guys are at a hundred percent of active learners. I’d love to understand what are some of your best practices for creating an engaging learning environment for reps?
KS: I think the first thing that sounds maybe simple is like, you gotta make it required. That is a simple thing and I think that’s a cultural thing. We want to assume you want to show up, and do well in your role. You want to grow in your role, right? So there is this idea of like culture and of wanting to develop yourself and train yourself. So you want to make it required. There are certain things that our sales teams cannot do. In front of a customer until they work through certain training material. And they want to be doing these things. We’re not asking them to do things that are not helpful for their role. So simple thing, the first customer might make it required, make it part of your culture, that this is what we do is we learn and we get better at these certain things.
Secondly, make it short. We fully believe that people shouldn’t have to, not even just sales, but all of us, most people don’t like sitting through a six-hour course on something, right? How do we make bite-size? Learning moments. And really we try to do that even with our own learning platform. And that’s really kind of come into how we develop learning and training at O’Reilly, excuse me, within our enablement team, right? I wanna make this as short as possible, so that way you feel it’s efficient, it’s helpful, but it’s also not taking you away from your work and what you need to do as a seller. So make it short. And then third, make it human anytime. That we in enablement with our training and our courses, if we can interject actually the people of enablement into the material, that’s always better.
It’s always better to have a real human talking over, let’s say, a PowerPoint versus them just reading a PowerPoint that has the text, right? So anytime we can have a more human connection in the learning modules that we’re creating, it’s always better. Because we have that relationship with, with the sellers and, and what they’re doing. So if they’re also then hearing it, seeing it from us, knowing that we support them, it’s always better. So make it required, make it short, you know, make it human.
SS: I love that you guys apply that filter to the way that you create enablement for your field teams. It just makes it resonate and land a lot better with your reps.
AG: And I would add to the make it human is use human language. So a lot of times when we’re putting scripts together and stuff, it’s really easy to kind of fall into that marketing speak. And it’s good because we can check each other and be like, Keith will be like, Alison, people don’t talk like that. We need to humanize this. And like, what would you actually say? And so we kind of use that filter as well. Like if I was talking to my friend, What would I say? Like, how would I say this and put that human element into some of the work that we do?
SS: Absolutely. So, you’ve talked a few times about how important it is to have the data to understand what’s happening and how to use that data to make optimizations to your strategy. I’d love to understand, how you go about measuring the impact of your enablement strategy. Allison, do you have any wins you might be able to share with us?
AG: Sure. So we look at a variety of metrics. Of course, we look across the whole sales funnel and how are we doing? And we look at things like conversion and pipeline being created and meetings being booked. And then how are the deals moving through? Where are they slowing down? If they’re not closing, why not? If we’re losing those deals, why not? Because all of that kind of touch points typically lead back to something we can do, right, to help the sales team, especially if it’s kind of in aggregate. Like if there’s a thing that’s happening in aggregate, then that’s signed to us that like, let’s jump in there and see what we can do. So that’s the big one. That’s sort of the data-driven one. The other one, which is really hard to measure, but equally important is feedback from sales leadership. How is this actually working in the field? What is actually happening? You know, we’re seeing this, but like, what are people’s boots on the ground saying? And this sort of goes back to what, you know, Keith was mentioning earlier about even going to individual sales reps and saying like, rolled out this new thing, is it working? Like, what are customers saying? What’s your experience with it? And so getting feedback loop, I think, It’s also important to sort of measure the impact of our strategy. Of course, we use the metrics from Highspot. Like what are people looking at? What are they using? What are they not using? That actually can even be more telling than what they’re using.
SS: Absolutely. Well, Keith, and Allison, this has been fantastic. I have one last question. Um, Obviously, the enablement space continues to evolve.
I’d love to get a sense from each of you on sort of how you plan to leverage some of the latest innovations like AI to continue to drive impact for the business. Keith, maybe I’ll send this one to you first.
KS: It is a really exciting area and at the same time. We often say at O’Reilly, when it comes to technology, that there’s a difference between what’s hype and what’s actually helpful. So I think that’s very true for Gen AI, large language models and how they can apply even for sales, sales enablement, marketing, what is actually helpful for us as an organization and us as an enablement team, what we’ve begun to explore right now, just custom GPT, right? So how do we take the great things that are happening with the different GPT models and services that we already know most of our team is, is Using, and we’re encouraging them to use, but how do we bring the data set that’s powering those GPTs behind our walls, so to speak, and actually drive change? Really unique situations and scenarios and for our sales reps. So whether that’s kind of role-play simulations that we can use in training where they can role play with like one of our potential buyers of what the, or our potential customer, what that could be like, whether that’s doing really deep account analysis, you know, Compared to the other customers that we have, let’s say a hundred within like healthcare, and we want to know what are their top five priorities in this area, in this time, we can figure that out. So exploring custom GPTs, I think is really interesting for us. Cause if we can. Streamline kind of the administrative work, our sales people. So that way they’re in meetings, right? If they’re in meetings, that is where they shine and we’re doing our best. So if we can actually output that nonmeeting time and get like a 70 to 80 percent quality, and then the reps can do the rest, that’s really huge for creating an effective organization. So that’s one area that we’re starting to explore right now.
SS: I love that. And that would be extremely helpful to your point. Allison, how about you? I’d love for you to close this out on this one.
KS: Sure. So I think, you know, from my point of view and I think sales and marketing both know this, but the way that people buy is changing, some of that’s being driven by technology. Some of it’s just being driven by some of the younger workforce coming in and things like that. And so things like prospects expect more personalized experiences. So trying to figure out how we use Gen AI to create Those personalizations and scale that, right? You know, we’ve got the sales team out there and so we want to have them work smarter, not harder. And so how do they leverage Gen AI for like some of that personalization work, right, or some of the research on an account so they’re not spending, you know, hours researching an account? Now they can spend minutes. And how to do we kind of package that up nicely instead of just saying like, yeah, I use chat GPT, you know, how do we package that nicely for them and show them how to use it to their advantage and really just, To get their productivity to go up and like I said, work smarter, not harder. And so I think over time, especially as more tools come out and AI is being incorporated to all of the tools that we use, so how do we use that and leverage that in our work as well? So I think over time, we’re going to see such a huge shift in not only the way people buy, but also how we as a marketing and a sales team operate.
SS: Absolutely. Absolutely. It’s exciting times. Well, Allison, Keith, thank you both so much for joining us today. I really appreciate the time.
AG: Thank you for having us.
KS: Glad to be here.
SS: To our audience, thank you for listening to this episode of the Win-Win Podcast. Be sure to tune in next time for more insights on how you can maximize enablement success with Highspot.
