According to research from Gartner, buyer uncertainty leads to a 30% reduction in a buyer’s ability to make a purchase decision at all. So, how can you create a buying experience that builds confidence, drives engagement, and ultimately improves win rates?
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 is Annabel Hosking, Global Sales Enablement Manager at LexiNexis Risk Solutions. Thank you so much for joining us, Annabel. Just to kick us off, I’d love if you could tell us a little bit about yourself, your background, and your role.
Annabel Hosking: Hi everyone. I currently work as a global sales network manager at LexisNexis Risk Solutions within the data services brand, so I’m very fortunate to work across.
Four different brands that will work within the data space. And within my role, I lead the sales enablement team. We’re a global team. We’re a small team, small but mighty, and we work across methodology enablement. So all about our sales methodology, how we go to market, how our customers. Experiences. And I also work across all of our onboarding as well as all of our tech stack as well.
So my role is really varied. I’m very lucky I get to work with some really great people across the world. And yeah, it was never a dull moment, I’ll say.
RR: Isn’t that always the case? Small scrappy teams. Wearing a lot of hats and it’s always exciting. We’re super excited to have you here because I know you have experience spanning a lot of core parts of enablement, so I think there’s a lot to dig into there.
Could you walk us through, because I think everybody’s story is different, maybe your professional journey and then how that background led you to enablement, and then how it’s kind of shaped your approach to enablement today.
AH: Absolutely. I have what I like to think of as, and it comes from a podcast I’ve been listening to recently, it’s called Squiggly Careers, and I feel like my career was like a very squiggly career of how I ended up in enablement, because I did not at school think, oh, I’m gonna become a.
Sales enabler whatsoever. But my background is very much actually in content management and platform management and communication. And how I moved into enablement was I was actually hired in my current company and one of the brands, the beginning of the pandemic. To essentially deliver enablement content.
So I worked on delivery of content, content management, delivery of our Highspot system as well. And that was how I started to move into the enablement realm. And I will say it was completely unknown to me originally. I. Wasn’t even clear that I was doing sales enablement per se, but at least a good 18 months in my role here.
I thought I was just delivering content and it wasn’t until working with vendors like Highspot where. That term enablement started to come out and it started to change, I suppose, how I delivered my content and it’s really come into its own where now I’m very fortunate where I’m have on my team who does phenomenal content and through my experience.
It’s really understanding who my audience is, understanding how they like to consume their enablement, but also how can we consistently stay, um, ahead of what the trends are and how people like to change, how they like to consume, what they’re seeing
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day to day, because that has vastly changed as well in the last six years.
So. Thankfully my background and being adaptable, working globally, working with a lot of different people has really helped shape that. Because you know, I always say if there’s one thing, so my career of, you know, working in content management and working with platforms, working in technology. It has really shaped who I am today because it’s all really embedded in those user Jo Journeys user stories, and that translates into what I hope is a good enablement experience.
RR: Well, amazing. I love the phrase squiggly career. I think I am certainly going to have to steal that one, and I think it’s such a good way to describe how so many folks end up at enablement. You start in one place and you bring all of that knowledge that you acquire in that early discipline. Into enablement programming that’s more effective for it.
And thinking about, you know, your background in content management and creating content and all of that fun stuff, I’d be curious to know how they kind of come together. So you recently spoke at Spark EA and highlighted the importance of the buying experience, so. What are you seeing as some of those biggest challenges in engaging today’s buyers and how are you addressing them?
Maybe through content, maybe through enablement? What does that look like to you?
AH: I mean, I think the buying experience today in 2025 is unlike anything we have seen. Ever. It is a completely different world for both salespeople and for buyers as well. And what I’m seeing is, you know, buyers are not only overwhelmed with information, they’re also inundated with it.
There is so much content out there for a buyer to consume and not just through their sales individual. This is content that they can easily go and either get themselves or with things like AI and Copilot, they can have. Harness and surface to them. So that makes the role of the seller that much harder because we don’t always know what the buyer is viewing and whether it’s of value to them, and that means that their time, the buyer’s time is so precious.
We are seeing that, you know, buyers, and I mentioned this when I was at Spark, there are so many people now involved in the buying decision. We’ve moved, I think it was from about three people a few years ago. We’re now at. Six to 10 people. And if you think about it, those are all new personas that sellers have to understand, have to get to know, potentially map out, connect with.
And what’s really unfortunate is we’re also seeing that for a lot of sellers, our buyers are actually taking. Long to make a decision that they kind of get to a point of no decision. We’re at this decision fatigue. We’re a information fatigue, we’re a decision fatigue. And I think on the whole, our buyers are they tired.
And I can talk as a buyer, myself as a customer, it’s really exhausting. And so what we try to encourage where I am in data services is sales have to differentiate themselves. If you wanna get in front of buyers nowadays, you have to think what are you bringing to the table that’s different from them?
That’s a unique experience, that’s an experience that makes ’em feel important, makes ’em feel, listened to, makes them feel like they really can understand why we are doing business together. And that starts in how we as enablement get that content to our salespeople. If we are not able to identify the value that we are bringing as brands into that conversation, it becomes really hard for sales to know how to articulate that to the buyers as well.
And so. As enablement, we are that bridge between the, a lot of other functions and the sales teams and the commercial teams of making sure that value identification is really clear. So by the time it reaches the buyer, they absolutely know why they’re having that conversation. They absolutely know what the value of that conversation is going to be.
And that really does start with how are you getting that information into the hands of your salespeople? How are you making that content? Really accessible, really palatable as well. I think traditional enablement, we defer to a lot of very wordy, very long documents, which from experience, no salesperson really wants to read or look at or go through.
So just as we’re seeing the buyers experience evolve, the enablement experience has to evolve as well in order to stay ahead of that and to give them the best experience to our salespeople.
RR: I think you’re absolutely right on all of that. It is only getting more difficult, and as things change externally, you need to adapt internally.
And so kind of thinking about how you’re making that change, and to your point, how you’re distributing materials in a way that is usable and usable for a sales audience that maybe isn’t gonna read 10 pages of written content. What would you say then is kind of the unique value for an enablement platform when it comes to helping sellers?
Create and deliver these impactful and differentiated buying experiences that you’re looking for?
AH: Oh, huge value, absolutely huge value. The power of enablement comes in the ability to be able to streamline that messaging. But in order to do so, we do need a channel to do that, you know, and that can’t exist.
In ad hoc documents that you just hold on someone’s computer. Our journey with Highspot started many, many years ago. I think it was about sort five or six years ago, very early days for Highspot even themselves. And we set out with a mission statement, which was that Highspot would be a single source of truth holding up UpToDate relevant sales content.
And I am happy to say that five years later we still maintain that mission statement. The platform has got bigger. There’s more people, there’s more content, as I’m sure you can imagine, but we have stuck to our statement that it is a single source of truth. It is up to date, it is valid information that sales are getting, but that all comes from having a channel with a witch to push that through to the sales audience.
It just makes your role as an enabler that much easier, you know, day to day. As you know, we spoke about at the top of the call is no one day looks the same for enablement. It will always be different. There’ll be different priorities. There’ll be different go to market, there’ll be different initiatives.
But if you know that at least you have somewhere that you can reliably put information in front of sales and then see how it’s being used, how it’s being impacted, how the seller is using it, how the buyer’s consuming it. Your role as enablement starts to become just a little bit easier. And so I would say for anyone who’s within the enablement sphere and looking at their tech stack, having a solid CMS is really gonna be a, a strong cornerstone of that.
RR: I love the perspective on an enablement platform as kind of a source of consistency. Almost everything is changing. Your day in enablement is different. Buyers are behaving differently. Reps need to do different things to engage ’em, but at least you have one place that is reliable. But I will say, I know that.
Strong buying experiences aren’t necessarily contingent just on technology. They also require a lot of hard work internally. And as one of the things that you, I’ve seen you mention on LinkedIn is that a core foundation of LexisNexis Risk Solution Services is ensuring that customers really recognize the value that you provide.
And that kind of starts internally. With sales and leadership alignment. So I’m curious, how are you aligning those internal stakeholders so that way your teams are set up for success when they’re shaping those buyer experiences externally
AH: with immense difficulty, I’ll say, and I think any enabler that sits here and says that it’s an easy job is lying through their team.
It is, I think, one of the hardest, the hardest roles. Of enablement is getting everybody aligned, getting everyone to agree, and especially I work, as I say, across a lot of businesses. You know, I have four MDs, I have four heads of sales, I have a lot of sales leadership and a lot of sellers, and I’m sure that’s the case for a lot of people working in large enterprise organizations, stakeholders.
Can be difficult to align, especially when you have a lot of different priorities and a lot going on. But what I would say is, is really identify what is the core value that you as a company or you as a business, as a brand can all agree on. Our MD has this thing, he says that all of our kickoffs, which is, you know, value is not on the lips of the seller, but is in the eyes of the customer.
And that mission statement as it were. Has sort of brought all the stakeholders together to agree that even if there’s misalignment or disagreement on how we do things, we can all agree that we want to give the best experience for our customer and the best value to our customer. And so for enablement, it’s then saying, okay, so we have this mission statement, we have this belief that we want to be customer centric.
We want to be value focused. What does that actually mean? For each internal stakeholder, what’s important for them? What are the metrics that they’re looking at day to day, month to month, quarter to quarter, and how is what we are doing with an enablement? How is it actually starting to impact that? Where is their focus?
What are they going after? And the only way you are really gonna get those answers is by talking to your stakeholders. If you’re an enablement and you’re not a people person, it’s probably gonna be quite a tough job because a lot of our job is just talking. It’s talking with people, talking, you know, at people, sometimes listening to people, taking in information.
I would say spend time with your stakeholders. You are there to listen first and foremost. You can’t solve every single problem that they come up with, and you shouldn’t try to. But if you can really understand what their world looks like and what’s really important to them, and what are the behaviors, what are the metrics that are gonna move the dial for your stakeholders?
You’ll eventually start to map out, which is what we did. But actually a lot of them start to align. And even though they might be saying different things, the reality is that for a lot of sales leadership, they want similar things. You know, they want to have better pipeline hygiene, they wanna have higher wind rate.
They wanna see, you know, large opportunity amounts more in the qualifying, the identify stage, that early sales stages, they wanna increase, you know, the ramping of new starters. We start to get these similar uniform metrics and so then we as enablement can start to work that into our strategy. Although we as enablement can really start to build what we are working on to align with our internal stakeholders and start to deliver for them.
RR: I really appreciate that you had some really tactical and helpful tips in there, but also that you led with, this is not easy. That’s the big part, is there’s so many kind of lofty initiatives that you are like, how do I even tackle this? And it sounds so overwhelming. So I appreciate the acknowledgement there.
Kind of wanna shift gears a little bit maybe towards some of the capabilities that you’re using and finding some success with. So one of the things that we’ve heard is that digital rooms have been a lever for kind of creating those differentiated buying experiences. So what are some of your best practices for creating effective digital rooms and then maybe getting your teams to leverage them.
AH: Mm, absolutely. We have a brand who is using digital rooms really fantastically, and they’re teaching our other brands how they’ve used them. So, you know, I, I wholeheartedly agree they can make such a difference in the buying experience and if you’re not using them, you should a hundred percent be looking into where you can use them.
So I would say when you are looking to start with a digital room is really understand. Why are you doing this? Like what’s the purpose of actually taking the time and the effort to work probably with your product marketing team or with your marketing teams as a whole to put together something that looks really professional.
Looks on brand, but is also really easy for sales to go in and start to customize. I would recommend not having sales do it fully themselves. They have very busy day jobs, and I think if you’re gonna say to any sales person, okay, over to you to go and create this, you might run. Some adoption issues, however, working, you know, this is where your cross-functional working really becomes essential, is working with the individuals who can make good content, who can deliver good, uh, visuals, good framework for the salespeople to literally just be able to, within their sales cycle, adopt this, lift it, and send it to the customer.
Because then we start to see, okay, where are we actually starting seeing the customer impact? Has it changed how the customer engages with the content? Are they revisiting? And so what we’ve seen is we’re actually looking at, you know, we see a much higher engagement rate when we have the customers viewing content through a digital room as opposed to simply.
Static content, and we can see that obviously with the Highspot metrics, which you know, are a real gold dust when it comes to that. We can also see that, you know, we have repeat visits, so something that we wanted to drive was customers coming back and revisiting the content rather than just clicking in, seeing it once and then never viewing it again, was actually having that revisit of them continually coming back to their individual microsite, if you will.
You know, we spoken a lot about a differentiated. Differentiated buying experience. And that can be challenging for salespeople because unless you are fortunate enough to only have you know four or five accounts, the likelihood is your book of business is probably quite vast. And so the expectation that you are consistently offering a differentiated variance for every single customer is just not sustainable.
And so using these digital rooms, you are able to. Have, you know, a differentiated experience that is scalable. That it makes a buyer feel like it’s a really individualized experience when the reality is for sales, it’s probably quite an easy thing for them to put together, but it does take some uplift front end with your other teams and your cross departmental functions.
RR: Yeah. I wanna double click it as something you said there, which was, if you’re asking reps to build it themselves, you’re probably not gonna see much in the way of adoption. I, I kind of wanna. Speak about that idea of what you can do to drive adoption more broadly. Because looking at the data, you’ve achieved a really impressive 82% recurring usage rate in Highspot.
So in addition to that kind of approach to digital rooms, how are you driving adoption more broadly across your revenue teams, whether that’s internal reps, partners, whomever, what are you thinking about that’s helping you? Get people in the platform and keep them there.
AH: Yeah. That’s been, you know, a metric we’re very proud of.
And it’s been something where, you know, going back to what I said earlier, which is Highspot was set out to be the single source of truth. As soon as we turned on Highspot, for lack of a better word, we pretty much turned off every single other site. So there was nowhere else. For sales to go to get this information apart from this one platform.
And I’ve seen this done various ways. I’ve seen people where they have, you know, duplicates and, oh, we’re doing a slow migration. We’re gonna keep SharePoint for a while, and then we’ll have Highspot as well. And you know, there’s no right answer to this, but ultimately, if you are looking to put out a message that this is your single source of truth, this is where you need to go to speak to sales.
Our adoption has come because we really drove that and we continue to drive that. If you want content in front of sales, if you want success stories in front of sales, whatever it might be, it has to live in Highspot because there just simply isn’t anywhere else to go. And this is for a couple of reasons.
The main one being that, you know, the actual management of the content is far easier. And if you think about the trickle down effect, the user needs the best experience possible. And so if they have all of this disjointed experience of going to multiple places to find multiple pieces of content that look different, that sound different, they’re not getting the best experience and they’re probably not gonna come back to Highspot.
So for us, it’s really making sure I’m maintaining. The consistency in the user experience, and that comes from feedback as well. So we will regularly have feedback forums with our salespeople, with our sales leadership, and we’re very open within our team to hearing, listen, this is actually getting quite complicated to navigate.
I dunno how to find content. And so then we as a team, as an enablement team, go, okay, what do we need to do to make it easier? How do we start to surface more content directly in front of our users? Because if they’re not having a good experience, then we are not doing our role as enablement. And you know, you don’t have to, if you do have a large sales team, you don’t have to have that verbatim feedback.
You can use things like the search reports in Highspot to see, you know, what are people searching, what are the terms they’re looking for and the pieces of content, how can you start to surface that in front of them in a much easier way? Putting it on the homepage, putting it into their specific areas, really thinking about how you.
Manage, maintain and govern that content to give your users a really solid experience. And that’s what we’ve done and it’s reflected, as I say, in the adoption and in the revisit rates as well.
RR: I really like that you called out that search results report because I think that’s such a great way to kind of get a pulse on your people without having to go dig around and have a bunch of conversations.
So thinking in addition to that, how do you leverage data and insights in the platform to help you inform and improve the programs you’re leading?
AH: Yeah, absolutely. I mean, I have actually had to learn to, I suppose, step away from data slightly. Um, so that’s been feedback I’ve had as I’ve moved more into a, I suppose a leadership role is actually the data can’t always tell the whole story, although my heart and enablement goes, yes, it can, it can.
But yeah, the. The, the scorecards that we have in high spots. So really for us, you know, looking at things like that play scorecard, we deliver a lot of sales plays. They’re the best way to get our enablement in front of people. They’re enjoyed and they’re liked by sales. But I can see very clearly what is the percentage of my audience that is viewing this play?
How long are they spending? You know, what are the outcomes of the, you know, the business impact? At what point in the sales cycle as well? If there’s external content in there, for example, the marketing collateral, are they deploying this collateral and is it actually having any impact on the customer?
Those sorts of insights. You just do not get anywhere else within any other content platform that we have. And so when it’s come to say, onboarding our marketing team or our product team into contributing content, being able to give them this insight helps them understand that the work they’re doing on building the content, maintaining the content is actually worth something because we can directly see the correlation with business outcome, which has always been one of our biggest challenges.
Beyond that, our company does a lot with actually pulling the data out of Highspot. So we make use of the Highspot data lake, and we’ve actually pulled that into our own BI platform where we’ve started to look at things around, you know, how many channels and how much activity per opportunity are we seeing within sales.
Something at the moment that we’d really drive on. Going back to that differentiated experience for the buyer is looking at a multi-channel approach when it comes to how we prospect and how we outreach. And that really started from using information that came from Highspot, looking at information that comes from Salesforce and going, okay, how many channels do people currently use when they’re outreaching?
We’re only maybe seeing a couple, you know, one or two channels. But we know in today’s buying world that it’s gonna take between six to eight. Channels to get through to a buyer and to actually have a meeting. So what can we do to start to move the dial and start to build our programs across driving that?
And so that’s how we use data and enablement is actually saying, what are we seeing today? What are the outcomes we want to see in the next quarter? What do we need to do in order to get there? There’s always a lot of talk on LinkedIn. I always see it about, you know, you need to be data driven and enablement.
If you’re not offering insight, if you’re not offering analytics, you’re not doing your job. And that can be kind of hard to hear when actually, I think there’s almost too much data sometimes, and it can be quite complicated to understand. And this is why I, I personally really like how it is viewed in Highspot because the scorecards make it very accessible, very easy to consume, but also it doesn’t matter whether you’re an enabler, a seller, or a senior leader, you can be presented a scorecard and you can very quickly see what you need to get out of that and what your conclusions you’re drawing from it.
RR: Yeah, I think it’s that. The difficulty of democratizing data into meaningful, actionable insights is sometimes impossible. You have so much at your disposal, and so making it useful is sometimes a challenge, so I love hearing that. You’re finding a way to use it well and inform your programs well. So we’ve heard a little bit about engaging buyers driving adoption.
Tracking your impact and seeing how it’s kind of helping you do the things that you need to. So just one last question for you to close this out. For other enablement leaders looking to improve the buyer experience in today’s very digital first world, what is the biggest advice you would give ’em?
AH: Oh, that’s a great question.
I would say if you are in a position where you’re fortunate enough to be the buyer, think about how you want to experience that life cycle. You know, as someone who is a buyer day to day, as well as an enabler. You know, I always ask myself through, when we do our methodology onboarding, I will go and speak to the sales people about actually what it’s like from a buyer’s experience today, and that really helps.
Give them that insight into what is sometimes a little bit of an elusive world that we know the buyer’s world, the buyer’s experience. So I would say for other enablers is how do you like to speak to your vendors? How often you know, what makes them stand out? What makes them noisy in your inbox, you know?
When do you get those emails or outreach that you think, wow, I really wanna continue a conversation with that person. What did that person do? How can you bring that into your go to market? How can you bring that into your sales team if you’re an enabler who is perhaps not in the buying cycle? I would say.
Spend time with your salespeople, really understanding the customer experience, and there are many ways that we can do this. Nowadays with technology, obviously everybody’s got call recording software, so we have a lot of our sales calls recorded. If you as an enabler are not digging in and really understanding what’s happening in those customer conversations, it’s going to be harder for yourself to be able to really get into the world of salespeople.
So I would say, you know, you really need to experience. What the customer is going through. And that can be simply by having a look at those calls. Where were they successful? Where was there a positive outcome? Where did the buyer enjoy it? But then also where did the buyer sometimes mention things that were pains to them or where they would like to see improvements?
What were the questions? That is where we really need our enablers to be on the front foot of really digging into the customer experience and almost spend as much time as you know with your customers, as you do with your salespeople, to really get that insight.
RR: I think that’s fantastic advice to close on, is to put yourself in the buyer’s shoes, understand what they’re going through, and know for yourself what good looks like to you and drive that in your own business.
So thank you again, Anabel. This has been a wonderful conversation full of all sorts of good insights that I really can’t wait to share with our community. I appreciate you joining us so much.
AH: Thank you so much. Thank you so much for having me as well. Fantastic questions.
RR: Amazing. Well, to our listeners, 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 successful Highspot.
