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-funnel materials, and then I would jump very quickly into technical documents. So I needed to be able to, like you said earlier, customize, and that was a gap that became pretty quickly consistent, that I needed to bring a middle-of-the-road option to help ultimately fast-track opportunities to close. It’s something that we’re still actively working through today.
RR: Once you had that line of sight, not only into real-world conversations, but the analytics into usage that we’re talking about, what difference did that make for you and other cross-functional teams? We have this example of middle-of-the-funnel content, realizing this is a necessity and maybe we aren’t serving it. But were there any other moments that made it very clear this was helpful?
JS: Yeah. It just gives me, and our whole company honestly, a much better shared understanding of what actually is happening in the field. From an enablement standpoint, it helps us see where reps were confident and where they needed support. Were they asking discovery questions? Were they connecting the message to customer priorities? It helped us figure out if there were gaps and ultimately skills I needed to help upskill.
For our leaders, it gives them more specific coaching moments. So instead of coaching from memory or only from a pipeline update, they have the ability to coach from real customer interactions without having to sit in live on 50 calls a week. It also helped open up a level of visibility across cross-functional teams.
Product marketing can come in and review whether messaging is landing, whether the decking is being used. They also get a great depth of understanding around customer questions, objections, and needs, more directly. So I’m not relying only on select feedback or the loudest feedback in the room. I use real customer conversation to keep improving our full enablement environment.
RR: And as you alluded to, you’re beginning to use Deal Agent to capture deal-level insights and start to act on them. So how do you see it adding value to the environment you’ve already built and the environment you’ve already got your sellers comfortable using?
JS: Yeah, Deal Agent is something we’re really excited about. We just launched it and had a full all-sales meeting with our Highspot customer success team, and it’s really that next layer of a foundation we’ve already built. We started with getting content and training all in one place. Now we’re layering in conversational intelligence, but Deal Agent is going to take that a step further for us by connecting the conversations and insights we’re gathering back to the opportunity level.
This is really important for us because our sellers and our leaders don’t just need to know what happened on a call, they need to understand what that ultimately means for the deal, for them to close business. Are they talking to the right stakeholders? Are priorities clear? Do we have risks we need to address?
For our sales reps, I think the value is that it can reduce some of the manual work and help them stay focused on the right actions. For leaders, it gives clear visibility into deal health and where they may need to coach. For the rest of the organization, it gives us another level of insight, so I can look to see what patterns are building across opportunities. The AI agents built into it are amazing too, because they’re helping eliminate some admin burden by building Digital Rooms faster, with the content needed at that moment for that deal.
RR: And I think what’s kind of interesting is that this is a vision you see, and you’re like, “I see so much value in this. I see what the potential is.” But it’s so new, and it’s such a new way of working for literally everybody. You’re not trying to roll out a program you’ve seen elsewhere, you’re on the cutting edge.
So how have you been tackling things like the rollout, the behavior change, getting folks accustomed to this very new way of working?
JS: Yeah. So for us, it was big. We didn’t really have any tools like this in place already. The biggest thing we’ve learned is that you cannot roll it out as just another tool. Sellers already have a lot of tools, and if something feels disconnected from their day-to-day workflow, adoption is going to be really difficult.
So we tried to anchor the rollout in practical use cases. How does it help a rep prepare for a meeting? Does it help them follow up faster, remember what the customer actually said? For our sales leaders, we’re focusing now on that next phase of coaching and visibility, helping them find a better way to understand what’s happening in their field and coach their teams appropriately.
But in all honesty, there is a bit of change management. It’s a different way of working for some reps. Some reps were super excited and dove in headfirst, and others really needed to see the value a few times before it clicked and became muscle memory. So I try to keep that adoption path clear and practical. I’m not asking people to change everything overnight.
We’re helping them build small habits: review call summaries, look at action items, use that deal-level information to pressure test next steps, use Digital Rooms or Pitches to send content and see what customers are engaging with. The key for us was making it feel useful before making it feel mandatory. Once people saw that it could save them time and improve their follow-up, it became less intimidating, and after a certain period of time, I was actually able to pull down any old resources they may have had a habit of going back to.
RR: And since you’ve gone live with both Highspot and Deal Agent, what have you heard from the field on how they’re responding to it?
JS: Yeah, so anecdotally we’ve heard that being able to get those next action items and the call takeaway was a really big piece. Being able to more easily share back the call recording also saved some steps from how they used to do it before. Deal Agent is still relatively new for us, but I think where we’re honing in is the ability to slice data in different ways, by our sales forecasting, by our sales stages, and then really pairing that with a lot of the intelligence and reporting we already have in Salesforce. That gives us and our leadership a much deeper understanding of what’s truly happening and where leaders need to step in.
RR: So to your point of don’t boil the ocean, there are a handful of use cases that your sellers like, that you like, that your leaders like, that are slowly building the muscle. And over time, things might change, new use cases might emerge, but as of right now, there are a few recurring things that it sounds like people really are finding useful.
Super cool, I love that. And you touched on this a little bit, but I’d love to hear a little bit more about how this is helping you solve for some of the guesswork you were feeling. We talked about building without knowing what was being used by the field and what was landing. So now that you have that combination of conversation, deal data, and usage data, how does that change what you and other teams are building and providing to your reps?
JS: Yeah. It really helped us move from a state of assumption to being evidence-backed. Before, I had a lot of smart people supporting the field, but we would build materials based on individual feedback or something needed for one deal, and assume it was scalable across all deals. It’s not necessarily a wrong way to do it, but it’s an incomplete way to do it.
Now that I’ve got conversations and deal data all in one spot, I can start to pull out patterns. Where can I look to see what customers are actually asking? Where can I look to see what customers are actually engaging with? Is it the same consistent objection that keeps coming up, and are we answering it in the right way?
For my team, it means we’re much more targeted. Maybe the answer is a new training. Maybe it’s a better talk track or coaching around certain areas of the sales process. It could be working with product marketing to create a new Sales Play, or a clearer way to help position our value. The biggest change is that we’re actively, every day, listening, learning, and adjusting based on what’s actually happening out in the field.
RR: I love that. And I think that middle-of-the-funnel example is such a good example of how you can stitch all that information together and recognize that there’s a component of your strategy you can really pull on that might be particularly valuable. So I love that we have that, not only the high level of what it’s doing, but how it comes into play in the actual work happening.
Okay, so looking back, a year ago now, a few months ago now with Deal Agent, from where you started to where you are now, what’s the biggest impact you’ve achieved, or the proudest moment that sticks with you?
JS: I think the thing I’m most proud of is that we built something literally from the ground up, and it changed how enablement shows up for our business. The biggest impact has been moving from a fragmented environment to a connected foundation that can be structured, measured, and embedded into how our go-to-market teams work.
I can actually see that in a shift in our numbers. When we first brought Highspot on board, it was specifically a sales-only tool. I didn’t have any other broader teams in the tooling, and now we’ve doubled our Highspot user base. I’ve expanded from supporting just sales to supporting the broader go-to-market team.
Training has been one of our largest wins. We’ve moved from one-off live training to structured onboarding paths and ongoing learning. We’re actually in the midst of a current go-to-market training refresh, taking everyone through our RL Datix 360, as we call it, and I went from maybe a 4% completion rate in the early days to now seeing nearly 100% completion. Last time I looked, we were at around 97 or 98%. That’s a huge shift in the consistency and accountability I have with my field.
For content, 91% of our internal audiences are viewing our content in Highspot, and I’ve got close to 500 opportunities actively engaging with our content. So it’s telling me this isn’t just a repository where things sit. It’s becoming embedded in their daily workflows, in how they prepare, sell, and engage our customers.
There’s also a time-savings piece. It’s a little harder to quantify, but I feel it every day. I’m still working toward maturing how we connect this directly to revenue outcomes like win rate and pipeline movement, but now I’ve got a solid foundation, a high level of adoption, and the visibility to keep building toward that.
RR: Jill, the volume of work that happened in one year, when we talk about building the foundation, that’s the year. But you took 365 days, built out the foundation, drove the behavior change, and now you’re already in the midst of that next phase of evolution and getting people on board. So bravo, I don’t know how you did that. Hope you’re sleeping.
I’d love to get a little bit of perspective on how you did it, for other leaders who are in that phase of building a strategy from the ground up. How would you recommend they get started, especially in an AI-first world?
JS: Yeah. We went live with the product really, really fast. I had a great team behind me, and we worked hard every single day to get things built. But my advice would be actually not to start with AI.
It’s probably going to be a little controversial, but I think you should start with the problem you’re trying to solve. It can be really tempting to jump straight into the newest tool or capability, but if your foundation isn’t there, AI can just make the mess faster. I would start by understanding where the friction is for your sellers and go-to-market teams.
Can they find what they need? Do they understand the message in training? Do they know what good looks like? Are managers coaching consistently? Do you have visibility into what’s happening in customer conversations? Can you tell what’s helping deals move forward or stall? Once you understand those gaps, you can be more intentional about where AI fits.
Can it help a rep prepare faster, summarize conversations, surface deal risk, build up Digital Rooms? It should really be tied to a true, real workflow and a business need. This is when AI becomes much more powerful, because it’s got the right context. It’s not just another tool. It’s a way to scale insight, reduce manual work, and help the team make better decisions faster.
So for an enablement leader starting from scratch, I’d say: listen first, build your foundation, solve the real frictions in your sales force, and then use AI to scale what’s already working.
RR: I really liked the question framework you threw out there. Because I think especially when people are starting to build, you have this insane arena of potential work to be done. And when you can start to ask the right questions that build toward the right purpose, you can get to the exciting work down the line.
Well, Jill, thank you so much for chatting with us today. It’s been really wonderful to hear a little bit about what you’re building, how you’re thinking about building, and I’m so curious to see what’s next down the line. We’ll have to stay in touch.
JS: Yeah. Thanks so much for having me. This was great.
RR: To our audience, thank you for listening to this episode of the Win/Win Podcast. Be sure to tune in next time for more insights on how you can maximize go-to-market success with Highspot.
