Win Win Podcast

Highspot
  • 5.0 (6)
  • Business
  • Updated Biweekly

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. Aug 12

    Episode 156: Building & Buying the Right Tools for Your AI Ecosystem

    According to Gartner, worldwide AI spending is forecasted to increase 44% by the end of 2026. Companies are investing in AI, and they are investing heavily. But knowing where and how to invest isn’t easy, especially with what feels like a million different AI tools out there and a million more different ways to build your own. So how do you figure out what to build, what to buy, and which investments will help you move the needle for your business? Riley Rogers: Hi, and welcome to the Win/Win Podcast. I’m your host, Riley Rogers. Join us as we dive into changing trends in the workplace and how to navigate them successfully. Here to discuss this topic is Cody Sims, head of commercial brand at Cox Communications. Cody, thank you so much for joining us today. Super excited to hear your thoughts on this one. Before we dive into what is quite a loaded topic, could you tell us a little bit about yourself, your background, and your role? Cody Sims: Yeah. So, hi, I’m Cody. I’m the head of commercial brand for Cox Communications, and it’s kind of crazy how I came into this role. So I actually started my career when I was 15 and was installing phone systems for my dad’s phone company. And after that, I had actually had two parts of what I thought was what I wanted to go into, and that was either musical theater or physics, because those were two things I really had a passion about. And when I got into college and had musical theater as my major and physics as my fallback, I realized that both of them left a part out of what I really enjoy. And so I ended up actually landing in marketing because it’s both analytical and creative, and that has served me really well over the years. So, across Cox, I have done all kinds of things from product management to market development to pricing to competitive analysis, and now in the brand world. It’s given me kind of a 360 view of the entire business from a marketing lens. I would say that I’m pretty much a transformation leader. I really enjoy breaking things and building them up new again. So, AI is happening right at the right time for me. RR: I love that story, and I love that it’s taking you to a place that especially now is getting more and more technical, more and more analytical. I’m very excited to get into that transformation leader side of things. But before we do, can you paint a little bit of a picture of your sales environment? CS: Yeah. So when I first came to Cox, it was very similar to most of what you would call a CLEC, or a competitive local exchange carrier, which is primarily internet service, voice services, and obviously because it was Cox, some cable TV services that were the triple threat. That was kind of what in the early 2000s was kind of the way that they went to market. But over time, the team at Cox realized that in order to stay competitive, they had to add to the portfolio to make sure that they were providing value to their customers, and I’m sure many would understand that and have gone through similar transformations. And so we had acquired several different other companies that added to our portfolio, and developed some of our own products, and over time that turned into a lot of products. But it’s not just 70 products. It’s 70 products, it’s nine customer segments that we have from a segmentation perspective. It’s six distinct buyer personas, industry verticals, what’s serviceable at that address. So you take all of these different components and it’s almost like three-dimensional chess for the salesperson. The way that I like to think about it is that the sellers, what they really need and what their challenge is, is that they’re not looking for specs. They’re looking for what are the business outcomes that my customer is trying to achieve, and then what do I have from my portfolio that will help them to achieve those results? So it’s no longer a world where they can memorize everything and know every product in and out, and be the technical expert. They really do have to have tools and systems that help them to have the right knowledge at the right moment for the right person in the right place. RR: Yeah, there comes a point when the human brain just can’t contain the context and the expertise that you need. So when you can’t ask for expertise, what you can do is provide, to your point, that just-in-time support. And one of the things that you alluded to was that that’s where you kind of started some of that AI investment as a way to bridge that gap. You’ve given us a little bit of a taste, but what kind of motivated that early initiative? CS: Well, I would say that, over time what we discovered was that we couldn’t keep track of all of our marketing materials, collateral, all of the pieces of information in just files, formats, and putting it online into a here’s-an-accessible-library. Because the library just becomes bigger and larger and more difficult to manage. But I would say that we didn’t set out to do AI. We didn’t sit down and say, “Oh, hey, AI looks cool. Let’s make sure we’re doing it.” We needed to transform our go-to-market strategy so that we were more nimble, we were more competitive, and that we could deliver the kind of experience that our customers were asking for. And so AI was the mechanism that would help us to get there. But what really triggered this whole thing was what I mentioned earlier, was our segmentation. When we sat down and said, “Let’s rebuild the way that we look at our audience segments,” and we did that based off of what is the value to Cox of each of these customer profiles, and then what is the technology sophistication of that client, of that business. And that intersection allowed us to create our nine different segments that we were working on. And so when we did the math, when we looked at all of that information and all of the things that we needed to be able to provide to those segments, we realized this was quickly going to turn into something that was far beyond any marketer’s ability to do. But what we knew is that the Gartner information we were tracking said that personalization was having much higher returns on the way that people respond to information. And not only that, but if you do personalization and you get it wrong, if I call you and I say, instead of, “Hey, Riley,” and I say, “Hey, Jonah,” you’re like, “Hmm, nice try.” So personalization is really important to being successful, but getting it right is even more important. So we realized that we needed to have some radical partnership between our marketing, AI, and sales teams, that we needed to make sure that this was not just an IT project, that we were going to go and pull a bunch of requirements together and everybody would be like, “Oh, hey, here’s this new tool. Everybody figure out how to use it.” And it wasn’t necessarily about optimization. It was about transformation, the way that we go to market, the way we think about our customers, and the way we show up. So I would say that AI definitely was part of the solution set, but we had to look ourselves in the mirror and say, “It’s time for us to actually think about this in a completely different way.” RR: That distinction comes through very well, and I think is very important because oftentimes when you’re in kind of the scramble to be keeping up with the market, keeping up with your competitors, there is this urge to just tack on AI because we have to. But when it’s not strategic and it’s not built into the things that you’re actually doing, to your point, it’s we put together some specs, good luck using it. But instead, now it’s something that’s really built into the way that you work. I would love to hear a little bit more about that specific use case, especially given the fact that a lot of teams are running into that question of how do we use AI and can we just build what we need ourselves? Given that you’ve done the math, answered the question, I’d love to hear how it worked and kind of where you landed. CS: It’s very easy to fall into the trap of, “Hey, everybody, here’s AI. We put it on your computers, now go use it.” And so then everybody starts using AI to try to figure out, how does this help me in the job that I already do, in the role that I already do, in the processes that I already do? And so then it really limits the impact that it can have on the business and the performance because either, A, you have a handful of people who are really smart, and they go crazy with it, and they create their own thing, or you have a bunch of people who are looking at it going, “Okay, came up with some ideas, but I still have to do my work.” What you end up with is there’s no standard. There’s no flag running up the hill to say, “Everybody follow me. Let’s go do it this way.” So, it required both the yes, we had to make sure that the teams were bought into using AI, but we also had to have a standardized way of approaching how we deploy AI. And that brought us to the question of do we buy or do we build? And because there were so many different parts of what kinds of functionality we needed, it wasn’t the same answer for every one of those needs. So in some cases, we have a tool, we have a partner, they already have AI integrated into their platform, let’s go see how we can use that. In other cases, and I’ll give you an example, in the case of content generation, that is where we started with our AI journey about a year ago. We sat down and started interviewing and reviewing all of the different providers who can do content generation. Every one of them had a different approach to content development, content generation, which were all very good, and they attempt to make sure that they are covering as

  2. Aug 7

    Episode 155: Shaping GTM Strategy with Deal-Level Intelligence

    According to research by Gartner, by 2029, sales organizations with AI-driven enablement functions will achieve 40% faster sales stage velocity than those using more traditional approaches. But getting there means building the kind of workflows that tell you what actually works, which is only possible when you can see inside the conversations that selling actually happens in. If you can’t, you might just find yourself scaling an AI-powered program that’s completely misaligned with how your sellers sell and how your buyers buy. So how do you understand what your teams need, and then build an innovative, mature, AI-powered enablement program to match? Riley Rogers: 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 Jill Sawyer, Director of Sales Enablement at RL Datix. Thank you so much for joining us today, Jill. I’m really excited to have you here. I think we’ve got a very fun conversation ahead. Could you give us a little bit of an overview of who you are, what your background is, and your work today? Jill Sawyer: Yeah, absolutely. First, thanks so much for having me. I’m super excited to be here. Currently, I sit as the Director of Sales Enablement for North America at RL Datix. I’ve been here for a little over seven and a half years. JS: My background is a bit non-traditional for sales enablement. I started more on the marketing and product marketing side. I moved into the enablement role a few years ago, a little bit over two and a half years ago, but I was really stepping into a function that needed to be built from the ground up. That meant figuring out not just what sellers needed to know, but how to help them actually use it in moments that matter. I’ve also recently gone back to school. I’m currently pursuing my Master’s of Jurisprudence in Health Law at Loyola University Chicago, which has been really valuable in this role. Our customers operate in a highly regulated healthcare environment, so understanding more about compliance, patient safety, risk, and legal frameworks helps me think differently about what our sellers need to understand and how we support them. RR: And you wear so many hats through it all. I’m really excited to see how all of this comes into play in your work today. But before we jump into what you’re working on now, could you give us a little bit of an overview of your sales environment? JS: Yeah. So the way I usually describe RL Datix is that we sit at an intersection of healthcare safety, risk compliance, and operational reliability. Our customers are health systems and hospitals that are trying to solve problems with very real stakes. They’re trying to either prevent harm, respond appropriately when something does go wrong, or maintain regulatory readiness. So it makes our sales environment really complex because those problems rarely belong to one department or one singular buyer. The buying committee can be really broad, and each stakeholder is looking at the problem through a different lens. So for our sellers, the challenge is being able to zoom in and zoom out. They need to understand specific workflows, not only within our product, but within the landscape. But they also need to connect that workflow to the larger operational and strategic priorities of our customers. This is where enablement for us becomes really important. I’m helping translate complex healthcare problems into clear, relevant conversations about value and outcomes and how RL Datix helps raise the standard of care. RR: So a lot for sellers to juggle, and a lot for you to help them juggle, especially because you built the enablement function largely from scratch. While doing so, you were learning what sales enablement as a concept is, what the function should look like, and how you should tailor it to your specific environment. So how did coming in without a more traditional enablement background change the way you thought about what to build, and was that kind of an advantage? JS: Yeah, so I think coming in without a traditional enablement background shaped our function in a really positive way. Since I’ve come from marketing and product marketing, I was always really thinking about our audience, message, positioning, and customer value. But when I moved over into enablement, I quickly realized that having the right message or right content was only part of the equation. I needed to help our field know how to use it in real customer conversations. I really came in thinking about what my sales reps actually need to be more confident, more consistent, and ultimately more effective. Of course, sellers needed content, but they also needed guidance, learning, reinforcement. Our leaders needed coaching and better visibility into what was working and what wasn’t. So in some ways, I approached enablement like building a product. My sellers were the users, the sales process was our workflow, and it was my job to understand their friction points and build them something that made it easier to have stronger customer conversations. RR: I love that. It’s enablement, but make it product marketing. You listed out some things that were important for sellers and things that were important for your leaders, and all of this you had to build from scratch. So as you were looking across what needed to happen, what your first few check boxes on the to-do list were, a key first step was assessing what you had and what you needed. How had RL Datix been supporting its sellers, and where did you start to see those first few gaps? JS: Yeah. When I first stepped into the role, we had a lot of strong subject matter expertise and a ton of people supporting the field in a variety of different ways. The issue wasn’t that our support structure didn’t exist, it was that it wasn’t really connected or, quite frankly, easy to scale. I had a lot of content, but it lived in a variety of different places. We had trainings, but much of it was event-based or dependent on live sessions and then going back and watching re-recordings. I needed to make sure my sellers were hearing the same message and had access to the same guidance on how we wanted our customers to hear about RL Datix and our offerings. And I needed visibility, not only for enablement, but for collaborative teams like product marketing and product, into what was actually being used, what was resonating with our customers, and where we still needed to support the field. So my final assessment really shaped the foundation that we built. It was truly creating what I call that connected enablement environment that could support sellers in the flow of their day-to-day work. RR: Yeah, and I think a recurring theme through all of this is that there were levers to pull, content to create, training to centralize, all of these things, but that wasn’t the end goal. The end goal was that when a seller hits the field, when a seller is on a Zoom call, they’re saying the right things, and they’re not just reading off bullets, they’re tailoring it because they know it and they know it well. So you’re looking at what you need to do. You have your content, you’re beginning to get it centralized and organized, your training is in place, you have data on what reps are using, you’re building. But you still can’t see inside the conversations that sellers are having to understand whether all of that work is, for lack of a better word, working. So what challenges did that lack of visibility create, and why did you start thinking that maybe a conversational intelligence tool was that next step forward? JS: Yeah. So when we brought Highspot in, we truly started with a baseline foundation. Before I could do anything more advanced, I needed to, step one, make it easier for sellers to just find what they needed and understand how to use it. It may sound really basic, but it was a huge step forward because it helped us connect content to the way sellers were actually selling. It also gave us a huge level of visibility. I could start to see what reps were using and what they were not using, to identify those true gaps. But the missing piece was actually our customer conversations. I could easily know if a rep opened a deck or completed a course, but I still didn’t know how that translated when they were in front of a customer. Were they asking strong discovery questions? Were they connecting the message to the customer’s priorities? How were we handling objections? What were we hearing? Without that level of visibility, there was still a lot of guesswork. Enablement, product marketing, product, and sales leaders were all trying to support the field, but a lot of times we were relying on anecdotal feedback or even secondhand information. Conversational intelligence really helped close that gap, and that foundation is really what made the next phase possible. Once we had the content, the training, and guidance all in one spot, I could start to think about how to layer other pieces in, like coaching, conversational intelligence, and eventually deal-level insights on top of it. RR: When you first had that line of sight into the field and what they were actually coming up against, was there anything that you didn’t expect that came through? Things that sellers were either saying that you were like, “Oh my gosh, have you been saying this for the last umpteen months?” Or that you had no idea they were running into that was a problem. You were like, “Oh, we should’ve been helping with this,” or, “We could be enabling differently.” JS: Yeah. I think for us, what it really helped open up was just the level of content that I needed. We had really great high-level intro, top-of-funn

  3. Jul 27

    Episode 154: Turning Skepticism Into Enthusiasm for a New Platform

    According to Salesforce, sales professionals spend up to 40% of their time searching for the information and knowledge they need to do their jobs. For go-to-market teams stretched across multiple products, multiple acquired businesses, and a sprawling tech stack, that number can feel like a conservative estimate. So how does a solo enabler cut through the chaos and build something an entire go-to-market organization actually uses and actually trusts? 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 Darling, senior sales learning and development manager at HSI. Thanks so much for joining us today, Heather. Super excited to have you here. Wondering if you can kick us off and just tell us a little bit about yourself, your background, and your role. Heather Darling: Yeah, absolutely, and thank you so much for having me, Riley. Appreciate it. My background actually started on the customer side. I spent a few years in customer success at HSI, working directly with our customers, building relationships, identifying growth opportunities, and helping them drive product adoption. So over time, I realized I really loved helping teams get better at that work and not just doing it myself. So I got my master’s, and I moved into the sales learning and development role, where I now design onboarding and ongoing learning for our sales reps and CSMs. And a big focus for me is practical application, so I spend a lot of time building programs around how to position our solutions with buyers, how to teach reps about our solutions without overwhelming them with information that they don’t need. Recently, I’ve been focusing on how AI can help sales teams show up more strategically with customers, so I’m really focused on how you turn enablement into something that actually changes behavior. And because I came from customer success, I think a lot about the full customer life cycle. So a lot of my work is in helping teams connect the dots across sales, onboarding, and long-term success. In enablement, I just think it’s important to focus beyond training and think about how we build a culture where people are continuously improving. RR: Your intro tells me we’re going to have a great conversation about how you’re bringing all of that to life. But before we do, I’d love if you could maybe give us just a little high-level view of HSI, just so we have a little bit of a framework as we’re going into the conversation. HD: HSI is a workplace safety training and compliance company in the environmental health and safety space. Ultimately, our goal is to help companies operate safer, smarter, and with less complexity. So we sell to SMB and enterprise organizations across a wide range of industries. Within those companies, our buyers are typically EHS leaders, HR and L&D teams, and operations leaders. So basically anyone who’s responsible for tracking workforce performance, compliance, and risk. RR: Love it, and that is, to your point, just about every company aims to do that, so broad customer base to serve, broad prospect base to target. One thing that you mentioned to me when we spoke last was that HSI’s growth has come from acquisition. So can you tell us a little bit about what’s challenging about working in an environment that’s constantly changing and trying to enable your teams through that change? HD: Honestly, it’s a tough environment to run enablement in. Growing through acquisition, you’re constantly dealing with new products, old branding, different messaging, new systems, and even different workplace cultures converging. So, it sometimes feels like nothing is ever fully standardized. You’re always evolving, working towards a moving target, and the teams are always needing to absorb new information. So you’re trying to help reps understand what to sell, how it fits together, and how to tell a simple story even when the business itself is still getting aligned. On top of that, priorities are shifting with a moment’s notice, products are getting rebranded, positioning is evolving. So enablement needs to stay really plugged into the business and be flexible. There’s long periods of waiting to bring a new product to market sometimes, and then suddenly it’s go time, and you need to be ready, and you have to get everyone else ready. At the end of the day, it’s just a balance between driving consistency and accepting that some level of change is always gonna be your reality. So if you wanna be successful without driving yourself crazy, you work to have a structure in place to bring consistency to your own role in those moments. RR: I would love to know what your personal process for creating consistency amid that chaos is. I think that’s something that’s often challenging to do. HD: That’s a good question. I spend a lot of time meeting with our leaders. I touch base with them at least once a month. I go to team meetings when I can. I just try to stay as plugged in as possible to all the different things that are happening within the organization. For me personally too, I have a mission, vision, and values for my team of one, and so it’s a touchstone for me to go back to. Like, “Hey, am I meeting the goals and the principles that I’ve set out for myself?” Make sure that we’re doing the things that are not out of scope, but also that we are doing the things that we need to be doing to address what’s happening at the moment. RR: I think that’s one of the things that’s really hard, and something that when you talk to solo enablers is probably one of the hardest things, is that wherever you are, enablement is a game of change. It’s a never ending project. There’s always new things for people to learn, always new things for people to do. But when it is just you, and when things are changing fast, staying true to those north stars and that scope that you’ve set, beginning of the year, beginning of fiscal, gets hard. So I really appreciate those tips for how to maintain structure, how to not go crazy, and how to keep yourself on a path that supports your work and the business. So thank you for that. You alluded to a little bit of this in your introduction. Acquisitions aren’t easy. They add new product lines, they add new collateral, they add all sorts of different branding, messaging, et cetera. So what are you seeing that cause for reps? HD: For reps, I think the biggest challenge is just suddenly they’ve got a bigger portfolio of things that they can sell, but it’s not always clear how the pieces fit together, what they need to lead with. If you’re not on top of that as an organization, rep’s confidence drops, your sales cycles get longer. You tend to see people fall back on doing and selling what they already know. People can be reluctant to bring up a new solution that they might feel like they don’t fully understand. And so again, I think that’s where it’s really important to make sure all those pieces are in place as much as possible before you bring the reps in, because they don’t fully understand something, they don’t feel confident in talking about it, so sometimes those new solutions, they don’t get brought up as much as they should. That’s definitely a challenge. For the broader go-to-market team, it creates a lot of inconsistency too. We’ve got different messaging, different positioning, overlapping collateral. It’s really easy for marketing, sales, and customer success to get slightly out of sync, and that shows up pretty quickly in the customer experience. Your risk really with that is not a lack of resources, it’s almost in having too many. It makes it hard for people to find or trust what’s relevant. So you might have reps sharing old collateral with legacy branding because they feel comfortable, they feel like that’s something that they trust. They’re measured on results, so when something is working for them, they don’t wanna risk messing that up. And so change can feel like it really slows them down or it puts deals at risk. So when you’re introducing new products, new positioning, or new tools, especially all at once, that can create some hesitation. Reps are gonna tend to default back to what they know, what they trust, what they’re comfortable talking about. RR: Hearing all of those challenges and also some of those questions that you asked, when there are so many priorities swirling around, so many new things coming in, how do you find that clarity, and how do you create that clarity? And I think one of the things that you shared was an answer to that was, “We needed some tooling.” And so you started looking for some tools to help with that, that problem of reps don’t feel confident with our new solutions. And so I think you were looking initially maybe for something more aligned to an onboarding tool, and then you wound up here with a sales enablement platform. HD: Yeah. Yeah, it was an interesting shift because early on I really was thinking about this as an onboarding problem. So how do we get new reps ramped faster, especially with how complex our business has become? But as I got deeper into it, I realized that the bigger issue wasn’t just onboarding, it’s ongoing development, coaching, creating and tracking certifications. So the challenge doesn’t stop after those first 30, 60, or 90 days. The business is still changing. We’re adding new products all the time, messaging keeps evolving, and that can be really a struggle for reps to keep up with. So there’s just so much information coming at them about buyers and products, and not to mention our internal processes that can sometimes

  4. Jul 24

    Episode 153: Decoding the “Build or Buy?” Question from the IT Perspective

    According to Gartner, at least 30% of generative AI projects will be abandoned after proof of concept due to escalating costs, poor data quality, or unclear business value. There are a lot of factors working against them, and too often failure happens when teams are right in the middle of building. They’ve spent significant time, money, IT capacity on something that may very well have been doomed from the start. So how do you know if something is actually worth building with AI or if you should just focus on buying instead? 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 Keith Weaver, Senior Director of Global IT and Enterprise Applications at Highspot. Thanks so much for joining us today, Keith. I’d love if you could just kick us off by telling us a little bit about yourself, your background, and your role. Keith Weaver: I have been leading our global IT team at Highspot. I’ve been in IT for, I think, getting close to 20 years now, just overseeing all kinds of different systems and specialties within those systems. Our IT team at Highspot is IT operations, making sure everyone has devices, equipment, all of that globally. We’re now in seven countries. As well as system engineering, making sure everyone has the right tools, that they’re optimized for the business. And then we have specific teams in IT that specialize in financial systems and HR systems. In the world of AI, it’s a whole new world and it’s a lot of fun. RR: So 20 years in IT, you’ve kind of run the gamut. But it sounds like the last two and a half years have crammed almost 20 years’ worth of change into a very short window. When we were planning for this episode, you mentioned to me that you read four or five newsletters every morning just to keep up with the pace of innovation. Can you walk us through why you’re spending so much time learning and how IT has had to evolve to keep up with this pace of development? KW: What I’ve seen is mostly it’s the same things that we’ve done, except it’s done at a much faster pace. It is kind of an unheard of pace that AI is moving. Every day, the reason I read five different newsletters is because there are so many new things getting released, whether it’s a new model or a new tool, and then there are things within the tools that are getting released. Trying to understand all those things, the new protocols that are getting released, the new ways people are building or executing on AI, or the new things people are learning, is just really critical. And all of that is at a speed that we’re just not accustomed to. So I think that the objective of what an IT team does to continue to keep the business unlocked, able to do their best work with the technology and tools while making it secure and scalable, those things are the same. It’s just the speed now that it’s running, and the speed from the business. The business is moving so fast, and their expectation is that IT continues to deliver at that pace. I’ll give you some examples. I get probably, me personally, not my team, but me personally, I probably get 20 to 50 requests for new connections, new skills, new tools every week. That’s in Slack, in Jira. It’s just nonstop, and that’s just unheard of before AI. It just didn’t happen. It would be like, “Oh, we have this big initiative, and we’re gonna do this thing.” And now it’s just like, “Can I have this? Can I have that?” And all good things, it’s just how do we do that, and how do we keep up? RR: So when you have 20 to 50 requests hitting your desk every week, it can probably start to feel a little overwhelming. And I wonder if the folks who are sending these requests your way maybe don’t know the considerations behind every single one of these ideas. I’d love if you could give us a view of what you’re seeing across the industry as both technical and non-technical teams are all noodling on the idea of how to build with AI, how to buy AI tools, how to bring them all together and create a combination that actually works. What are you seeing? KW: Well, I think if you think back a year to a year and a half ago, mostly people were buying tools. Building was… It’s so funny ’cause we’re talking about a year ago or a year and a half ago, but building was much harder. And really with Claude, the Opus class models that came out, it really started unlocking the ability for everyone to start building. And so since then, the conversation shifted from, “Yeah, we can go buy this tool,” to “We can build this internally.” And there’s a lot of excitement to build because building’s fun. The pendulum just swings often on these things, and so we’re kind of in that wave where everyone’s super excited about building something. And I think we’ll end up in a place that is more normalized, where we’re building some, we’re buying some. We’re doing a hybrid approach. I think that is where we’ll end up. It’s just, it has swung really far to, “Look, we can just go build that thing.” RR: So it sounds like we’re kind of in the early phase of a cycle that you’ve seen time and time again, where surrounded by enthusiasm, but maybe we don’t have much direction. And like you said, building is fun, so I imagine you probably hear a lot of, “Hey, look what I built,” or, “Why can’t we just build this?” So when something like that lands in your inbox, what’s the first thing that goes through your mind? KW: If it’s, “Look what I built,” there’s lots of questions, like how is it being deployed? What’s the next step with this? Who’s gonna own it? How is this actually out in the world, and how are we gonna make sure that it’s as scalable and secure? If it’s a conversation, I would say this is more so where we hear, “We want to build this thing,” or, “We can just go build this thing. Why would we buy this?” I think the thing that I would ask is, what is the long-term path for this? Because deploying is just the first step. It’s the iteration. It’s the test. It’s continuing to deploy it. It’s maintaining it. It’s supporting it. It’s the full life cycle of any software project. What resources are gonna do that? How are we going to maintain this and support this long term? Those are usually the questions that I start asking. RR: And you’re quite equipped to speak to the build side of the equation because you’ve done it. You’ve tackled the planning, the deployment, the maintenance, the ongoing support, the full life cycle, like you said, of a software project. And you’ve done it with AI. I’d love if you could walk us through your first test case. Tell us a little bit about what you were thinking going in, and what you learned along the way about what works, what doesn’t, and what was surprisingly difficult. KW: Yeah. So we built an IT AI agent and an HR agent, and we did that with a cross-collaborative team. I think we started it last fall and then deployed it in February or March this year. And I would say the main objective there was not that these are the tools that are gonna change the way we function. The main objective was a learning. It was an R&D investment. So we knew that we had to, as an IT team, be able to help the business deploy these agents, and we found some use cases that we could. The IT one we can own in-house. The HR one, we already collaborate with them very closely on a number of things. So it felt like a good first step for us to dip our toes, learn a lot about how to build these, what works, what doesn’t. And these agents are more than just chatbots. They really were taking actions in tools like Jira and Workday, Highspot itself. And we built them using the Workato platform, and what we learned through it is it was actually really exciting and really easy to get to a place where this mostly works, and this is pretty, it feels like this could be really powerful. That was, like, the first three weeks. The rest of the time was, “Oh, gosh, how are we going to get this thing so that it doesn’t give somebody some really poor answer from a security standpoint or an HR answer that needs to be rooted in truth?” And then how can we make sure that it repeatedly does these actions no matter what people prompt, that it’s really controlled? I often described it to my team like it was training a four-year-old. I have four kids and they’re all older now, but it was like I was back in those toddler stages. Like, “Why’d you decide to do that? That was a bad decision. Stop.” And trying to train it and get it to that point, it just took a massive amount of time. And since we’ve launched it, it’s a lot of resources to read the conversation, understand what was asked, understand what it did and where it went wrong, then refining it, then retesting it, then redeploying it. It’s a cycle. It’s this continual cycle, and that takes a lot more resources and time than I originally thought it would. RR: Ballpark, what did that investment look like? How long did it take you to build? How many queries did you have to manually validate before you trusted the thing? And how much are you still investing today to keep it alive? KW: In the beginning, you just start giving it manual prompts and testing it to see what it does. Then you produce your test cases, and you manually go through those test cases, and every time you make some major changes, you go through those test cases, make sure that it’s still hitting. Because just changing one little thing, for example, if you take a tool and change the prompt or the description of that tool, you actually have to do regression testing on all the t

  5. Jul 20

    Episode 152: Upleveling Execution Through Practical AI Application

    According to research by IBM, just 16% of AI initiatives have achieved scale. Why? Because few organizations have the structure and data to support long-term AI investments. So, how do you build an AI-ready system? Riley Rogers: 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 Rich Weymer, Senior Director of Go-To-Market Strategy and Transformation at Yubico. Thank you so much for joining us today, Rich. I’m super excited to have you here to dig into all the expertise that you’re gonna bring to the table. As we’re kicking off, I’d love if you could just tell us a little bit about yourself, your background, and your role. Rich Weymer: Yeah. First off, thanks for having me. A repeat customer with Highspot, so excited to get invited to this, as we’ve worked with your organization for some time now. Like you said, Rich Weymer. I’ve spent time pretty much so in tech for most of my professional career in one form or fashion, from my earlier career days at Microsoft working in consumer goods, where I’ve worked on video games, your Office products, all your devices, through where I’m at today in the security world. RR: Well, amazing, and bravo, tech veteran. Not easy. RW: Yeah. It looks a lot different today than it did when I started, that’s for sure. RR: And I think that is exactly what we’re gonna talk about today. But before we go into where the world of tech has been to where we are today, I’d love if you could give us a little bit of foundational context for folks who might not be familiar with Yubico. Could you give us a little walkthrough of who your company is, what you do, who you serve? RW: Yeah. So Yubico does phishing resistance hardware MFA, which basically means we ship you a little bitty key that helps control access to all your online portals and logins and everything along those lines. RR: As somebody who is password challenged, I certainly see the value of that one. I wish we had a wonderful little bitty key that got me set up for success every single day. One thing that I think you set up early on is that Yubico, and pretty much every other organization in the industry, is moving fast, and it has to. Security in this day and age is harder than ever. And when it comes to working in a fast-moving organization, teams like yours also have to move fast. I’d guess that that pace of change is part of the reason why you have a really forward-looking approach to enablement and to go-to-market strategy. So why do you think it’s important to think critically about how technology can transform traditional workflows, processes that you’re accustomed to, things like that? RW: Again, to your point, things are moving so fast right now. That’s the biggest underlying factor that organizations really need to think through. Decisions that you’re making today are almost obsolete by the time you’re done signing the paperwork on whatever decisions or procurement you’re going through. So you need to be really thoughtful about the foundations that you’re building, the integrations that you’re gonna lean on, and the partners that you’re gonna select that are gonna be around for the long run. Measure twice, cut once, and also understand that there’s different types of decisions that you’re gonna be making. I use the analogy of a hat, a haircut, or a tattoo. What type of decision are you making when you’re thinking about your technologies? If it’s a hat, you can switch it in and out real quick. If it’s a haircut, maybe it takes a little bit of time to unwind. And those tattoos are the ones that you just can’t change. They’re gonna be– They’re– You’re gonna live with them forever. So you really gotta just understand the lens that you’re making the decisions through, as well as having an industry understanding of where things are heading. And as you look at your partners, thinking, “Hey, at the pace at which innovation is happening, is this someone that’s gonna be relevant six months, 12 months, 18 months from now?” RR: I have not heard that decision-making framework before, hat, haircut, tattoo. RW: It’s an easy one, yeah. A lot of organizations think everything’s a tattoo. So you make every decision like it’s the last decision you’re ever gonna make in that space. And it’s right for a lot of things, but framing it goes a long way, especially when you’re trying to move fast. Being able to categorize those decisions pretty quickly goes a long way. RR: Yeah. And it helps you avoid the problem of when everything’s important, nothing is. You mentioned systems, data, processes, having the right tools in place to move quickly. So with that perspective in mind, how are you thinking about layering on AI? RW: I think about it every day and night, in every meeting I’m sitting in, and every conversation I’m having, and every free minute when I’m thinking about work. The big thing is automation and AI for the sake of AI, and automation for the sake of automation, it really doesn’t mean anything unless you have a strong foundation and an understanding of your data. So to me, it all just boils down to a strong foundational data set and understanding what to measure and what moves your business, and then building around that first and foremost before you do anything else. RR: What do you need in that foundation before you can start building AI on top of it in order for those initiatives to be successful? RW: If I were to think through how I structure this, there’s no shortage of ways to measure the business, but landing on one that’s influential and helps you adjust the dials as you go is really important. So the way I operate is through the lens of sales velocity, which is a time-tested mathematical problem to give you a temperature check on how the business is doing. It’ll let you know whether you’re going up, down, left, right, staying center, or whatever it is. But where organizations stop is they stop at the top four measurements, which, if you think of sales velocity, is open opportunities, average deal size, win rate, and then you divide that by your deal cycle length. That gives you a daily throughput, which tells you part of the story because you can help understand your forecasting. When you take your close one business, you can use that to forecast days left in the quarter, what those numbers would look like. But where it gets really powerful, and what I think a lot of organizations haven’t spent the time to do, is go deeper on the leveling of those metrics. So if you think through the process lines, L1 is your executive metric. That’s the all-up number. Your L2s are your leadership numbers, where your managers need to understand those. But your L3, four, five, six, and you can keep going down the rabbit hole, really start impacting how your frontline folks operate. One of the things we’ll talk about today is AI Role Play, and when we think of it, we look at diagnosing issues in our win rates, and we think, “How is our competitive wins doing? What are we, we get very, very granular in how we look at those.” And then we can actually start layering on recommendations and automation. So we do that across probably close to 100 different metrics through the various layers that are our leading indicators. And this really helps us when we think through automation of where we go from here, ’cause once we understand those, we know how are we doing against certain competitors? Are we getting the right amount of MQLs? Are we talking about the right things? Do we get caught up in legal, security? We can understand all those different variables of the business, and then we can take a proactive approach to coaching where we need to coach, and then adjusting the business where we need to adjust the business. And you can’t really do that unless you have that entire foundation laid out and actually understand what all those levers are. So to me, taking the time to do that is really just beyond critical. RR: Yeah. Yeah. You know what you need to do, and you can start driving really aggressively against it, which I– it sounds like you alluded to an example there with AI Role Play, you’re doing the work to do. In that, you’re beginning to layer some of these new technologies, new tools on top of that foundation. What were some of those first use cases that you prioritized, and why did you start where you did? RW: I think the first win you always wanna go for is really a practical application of any new technology and how that can move the needle for the business. So when I think of practical applications, I think of AI Role Play as being a very early one. As an enablement team and a training team, how many times have people walked through certification programs, the one-on-ones with managers, all the Role Plays, all the back and forth and the headaches and the objectivity that goes into those exercises. That’s just a quick win that you can pick up and take care of almost all of that. The time saving alone and the cost of having a manager do these one-on-ones time and time again, it just drains an organization when every organization right now is trying to be lean, mean, focused on sales efficiency. So anything we can do to give back and level the team up, I think is just a no-brainer. So AI Role Play is a huge one for us. We looked at a lot of different places. We tried a lot of different things, and we landed on the Highspot implementation of that because it’s important to be able to do that stuff, but also it has to be within the context of everything you’re doing and all the content and everything that you do have. It can’t b

  6. Jun 29

    Episode 151: Designing Deal-Winning Buyer Experiences

    According to Corporate Visions, 74% of buyers say they faced too many competing options in their last major purchase decision, and instead of selecting a vendor, they just checked out entirely, gave up, and moved on. So, how do you create a buying experience that makes those decisions feel easy? Riley Rogers: Hi, and welcome to the Win/Win Podcast. I’m your host, Riley Rogers. Join us as we dive into changing trends in the workplace and how to navigate them successfully.  Here to discuss this are senior enablement program manager Lisa Monahan and account executive Madison Leatham from Pluralsight. Thank you guys for joining us. I’m super excited to talk through this topic with you. I’d love to just hear a little bit about yourself, background, and role. So Lisa, wanna kick us off? Lisa Monahan: Yeah, absolutely. My name’s Lisa Monahan. I live in the suburbs of Austin, Texas, and I’ve been at Pluralsight two and a half years, and I’ve been in enablement for, I guess that’s coming up on four years now.  I currently serve our go-to-market tech stack from a strategy and execution standpoint, and that is where I learned about everything I know and love about Highspot. So big Highspot fangirl here. Happy to be here. RR: Amazing. We’re happy to have you here. Madison, can you tell me a little bit about you? Madison Leatham: Yeah, of course. Happy to. I am based out of Salt Lake City, Utah, and I am an account executive on the public sector team here at Pluralsight. I started out as a BDR on the public sector team, eventually moved into a manager role, where I led the same team that I started on as a BDR, as well as our team in Australia, and then more recently became an account executive supporting our higher education partnerships specifically. RR: I can’t wait to dig into all of this wonderful work and experience that you guys have, and then all the complexity and challenges that kind of come with that. So Lisa, I’d love if you could set the stage for us: who Pluralsight is, what you do, who you serve, all that goodness. LM: Absolutely. And Madison, I’m gonna ask you to keep me honest, ’cause I’d love from a seller’s perspective how you would change my pitch. But we are an online learning and workforce development platform serving businesses and individuals alike with on-demand courses, hands-on labs, and skill assessments that help bridge the skill gaps in areas like AI, cybersecurity, and software development, and so on.  RR: With that context in mind, I think I’d like to jump into what that world of work kind of looks like today. So Madison, from a sales perspective — BDR and AE roles, managerial roles, helping BDRs succeed — you’ve kind of seen it all.  When we look at where we are today versus where things were when you started, what’s changed most about selling over the last few years, and where do you see sellers still struggling the most? ML: So just to talk about both sides of it, starting with prospecting, there’s definitely more of an expectation of personalization and effort. The spray and pray tactics just don’t work. People are a lot more risk-averse. They’re just more busy.  You have to do something different to really cut through the noise, prove that you’ve done your homework, and that you deserve their time just based on the research that you’ve done. So finding ways to do something different is always a challenge. It takes more time. I think personally prospecting and getting your foot in the door is really the hardest it’s ever been.  And on the selling side, this might not be really new news, but they say it takes a lot more people to decide on purchasing a product nowadays. You’ll see different studies saying different things, but they all just show how the buying group has jumped up in numbers, so there’s a lot more need for collaboration on both sides of the fence for communicating the value to different stakeholders that might have different goals. And then I’d say multi-threading, getting in front of decision-makers is just consistently one of the most challenging aspects. Sometimes it’s tricky because you wanna keep the relationship strong with your main point of contact, not overstep, but you wanna make sure that the value is still being communicated and the pain points are still being properly uncovered and discussed. And you kind of lose control of that when you’re just relying on one person. So I really see that across all the AEs I’ve talked to, all the AEs on my team, that need to multi-thread and how tricky it can be to communicate that value across different stakeholders and throughout the buying group. RR: So it sounds like there are a lot of challenges out there, and it’s a fine line to walk when it comes to balancing your initial point of contact and then doing all of the work that makes a deal successful. Thinking specifically about the AE challenges that now you in this new role are facing, in your day-to-day, some of these things that we talked about, what would you say is most difficult for you when you’re working deals and trying to keep things moving forward? ML: Just visibility into what matters to those fringe stakeholders. So when I say fringe stakeholders, the ones that you know have some sway, but you don’t have that direct contact with. Maybe they join one call, and they were off camera. And then just trying to figure out how do their goals align with the solution? How can I make sure it’s not just that game of telephone, that everyone understands the vision of the solution and the implementation of the solution so that we can really start to focus on aligning the logistics and next steps. So I’d say it’s just being able to get clear communication and more visibility and more people involved to really get those discussions, give them a little bit more oomph and value with each person that has some sway in the deal. RR: Yeah, because if you can’t find those fringe stakeholders, you’ll kind of go sideways, and you lose the momentum that you spent all that time building. One thing that’s funny here, Lisa, are you taking notes? LM: I am. This is on the fly, and I’m like: “Oh, this is so interesting to learn.” RR: You’re sitting here taking notes, hearing these challenges, and being like, “Hmm, how do these fit into my programs? How can I support this?” So when you’re hearing challenges like this from the field, how do you start thinking about solving them? LM: So it’s about making sure that the field is empowered with the tools that can really help them do that deep, intelligent research so that they can speak to the needs and the pain points of these accounts.  It can’t just be this very generic as you said at the start of the call spray and pray. It can’t be that anymore, and we know that to be a fact. So it’s ensuring that they have the tools available to them, but also knowing all the different ways that those tools can work with them, not against them, so that it can be simplified.  One of the biggest things I care about is reducing tool swivel, making sure that it’s easy for them to get as much done in one place without feeling exhausted by having to go from Gemini to LinkedIn Sales Navigator to Highspot. So trying to make sure it’s as simplified as possible. RR: Having that conversation of swivel chairing has changed so much over the last year. Now there are so many different AI tools that you can layer in, and somehow it seems like the number of tools has shot up. So making it simple is almost harder than ever and a bigger priority than ever. Today, what are you prioritizing, Lisa, to help sellers break through? What’s new? What are you working on to help them cut through that noise and engage buyers effectively? LM: Definitely AI at every step right now, because as you just mentioned, every tool that we use has some level of AI, and making sure that they understand which one is the best one to use in what workflow, in what step: prospecting, outreach, anything like that. So really working hard. And as you said, it feels like the functionality is changing so much right now that I feel like every half day, my strategy of how we’re going to market with AI for our sellers changes. RR: Yeah, and I love that point of utilizing a tool to its fullest. You invest in these things, you need them to work for you. And one of the things that over the years you’ve spoken extensively about is using Digital Rooms as part of the way of simplifying the buyer journey, making it easier to engage your buyers, and then, to your earlier point, Madison, track what’s interesting to them, track who’s in there. So Lisa, with that being a key part of your strategy, can you walk us through why you leaned into that approach? LM: When I was previously at SAP Concur, Digital Rooms were such a huge part of their strategy that they had an entire team dedicated to that. And so when I was there supporting Highspot, I actually didn’t have an opportunity to touch it. It felt like this really powerful feature that seemed unattainable to me. And then when I came to Pluralsight and I was rolling it out here, I had to very quickly learn Digital Rooms, and I have to admit, I was intimidated because of the way that it was handled at my previous employer. But once I came here, I was like, “Oh, it’s actually super easy.” Digital Rooms are very easy to use. It takes just a few minutes to customize one.  And what I think is really important about Digital Rooms is what Madison was saying earlier, we don’t have a lot of opportunities to break through and stand out right now. You can send a link to something, you can add an attachment to an email, but being able to build out this very personalized space like a Digi

  7. Jun 3

    Episode 150: Enabling Sellers to Show Up as Trusted Partners in Every Deal

    According to research by Salesforce, 86% of business buyers are more likely to buy if companies understand their goals, and nowhere is that statistic truer than in the nonprofit sector. So, how do you ensure that your sellers are ready to show up the right way for every buyer?  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 Carly Foerster, principal enablement manager, and Conner Smith, mid-market account executive at GoFundMe. Conner, Carly, thank you so much for joining us. We’re super excited to have you here today.  As we’re kicking off, I’d love if you could just tell us a little bit about yourself, your background, and your role. Carly Foerster: First and foremost, I just want to say thank you so much for having us on here. We are honored as always to work with Highspot and to be featured—how exciting for us.  So, my name is Carly Foerster, as you just shared. I am on our revenue enablement team over here at GoFundMe. I’ve actually been here for almost 10 years now, so about a decade of experience with this team, and one fun fact is that I started on the actual sales frontline side at one point way back in the day, which meant that I was working directly with our nonprofit organizations.  I share that because it’s really helped shape how I think about enablement today. I’ve been in that seat. I’ve been where Conner is. I’ve worked and navigated really complex and unique buying cycles here. And what’s really kept me with this team is our mission. It’s this incredible mission to help people help each other, and I also have this incredible opportunity to partner with purpose-driven individuals, just like Conner. You’ve brought the right person on the call here today. It’s been such a privilege to work with these incredible nonprofits and help drive real impact in this world. And one of my favorite parts is I’m still learning every single day, so I hope that I learn something through this podcast. And with that, the person I’m probably going to learn from is Conner, so I’ll toss it to you. Conner Smith: Yeah, Riley, thanks so much for having us on. I’m Conner. I’m a mid-market account executive here at GoFundMe, and I sell fundraising software for nonprofits called GoFundMe Pro, which is the artist formerly known as Classy. It’s the entire arm of GoFundMe that specializes in helping nonprofits just raise more for their missions. I got into sales about four years ago after being a pastor for four years, actually, so I navigated a pretty significant career shift when I went from leading a nonprofit to selling windows, then while I was selling windows, I learned about tech sales and had to go Google what SaaS was and what an SDR was and what an AE was and all those things. I learned and realized, “Okay, I think this is a pretty good path to success and the lifestyle that I’m looking to build.” So I entered as an SDR back in 2023 and quickly moved into an AE role that I then leveraged just a few months after that to ultimately land a spot here at GoFundMe. And it’s really been a great fit because I know the nonprofit world pretty well, and now I get to meld my nonprofit and sales experience together to really help amplify the impact of nonprofits by giving them the tools they need to, like I said, raise more money for their missions. The cherry on top? I get to work with and learn from pros like Carly. RR: You know, I was going to say that was a great introduction to have to follow, and you smashed it. You guys both—those were incredible introductions. I’m super excited to dig into all of this experience that you just kind of high-level skated across. I think there’s a lot to talk about, and I hope a lot to learn.  One thing that you both touched on and that is very apparent throughout both of your career journeys is this shared love for continuous ongoing learning and self-development.  Can you talk to me about where that mindset comes from for you, and then how it shows up in your work? Conner, I’ll toss it to you to start us off. CS: Yeah. I mean, going back, in my previous role in the nonprofit space, learning was a big part of that. You had to wear a whole lot of different hats, and so learning on the fly was a regular part of the job. I think that’s where it comes from for me. But then coming into sales from a different background, I didn’t really have a playbook either. I had to learn fast. I had to learn through trial and error, through feedback, and through a whole lot of mess-ups and failure. And I think that mindset really shows up now in really practical ways. For me, that looks like things like call recordings and listening to those on a regular basis, looking at engagement data, experimenting with different approaches, and not being afraid to fail. You need to be quick to fail.  I had a manager tell me that early on, and I think that was some of the best advice I got. Just get out there and do it. Don’t be afraid of failure because it’s the quickest way to learn. RR: Yeah, and that’s fantastic advice. And I think you built the learning muscle because you had to, and now it’s stuck, and that’s just how you continually improve over time, so I love to hear that. Carly, what about you? CF: Yeah, absolutely. Love learning. We’re big learning fans over here, and Conner, I was going to say, I love that mindset. I think you and I have talked about this, this sentiment of fail fast, fail hard, learn quick, right? That’s a huge part of what we understand as the learning process here. For me in particular, I’m going to take this on a little bit of a personal journey. So one thing you should know about me is that I have very strong core values personally, one of which is to always be learning. So this is really at the heart and core of who I am as a person.  I’ve always had this real natural curiosity in life. I yearn to do and see and experience everything that I can, and I think it’s that sort of innate drive that makes me want to keep growing, to really have that growth mindset. A couple things I wanted to share from a sales lens first. Back when I was a rep, one of my biggest learnings, since Conner shared a few, was that if I were to look around and see who was the most successful on the team, what I could tell you is that the most successful people were not always the ones that had the answers right away. It was often the people who were asking another question, better understanding what they were trying or being asked to do, and then adapting real quick. When I think about our role in enablement now, where that shows up is really how we build our programs. So we focus on the fact that we’re not creating static systems. We’re not creating one-and-done trainings. We’re trying to create systems that are constantly evolving. We try to. We’re not perfect at it, but that is the end game for us. We’re constantly looking at what’s working, what’s not, how we can iterate. Conner even called out a couple of things. We’re looking at recording data, information from Highspot through reporting and analytics to help inform what that looks like. RR: Learning doesn’t always have to be external. Sometimes it’s asking that question of yourself every single day, “How can I be that little bit better? What can I do a little bit differently to serve my customers, to serve my nonprofit partners that little bit better?” And I think that is such an important mindset shift to just be open to that question. On the topic of growth, Carly, you’ve mentioned a couple times that you started your journey at GoFundMe as a seller.  So, having experienced the nonprofit space from both angles, both the sales and the enablement side, what obstacles do you find that your sellers most often encounter now that you are in this place to help them through it? CF: Great question, Riley, and it’s something we’re thinking about every day, right—how can we overcome barriers and friction in our sales process so that we can better support and serve our customers? I think one of the biggest challenges that I learned very early on as a rep and continue to hone in on as an enablement professional in our specific sector is that we’re a little bit off the beaten path from what it means to be in a traditional sales role. It’s because we’re not just selling a product, we’re actually partnering with organizations that are deeply mission-driven. They are incredibly thoughtful about every single cent, every single dollar that they invest, and that’s rightfully so, because so many of the nonprofits we work with are supporting critical solutions for some of the biggest problems in this world. So they have to think about every single dollar that they invest. And so for us, what this sometimes translates into is longer sales cycles, a higher bar for trust. So we are designing our enablement program around those realities.  We’re helping reps to tell as clear of a story as possible, to help personalize our outreach at scale, and to use tools like Digital Rooms through Highspot to create this really thoughtful, almost through-line experience during that deal cycle. At the end of the day, I would almost position it as transitioning from selling to serving. We are here to support nonprofits through this decision to show how we can partner and then to prove ourselves as a partner when they become customers. RR: You know, I think something that comes through as the through line of all of this, just listening to you both speak about your work and the passion that you have for it, is just how important it is to work for a mission-driven or

  8. May 26

    Episode 149: Transforming Strategy into Real-World Execution

    According to research by Gartner, 84% of business leaders report their company’s identity must significantly change to achieve strategic objectives. But how do you know when the time is right? And more importantly, how do you ensure that change goes smoothly? Riley Rogers: 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. According to research by Gartner, 84% of business leaders report their company’s identity must significantly change to achieve strategic objectives. But how do you know when the time is right? And more than that, how do you ensure that the change goes smoothly? Here to discuss this topic is Shelly Luciano, Vice President of Strategy and Operations at Leah. Thank you so much for joining us today, Shelly. I’d love if you could just kick us off by telling us a little bit about yourself, your background, and your role. Shelly Luciano: I’m Shelly Luciano. I’m Brazilian. I studied industrial engineering in Brazil and France. I started my career working in infrastructure and R&D, so that experience gave me a strong foundation in execution early on. Back in 2014, I moved to the UK to pursue my MBA at London Business School. I used business school to transition from a technical background into strategy on a global scale. After my MBA, I spent three and a half years in strategy consulting. That work helped me learn how companies compete in larger markets. What I realized is that although strategy consulting is intellectually fascinating, I was being more and more drawn to the business. So I transitioned into tech about five years ago. I joined what was then ContractPodAI, which is now Leah. Today, I’m Vice President of Strategy and Operations. My team focuses on aligning strategic priorities, supporting cross-functional execution, and ensuring our go-to-market approach reflects both where the company’s headed and what our customers need. One of the most valuable parts of my role is staying close to our customer base. These conversations give me and the company a lot of valuable insight into how the market is evolving and how organizations are actually adopting AI. I then bring these insights back into the organization, back into Leah, to inform product direction, enable our customer success team, and ensure that our strategy remains grounded in real market needs. Ultimately, my role sits at the intersection of strategy, go-to-market execution, and customer insight. RR: I think you have a fascinating role, to be quite frank, and also a really wonderful story. To go from “I’m trained as an engineer,” to “now I’ve got my MBA, I’m in consulting, and today I work in tech and have for the last five years,” that’s really an incredible journey that I imagine must have given you a real wealth of experience that serves you very well at Leah. SL: It’s funny because if you asked me when I graduated in Brazil what I’d be doing now, I wouldn’t have guessed. The world has changed so much. My world has changed so much. So I feel very lucky and blessed to do the job that I do. I really like it. My company’s fascinating. My role is fascinating. My company gives me room to change as long as I’m adding value and my team is adding value. So I’m really happy. RR: Yeah, and that’s certainly evidenced by the fact that you spent five years in one tech company when the average tenure is just over two, so something really must be going right. I’d love to dig a little bit deeper into this exciting, challenging, and evolving role that’s been keeping you at Leah for the last few years. You’re there to keep an eye on what’s happening in the market so your reps can tell a story and your engineering teams can build a product that the market both wants to hear and to see. More than that, you’re also there to break down silos and operationalize your strategy so it really shows up in everyday workflows. In this work, what kind of things tend to crop up—challenges or obstacles that make it difficult to build the connections that bridge that gap between strategy and execution? SL: For me, there are two major challenges I see in equipping internal teams to drive growth. First, strategy and execution often evolve at different speeds. A leadership team can align relatively quickly on a strategic direction, but translating that direction into how hundreds or thousands of people operate day to day can take much longer. For me, strategy only really lands when it keeps showing up in customer conversations. What you portray needs to align with what your client base and the market are seeing. If the people talking to customers every day don’t understand the problems that your company is solving and why, then your strategy hasn’t really landed. It’s just a deck. It’s lovely to build these ideas, but you’ve got to be able to execute on them. As companies scale, the complexity increases much faster than people expect. You have more industries, more personas, a larger product portfolio, and if you don’t have the right systems and alignment, that complexity can create a lot of confusion internally. And if your team is internally confused, then everyone else is too. RR: So your job is to keep an incredibly close pulse on the market and on technology as they both evolve. And it’s a little bit of an endless task because the market will always shift and technology will always evolve. So you’ve got to be right there with it as the voice of reason for the organization, telling everyone, “Okay, here’s what’s happening, and here’s how we’re going to move with it.” As someone who, by job description, is very comfortable with change and evolution, can you share with us how you’re thinking about how Leah, as an AI-first company, is keeping pace through major technology shifts, and then how other organizations should think about translating these shifts into their own organizational and operational processes? SL: Leah has been an AI-first company for years, way before LLMs. What changed with LLMs is the speed and scope at which we can execute our strategy much faster. We’ve been using machine learning in our platform for a long time, so the foundation was already there. We already had a really strong team. What LLMs did was introduce a step change, and our founder, Sarvarth, is a visionary. He saw straight away how that was going to change the game. All these changes in the past few years did not change our direction, but for the client base, what they can really see is that LLMs have expanded the use cases that we can deliver. And I think that’s what matters to customers—how can we solve more of their problems? With Leah, we’ve moved from traditional automation into what we describe as an agentic operating system. That means our AI is not just supporting workflows. We can do much more than that. We can now reason across data, understand context, and orchestrate actions. That is so exciting, as you can imagine, for someone who works in strategy because it feels limitless. Going beyond static workflows, you now have systems that can adapt dynamically to the problems that we’re solving. And that’s where the speed and pace of innovation really comes in. Once you move into an agentic model, you’re no longer limited to predefined use cases. You can continuously expand how AI is applied across not only our internal organization but also our client base. From a strategy and operations perspective, the challenge is not adopting the technology, because we’ve been able to do it and we continue to do it. The challenge is how do we operationalize it? Strategists love frameworks, so if I had to group it, I’d say there are three ways I think about this. The first part is strategic focus. The risk with AI, within all this opportunity, is diffusion. So we need to be deliberate about which use cases we prioritize. We need to define where we can deliver the most value, because being AI-first doesn’t mean doing everything. It means scaling the right use cases. The second part is how do we translate that into go-to-market execution? As I mentioned before, strategy only really lands when your customers can speak about you. Organizations need to understand how to position AI. We need to be able to explain it clearly so we can apply it across different industries and contexts. That’s where systems like Highspot can really help us translate this within our organization and externally. The third thing is continuous customer feedback loops, because customer proximity is the most valuable strategic signal we can have. To be a strategist in tech, your goal is not to define a static AI strategy. You’re always on a feedback loop, and you need to be agile. The tools and teams that support you need to be comfortable with always learning and always putting our best foot forward. RR: So as you alluded to, you and the team actually recently went through a rebrand. From ContractPodAI, you became Leah, named after the organization’s flagship AI offering. I’d be curious to hear how, with these challenges to strategy-aligned execution in mind, you and the team made sure that everyone was telling the same story and supporting the same strategy, even as the brand message and narrative shifted so drastically. SL: Leah was already a product of ours that had taken a bigger and bigger piece of our client base. So moving from ContractPodAI, which was very contract-focused, into Leah made sense because the Leah product had become a much bigger part of who we were and our identity. When we came into becoming the Leah brand, we were ready in many ways. You’re never fully ready for a full rebrand. There’s still a lot of work. But we had t

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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
    152
  • Rating
    Clean
  • Show Website
    Win Win Podcast