Win Win Podcast

Highspot
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Welcome to the Win Win podcast by Highspot. A short show where we dive into changing trends in the workplace and best practices to navigate them successfully.

  1. 3H AGO

    Episode 142: Designing Enablement for Scale in Healthcare

    According to research from the State of Sales Enablement Report 2025, businesses with well-integrated enablement tech stacks are 42% more likely to increase sales productivity. So, how do you go about building an effective, well integrated tech stack? 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 Nicole Cost, director of enablement and operations, and Becky Garcia, enablement operations manager, at Lantern.  Thank you both so much for joining us; it’s so exciting to have you here. I think there’s probably a really wonderful conversation to be had, and I’m excited to jump into it. I’d love to start by learning a little bit about yourself, your background, and your role.  Nicole, would you mind kicking us off? Nicole Cost: My name is Nicole Cost. I’m the Director of Commercial Enablement and Operations at Lantern. At Lantern, our department’s primarily responsible for supporting our commercial new hires with their onboarding experience, process strategy, collaboration, and communications, and then in-person meeting operations and logistics. I’m based in New York. I’ve been in this space for about four years, but prior to working at Lantern, I was at Carrot Fertility and I worked in a totally different industry in sport and entertainment; I was a teacher and worked on the business side in a very different world. RR: Becky, would you care to tell us a little bit about yourself? Becky Garcia: Yeah, definitely. So, I’ve been in the industry now, I’d say I’m going on my seventh year in the health services and health tech space. I’ve been kind of all over in terms of my background, but in the last seven years I’ve really been in an operations role.  Part of what I love doing here at Lantern is helping companies grow and scale. That’s really what I love to do. RR: It sounds like you guys have been here before. This isn’t your first rodeo. You’ve spent the time not only in the industry, but also specifically in healthcare spaces, both at Lantern and in previous roles. I’d be kind of curious to dive into those previous roles and how they kind of affect today before we jump into your work at Lantern. So, Nicole, what challenges have you noticed pop up that people in other industries might not expect? NC: What I loved about this question to kick us off was because I was actually, like I mentioned, one of those people in another industry for about 10 years before pivoting to healthcare, and I will never forget my first manager asking me: “How much do you know about healthcare?” And I responded—I remember it vividly—I responded with: “I know I have great benefits.” I quickly learned that great benefits were not a normal thing, and that is why so many companies either are being created or evolving to provide healthcare benefits that most people in the United States do not have access to. And usually these gaps are incredibly expensive. They’re very emotional, and they’re non-linear in their journeys if everything is just very complex. So one could say that selling in healthcare is more difficult than many other industries. But when we ask our new hires—we ask: “Why did you choose Lantern?” And I would say almost 100% of them say they wanted to be part of a mission-driven company because the work is meaningful. It might be more complex, longer cycles, everything’s a little bit more difficult and nuanced, but it is mission-driven and really meaningful.  All of this to is say that our enablement approach at Lantern focuses on collaborating with our friends in learning and development and our cross-functional partners to arm our internal team with tools that they need to succeed. RR: I like what you said there about nuance. I feel like a lot of the time when we talk about difficult selling environments like healthcare, challenging, obstacles, difficulty—this is all kind of what pops up. Those are the words that we use, but I love that reframe of like, “It just is what it is. This is normal and we’re doing our best to help people.” It’s nuanced, it’s not challenging. I love that reframe. As we talk this through, from your perspective, Becky, I know you’re coming in with a background in operations, which likely gives you a bit of a different perspective. Can you walk us through what it means to drive operational excellence in the healthcare space and, again, maybe how that differs from other roles you’ve held? BG: Definitely. From an operations perspective, I think driving excellence in healthcare really means building reliability into a very complex system. So as Nicole mentioned, healthcare isn’t linear and there are many moving parts. There’s handoffs, regulations, nuance, and a lot of emotion for people that are going through it. So excellence really isn’t just about efficiency, it’s about making sure that the right thing happens consistently, even as you are scaling. Operational excellence is also what ensures that we can deliver on process, discipline, documentation, reporting. And if that’s not strong enough, that’s really where scale breaks down. That’s where enablement comes in. And tools like Highspot really help us turn our best practices into the standard of work, and they help us give our teams confidence that what they’re saying in the market really matches what the organization is expecting. At the end of the day, operational excellence is really how you make impact repeatable, and that’s gonna be for patients, it’s gonna be for customers, and it’s also going to be for our teams who are doing the work. RR: That’s a great answer and I like how you look across excellence to understand how you build the systems to support it. And for whatever environment you’re in, that’s the goal. How you get there maybe differs a little bit— and it probably differs a lot when you’re dealing with, like you said, highly emotional, highly impactful scenarios—but at the end of the day, you’re still driving toward the same things.  I’m excited to hear how you’re driving towards those, especially knowing that just a little bit ago, Lantern hit a period of extremely rapid growth. What kind of challenges did that create for the team? NC: Growth is exciting. It’s a privilege. We’re excited to be part of that. And what was great is we already had the building blocks in place for our new hire onboarding experience. They were in place, and we were welcoming new hires on a weekly basis with custom 30, 60, 90 day plans. But we learned quickly that that just was not sustainable for our small team to maintain a level of excellence that we pride ourselves in Just. Wasn’t gonna work because our new hire numbers continued to grow and our team is still the same: It’s Becky and I. So the biggest challenges that we faced, I would break into probably three categories: process lag, quality control, and then updated content and assets. So, we continue to bring in the best talent and the industry, but it was incredibly important to us that we recognize these challenges as opportunities to redesign how the work gets done. So this is when we started to evaluate tools like Highspot. And even as recently, like our colleagues in marketing sing Highspot praises because it helps make their content more discoverable. RR: Becky, can you talk to us from an operations perspective, you know, hearing some of these challenges, how did they influence the decision to invest in a platform and, and why was Highspot kind of the right answer for you guys? BG: From my perspective, I think the biggest impact of rapid growth was really fragmentation. We were scaling headcount, products and processes all at once. Information started to live in too many places. There were decks here, documentation there, and there was really a lot of knowledge in people’s heads. The lack of consistency really created friction fast. It resulted in people not being confident about what the latest and greatest was. At the same time, like taking a step back, we were also going through a rebrand of the company, which actually made it a perfect inflection point. So we had an opportunity to really step back, refresh our message, and our resources all at the same time. And we really got to be intentional about how we showed up both internally and externally. So rather than just updating assets that were in place, we wanted to start with a fresh source of truth. And that’s ultimately what helped us drive the decision to invest in Highspot as we discussed. Like we’re growing so significantly, we’ve doubled in size from our commercial team, and so we needed to onboard a lot of people with very unique roles and then also operationalize best practices as we grew.  RR: I knew a little bit about those early days. You’d mentioned hypergrowth and things like that, but knowing that you had doubled headcount, you were going through a rebrand, and you were implementing a new platform and evaluating a new platform at the same time, and it’s the two of you doing all of that. I think there’s probably a lot of people that will listen in and be like: “How?”  Because that sounds like quite a lot. We’ve heard about all of the work that was being done, all of those initiatives that were kind of coming together to prioritize the need for a platform, the need to get reps up to speed quickly. So, what did onboarding look like before and why was it kind of time to make a change? NC: So as I mentioned from just the beginning, but our commercial onboarding experience has always had a formalized program, and we’ve always had our building blocks that work really well to

  2. FEB 12

    Episode 141: Designing Curated Enablement Experiences

    According to research on organizational alignment led by LSA Global highly aligned companies grow revenue 58% faster and are 72% more profitable than misaligned companies. So how can you cultivate an aligned culture ready to drive improved outcomes?  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 Julia Juliano, manager of sales enablement at Cencora.  Thank you so much for joining us, Julia! I’d love it if you could kick us off by telling us a little bit about yourself, your background, and your role. Julia Juliano: Yeah, of course. Thank you so much for having me. I’m excited to be here today. My name is Julia Juliano. I live in the Philadelphia area with my husband, daughter, and two dogs.  I’m actually coming up on my seventh year with Cencora. I’m now a sales enablement manager, and I started with the company in generic sales within the New York Metro Territory, where I was a top performing rep. That experience really ignited my passion for empowering sales teams to succeed, which ultimately led me to transition into sales enablement. I entered the enablement world as a specialist about four years ago, and worked my way into my current role as a manager. Over the years, I’ve had the privilege of supporting both community retail pharmacies and more recently our specialty distribution business. These experiences have given me a comprehensive understanding of the challenges our teams face and the tools and strategies they need to excel in such a competitive and highly regulated environment. RR: Well, we’re super excited to have you here and to dig into a couple of those things you’ve mentioned—transitioning into that sales enablement role from your desire to help sales teams win, navigating competition. So excited to dig into all of that. I want to start with one of the first things you mentioned, which is that you’ve run the gamut from sales to sales enablement. So, can you take us back to your time as a pharmaceutical sales rep at Cencora? What challenges did you experience that shaped how you enable today? JJ: Yeah, you know, it’s a really unique experience to be able to go from sales to sales enablement. As a pharmaceutical sales rep, I experienced firsthand the challenges of accessing the right resources at the right time.  Whether that was finding compliant marketing materials, navigating product specific information, or understanding how to position solutions for different customer needs, there was often a disconnect between the tools available and the realities of working in the field and the conversations that I was having with those customers.  That experience really allows me to approach enablement from the rep perspective, knowing that every minute they spend searching for content or trying to interpret complex messaging is a minute that they’re not spending with their customers. My goal is to streamline their workflows, ensure they have what they need at their fingertips, and create alignment between the tools we provide and the outcomes that they’re driving in the field. RR: I think that’s such an important call out: Every minute that you’re distracted with non-essential tasks takes you away from the work that really matters both to you and to our business. I think bringing that kind of lived experience and empathy that comes with it to the table is so huge and helps you kind of build the programs and support arms that you’re like: “I wish I’d had that.”  And I know it probably can’t be easy to build those programs because Cencora unites six distinct business units under a single brand. So, from an enablement perspective, what kind of complexity does that create for you? JJ: Yeah, so the complexity really lies in balancing the enterprise wide alignment with the unique needs of each of those six business units. So, the six business units are specialty, GPO, community, retail health systems, animal health, and corporate partnerships. They each serve distinct segments of the healthcare ecosystem; their customers, products, and sales strategies vary significantly, which means that their enablement needs are equally diverse. At the same time as one unified brand, we have to maintain consistency and messaging, compliance and governance across the organization. So from an enablement perspective, this requires a strategic and thoughtful approach to content structure, governance, and collaboration to ensure that we’re effectively addressing both the enterprise and each individual business unit’s priorities. RR: When you’re looking across these priorities and trying to stitch everything together into a clear strategy and message, it’s obvious that alignment doesn’t happen by accident. It’s a very intentional, thoughtful thing that you have to cultivate. So how do you use Highspot to break down those silos that could potentially appear, and then make sure that everybody’s running to the same drum beat at the same pace? JJ: We’ve accomplished this by building a centralized Spot architecture that balances enterprise-level consistency with business unit-specific relevance. So at the enterprise level, we house shared resources like compliance guides, org charts, corporate initiatives—things like that. At the business unit level, we provide more tailored content and tools designed to meet those unique needs of each team for their specific solutions.  Highspot Analytics further enables us to identify content gaps and redundancies, which allows us to continuously refine and optimize our approach By centralizing any efforts on Highspot, we’ve established a single source of truth that fosters alignment while maintaining the flexibility needed to meet those diverse needs across our customer segments. RR: There’s so much in what you said that I really want to dig into in just a second. You know, about how you structured those Spots, how you determine what gets a Spot, what doesn’t, alongside the kind of specific, tailored tools that you’re building for solutions. But I want to start with the foundation, the baseline for all of this, which is that as part of your work, you led the creation of a formal structured governance plan. Why did you see governance as foundational for driving alignment and helping Cencora drive a shared strategy? JJ: Governance is truly the backbone of any successful enablement strategy, especially in a complex organization like Cencora. Without it, you risk content duplication, outdated materials, and a lack of visibility into what’s working and what isn’t. When I joined the team, we had a ton of great content, but it wasn’t always easy for reps to find or trust that they were using the most current and up-to-date version. By implementing a formal governance plan, we established a clear process for content creation, approval, and maintenance. And this not only improved findability and adoption, but also ensured that everything we provide to our teams is compliant, up to date, and aligned with our strategic goals, RR: So, you knew what it could achieve for you, and you’re starting to see those outcomes. Specifically you’re seeing that in the data. You know, as a result of this governance strategy, you’ve seen meaningful improvements in content views, downloads, findability, and even platform adoption. So, what actions or parts of this strategy do you think made the biggest difference in achieving the results that you’ve named? JJ: We implemented a consistent taxonomy or naming convention across all the different business units, which made it easier for reps to navigate and find what they need. We also introduced regular content audits on a quarterly basis to ensure that everything in Highspot is relevant and up to date. Another key action was also leveraging Highspot analytics to identify gaps in content or areas where reps were struggling to find resources. And by addressing those gaps and continuously refining our approach, we saw significant improvements in engagement metrics, like you mentioned, the content views, downloads, and overall adoption of the tool. RR: How did you identify those gaps in content that reps couldn’t find? JJ: So, we created sales surveys and worked with our marketing partners and our solution owners to identify which solutions were being most searched for by reps, what materials they needed to aid in the customer conversations that they were having. Then, you know, in the surveys we addressed: “What would you like to learn more about? What type of content are you unable to find that would be helpful in your day-to-day role?”  And so we took those surveys, partnered with marketing and those solution owners, like I mentioned, and were able to create those resources to better drive, you know, adoption and findability within the platform. RR: Okay, amazing. I think that’s such an important approach where you’re building from the perspective of your users. It’s not just: “Here’s what we think works.” It’s: “Okay, what does this actually look like in your day to day and how can we make it better?” And actually that kind of leads me to that Spot architecture that you touched on, which includes enterprise-level and then business-unit specific spots. So, how did you create this structure and then how does it help you create consistency like we talked about, but also keep things relevant to reps’ day to day? JJ: Yeah, so we started by clearly defining what belongs at the enterprise level versus the business unit level.  Enterprise level Spots include resources that apply across the entire organization—this is our compliance guidelines, corpor

  3. JAN 8

    Episode 140: Creating Clarity in a Complex Sales Environment

    According to the State of Sales Enablement 2025 Report, 20% of organizations see the sales process as a key strategic priority. So how can you optimize your sales process and drive higher win rates for your team? 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 Aaliyah Patel, senior specialist, customer marketing at Ansell. Thank you so much for joining us. Aaliyah. I’d love if you could start by telling us a little bit about yourself, your background, and your role. Aaliyah Patel: Absolutely. Well, thank you for having me. My name is Aaliyah Patel. I’m a senior customer marketing specialist here at Ansell, where I’m a part of the customer marketing team. My role really centers on leading our sales enablement in digital MarTech operations, so ensuring that our systems, processes, and data flows that support our go-to market motion are aligned, connected, and easy for our teams to use.  A large part of that includes overseeing the digital tools like Highspot in our tech stack, supporting content governance and building scalable frameworks that help reps access the right insights, messaging, and assets across the buyer journey. The goal is to ultimately empower sellers and partners with the clarity tools and visibility they need to drive growth and deliver consistent customer experiences. RR: Just from what you mentioned there, it sounds like we have quite a lot of ground cover  in terms of your experience, your background, and then the work that you do with Highspot. Before we kind of jump too far into the deep end there, I always kinda like to start by getting a sense of the environment that you’re working in. So I know that Ansell manufactures and distributes a really wide range of products.  What are some of the unique challenges that go-to-market teams face when selling in this environment? AP: Absolutely. So, Ansell serves an extremely diverse markets, so anything from industrial safety to scientific to healthcare. And each customer group has different expectations, buying cycles and safety requirements.  Reps often need to shift between very different conversations throughout the day. And the challenge isn’t necessarily complexity, it’s clarity. Reps need to quickly position the right solution, especially when our portfolio is broad and customers span multiple industries with unique needs.  There’s also the constant need to stay current on new product developments and differentiators across categories; our priority has been making sure that our teams have a unified way to access information, understand messaging, and communicate competently no matter what business they’re supporting. RR: I love the shift that you mentioned there: it’s not necessarily complex, instead the challenge is making things clear and easy to navigate because yes, there’s a lot going on. You can’t change that, but you can pull certain levers to make it a little bit easier for your teams. Knowing that’s kind of where you’re at, I’d like to turn towards some of the actions that you and the team are taking. So, what are some of the key go-to-market initiatives that you’re focused on? And then how are you enabling reps to find clarity in Ansell’s sales environment. AP: A major focus for us has been simplifying how our teams access and leverage content to drive more consistent, confident customer conversations. We’ve strengthened our content governance, we’ve centralized materials, and we’ve made it much easier to connect the right message to the right audience.  We’re also aligning more closely with sales to ensure that our go-to market initiatives are really grounded in real customer challenges. Whether through targeted campaigns, sharper product positioning, or ongoing training and enablement, everything that we do is centered on helping our teams articulate our value across the diverse markets and products that we sell in.  We’re seeing the impact of that work in real time: We’ve had over a hundred thousand content views with almost a 90% reoccurring usage rate, which tells us that the structure we’ve put into place is resonating and helping our teams move faster and stay aligned. RR: I love that you came in with the data to back it up—actually, not just the data to back it up but great data to back it up. That’s super impressive, especially knowing that you guys are a little bit early in your journey, that you’re already finding that significant success.  One of the things that we’ve heard is that a key focus is the sales process. So in your experience, what are some of the essential building blocks for creating a sales process that’s driving these business results that you’re seeing? AP: For us, the foundation comes down to three things, so it’s simplicity, alignment, and insights.  When you bring clarity, consistency, and real data together, you create a process that’s scalable, repeatable, and tied to business outcomes, and it allows teams to adapt their approach, depending on the customer segment that they’re working with that day. RR: I think you touched on some really compelling aspects there, and I think I’d be curious to double click into a little bit more of what you said and about how you’re bringing some of those building blocks to life, especially with a platform like Highspot.  So, can you talk about the role that an enablement platform plays in helping you streamline that sales process? AP: So the value is truly structure and connection. An enablement platform brings content, people, and insights together, and it gives everyone one place to operate from. It reduces the time the seller spends searching for materials; it makes sure that our messaging is aligned across our campaigns and launches, and it also creates visibility into what resonates in the field. So, it’s truly become the backbone of how we support consistent execution across the buyer journey. RR: I always love to hear that consistency is kind of what’s coming out of your usage of an enablement platform. I think that’s really the goal, right, to help standardize your messaging and bring consistency to your teams. I would love to dig a little bit deeper into that and kind of the benefit that you see of partnering with Highspot. How does this partnership help you drive some of those core initiatives? You touched on this a little bit already. AP: Partnering with Highspot has been incredibly valuable because it gives us a partner who truly understands the complexity of a modern go-to market environment that helps us operationalize our strategy in a really scalable way. For us, the benefit is twofold. First, Highspot provides the structure we need to centralize our content, our launches, our campaigns, and our customer facing materials, so our field teams can execute with confidence. It creates alignment across marketing and sales, which is essential when you’re supporting multiple markets and product categories. Second, the partnership helps us accelerate our core initiatives. Whether we’re rolling out new product messaging or enabling our teams on evolving customer needs or programs, Highspot gives us the platform, analytics, and support to execute and quickly measure the impact. We’re not just using the platform, but we’re truly maximizing it, and the collaboration has helped us build stronger governance, improve adoption, and really tie our go-to market strategy back to real behavior and engagement. It allows us to deliver a more consistent story, support our reps with clarity, and really create a unified experience across every touchpoint.  RR: That certainly makes me, and I think all of our teams happy to hear. One of the things that’s really interesting about what you said is that earlier you gave us the data to kind of back it up and say that yes, we’re seeing these things anecdotally, but we’re also seeing them empirically.  Thinking of that data, I know that it kind of speaks for itself when it comes to the work that you and the team are doing, but we’ve heard that Digital Rooms have been a key driver in your enablement strategy and in your strategy with Highspot. In just 90 days you’ve generated like 3,000 views with your Rooms. How have you and your teams been leveraging Digital Rooms? Can you talk to us about what impact you’ve been seeing so far? AP: Digital Rooms have become a core part of how we help our teams go to market. We use them to create curated experiences that package our messaging assets and resources into a structured, easy-to-navigate format that aligns with the story we want to deliver so reps can use them to deliver a clear and consistent narrative and everything they need is in one place.  This helps our teams guide customers and partners through a cohesive experience. That visibility supports stronger account planning, more intentional communication, and better alignment with customer needs. The engagement has been strong. We’ve created over 500 Digital Rooms with an average of 30 minutes of viewing time per Room. Some have accumulated between 20–60 total hours of engagement, and several have been shared externally more than 40 times, which shows us that our customers and partners are engaging with the content in meaningful ways. RR: I love to hear how you’re using that Digital Room scorecard to keep a pulse on how they’re performing out in the wild. When you are supplying go-to-market teams with these Digital Rooms, is it the marketing team that’s building them? And if so, what kind of use cases are you building for? AP: It’s in partnership with both marketing and sales, so we can help them

  4. 12/12/2025

    Episode 139: Strengthening Agency Partnerships Through Enablement

    According to the State of Sales Enablement Report, 2025, 29% of companies still rely on multiple disconnected GTM tools. So how can organizations leverage a unified platform to scale sales readiness and achieve GTM success? 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 Heather Hubner, advisor distribution and agent relations at Priority Health. Thank you so much for joining us, Heather! I’d love it if you could just start by telling us a little bit about yourself, your background, and your role. Heather Hubner: Thanks for having me, Riley. Again, my name is Heather Hubner, and my role is a somewhat newer role in our company, but I came from the employee benefits side of the industry and then moved into sales. So I was a sales rep for several years for priority Health and that has evolved into the distribution side. Really my role is to ensure that our agent partners have a very aligned message as far as our products go, and just ensure that we are giving them the tools they need to represent our product in the field appropriately. RR: I kind of wanna double click into something you mentioned, which is that you started on the sales side of the house at Priority Health. So with that background in mind, can you walk us through some of the unique challenges that reps in the healthcare industry face, and then maybe a little bit about how enablement can help them overcome those things? HH: Yes, and I love this question. Being a sales rep in this industry—I think anyone who has worked in it understands the complexity—-is complex, it is fast paced, it’s somewhat seasonal, but we’re also learning that those seasons are no longer such. It’s just a high pace all year round.  As a rep, one thing that I really learned was we have time wasters: we’re looking for a certain material that an agent wants, we’re reeducating ourselves on a product because maybe it’s something that we don’t delve into on a regular basis, we just need to reeducate ourselves as a rep.  Before Highspot, so much time was spent digging around for that information and therefore less time was spent selling and building relationships and building trust with the agents. That was, that was very challenging. You know, I always thought: “Goodness, if I had everything at my fingertips, frankly, I could sell more for our company because I would be spending my time in a valuable way.” So I would say about four years ago, that’s when we first started using Highspot and it was an absolute game changer. I mean, it changed our world. We could get everything in one spot, and there was a lot of emphasis on making sure we had a source of truth.  Reps know they know to go to Highspot, they can grab what they need when they need it, send it to an agent, reeducate themselves, and there isn’t any more guessing about where to look at our system, which drive, how do we find out who has the most up-to-date information. It really has been an amazing alignment tool. RR: I love that you’ve walked the walk so much so that you’re like: “I know what was hard, and I can now have the agency and also the tooling to go in and fix it.” I think that’s wonderful. And I think that’s always the goal of enablement, right? But when you have that background, you’re so much more in touch with what your reps need. So now that you’ve kind of made your way into this new role, I’d like to dig into what you’re working on now. So, what are some of those key initiatives that you’re focused on driving for the business this year? How are you hoping to decrease complexity like we just talked about for Priority Health’s reps and agency partners? HH: To give you an idea of our journey so far, we started using Highspot for our reps and really went hard this year on ensuring that we had similar tools for our agents creating pages, specifically for our agents by market segment. We have created digital pages, so to speak. We call them engagement pages from an externally facing standpoint, and we have tailored the tools that those agents specifically need. This is important because, you know, if you are a small group agent, you generally don’t have all the complexities that large groups have, and therefore you don’t wanna weed through all those materials.  So it really is the same principle applies, right? It’s giving them the tools they need when they need it, without having to sift through a lot of things that they don’t need. So creating very tailored pages for them has been really important.  We’re going to take it a step further this year. So, to get to your actual question, we’re gonna focus on training. So when we get new agents in the field, they are the ones that we count on in order to sell our product, and oftentimes they are getting in the trenches, learning about all the carriers all at the same time. It’s a lot to digest.  What we are gonna focus on is working on our training and our onboarding experience for our agent partners, and that way they can get in the field quicker with the right type of information, stay compliant with what our product actually is offering, and feel more comfortable. The hope there is truly we’re gonna sell more, more quickly, and they’re going to feel more comfortable repping our product. RR: I love the kind of internal enablement philosophies that are being extended out to the partner network—we know what you need and we want to give it to you in an easy, digestible way that is tailored to your workflow, because I’m not going to make you dig for something that you don’t even need. Keeping that in mind, I’d love to know what some of those other key building blocks for effectively equipping agents and building strong partner relationships are for you. HH: Gosh, the biggest piece is trust, right? They’re building trust, um, spending time with them. Listening. Listening is the biggest piece. When agents are telling us things, we have to listen to them and act upon them. Otherwise what’s the point? The fact of the matter is in our industry—and anyone that works in health insurance knows our agent—partners are very direct. Sometimes too direct, but they’re very direct. So when they’re telling you something, they mean it and they are going to be truthful because their livelihood is also reliant upon the information we give. But I would say relationships are the strongest one. Trust, transparency. You know, being honest. If we are, you know, if an agent questions us on something, or frankly, sometimes they’ll compare us to other carriers: “Hey, this carrier does this. How come you guys can’t do that?” Be honest about it.  But it really goes back to listening and forming those bonds to where they trust you. Because the more an agent trusts you, the more willing they are to say: “Hey, this group is a really good fit for your product. And I feel confident that you’re going to onboard them smoothly. I feel confident you’re going to take care of them from a customer service standpoint. And I feel confident that when there’s a problem, I’m going to call you, you’re gonna answer and you’re gonna help me solve it.” RR: So, you mentioned listening and building trust and transparency, and then using what agents are saying to kind of build your programs and how you support them. How are you kind of creating these channels to get in touch with your agents? Is it just getting on the phone and talking to people and then taking that information back to your strategy? How are you kind of creating that feedback loop? HH: So our team, I wanna give a little, um, shout out to the team a little bit. We are very unique, so we’re a newer team. There was not a distribution and training team before. We’re really working on the strategy for exactly what you said. How do we strategically get out? How do we make sure that our interactions are meaningful, and how do we enable our sales team to do the same?  So what we have really come up with—and it seems to be quite successful—is we’ve created a premier partner program. What that means is we’ve got different levels, essentially of our partner groups: gold, silver, and bronze. For each one of them, we provide different levels of service, so to speak, but it’s really rewarding them for their business with us.  With that, we’ve created a strategy on formal meetings. So formal meetings are when we actually go to the agency, we’re bringing our team of leaders and some of our reps, and we’re spending time with them in person and talking about our new products, some of the intricacies and nuances about what to expect, getting feedback about what they’re seeing in the industry and what they need in order to keep their clients in the space that they’re hoping to be for their employee benefits. We do that twice a year, and then we have kind of the other agency partners who we hit once a year. But on top of that, you’ve got kind of this less formal interaction, and that’s where we really come into play from an enablement standpoint. We want to make sure our sales reps have what they need when they need it. We help create some content for them so that when they are having more informal meetings—maybe they’re going to lunch, they’re going to breakfast, and they want to build a relationship, but they also want to bring some value and bring some meaningful messaging. That’s really where we’re focused. We understand that there’s different levels of that relationship building. You know, those individual reps, it’s so important that they have those relationships, but as an organization, as a whole, it’s im

  5. 12/05/2025

    Episode 138: Developing a Reliable, Repeatable Launch Process

    According to Forbes, sales reps spend 35.2% of their time selling and 65% of their time on literally everything else. So how can organizations cut through the noise and focus reps on the activities that matter most? 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 Yvette Boucher, Director of Sales Enablement at CentralReach, and Chelsea Louro, Senior Manager of Sales Enablement at CentralReach. Thank you so much for joining us, both. Just to kick us off, I’d love if you could tell us a little bit about yourself, your background, and your role. Yvette, would you like to kick us off?  Yvette Boucher:  Yeah, thanks for having us. I’m Yvette. I’ve been with Central Reach for about six years now, building out our enablement programs. We’re an AI-powered platform for autism and IDD care providers. Our end-to-end software and learning solutions help organizations deliver quality outcomes to help every client succeed. I’ll pass it over to Chelsea. Chelsea Louro: Thank you. I’m Chelsea Louro, senior manager of sales enablement. I’m also approaching six years here at CentralReach. And then prior to coming to CentralReach, I was a teacher for a little over a decade. I also did teacher training and recruitment and then education sales, then that brought me here where I was in SDR, an account executive, and then also now in enablement the last three and a half years. RR: Amazing. Well, we’re super excited to have you here, especially knowing that you guys were both up for a Spark Award this year. So you are doing some really wonderful work that I’m really looking forward to digging into as we kick off. I’d love to start with you, Yvette.  Let’s open with what’s difficult, what you’re up against lately. So, what are some of the core challenges to GTM success that you’re seeing, and how have those challenges kind of evolved throughout your enablement career? YB: One of the biggest challenges we’ve seen recently is just how short the timelines have become between a product announcement and when reps are expected to start selling it. We’re moving faster than ever, especially with our new AI products.  That means enablement has to get the reps the right information, the right messaging, and the right training almost immediately. It’s been a constant balancing act between speed and depth. We want reps to feel confident and well prepared, but we also need to deliver that enablement in a really agile way, so they’re ready to have meaningful conversations from day one. So the pressure to move fast has definitely shaped how enablement operates today. For us, it’s not just about building training, it’s about building our systems and processes that can scale and flex with the business. RR: I think you’re certainly not alone in some of those challenges. Organizations across the board are struggling with similar things, and everyone’s kind of looking for that silver bullet. Chelsea, I wonder if you can maybe help us kind of build on this. So, from your perspective, how does an enablement platform support you and the team in addressing these challenges and helping reps focus on selling? CL: Yeah, so I’ve been in roles at other companies where there wasn’t much organization. There was no enablement platform at all. Both as a seller and a leader, I spent a lot of time trying to find the resources that I needed, and sometimes just—out of pure frustration—had to create my own. I know a lot of sales reps come across that as well.  So, having a platform like Highspot gives us kind of that single source of truth so we can get all of our content guidance training all together in one platform, one workflow. Our reps aren’t spending time trying to find things and they can focus on what they really need to do, which is sell. It also helps us deliver insights back to our leadership, um, and lets us see what content and sales plays are actually driving our sales.  That visibility allows us to continually refine and to make sure that the reps are supported and then focused on selling. RR: Kind of moving forward, I would love to maybe focus on some of the ways that you’re using an enablement tool. I’ve heard that you and the team are doing some really wonderful things with Sales Plays, and that’s kind of part of what earned you that Spark Award nomination.  Yvette, knowing that Sales Plays are playing such a critical role in supporting some of your AI-centric product launches this year, I’d love to learn a little bit from you about what that strategy is, and how you’re using plays to streamline rep workflows. YB: We’ve really built our Plays with simplicity and speed in mind. So, the idea is that we get the right information in our reps hands as quickly as possible with who to target, what to say, and what resources they can use so they can jump straight into the action instead of digging through multiple tools or decks. When we launched our AI solutions last year, the Plays became a living guide for the team. And because the plays live right in Highspot, reps can easily pull them up in the moment. So as our products continue to evolve, the Plays evolve too. So they’ve become a go-to reference point that helps stay, keep everyone aligned and stay confident in how they’re positioning our solutions. RR: It’s funny because you know, a Sales Play is such a humble thing, but it can be so powerful if you use it right. It’s not just the strategy that I think is really impressive with what you guys are doing.  Chelsea, I’ve heard that you and the team have driven a really incredible 99 again, 99% adoption rate of your Plays. So can you walk us through how you maintain such high sales play adoption? CL: I think a lot of it is just constant repetition and reinforcement. Our teams have kind of become used to our enablement and go-to-market communications, so adding in Sales Plays was just a nice easy process.  Every time we roll out a new Sales Play, we emphasize the importance to them. We let the team know that any changes or updates will be made in that Sales Play. So that’s where they need to go to find their source of truth.  I put out a weekly newsletter called the CR Morning Brew every Monday, and in the Brew we share new marketing content, any updates to those Sales Plays, any initiatives, things that they need to know. Then we have a live sales meeting on Tuesdays where everything that was shared in the Brew is reinforced. So again, the reps are reading it, they’re getting it in sales team channels—because I share out that Brew in every single sales team channel—and then that live, vocal repetition and just making sure that they’re paying attention and, and they know what’s happening. RR: I think one thing that’s really important that you called out there is that yes, you’ve driven really high adoption, but you also built the foundation of communication beforehand. So you had these levers in place that you could pull and be like: “You trust us. You know where we’re coming from, and now I can send you to the right places.”  So, you’ve built a strategy. You’ve seen near unanimous engagement with it, but it goes further than that.  Yvette, you shared that using Sales Plays during a recent product launch led you to influence over 900 opportunities. Could you walk us through how you drove those results and then how that impacted the launch outcomes? YB: I think it really came down to how we set up the Plays to begin with. Like it came down with that alignment and teamwork. So prior to the launch we worked cross-functionally with product marketing, sales leaderships and our SMEs to make sure the reps had everything they needed for messaging, positioning, and the hands-on product support, which I think was key there. They needed someone that knew that product. We also knew we would be learning in real time. So every team at CR leaned in to help them, everyone. By the time the Play that went live, we were already making edits and updates based on early feedback. Every update and change was communicated in our Morning Brew. sales team meetings, and individual team meetings, and we continued that communication and support from our SMEs, and that’s really what helped us influence those opportunities. It’s also great that it was a great product for people to have. RR: That is the kicker—it’s hard to sell when you don’t have something exciting. So I’m glad that both cylinders were firing there. You guys were doing the right things and so was the product.  Now, I feel like we could probably continue digging into Sales Plays, there’s a lot there. Again, like I said, they’re one thing that gets overlooked, but they can be really, really high impact.  I would like to maybe switch gears to another win that you’ve shared with us. Chelsea, you leveraged Highspot to redesign your onboarding program, achieving a really impressive one hundred percent adoption of required training and reducing ramp time by one to two weeks. Can you walk me through what you were thinking about as you were improving this program? What impact has that has had on rep productivity, ramp time, and all of those good things? CL: Yeah, so we kind of reimagined the onboarding program to be a little bit more personalized and performance driven. Using Highspot’s training module, we built out role-specific Learning Paths that kind of combine product knowledge, our Sales Plays, and then real world scenarios. We also created an onboarding homepage. So when a brand new rep first joins the team, they log into Highspot. They have an onboarding h

  6. 10/30/2025

    Episode 137: Unlocking the Value of Content Through Effective Governance

    According to research from Forrester, 70% of marketing content goes unused. So how can you effectively structure and govern your content to unlock its value and drive measurable business results? 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 Chanique James, marketing lead generation and enablement specialist at MSCI. Thank you so much for joining us, Chanique. To kick us off, I’d love if you could just start by telling us a little bit about yourself, your background, and your role. Chanique James: Sure. Thank you so much for having me. I’m excited to be here. I have several years of experience in brand and product marketing, focusing on promotions, trade marketing, and event management, as well as sales enablement. Over the years I’ve managed from product marketing initiatives across both B2B and B2C environments, developing integrated strategies that connect creativity, storytelling with measurable business outcomes. I’ve always been passionate about connecting strategy with people and finding the balance between creativity, data, and impact. That perspective has shaped how I approach marketing and enablement today. In my current role, I focus on marketing, lead generation and enablement. Ensuring or grow to market teams have access to the right content at the right time, along with insights and tools to engage clients effectively. I see my work as connecting digital strategy with operational excellence, bringing clarity, consistency and impact to how marketing and sales collaboration. RR: Amazing. Well, from that background, it seems like there’s a lot of ground we could cover here. A lot of experience across a lot of different arenas that I’d love to dig into. So let’s just start with maybe a bit of background on kind of the environment that you’re working in. So I know that MSCI provides a pretty broad range of services to the global investment community. So what are some of the unique challenges that your go-to market teams face when activating at scale across global regions? And then to your point, how does digital enablement help address them in global environment? CJ: I believe that scale introduces complexity from different regulatory environments to language nuances and varying buyer expectations. Go to market teams face similar challenges across regions. They have to balance consistency, compliance, and connectivity. Ensuring that messaging feels unified, yet relevant in diverse markets. Managing that balance requires both structure and flexibility, and that’s where digital enablement comes in. By centralizing content, data and workflows, digital enablement gives team visibility into what’s working and empowers them to adapt quickly. These tools make it possible to deliver localized content and timely materials to client facing teams around the world, helping them navigate campaigns efficiently as well as, I would say more confidently. RR: Amazing. It sounds like you’ve got a lot on your plate, so I’m excited to dig into kind of the strategies for approaching those obstacles and those challenges of scale beyond kind of some of the unique obstacles that you encounter as a global organization, as a financial services organization, I’d like to focus on some that pretty much every organization is gonna face, which is the disconnect across the go to market organization. So as a marketing leader. What go-to-market initiatives are you focused on to better align your marketing and your sales teams? CJ: For me, I would say alignment starts with visibility and connection. It’s really about making sure marketing and sales teams are working from the same playbook as well as working together so that content, messaging and data tell one cohesive story. That alignment creates focus and efficiency. It means simplifying access to marketing and enablement tools, making insights actionable, and keeping collaboration front and center with both sides. That is marketing and sales are connected around shared goals and clear communication. Everything else from productivity to performance naturally improves. RR: Absolutely. And I think one of those key levers that you can pull on is the content that you’re sharing across. When it’s well managed and well socialized, you unlock really strong cross-functional collaboration when it’s not, we know the consequences in your work. One of those key focuses is content management. So from your experience, what are some of the common pitfalls that financial services organizations like yours might face when developing and managing content, and then how can maybe they avoid them? CJ: I would say possibly a big, or the biggest challenge that we have is fragmentation content often live in silos owned by different teams, sometimes with different goals that can lead to duplication, outdated materials, or even inconsistencies in messaging and compliance. Key, however, is strong governance and collaboration, establishing clear processes around how content is created, reviewed, distributed, and even maintaining open feedback loop across marketing, compliance, and sales can actually help us ensure that every piece of content is purposeful, consistent, and UpToDate in addition. I believe that when organizations take that structured approach, they move from managing content reactively to managing more strategically, and this can actually turn into a real advantage for the business. RR: Can you talk to me a little bit about like the value of that strategic approach as opposed to a like reactive approach? CJ: So I ultimately believe that in terms of content management, you really need to think strategically, how are teams accessing it? How are they using it, and also is it relevant for your market? I believe that one of the key things that we can do is always leverage the data. Enablement tools allow us to get a lot of insights not just into client engagement with content, but also how our sales team are actually using it. When we actually leverage that data, that helps us to drive strategy and that strategy actually helps us improve over time. The content that we continuously create and the content that we also continuously share with our clients. And I think that’s a big portion. That’s a big part of actually making sure that we’re not just reacting to things, not be being used well, but also strategically ensuring that moving forward when we see certain metrics, we use that to create better content, to have better client relationships and conversations for our sales team. RR: Yeah, I think that’s such a great perspective. I think sometimes as marketers, you get really caught up in like what you’re excited to create, and sometimes you have to take that step back and go, what is actually useful? What are our reps like, what are our clients like? And how can I lean into that? So I, I love that you’re taking that approach. Um, and I know good governance and good content creation strategies can be really, really crucial, but they can also be really difficult to maintain. So I’d like to talk a little bit, maybe about. The impact of taking the time to focus in on that. So what do you see as the value of having compliant up-to-date content and how does that enable reps to succeed in the field? CJ: Sure. I believe that having quality and compliant content is very essential, and also having enablement platforms actually serve as a great deal in terms of ensuring that the content is easy for sales reps to access. Enablement platforms are transformative because they turn content from status assets into living resources. They centralized content distribution, enforce compliance, and provide clear insights into engagement and performance. For financial organizations where accuracy and timing are everything, this gives our sales team confidence that what they’re sharing with clients have been approved and is also relevant. So I would say that it’s not just about access, it’s really about assurance, agility, and trust. RR: I think that that last call out is so key because it’s ultimately just about trust, right? Your reps need to know that your content is reliable and aligned to their needs. Your business needs to know that you’re compliant and aren’t gonna create unnecessary risk that nobody wants to deal with. If you can prove that and build that brand of trust. You’re set. And maybe that’s kind of how you’ve achieved such a high recurring usage rate in Highspot. So can you walk me through, in addition to some of the governance pieces that we’ve been talking about, but what best practices have been effective in helping you drive strong adoption? CJ: Adoption thrives on relevance and experience. We treat our environment as more than a repository. It’s really a dynamic workspace that grows with our teams. We’re focused on building a clear content structure so users can easily find what they need, and we partner with champions who will help drive awareness, as well as share best practices. We also offer focus training and share success stories with our new users. That highlights real results. In addition, we integrate with platforms such as Salesforce so that the tool actually fits naturally into the workflows of our sales teams. I think that when people see genuine value in how it helps them, it actually allows them to work smarter and adoption really naturally flows from that. RR: I love touching on the ecosystem piece and creating an environment that works for people. ’cause a lot of the time when enablement feels like a mandate or it’s not built with workflows in mind. You don’t see that adoption, so love to hear the best practices that

  7. 10/23/2025

    Episode 136: Bridging the Gap Between GTM Strategy and Execution

    According to the GTM Performance Gap Report, 98% of leaders say their GTM strategy is active, but only 10% see it driving results. So how can organizations bridge this gap and turn strategy into meaningful execution that drives outcomes? Riley Rogers: Hi, and welcome to the Winland 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 Becky Payne, Vice President of Sales and Success Digital Enablement at Sage. Thank you so much for joining us today. Becky, we are super excited to have you. As we kind of get things kicked off, I’d love it if you could just start by telling us a little bit about yourself, your background, and your role. Becky Payne: Absolutely. Well, thank you so much for having me on the Win-Win podcast today. A little bit about me and my background. I’ve been at Sage for seven years. I’ve been in corporate America for almost 17, and what I can tell you is. When you really get under the hood of go-to market, that’s really what makes an organization home, right? And so my experience and my background is a lot of understanding the channel, a lot of understanding how go-to market works in real life, which is a phrase I like to use quite a bit. As well as then understanding how that connects into our strategy as we think about where we need to drive transformation to get to our ultimate outcomes along the way. My role at Sage is very unique. I sit in our routes to revenue organization, and so I get the privilege of enabling our go-to-market teams to drive the revenue that they need to and the various motions and go-to-market aspects of what they do every day. RR: Amazing. First of all, I love the Routes to Revenue team. That is the best team name. Based on what you’ve said here, it seems like we’ve got a lot to dig into. As you mentioned, you’ve got a pretty extensive experience in both channel and sales enablement, so can you walk us through how you journeyed into sales enablement, and now that you’re here, how that background influences your strategy today? BP: Well, I think my experience is probably a little bit of a unique one, but I’m happy to share it. So prior to this role, I actually served as our chief of staff or business executive in the North America space, and prior to that actually for our global partners and Alliance leader. So I have spent a significant amount of time in both of those spaces, and what I was able to identify is that. We had the most brilliant pieces of technology out there. We had the most brilliant strategies out there, but we didn’t have a great way of connecting those into the workforce every day to get them to drive the outcomes that the business really needed to see. So coming into this role, first of all, I think I have the best role at Sage, so I love to brag about what my team does. But what we get to do is we get to connect in with solving real world problems. We get to work with these sellers and these channel partners every single day to be able to deliver incremental value into what they do directly in relation to the customers, but also then how we make them operationally efficient in their day-to-day activities to be able to execute on that go-to-market strategy. RR: It seems like we got the exact right person to talk about the strategy and execution gap. I think you mentioned everything that I hope to cover, so super excited to dig into how you’re making that all this happen. Before we get into kind of the fix it strategies, I’d love to start with where we are today. So as you’re looking across the go-to-market stage and seeing some of the obstacles that pretty much every team is encountering in their day-to-day, what are some of the top challenges to sales success that you’re seeing? And then how are you addressing those challenges for both internal reps and channel partners? BP: Well, I don’t know that we have enough time today to get into all the details, but, but when you really think about it, it’s common in a lot of places, right? Yes, we might be in the high tech world, but a lot of what we’re experiencing is what is happening across the globe today. So if you think about it, a lot of our, both internal sellers, as well as our channel executives and partners, actually are experiencing information overload. And quite honestly, they’re not able to make the understanding of where that information overload then meets the relevance. Impact driver for what they’re dealing with every day. You know, a lot of our colleagues are flooded with content tools, data galore. We have a very, very data rich infrastructure here, which is amazing. However, the challenge isn’t access. To that, right? It’s really the precision and the action that they’re taking on that. We also have a bit of a previous history in having some consistency gaps when you think about that, right? So both direct teams and our channel partner teams that are out there selling and they’re engaging with these customers. Until recently, we didn’t really have a global blueprint. We didn’t really have a ton of global sales place, so we had a, a large inconsistency in how things were showing up, which their format, how we were measuring those outcomes and those impacts couldn’t be aligned on the day-to-day basis. We also are seeing a ton of pace of change. I mean, every organization is experiencing not only the AI transformation and AI change, but overall as a team at Sage, we experienced a significant amount of transformation in the last 24 months. So we’re kind of embracing that as we see a lot of the challenges as we embrace the AI transformation that’s on our doorstep. RR: You called out a couple things that I think most teams are gonna resonate with. Information overload, crazy pace of change, consistency issues across your channels. There’s a lot of noise out there, which makes it really difficult to create enduring, trusted relationships that drive the results you’re looking for. So from your perspective, what are some of the key building blocks behind a strong, effective partnership with your channel teams? BP: All right. This is one that goes a little bit like near and dear to my heart, right? What we have such a great ecosystem around us at Sage and such a great channel partner team, both internally and with our partners directly, is the clarity of the purpose. And the incremental value that they add to Sage. A lot of times our managing director of North America, Mark Hickman, he references the one plus one equals three equation, and that’s generally how we feel with our partner ecosystem. We have the best partnerships and those best partnerships start when both sides are really clear on the outcome and the impact that we mutually drive together. And what we’re able to see is when we do that in a very cohesive, consistent, and aligned strategic way from the leaders all the way down to the front line, we’re able to see incremental value driven through with and to our partners as well as back into Sage when you think about that bigger ecosystem play. RR: Okay, so we’ve covered a little bit of the philosophy of alignment, outcome, shared outcomes. I’d like to talk a little bit about the execution piece, so how you’re bringing that strategy to life with technology. Can you walk us through how an enablement platform helps you better equip both the internal and the partner side of the house? BP: Yes, this is where I nerd out just slightly ’cause this is absolutely what I love. So when you think about it, it does absolutely start with a unified go-to-market motion, which we have been able to deliver over the past year with my partner in crime, Mark Jackson. But we also have now, literally a couple weeks ago, launched our global unified enablement platform, which happens to be Highspot. And what we were able to learn from that is when you take a consistent blueprint and go to market mission, right, and then you add that. The best platform that we can. Not only can we surface insights and leverage some of the AI technologies that Highspot is offering, but we also have an ability to have mutually shared documents, mutually, you know, shared Digital Sales Rooms. Things that allow us to go to market together in an effective way that we’ve never had before. We really feel like this is a game changing strategy for us and really is a way for us to bring our blueprint, right, and that kind of strategy to life in the day-to-day execution. Some of the genomics aspects of your platform bring visibility into some of these sales plays and other items that we’ve never had before. We can now go in and we can see what partners are engaging with us, who within those partners are engaging at a different way, allow us to provide reporting to senior leaders, but also at those frontline sellers. So they’re going into their weekly strategic team meetings with these partners with a strategy that’s very clear. They’ve got content they can reference. They have points of which they can then articulate what is or is not working in sales plays and other things, and we’ve never had that capability before. RR: Well, that’s absolutely what I love to hear that the platform is becoming such a game changer for you guys, and you’re already seeing that difference between before and after. One thing I’d like to double click into what you said there was that you’re starting to dig into Highspot AI capabilities. So can you share how you’re building some of those features into your enablement strategy and then where you’re eventually hoping to go with them? BP: The future’s endless, right? Endless possibilities is where we’re hoping to go. But if you think about something like Sage, we are a global busi

  8. 09/25/2025

    Episode 135: Elevating the Buying Experience for Today’s Digital Buyers

    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 we can consistently stay, um, ahead of what the trends are and how people like to change, how they like to consume, what they’re seeing 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 have 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 up-to-date 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 prioriti

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About

Welcome to the Win Win podcast by Highspot. A short show where we dive into changing trends in the workplace and best practices to navigate them successfully.

Information

  • Creator
    Highspot
  • Years Active
    2021 - 2026
  • Episodes
    141
  • Rating
    Clean
  • Show Website
    Win Win Podcast