According to Corporate Visions, 74% of buyers say they faced too many competing options in their last major purchase decision, and instead of selecting a vendor, they just checked out entirely, gave up, and moved on. So, how do you create a buying experience that makes those decisions feel easy?
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 are senior enablement program manager Lisa Monahan and account executive Madison Leatham from Pluralsight. Thank you guys for joining us. I’m super excited to talk through this topic with you. I’d love to just hear a little bit about yourself, background, and role.
So Lisa, wanna kick us off?
Lisa Monahan: Yeah, absolutely. My name’s Lisa Monahan. I live in the suburbs of Austin, Texas, and I’ve been at Pluralsight two and a half years, and I’ve been in enablement for, I guess that’s coming up on four years now.
I currently serve our go-to-market tech stack from a strategy and execution standpoint, and that is where I learned about everything I know and love about Highspot. So big Highspot fangirl here. Happy to be here.
RR: Amazing. We’re happy to have you here. Madison, can you tell me a little bit about you?
Madison Leatham: Yeah, of course. Happy to. I am based out of Salt Lake City, Utah, and I am an account executive on the public sector team here at Pluralsight. I started out as a BDR on the public sector team, eventually moved into a manager role, where I led the same team that I started on as a BDR, as well as our team in Australia, and then more recently became an account executive supporting our higher education partnerships specifically.
RR: I can’t wait to dig into all of this wonderful work and experience that you guys have, and then all the complexity and challenges that kind of come with that.
So Lisa, I’d love if you could set the stage for us: who Pluralsight is, what you do, who you serve, all that goodness.
LM: Absolutely. And Madison, I’m gonna ask you to keep me honest, ’cause I’d love from a seller’s perspective how you would change my pitch.
But we are an online learning and workforce development platform serving businesses and individuals alike with on-demand courses, hands-on labs, and skill assessments that help bridge the skill gaps in areas like AI, cybersecurity, and software development, and so on.
RR: With that context in mind, I think I’d like to jump into what that world of work kind of looks like today. So Madison, from a sales perspective — BDR and AE roles, managerial roles, helping BDRs succeed — you’ve kind of seen it all.
When we look at where we are today versus where things were when you started, what’s changed most about selling over the last few years, and where do you see sellers still struggling the most?
ML: So just to talk about both sides of it, starting with prospecting, there’s definitely more of an expectation of personalization and effort. The spray and pray tactics just don’t work. People are a lot more risk-averse. They’re just more busy.
You have to do something different to really cut through the noise, prove that you’ve done your homework, and that you deserve their time just based on the research that you’ve done. So finding ways to do something different is always a challenge. It takes more time. I think personally prospecting and getting your foot in the door is really the hardest it’s ever been.
And on the selling side, this might not be really new news, but they say it takes a lot more people to decide on purchasing a product nowadays. You’ll see different studies saying different things, but they all just show how the buying group has jumped up in numbers, so there’s a lot more need for collaboration on both sides of the fence for communicating the value to different stakeholders that might have different goals.
And then I’d say multi-threading, getting in front of decision-makers is just consistently one of the most challenging aspects. Sometimes it’s tricky because you wanna keep the relationship strong with your main point of contact, not overstep, but you wanna make sure that the value is still being communicated and the pain points are still being properly uncovered and discussed.
And you kind of lose control of that when you’re just relying on one person. So I really see that across all the AEs I’ve talked to, all the AEs on my team, that need to multi-thread and how tricky it can be to communicate that value across different stakeholders and throughout the buying group.
RR: So it sounds like there are a lot of challenges out there, and it’s a fine line to walk when it comes to balancing your initial point of contact and then doing all of the work that makes a deal successful.
Thinking specifically about the AE challenges that now you in this new role are facing, in your day-to-day, some of these things that we talked about, what would you say is most difficult for you when you’re working deals and trying to keep things moving forward?
ML: Just visibility into what matters to those fringe stakeholders. So when I say fringe stakeholders, the ones that you know have some sway, but you don’t have that direct contact with.
Maybe they join one call, and they were off camera. And then just trying to figure out how do their goals align with the solution? How can I make sure it’s not just that game of telephone, that everyone understands the vision of the solution and the implementation of the solution so that we can really start to focus on aligning the logistics and next steps.
So I’d say it’s just being able to get clear communication and more visibility and more people involved to really get those discussions, give them a little bit more oomph and value with each person that has some sway in the deal.
RR: Yeah, because if you can’t find those fringe stakeholders, you’ll kind of go sideways, and you lose the momentum that you spent all that time building.
One thing that’s funny here, Lisa, are you taking notes?
LM: I am. This is on the fly, and I’m like: “Oh, this is so interesting to learn.”
RR: You’re sitting here taking notes, hearing these challenges, and being like, “Hmm, how do these fit into my programs? How can I support this?”
So when you’re hearing challenges like this from the field, how do you start thinking about solving them?
LM: So it’s about making sure that the field is empowered with the tools that can really help them do that deep, intelligent research so that they can speak to the needs and the pain points of these accounts.
It can’t just be this very generic as you said at the start of the call spray and pray. It can’t be that anymore, and we know that to be a fact. So it’s ensuring that they have the tools available to them, but also knowing all the different ways that those tools can work with them, not against them, so that it can be simplified.
One of the biggest things I care about is reducing tool swivel, making sure that it’s easy for them to get as much done in one place without feeling exhausted by having to go from Gemini to LinkedIn Sales Navigator to Highspot.
So trying to make sure it’s as simplified as possible.
RR: Having that conversation of swivel chairing has changed so much over the last year. Now there are so many different AI tools that you can layer in, and somehow it seems like the number of tools has shot up. So making it simple is almost harder than ever and a bigger priority than ever.
Today, what are you prioritizing, Lisa, to help sellers break through? What’s new? What are you working on to help them cut through that noise and engage buyers effectively?
LM: Definitely AI at every step right now, because as you just mentioned, every tool that we use has some level of AI, and making sure that they understand which one is the best one to use in what workflow, in what step: prospecting, outreach, anything like that.
So really working hard. And as you said, it feels like the functionality is changing so much right now that I feel like every half day, my strategy of how we’re going to market with AI for our sellers changes.
RR: Yeah, and I love that point of utilizing a tool to its fullest. You invest in these things, you need them to work for you.
And one of the things that over the years you’ve spoken extensively about is using Digital Rooms as part of the way of simplifying the buyer journey, making it easier to engage your buyers, and then, to your earlier point, Madison, track what’s interesting to them, track who’s in there. So Lisa, with that being a key part of your strategy, can you walk us through why you leaned into that approach?
LM: When I was previously at SAP Concur, Digital Rooms were such a huge part of their strategy that they had an entire team dedicated to that. And so when I was there supporting Highspot, I actually didn’t have an opportunity to touch it. It felt like this really powerful feature that seemed unattainable to me.
And then when I came to Pluralsight and I was rolling it out here, I had to very quickly learn Digital Rooms, and I have to admit, I was intimidated because of the way that it was handled at my previous employer. But once I came here, I was like, “Oh, it’s actually super easy.” Digital Rooms are very easy to use. It takes just a few minutes to customize one.
And what I think is really important about Digital Rooms is what Madison was saying earlier, we don’t have a lot of opportunities to break through and stand out right now. You can send a link to something, you can add an attachment to an email, but being able to build out this very personalized space like a Digital Room, and share highly specific material that reflects the conversations that you’ve had with these accounts, that to me is a huge selling point and why Digital Rooms are so important to have in the seller workflow right now.
RR: I would be curious, Madison, because you’ve been here, you’ve traveled through the BDR to AE journey, and trialed all of these different processes at different stages of the sales cycle. From your experience hearing about this Digital Room strategy and thinking about how it shows up in your day-to-day, what kind of changed for you when you started using Digital Rooms?
Did you notice a difference in some of those challenges that you talked about earlier?
ML: I’ve used it on both the BDR level and the AE level, and it was really cool to see BDRs start to really lean into this because you’re really bringing that research to the prospect. You’re distilling down what aspects of the solution might be the most impactful, and then you put it in a Digital Room, you wrap it in a bow, and then you send it out.
And it was cool to have the BDRs get involved with this because when you come in as a BDR, you’re typically newer in sales, newer to the product, and you’re still learning the best way to pitch it. So that was a little bonus from leveraging the Digital Rooms, getting the BDRs to start to really read the one-pagers, learn about the different capabilities so that they could use that in their pitches. And then, yeah, it’s a good way to stand out.
If you’ve mentioned that you’ve made a custom Digital Room for someone, it could really pique some curiosity, and it also shows that you put in that work.
And so I really think that this changed the mindset as well to really recognize that we need to deliver value even in those initial touch points, and that just gave us a way to do that. And then as an AE, to pivot: I always make a Digital Room for my primary contact. Even if it’s just a quick conversation, a really small team, no matter what, I’ll say it’s for them to reference and also for them to share out with their team.
So I think it’s an easy ask for them to just share a link internally, and then all the relevant resources are there on their end. I’ll add custom content as well, any slide decks or proposals, so that it’s not just on my contact’s shoulders to consolidate all the information and try to share it out or create a business case. Everything is right there for them to really just be better at doing that internal selling. Because that’s what it comes down to: how well can you communicate the value to your main point of contact so that they can do it to the fringe stakeholders?
RR: I love the story of selling as a game of telephone because you have enablement that needs to help your BDRs be successful, and this Digital Room helps them learn the ropes.
And Lisa, I’m assuming you’ve built templates that kind of already explain that narrative. So as a BDR sending that out, they’re also getting enabled a little bit. And then on the other side, you have you as an AE working with a point of contact, telling them a story that maybe as it goes through the works internally gets a little garbled, but now you have control over the fact that it doesn’t.
I like that it’s a solution to that very tangled web. I would be curious: you spoke about the alignment element. How are you using things like engagement data, the buyer signals that come out of a Digital Room, to shape what you do next?
ML: Good question. In the BDR role, we could track to see if the Digital Room was being viewed.
A lot of the times in BDR, you can go a long period of time just sending things into the abyss and not knowing if people are even seeing them or reading them. So with the Digital Room, sending a link instead of that radio silence, you’re able to at least see if they’re clicking into the Digital Room, and then see if there are specific things that they are clicking on within it, which could help guide other outreach. That’s really valuable.
On the AE side, from sending out a Digital Room, I can see what’s being downloaded and what’s being viewed, so I can leverage that when prepping for upcoming calls as well. It’s really great information to see what’s getting the attention, and it can help guide my prep.
RR: One thing that comes up as you’re talking about these different use case: I’d be curious how you, especially as a solo enabler building this a little bit from the ground up, identified what those Digital Room templates specific teams needed, and then how you started thinking about building a structure that is useful to both your teams and the people that they’re engaging with.
LM: That’s a great question. I started with the existing teams that already had it: our pre-sales team. Because of the full relaunch of Highspot, a lot of things were out of our brand scope. So I started with the team that was already using it, rebuilt their templates to reflect the brand standards, and then began working with sellers to understand what they wanted in these new templates.
So, aligning very quickly around a simple, easy-to-use quick Digital Room, but then a full one where they could add demos and one-pagers, sections pre-built for all of that. But they would be plugging all that in based on the conversations they’ve had with their accounts. Also, preloading customer stories in there so that it didn’t just go out there with nothing, it already came included with how we’ve helped other customers as well.
As it’s evolved, I have a really strong connection with the entire field, and they always come to me when there’s a need for a new template. But that’s how I worked with them. I worked with product marketing to make sure that all of our solutions were in line, that it aligned with brand guidelines, and then it’s just been an ever-evolving process since then.
RR: So it really is a very cross-functional process. You’ve got the right message, the right content, it’s structured in the way that sellers like and would use, and then ultimately it drives that engagement that Madison, you’re using to continue progressing your deal.
I think that’s one of the things that’s kind of hard sometimes when people are thinking about getting started with Digital Rooms: “Okay, I have a blank Smart Page. What do I put on here? What is useful?” So I think that’s really helpful information.
Kind of switching gears a little bit, Madison, can you share a specific example, maybe a recent deal where you used a Digital Room to move a conversation forward, deepen a relationship, or catch a risk, where it was really key and you were like, “Oh, I’m glad I have this”?
ML: Yes. Just for some background, we have a solution package called AI Academy, which is this end-to-end program for AI literacy across the organization. It’s not always what we start on when entering into the conversation (our core product might be the point of focus) but I will always put a one-pager on AI Academy in the Digital Room, even if it wasn’t part of that initial conversation.
So I actually have an upcoming call with a customer for a follow-up on a deal focused on our core product. And I saw that they had clicked on the AI Academy one-pager in the Digital Room several times, so I know I’m going to prep some questions around their AI goals, make sure I get my pitch perfect for AI Academy, make sure that’s really sharp, and then determine if that solution would be a fit for them during this call.
And that was all guided by them clicking on that one-pager so many times, and I would get a notification every time in my email that they had clicked on it, which is always a good dopamine hit.
And then another example is a pricing model that we’ll share over a deck during a call, and I had put it in a Digital Room. It was custom to this prospect, and I noticed it was downloaded from the Digital Room, and I got sent that email. I reached out right away right after I got that email I sent a tailored follow-up email, and they were like, “Oh my gosh, you’re a mind reader.” So that was fun. I let them think that.
RR: Yeah. It’s a fine balance between “Ah, this helped me fuel my strategy,” and “I feel a little creepy,” but that’s okay. I love those examples, particularly that first one with that cross-sell element, where you would never have known that interest was there otherwise. And so it’s very helpful for you to deepen that relationship, go a little bit further with the opportunity and where you thought it might take you.
So that’s super cool to hear. And Lisa, I hope good for you to hear, too, just seeing all the different minute ways that this shows up in a specific deal. I know you see the impact in the usage data, in the adoption data, but here it is in a specific deal, how well it works.
Looking across this time where you came in, started rebuilding to now, what impact have you seen across the business since rolling Digital Rooms out, and what are you looking at to tell that it’s working?
LM: Well, metrics aside, I’m able to tell that if I ever had to step out for a business month, Madison would be able to run all my Highspot trainings on my behalf and sell Digital Rooms so that’s an impact right there that makes me feel better. But from the start of me entering Pluralsight and relaunching Highspot, we’ve seen an 81% increase in creation of external shares. We’ve also seen a 147% increase in external view time in that same time period, and we’re averaging about 17 views per external share. So the uptick has been massive, and people are engaging with the content that we’re sharing.
And also, I continually hear feedback from sellers they come to me and say, “Look at what I built.” A side note from all of that: the fact that I have people who are championing the use of Digital Rooms even when I’m not in the room shows me that it’s had an impact.
RR: Yeah, that it’s not behavior change you’re driving. It’s a useful strategy that you’ve handed over and they’ve just run with. I love that 147% increase in buyer view time stat, not only because that’s great for the business, but also because it speaks to one of the challenges you mentioned at the very top, Madison: earning attention. You’re asking for people’s time. You need to put the work in to show that “I’m not wasting your time. I’m giving you something valuable.” And that engagement has shot up so much tells you that your buyers are feeling that, they’re seeing, “This is something built for me, and it’s worth my time to engage,” which is always what you’re looking for.
And Lisa, to the point of solving the hard problems and giving sellers what they need, sounds like you’ve done it. I would love to hear a little bit about how you did it. As we’re kind of closing out, I want to hear from both of you on some of the really actionable things that listeners can take away and start doing.
So when you were spearheading this rollout and reinforcement process of Digital Rooms, what was your approach?
LM: I began working initially with a person who was, at the time, overseeing Digital Rooms for the pre-sales team. I wanted to understand what ownership looked like, what the structure she already had in place looked like, and how we could work together as opposed to me just taking this away from her.
So she’s still an avid contributor to Digital Rooms for her org. And beyond that, it was working to very closely align new templates with the branding and making sure that it reflected the Pluralsight that we want to go to market with. That was probably the biggest one.
But then I would say the Highspot relaunch in 2024 was a three-phase process: the content side showing them the new structure, the second part was pitching, and the grand finale was Digital Rooms. And that was a full live training where I walked everyone through.
And I would say that beyond just that grand finale of showing everyone what Digital Rooms were and how to build them, it was the support mechanism on the back end that I think has made them so successful, and that would include this Digital Rooms Play I’ve built. I think it’s probably the most viewed Play on Highspot at this time, where it has an overview of what Digital Rooms are, why they’re different from pitches, how they’re different from pitches, use cases for different roles, and then showing them different use cases even beyond that. So if I’m a CSM, I can share events with them, I can share renewals and pricing and everything there as well.
But I would say I also have a biweekly office hours for Highspot, where I allow people to just come in and ask any questions and that has been widely, widely used. And the final thing is that Highspot and Digital Rooms have a full hour dedicated to it in all revenue onboarding cohorts. Everyone gets an hour with me, and I spend 10 or 15 minutes showing them the platform, but then I stop sharing my screen and re-engage everybody eye to eye.
And I tell them a story similar to what Madison said, I engage them by saying, “When was the last time as a seller you sent a really important pitch or pricing documentation over to someone as an attachment via email, and you have no idea what happened to it after you hit send?”
And that’s how I get their interest, and I begin to deliver the value of what you can get by using Digital Rooms, the analytics that are a game changer. So that’s how I position it in revenue onboarding and make sure that it’s sticky with them. Then we go through the process of building one. They all have one after that training is over, and then they know all the support mechanisms that exist on the back end after that. Just continual support.
RR: Having seen said Digital Rooms Play, I have to plus one that strategy. It’s beautiful, and I don’t know if anyone can build as nice a Smart Page.
But what I would say is that it is very challenging, I think, to be a rep and be handed a Digital Room and told — even with a template — “Figure it out.” But having such a structured process of what it can look like, what it can do for you, and how you really get there is so helpful, and I imagine a very useful tactic that anybody starting to launch Digital Rooms or thinking about launching Digital Rooms should put in practice.
So plus one-ing that.
LM: Yeah. And if I may add, I make sure that even in all the trainings I’m like, “This is yours. This is your jumping off point. Take it, make it whatever you need it to be. I’m here for support, but this is your jumping off point.” Because I don’t know the best thing that works for my accounts at the end of the day. My sellers need to be able to be very adaptable and creative, and I don’t wanna take that juice from them because that may be the thing that makes or breaks their usage of this feature.
RR: And because you’ve given them the skills and you’ve really built that foundation, you know that when you give them the keys to the castle, they’re gonna do the right thing with it.
One last thing on the topic of launching. When you look back at this process, was there anything that you were like, “This worked really well,” and anything that you were like, “Maybe I would’ve done that differently”?
LM: The relaunch happened in four months. That was a full content audit of the entire platform burning everything down, rebuilding it, and also learning Digital Rooms.
So I wish I’d had maybe even just one more week to get a little bit more comfortable ahead of that Digital Rooms training. That’s just a personal one. But even to this day, I wish I had more people contributing to the templates, because I don’t ever wanna feel like I’m the gatekeeper there, but I kind of by accident have become.
So ideally in the future, I would love to make sure that I have other parties, even our product marketing team, involved in creating those so that there’s more proactive, not reactive, template creation. As opposed to, “Oh, we just launched a new solution, I need to get a new template made,” it could already be ready to go with the new solution launch as well.
RR: So it’s giving yourself the right amount of time, creating thoughtfully, bringing in all the people who can inform them, make them as good as possible. That’s great advice.
As we’re thinking about building, Madison, as somebody who’s always in the weeds with these, and to your point, you make one for every main stakeholder in every deal, you probably know better than most what a good Digital Room looks like versus a not-so-good one.
So when you’re talking to new BDRs or other sellers who are just getting started with Digital Rooms, what do you share as what good looks like?
ML: Well, first, I am very grateful that Lisa gave us all keys to the castle. I’m trying to make sure that I don’t abuse those, because I do love just being able to play around with it as much as I possibly can.
What I can share, and I’m always looking to improve how I’m doing it as well, some things that I will always do: I’ll always put the logo of the organization at the top of the Digital Room. That’s a given. It really doesn’t take very long, and I like that personal touch with every single one. And then I group sections together so it’s not an overwhelming dump of resources. And I’ll make sure to put my bio at the top just a quick note that sounds pretty personal, but is something that I can easily swap out names on so I’m not spending a lot of time crafting a different message for every single Digital Room.
I’ll put my scheduling link at the top, and then just for the sake of time, because I do wanna send a Digital Room out to every single person I talk to I’ll just copy the last Digital Room I created and edit it a little bit to customize. I just think that it’s more important to be consistent with it than to take a lot of time to build it out super custom.
So find a way that works for you where it seems really custom, but it’s more or less just copied and pasted with a few things changed, because you wanna be able to get them out. You don’t wanna drop that part of your process. And then it’s nice that as the deal progresses, you can always edit and add along the way it adds a reason to reach out, another touch point.
Even today I told someone, “Hey, I just added this one-pager to the Digital Room. I think that you might find this interesting in your conversations” don’t forget to have them internally and tell people about Pluralsight. So that’s always helpful too it can continuously evolve as a deal evolves.
RR: Yeah. That’s such a good approach copy the previous one because it saves you so much time. But then you strike a good balance between keeping your deal progressing, still giving attention to all of the other million things on your to-do list, but also giving that gesture of, as a buyer, my time and my attention to give you something more custom.
And I also like the point that as the deal progresses, as the conversation continues, it’s gonna become more and more customized, and so that thing that began perhaps a little bit copy and paste is eventually going to become something tailored and 100% unique to this buyer. Great tips there that anyone starting with Digital Rooms can use for their very first one.
That is Digital Rooms packaged up in one big life cycle from the enablement to sales perspective, how you built it, how it shows up in the field. That’s incredible. The Pluralsight team never fails to amaze us. You guys are doing such incredible work, and I love hearing how it shows up for you, Madison, because Lisa, we’ve heard the journey the last two years, and seeing the conclusion of it is so cool.
Thank you both so much for joining me and telling me a little bit more about it. It was so fun to hear about what’s hard, what you’re figuring out, and how it’s working for you guys.
LM: Thank you so much for having us.
ML: Yeah, it was great.
RR: To our listeners, thank you so much for tuning into 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.
