According to research by G2, organizations with a sales enablement strategy achieve, on average, a 49% higher win rate on forecasted deals. But to see these kinds of returns, you first need to get sellers, leaders, and the business itself bought into the value of enablement. So, how do you build confidence in the function’s value across stakeholders at every level of the business?
Riley Rogers: Hi, and welcome to the Win/Win Podcast. I’m your host, Riley Rogers. Join us as we dive into changing trends in the workplace and how to navigate them successfully. Here to discuss this topic are Mateo Perretta, senior director of revenue enablement, and Bety Garcia, sales enablement program manager at Loopio.
Thank you both so much for joining us. I’m really excited to have you here and to learn a little bit from your expertise.
Before we kick off, would you mind telling us a little bit about yourself, your background, and your role? Betty, maybe can we start with you?
Bety Garcia: Yeah, no, thank you for having us. I’m a sales enablement program manager here at Loopio. I’ve been in enablement for a little bit under a decade at this point.
I’ve always been part of pretty small teams, so I’ve had to be pretty creative when it comes to, you know, how do we get a whole bunch of different initiatives done across the board.
RR: The story of scrappy teams and figuring it out is one that a lot of folks in enablement know well, so I’m sure there will be a lot of similarities in what you have to share.
Matteo, would you mind telling us a little bit about your journey?
Matteo Perretta: Yeah, absolutely. And thanks for having us today. You know, it’s interesting. I tell a story about, I started my career in telemarketing. I was in sales support did sales myself.
I became a sales leader. And then I stumbled into this thing called sales effectiveness, sales excellence, sales enablement. It’s changed over the years, but probably in 2010 when I stumbled across it. And what I’d like to say is I’ve moved from the game of quantity to quality.
RR: From your perspective, having now stumbled into sales effectiveness, now sales enablement and led it at several different companies, how would you define what great enablement looks like, especially for growing GTM organizations like Loopio?
MP: I’ve walked into sales organizations and the first feedback I get is, we’ve done way too much enablement. We really haven’t had any time to digest it. And that’s usually a symptom of teams being reactive.
What I mean by that is sales leaders and salespeople will come to you and tell you they need all this enablement and you just keep filling that funnel and you almost become a catch-all for everyone versus being proactive and really looking at, you know, data and insights to kind of figure out what do we need to do and how does that actually align to the KPIs or the results and what the organization’s ultimately trying to do?
And so for me, it’s really understanding: “What do we have, what are our assets, and how do we align them to our goals?” When you do that, you become a partner and you show them with insight what’s important versus just, you know, being this order taker and doing a lot of enablement that just isn’t resonating.
RR: The other piece of the puzzle is giving enablement the agency to kind of direct course and build a strategy with sellers in mind, but also not built for every single thing that every single seller needs, because that is an endless hamster wheel that you will never escape.
So I love that call out and I’m curious to hear how technology fits into that when it comes to building a great enablement strategy. Betty, you’ve been with Loopio through a couple of enablement tool changes, including when Loopio made the decision to step away from a previous tool and kind of run without one for six months.
Can you walk us through what wasn’t working then and why for a little while maybe no tool was better than the wrong tool?
BG: It wasn’t so much that we had issues with the tool itself, but more so what it had become at the time. Right? So like we have a ton of unorganized, outdated content in there. And the problem with something like this at the time is that users don’t tend to be loud about those issues. They tend to just find workarounds.
On one hand, you might have, you know, top performers starting to create all of their own content that maybe they share with a few individuals and those individuals might share with others. On the other, you have the opposite of that, where you have a whole bunch of outdated content out there that’s just circulating.
And so what this creates is a few different challenges for the team that doesn’t necessarily go noticed right away, which is that the messaging becomes completely random depending on, you know, who knows what, their experience level. That then translates to performance.
So, now it’s not just an issue of, you know, do we have a good source of content for everybody to draw from? It’s, you know, how do we get everybody back to performing at the same level with the same level of knowledge and the same level of information?
So that was sort of like, you know, stepping back. That was the real challenge that we were looking to solve. And part of what, having that time in between not having a tool and then looking for a new solution to bring into Loopio was having the time to plan for that, right?
If we’re gonna do this, how are we gonna do it? There was a lot of planning involved in that and really trying to make that decision and, and started to tie it to the real business challenges that we had there, which was how do we get everybody working at the same level once again?
RR: Yeah. And I’m really excited to dig into how you rebuilt that trust, because that’s not easy. So, we’ll touch on that in a minute. I want to start with the decision over that six-month period to strategize how we’re gonna rebuild and then who we’re gonna rebuild with, and eventually that decision led you here to Highspot.
Bety, you mentioned that you’d launched Highspot at a previous company. What made you confident over this time as your planning, planning, planning, that this would be the right tool and you’d be able to build that trust in that confidence with your users with it?
BG: I think it, I mean, I had a huge advantage, right? Because I had done it a few times, and I mean, had a great positive experience working with the team at Highspot, but also I knew that it was a really great tool, right?
It sort of sells itself when it’s launched correctly, right? So instead of evaluating the tool itself, from that standpoint, it was like, great.How do we get strategic about doing a launch that’s gonna be really impactful.
And that looked like doing cross-functional partnerships. So working with marketing and product, it wasn’t just an enablement initiative anymore. We really did spend a lot of time doing a ton of content review across the board and reevaluating what it was that we wanted to arm the team with. And then in fact, actually starting to anchor some of our own enablement initiatives into the launch of the tool itself.
So when we did launch Highspot at, we actually also relaunched our onboarding program and we launched a whole new product to enablement program. Now, we were touching on the needs of marketing, the needs of product, the needs of our sales organization when it came to even just onboarding and starting to ramp up ours. And we could really start to show that impact very quickly across many different areas.
RR: So from that moment, you’ve reached a pretty stable place with the platform and have built out a really robust environment that, just looking at the data, is well utilized by your teams. Matteo, from a leadership perspective, as someone who came in a little bit post-launch: When you joined Loopio and started looking at what you wanted the strategy to look like and the enablement approach to look like, how did Highspot start fitting into your vision as you were thinking about high priority initiatives, things like onboarding, things like, you know, Loopio’s, monthly product launch cadence?
MP: Yeah. I mean, I think it’s interesting when people say enablement or to define enablement, it’s what’s the modality? And I think a lot of times. People see enablement with a classroom and an instructor up all the time.
And one of the things, you know, I kept saying was, you know, it can’t be Bety and me in a classroom every time doing this. And so really Highspot allows us to give them different modalities and look at ways of giving people what they need when they need it. And so I think that was part of the strategy.
The other thing was, you know, I’ve spent some time with a Highspot team, like, how are we gonna measure this? How are we gonna prove ROI to our leaders so that we can get them to buy in? I know in speaking to other sales enablement leaders, one of the biggest challenges is actually getting people to complete the courses, and so we’ve gotta make it easy for them. So with Highspot, we can quickly pull reports, help people understand who’s completing, who’s not, but then take it one level deeper.
Some of the work that Bety’s done, we’re actually able to look at who are our top performers and how much time they are spending in Highspot versus those that aren’t top performers. There’s a correlation there.
To me, that’s the most valuable thing, being able to go back to our leaders and saying: “This is working, this isn’t working. Here’s why we need to change and, and here’s the insight behind it.”
RR: You mentioned something interesting there, which is the ability to, at a very granular individual level, see what users are doing, how they’re behaving, what they’re completing or what they’re not completing, and then kind of act on that.
And that comes back to what I wanted to touch on, Bety, is driving that end-user adoption. So, how have you gotten reps to see Highspot as a value-add in their day to day, and maybe a little bit more depth on what Matteo touched on in terms of the impact you’ve seen on those high adopters, those high users.?
BG: I think it becomes, uh, sort of self-explanatory when you can show what top performers are doing to the rest of the team.
Because the minute that you can point to, you know, these people are doing all of these things as well, people get curious. And so it doesn’t have to be enablement asking them to do it. And you also have leaders asking them to do it.
A really good example, early on what we did is we ran a Digital Room challenge. So yes, we had a few initiatives that were tied to the launch of Highspot, but I also knew from experience that the more they used Highspot, the more likely we would be able to get that adoption, which then gives us the analytics and gives us the feedback loop that we need to be able to get even better and make an even better experience for them.
So we created this competition and had them start using Digital Rooms where, you know, now there was all of this buzz just in terms of like the engagement analytics that they were getting. Top performers shared what they were doing, reps were getting curious about, you know, what was being shared, what was resonating with prospects.
And we didn’t have to do any of that. That was a pretty low effort initiative from our end. That was, I would say, more so on the side of how do we, again, build that credibility and get everybody changing the behavior of coming to Highspot all of the time for everything that they need with the understanding that they’re getting the right content at the right time.
When we move into sort of ongoing enablement, now that we’ve established that. How do we then also make the same sort of correlations between the top performers who are completing all of the courses or reviewing all of the content that we’re launching in Highspot?
People get excited about being able to do something a little bit better, and then that knowledge sharing starts to happen just organically across the board where people will start asking each other: “How do you do this?Can you share this with me? Where did you find this?”
RR: I really like the approach where instead of, you know, it being a conventional top-down mandate that maybe doesn’t land with reps as well or feels like a forced addition to their workflow, it was instead more of like a grassroots initiative led through seller competition, which is gonna be there naturally.
One piece that you did say is, you know, getting leaders to help you in that mission of getting reps to do the right things. Matteo, can you talk to us about what it’s like to get your leaders bought in?
MP: Yeah, I mean, I think it’s interesting. I had a sales leader who once said to me: “Am I flying a plane or am I running a sales team?”
And he was making reference to the fact that he had so many dashboards and he didn’t know what to start with. Highspot gives us the ability to pull reports and, and, and track success very quickly so that I can send it to a leader to be able to say, I need you to take action on this. They know exactly what they do, and they know exactly how to act on it.
When they’ve got a team of ten and we’re showing that four people are spending more time in Highspot than everyone else, and those four people happen to be performing better than everyone else, you get the leader’s attention and now they know they have to action it because it affects their bottom line and it affects their team performance.
Leaders are busy. Tools are supposed to make their lives easier, but if they’re inundated with it and they don’t know what to do with it, that’s where we as enablers need to empower them, give them the resources, give them the insights to be successful. And with the analytics and reporting that we can pull out of Highspot, the tool sells itself and, and they action it because they realize the value.
RR: To the point of data. I think a lot of times when you talk about leadership engagement and earning sales, leadership buy-in, it’s really a conversation of like: “Can I convince them of the value?” And more often than not, what is going to convince them is hand them a number and say you can look at it and see that this is what you need to go run and do. So I love that. It’s really just I have a dashboard that tells you how to win. Are you gonna work with me on this or not?
When did you feel that shift kind of happening and that accountability shifting from enablement-only to some of the onus going on to sales leaders?
MP: One, we track monthly product enablement completion rates. When we made it important to them, they made it important to their AEs and CSMs. All of a sudden you see the completion rates going up.
Not only that, we also track, you know, are they mentioning that product enablement from the previous month in their calls? We can start to track their calls and find out, hey, they actually are taking the information.
And so for us, it’s not just a completion rate because, let’s face it, people can create a lot of click-through training and they’re just completing it to complete it. We’re actually going one step further or measuring that success or the validity of it, or whether or not they’re using it in their talk tracks.
Again, all those numbers go back to the sales leaders, which makes it important to them, which means it’s important to the sales reps because the sales leaders are looking at it, and all of a sudden you’ve got better completions, better progress, and success in winning more because they’re using the assets and the training that you’ve shared with them on Highspot.
RR: How are you kind of drawing that conclusion? What are you looking at when you are correlating that top users of Highspot are also our top performers?
BG: I mean the, the most straightforward answer to that is that you look at, you know, our Salesforce data to take a look at win things like win rates, deal velocity, ARR, and then look at utilization metrics within Highspot.
Beyond that, when you’re thinking about enablement as a whole, it’s almost like there’s a few different stages when I’m thinking about a program in terms of measurement, because the biggest shift that I think we’ve done from an enablement success metric standpoint is really thinking about outcomes, which is what Matteo was sort of alluding to, right?
Like enablement always gets stuck in the measurement of completion rates and attendance rates, and that’s a really hard thing to then translate into impact to the business. And so when we’re thinking about outcomes, we’re leveraging a few different tools across the board to build that story.
So how do we first deliver the learning? Then, how do we measure how they adopted the learning? And then do we have a way to measure that the behavior has actually become consistent?
And so, looking at milestones, if you think about them from that perspective, to be able to measure how we’re doing every single step of the way. Yes, we can, you know, share that the team maybe hasn’t completed something for whatever reason.
But when we start to show the outcome of these things, right, like these are the behaviors that are driving the right kinds of numbers that we wanna be able to see in terms of win rates, then it’s not really an issue. Right? It’s sort of like a self-serving argument at this point because it’s such an easy thing to sell to them.
RR: It does often happen that I chat with enablement teams and measurement and real outcome and impact mapping is very much kind of a North Star still, and it seems like you guys have comfortably landed in a place where you can consistently point to: “Here is the initiative we’re running, the programs we’re driving, and here is exactly over the course of, you know, today, a month from now and then quarter over quarter, what that impact has had on our reps.”
So I would be curious to hear from each of you in terms of the impact you’ve seen over the last, you know, year and change of running with Highspot, executing initiatives through the platform. What have you seen that do to your business outcomes?
MP: There’s a lot of ways to measure that business outcome for us. And you know, I’ve heard other enablement teams struggle with how do they actually measure it? For us, every quarter we’re looking at what are our targets, what are we doing, what are the KPIs behind the targets, and how do we align to that?
And so we closely manage and monitor our impact and what we’re doing to, what those KPIs are and what the business metrics are. And so when a request comes in, we actually look at it and say: “Hey, what’s the impact?” And if it doesn’t fit within that, rather than put it through Highspot and, and get people to do it, we kind of deprioritize that.
I would say that’s probably one of the biggest impacts. The other one is one that I said earlier, which is that we have struggled with product enablement in the past and getting completion rates as most companies do.
But I think now with this tool and the insights that we’re able to prove, and the validity and the ROI behind it, we’re seeing better completion rates. And those completion rates, again, are correlating in performance. And that’s really the piece that we continue to drive.
RR: Bety from, from your end of things, anything you’d like to add to that in terms of. The impact or outcomes you’re seeing?
BG: I mean, one I would say that I could point to is our onboarding program.
I think that’s usually the easiest one to measure. The fact that, you know, we were able to launch a really structured, self-led onboarding program within Highspot meant that, you know, even though we have a really small team, I did have time to then focus on business as usual enablement, skills enablement.
But you know, being able to rely on that also meant that our ramp became a lot easier to predict. And so even thinking back to, you know, a year ago or so before we had our onboarding program launched, we probably cut the time to get reps to the field by about 25%. Right? And so that’s huge. I, as an enabler, who’s doing all of these different things to be able to rely on things like that when we have a growing team if we’re gonna be successful at anything else that we’re doing.
Otherwise you’re, you’re spread too thin and you’re not able to accomplish anything. It’s really great to be able to show from an organizational standpoint that what we are putting out from an enablement side is impacting other initiatives across departments. Right?
So the biggest questions we sometimes get is like: “Great, we did all this training, but is the team actually selling that? Or we have new messaging, like how do we ensure that everybody is actually working on that? When you’ve been able to tie some of those behaviors to, well, we started here, right?”
We were not just focused on whether or not they were looking at the content. We were actually focused on whether or not they actually learned something from it. That it’s part of their overall deal management.
RR: So it sounds like kind of the broad, overarching theme there is that you’ve been able to drive consistency. You have folks ramping at a standard time, you can reliably say, our program is working and it’s working faster on ongoing training. People are completing the work that they need to, to be ready for all of these product launches, and then all of that work is translating into better returns in the field down the line. So it’s kind of just a full end-to-end process that gets a rep ready to go and delivering better.
Looking back at all of this work, Matteo, I would love to hear from you. What, if any, other signals are you looking at that tell you that this is, this is the right approach that you and the team have developed something that really sustainably works?
MP: I think sometimes if you’re not getting people training or not getting people completed, it’s because it’s too hard. They couldn’t find it, they couldn’t locate it. You know, I wish we had everything in one central, you know, repository. With Highspot, we have that, and ultimately the experience for the AEs and the AMS and CSMs to complete training is much better because of a tool like Highspot.
Ultimately, that’s the, I think, the best measurement, and that’s why we know it’s working well.
RR: To go way back to the very beginning about what you were saying, Bety, with the earlier solution that maybe just had kind of broken down and folks were quietly unhappy, not saying anything to go to a point now where you have people coming to you and telling you: “This works. I like it. Please keep going.”
I think you’re right to say that that is the best signal and that tells you that everything that you’re doing is delivering exactly what you would hope it would. So fantastic to hear, especially knowing that you both are running this from a relatively small team.
So I’d love it if you could close us out with some advice for other folks, maybe working on small teams. What advice would you give them when it comes to developing a scaled program that they can run consistently and reliably?
BG: I think I kind of said this at the very beginning, like, you do need to get creative. Anytime that you can do more with less, I guess is the best way to put it, you’re going to get so much more return for your effort.
And what I mean by that is, you know, I mentioned, you know, having onboarding, product enablement, everything tied in into the launch of Highspot. That was very intentional. If I’m doing something to make a launch a success, but it’s also benefiting other initiatives that I’m also responsible for, then I’m multiplying the effort that I’m putting into that work.
And the other piece is you, and you kind of touched on this, the positive feedback from the team is super important with any sort of implementation for a new tool. Your biggest, biggest challenge is first credibility, and the second is adoption. I would say like, celebrate your wins often and, and like in as many ways as you can.
So, you know, the Digital Room, while that was, you know, just a fun challenge to put out there to the team, what it actually did is it created a ton of buzz, right? And so people were essentially showing the rest of the business, like leaders and others around them, that this was a tool worth looking at and worth implementing into their day to day.
If you can get creative there, in terms of not just showing the numbers. But actually having people talk about how great something is, that’s huge. And so really always celebrate the wins in every single way that you can.
RR: That’s such great advice because it recognizes the people who are doing what you want them to and gives them a little bit of a thank you for it. And then it also, to your point earlier, drives that competition for everybody who’s trying to achieve those exact same outcomes.
Matteo, any advice from your time here now at Loopio that you, you’d like to share?
MP: Yeah, I mean, I think with smaller teams, there’s two things that come to mind. One, if you can’t measure it, ask yourselves and your leaders, why are we doing it.
The second one is you have to enable your managers and your leaders to be enablers. That’s the way you can scale, and we spent a lot of time, Bety and I, meeting with the managers, collaborating with them, coming up with agendas, coming up with ideas, but then also delivering workshops together in tandem.
And so if you’re gonna have any tool or anything that you’re trying to drive, you’ve gotta get their buy-in, but then also help them be enablers and, and when you do that, you can scale.
RR: Yeah, maybe your team isn’t huge, but if you have champions across the organization advocating for you, well, all of a sudden you’ve doubled your capacity somehow. Bety, Mateo, thank you so much for joining us today.
MP: Thank you for having us.
RR: 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 go-to-market success with Highspot.
