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. 2d ago

    Episode 159: Outpacing the Market with Agile GTM Enablement

    According to LinkedIn’s Workplace Learning Report, 49% of L&D professionals say their executives are concerned that employees don’t have the right skills to execute their business strategy. And in busy, fast-paced industries, that gap is becoming a real problem. Because if the product, market, and go-to-market motion are all evolving at once, organizations are left asking the same question: what does it actually look like to build an enablement and a go-to-market model that can keep up and build those skills as they’re needed? Riley Rogers: Hi, and welcome to the Win/Win Podcast. I’m your host, Riley Rogers. Join us as we dive into changing trends in the workplace and how to navigate them successfully. Here to discuss this topic is Julia Townsend, Go-to-Market Enablement and Business Development Leader at DataRobot. Julia, thank you so much for joining us today. I really appreciate the time. Super excited to hear about the work you’re doing in this arena today. Before we jump in, though, I’d love if you could tell us about yourself, your background, and your role. Julia Townsend: Yeah, great. Thanks for inviting me, and Riley, really appreciate it, and excited to share more about what I do at DataRobot. So yes, I lead the go-to-market enablement and business development function at DataRobot, and if you’ve not heard of us, we are the only end-to-end agent workforce platform for secure, scalable, and production-grade agents. We are based out of Boston, although I am based in the UK, so we do have a global workforce. So when it comes to enablement, I own it globally. Plus, as I said, I also have the business development piece. Pretty interesting role that is fairly unusual within the enablement space. But day-to-day, what that means is a few things. So I run our enablement team, so within that, I have a BDR and sales revenue enablement specialist, I have a go-to-market readiness specialist, and I also have a technical enablement data scientist, which is brilliant. And then I also have our BDR team who are based in Boston. So a little bit about me. So prior to making a career change to working in enablement in the AI ML space, I actually did start out as a BDR myself, then I was an enterprise seller in the SAS observability market for many years. I’ve been with DataRobot for five years. I’ve been through quite a few different distinct eras of where we’ve been. And so started out very early with very hiring-heavy model. We did a lot of in-person boot camps, then we had a bit of a restructure within our business, which is very typical within the AI space. It’s very much up and down, so we had to rebuild the enablement in a much more of a leaner type of practice. And now within the AI agentic era, where the products in the market are moving so, so, so quickly, any of the other early enablement models that we’ve had, it’s really, there’s been a lot of changes. RR: And that leads us very well to kind of the first topic we were gonna touch on, which is the fact that change is abundant and everywhere, especially when you’re working in the AI space. So as you’ve been navigating the enablement journey for the last five years at DataRobot, what has shifted about how you think about enabling sellers from when you first started to what it looks like now? JT: So I guess the biggest shift when I think back to those years is moving away from a very calendar-driven compliance type model towards something that’s much more embedded where the seller is and is very continuous. In previous older years, we were very much all about completion tracking, which in hindsight looks a lot like compliance monitoring. So there were lots of weekly reports on showing who had or hadn’t finished a learning module. We were very big on the stick piece back in the day. And then I guess after we had our organizational restructure a couple of years back, our hiring volume dropped and the business model changed, and the need for big recurring cohort in-person boot camps really evaporated. So that meant that it forced enablement to start pivoting towards much more of a leaner targeted delivery. Tracking forward to today, enablement definitely lives now inside the same sorts of tools and the cadence that sellers already have. We use Highspot, we have the content management and the learning management modules. So that means we’re able to offer very much bite-sized content. So it means that rather than the field having a separate training destination that they have to go into, what we’re providing is very much just part of the weekly workflow for them to be successful. So they’re not visiting stuff occasionally, they’re always in it. So it’s less about building a big curriculum and running it once a year, and it’s much more about treating enablement like a live product. RR: We kind of talked about what it means for enablement as a function to be working amidst this change, but like you alluded to, DataRobot is a company in a market that never really stops moving. So what does that kind of environment demand from you? JT: It is really about speed because we operate in a very competitive environment. There’s a ton of companies out there that are specialist agent builders, they’re there to sell you some sort of agent to help you in a day-to-day life. But then there’s also companies at our level who are also providing platforms, and it’s very, the language is very similar, so it’s very hard to stand out. So when you have an edge with your product development, those USPs, you really have to get the sales team on board with it and talking that language, that new messaging, that new positioning to customers as soon as it’s been created. So speed is very important. What that means for enablement and content is that it has to ship in days or weeks, not quarters. For example, two Sales Plays that we launched last quarter, our Dell seller-to-seller play and our customer expansion play, they both went from kickoff, initial conception, to the field launch on very, very tight dated project plans with weekly status checks, which meant we could launch them in a matter of weeks, whereas in the past, it would take us a lot longer to do that. RR: I’d love to drill down into an example that you mentioned as you were speaking to the speed piece, in a recent instance where that became a necessity. So the Dell partnership. You shipped a Sales Play for it, you enabled the team quickly on the messaging. What did that look like to build, and can you tell us a little bit more about the scenario around it? JT: So DataRobot, we have a fairly new strategic partnership with Dell and Nvidia. As this was a new business drive for us, we had to create a very specific Sales Play that was focused on our reps engaging with Dell reps. And I think this is a little bit different maybe to other enablement functions or what we also did in the past, where plays tend to more focus on the sales process, so things like objection handling play, first meeting play. Whereas this play had a pipeline generation target attached to it, and so the play centered on building early-stage pipeline with Dell sellers, and it was very, very specifically around that. The Dell engagement with our Sales Play ended up being quite a few different types of enablement requirements that are stacked on top of each other for different audiences, but all around roughly the same timeline. So for example, we first launched the Dell seller-to-seller play. This was equipping our own sellers to target and partner with the Dell sales team. We launched this towards the end of Q1. But then coupled with that, we then did some event-specific BDR training. Our BDRs were going to some of these Dell networking events with the sellers and meeting them, and they needed to have the right narrative. They needed to understand some of the vertical specific use cases that would get a Dell seller interest. So we did lots of live role play practice with them to make sure they were able to do that effectively. But yeah, I guess to summarize that piece, it wasn’t just one enablement deliverable, it was four or five different audiences that were wrapped into one Sales Play, but it was very much focused on a pipeline generation target. RR: What was the timing like from we have this partnership to now I need to enable the field to I have enabled the field? How does that differ from maybe a year ago what that would’ve looked like? JT: Yes. So I guess a year ago, it felt like there was more luxury in terms of time, because the Sales Plays then weren’t so much aligned to a specific pipeline target. So if your Sales Play is more around objection handling or first meeting deck, that’s important, but it doesn’t quite have the same impact on what the business needs in terms of a north star metric that will translate into real business revenue and deals closed. So that was one thing that was different. In terms of the timeline, probably took us about four weeks. We really put the heads down with the team. We had a daily project call to work on the content, test it, and ship it out. We ran it like we would a product launch, so using the same sorts of methodologies around that with reviewing, iterating, building, testing, those sorts of things. So that was also different. We had a very tight project management approach to it, which enablement led. Because this was tied to a real revenue metric, it really had the ear of the CRO. It was his prerogative to drive this. So that also was super helpful, was having executive sponsorship all over it, encouraging the reps to lean in, and being the voice of enablement, helping us amplify what we did to help them, and that’s all because the Sales Play was attached to a real revenue goal. RR: Four weeks, that’s a pretty crazy turnaround, I

  2. Sep 4

    Episode 158: Bringing a Human Touch to GTM Workflows

    According to Gartner, 73% of B2B buyers actively avoid suppliers who send irrelevant outreach. That tells us two things. One, personalization is prolific. Many teams are trialing different plays and finding varying degrees of success. Two, personalization is a risky play. Get it wrong, and you might actually do more harm than good. So what does it actually look like to show up in a way that earns a buyer’s attention? 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 are Molly Donlon, sales activation manager, and Tommy Dauphin, senior account executive at Paylocity. Thank you so much for joining us, both of you. I’m super excited to dive into all of the fun and unconventional ways that you guys are capturing attention, driving engagement, and tackling the beast that is today’s modern buyer. Could you help me kick things off? Just tell me a little bit about yourself, and Molly, I’ll kick it over to you. Molly Donlon: Tommy would have insisted that I start anyway because he’s a gentleman from the South. So I started out in sales as a business development representative in my corporate career, and I actually used Highspot as a BDR. I stayed in sales for three and a half, almost four years, and then fell in love with the strategy behind sales, and especially personalization. I almost felt like an investigator, where I could go and do the research and find something that told me that this person actually would benefit from what we are providing, and then explain how I made that connection. So I decided to help my teammates and my colleagues within sales, rather than put that into practice with clients. It’s been an amazing company and a great journey. RR: Amazing. Well, I’m super interested to hear more about the buyer engagement private investigator lifestyle. Before we do, Tommy, I’ll kick it over to you. Tommy Dauphin: Excellent. Thank you so much, Riley. And, Molly, you are absolutely correct. I was not going first on that one. You were definitely gonna get the first intro there. So Tommy Dauphin here from South Louisiana. Been at Paylocity, it’ll actually make eight years next month. And then before that, I worked at Cintas for 10 years, primarily on the operations side. Paylocity was my first outside sales job. So not only did I have to learn the world of sales, but also the world of HR tech, and all of the things in between. So it’s been quite the journey, but like Molly said, fantastic place to be, and very excited to be here today. RR: Well, I’m looking forward to learning more about everything happening at Paylocity right now. And Molly, I’d love to start with you. You mentioned that one of the things that you loved was doing your own research, and it sounds like it’s not just sellers that are doing their research, it’s also buyers. So when buyers are learning, researching, Googling before they ever talk to a seller, how do you actually get their attention? MD: In a Forbes article, it said that about six in 10 B2B buyers prefer to go through most of the buying process without a sales rep intervening. And HRIS, human resources information system, what we sell, is very complicated, and it has an impact on the whole company. So I find it hard to believe that sales reps will be completely free of participation in the sales process. But I do think we should be leaning into the behaviors and the desires that we’re hearing from buyers. They want to see all of the information available, and that’s why we’ve had such great success with Digital Rooms, for example. The best way to accommodate this behavior is here are the trustworthy resources, so that we can meet you when you’re ready to talk to someone. RR: Okay, so you mentioned needing to create a place where when buyers are researching, they land in a location where they get everything they need, the right messaging that you want them to have, and that then leads them to an actual person that can then usher them through that back half of the sales cycle, or whatever point they reach you. Tommy, I know that you have more than a handful of creative tactics for those get your foot in the door moments. So how do you make a meaningful impression before the conversation starts? TD: I think the number one piece is providing value in every step of the way. In every interaction, there’s gotta be something that I’m bringing to the table, and me showing up and dropping off a business card or a pamphlet or a brochure or something is not cutting it. You have to do more than that. And it’s also a situation where not every person knows how to go through a buying process, because sometimes I’m talking to people who have evaluated their process every 18 months, every two years. But every once in a while, you run into that person who’s said, “We’ve been with our current provider for the last decade.” Well, a lot has changed in the last decade in the world of HRIS, so not only do you have to learn how to buy this product, but you have to then compare, contrast, and figure out the differences, and it can get confusing. The waters get muddy. Everyone starts to look and sound the same, and we have the phrase internally of the sea of sameness. We don’t wanna fall into that trap. So we really do try to differentiate ourselves right off the bat, and one of the ways that I do it is I like to drop off fudge, chocolate peanut butter fudge. And yes, it is something that I make myself. This is a recipe my mom’s been making for over 40 years, and I’ve been making it for seven and a half years. My tactic has changed over the years, pre-Highspot and post-Highspot, because before I didn’t have a good way of getting the information to the prospect about the recipe. But now I do. So what I have done is I have branded a QR code that takes the prospect to the recipe, and it’s housed in Highspot. So I can see who and when they click it. If I wanted to make it unique URLs, I could do that. But also, I can see when they’re accessing it, and then for how long they looked at it. So when I go to drop it, and number one, I always drop to the receptionist as well as to the prospect, before I get to my truck, I get an email saying that recipe has been scanned. I feel like I’m gonna be getting at least some sort of phone call back or return email for me to be able to have that additional conversation. Not having a tool like Highspot, I couldn’t do that before. It wasn’t nearly as easy. Now it’s a plug-and-play thing, and I’m rocking and rolling with it week in and week out. RR: I still can’t get over that approach. It’s so good, and it is so unique. I can’t imagine that there is anybody else that does that, and that is exactly why you get out to the parking lot, and already you’ve got someone on the line going, “Who is this?” Or, “You know what? I’ll take a call.” So I love that strategy. And I also love the call out to engagement data, of how you’re using that to intuit what’s happening in the mind of your buyer or in the mind of your prospect. So when a buyer engages with something that you’ve sent them, whether that is a fudge recipe or a brochure or whatever the case may be, what does that tell you? And then how do you use that to decide what to do next in a deal? TD: Number one, all I’m looking for is them to engage. Whether they like the fudge, they don’t like the fudge, they’re diabetic, or whatever the case may be, it sparks a conversation, and I’ve actually changed my process with that over the years. I used to drop the fudge, and then I would say, “If you want the recipe, just email me.” Well, no one willingly emails a sales rep. So it is definitely one of those things where I had to adjust. Now I can do my outreach. I can call, I can email, I can even text if I do have a cell phone number or something like that. And number one, I just wanna make sure they got it. Did they enjoy it? And then number two, if I find out too, because I’ve gotten this before, “Oh, sorry, I’m allergic. I can’t have peanuts or anything like that,” well, now I’m coming with one of the other drops that I have that is not food related. It gives me access and ability to have a conversation, be unique from the jump, and then after that, that’s when we bring in Digital Rooms or a brochure that we have tied to Highspot or something like that, where then I can interact with them in a more professional manner, talking about the products and services that we offer. It gives me the ability to adjust on the fly and do it from my phone if I need to, do it from a computer or an iPad, and it gives me the flexibility to build something specific for them. It’s not just the generic everyone gets the same response, and hopefully something sticks. I can have that personalization that you talked about at the beginning of the episode. RR: I love that, and I’m really curious too. So we’ve heard a little bit of the individual approach, of the very unique thing that you do, because I can’t imagine that every single rep at Paylocity is roaming around the continental US with fudge in their truck. Molly, I’d love if you could tell me a little bit about how you’re thinking about doing this at scale. What does your process look like for building something that you think, A, sellers will use, and that, B, buyers will go, “Hmm, maybe I should actually look into that”? MD: And one of the great things about Paylocity is our sales reps are gritty. And like Tommy was hinting at earlier, he tested the fudge approach. It’s the same with the Digital Room templates that we build. We know that when we put a Digital Room template out there, our re

  3. Aug 24

    Episode 157: Embedding GTM Enablement into Every AI Tool

    According to Salesforce’s State of Sales Report, sales teams use an average of 10 tools to close a deal, which then leaves 66% of reps to say that they’re overwhelmed by the sheer number of platforms they’re expected to juggle in their day-to-day. So when an enablement team goes to roll out new tools, reps more than likely just stop listening because it feels like it’s just another login that they’ll slowly stop opening over time. So how do you introduce something new without asking reps to change how they already work? 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 Ryan Costello, go-to-market senior enablement tools specialist at Enverus. Ryan, thank you so much for joining us today. I’m super excited to have you here. As we’re jumping into this topic, and a little bit of a loaded one, could you kick us off just by telling us a little bit about yourself, your background, and your role? Ryan Costello: Thanks for having me, Riley. So I’m Ryan Costello, coming to you from Indianapolis, Indiana. I started my professional career as a high school English teacher. I taught for 18 years, and then I left the classroom. I spent a couple years as a learning consultant at Lessonly and Seismic, and for the last two or three years, I’ve been working at Enverus. We’re an energy technology company, and I’ve been on our sales success team, helping our reps use the tools they’re asked to use more efficiently. So I manage our content and learning management systems, as well as our call recording and social selling softwares. That’s the quick version of me. RR: So sounds like you’re the right person to talk to when it comes to tool adoption and long-term tool adoption. As we’re thinking about how you’re making that happen in the specific environment that you’re working in, I’d love to get a little bit of background on the challenges that you’re coming up against. So what is it that makes your go-to-market motion complex, and how are you trying to solve these challenges or simplify these challenges with tools? RC: Enverus is a company that helps all fields in the energy industry. So that means that we are helping solar companies, oil and gas companies. We’re helping people that are investing in new energy technologies. And so there are so many different fields within the energy industry, and we have hundreds of products and SKUs that sometimes overlap with those various segments, that it can become a real challenge to get all of that information to the right reps. And so what we’re trying to do when it comes to helping them leverage tools is making sure that as we continue to offer more and more for our customers, we want to make sure that as that haystack grows, their ability to find the needle, to find the piece of content they need, or the training to get better at selling, doesn’t take away from their time with customers. That’s really what we’re ultimately focused on. RR: As you’re, again, helping reps find the needle in the ever-expanding haystack, it does sound like there are many avenues through which your sellers, your sales managers, anybody who’s looking for information can go try to access it from the bajillion platforms that we all have. So where do your teams today work from? RC: First and foremost, we’ve had Highspot for years, and our organization is really comfortable with it. The reps understand its value, but they’re often in other platforms. So one example I’ll use is, they’re in Salesforce a lot. And so for a while now, we have incorporated a Highspot widget in Salesforce so that they can search for content from that platform, and many of them have grown accustomed to it because they just, for whatever reason, live in Salesforce more. But like everybody else right now, companies, including ours, are starting to give them access to AI platforms. And so our entire go-to-market organization right now is in ChatGPT, and then our sales leaders and marketing, my team, is also in Claude. So when I’m primarily serving the reps, the main need that we found was that the reps are being told, “Use ChatGPT.” And so what we found was they were spending more time in a platform like ChatGPT. So to have an option where Highspot could essentially follow them there, any opportunity we have for Highspot to be where they’re naturally at is something that we’re interested in. When they were spending more and more time in ChatGPT, we needed something that let them more easily get to Highspot without having to travel there, basically. RR: So since you’ve started using the Highspot MCP Server to, like you said, bring Highspot along with you wherever your teams are working, whether that is Claude, whether that’s ChatGPT, what kind of use cases are you seeing sellers using that for? And maybe what kind of use cases were they trying to use these tools for previously that were kind of difficult because they didn’t have enough context to really deliver them? RC: One thing that they’ve really enjoyed within the platform is that now you can use the search bar and ask it a question, and it’ll give you an AI-generated response, and you can have that conversational experience. They were still saying, “Yeah, but I need to combine the information on our products that we have in Highspot with the information that I’m getting from a call transcript with a customer or some information in email correspondence that I’ve had with them.” And so what we’ve started to see with the Highspot MCP and ChatGPT is the ability to combine the information in Highspot with the capabilities that exist outside of the platform. But by having Highspot present in ChatGPT through the MCP connector, they’re able to do things without jumping around and having to manually synthesize it themselves. RR: I know you spent a lot of time testing it yourself before you launched it out to the field to make sure this was something valuable, something they would use, something that fit into their workflow. Can you walk me through what the process of evaluating this looked like? RC: When it became available, we met with our Highspot CSM and a Highspot TAM to talk through what the MCP was designed to do. And before I wanted to have our reps try it out, I wanted to make sure that it would serve their needs. And so the Highspot team gave me a whole set of sample scenarios. Here are the types of questions that we think reps would be served by. And I took quite a bit of time. I tested every sample prompt, every scenario that Highspot gave me. So I took the time to see, are the prompts and scenarios that Highspot has designed this MCP to help with, are they landing with the content that we happen to have? That was a really important process because I certainly identified some prompts and scenarios that just because of the nature of our business, didn’t quite land. So that was the first step, was let me try these out and see what lands and what doesn’t land, so that I could identify what to unveil this with to ensure that the first time a user tries it, it hits. So that testing allowed me to prepare resources that would lead with what it’s best at and give some troubleshooting right off the bat so that if they stub their toe, they had a quick solution. So that was all just the testing phase to then get to resources so that I could create a how-to video and a how-to guide so that they could step by step set it up and try it out. RR: To the point at the top, you launch a tool, it sounds scary, nobody uses it. If you can make it easy, or at least feel digestible, you give yourself a little bit of an edge. So I’d be curious, in addition to the resources that you built and the thoughtfulness with which you approached what works, I’d love to know a little bit more about what the rollout to your teams looked like. RC: So after I had tested everything, we did what I would consider a soft launch. We let all of our Highspot users know that it was available, and we designed those resources so that whether they were using ChatGPT or Claude, the resources focused more on what the Highspot MCP could do regardless of the platform. All the information was essentially the same so that we didn’t have to create two different versions of everything. But once we had tested and had those general resources, we let everybody know via email and our Teams channels, “This is now available. Try it out.” And that probably lasted a month and a half. And while that was happening, I was asking, “If anybody’s trying this and you’re having success or not, let me know.” Because before we did a full rollout, I needed to know the real-world application and value of the MCP, which I just can’t do myself because I’m not a rep and I’m not talking to customers. And so during that soft launch, our reps who were always up to try something new, they were our guinea pigs, so that when we did a full launch about a month and a half later, I could have more specific use cases. And so the full launch had resources that were more specific to us, and I was just more aggressive. So we again fully launched through email and Teams channel communication. And then every week, I would provide specific examples from our guinea pigs earlier, knowing that it had genuinely helped them, and that would ultimately give this more credence. And so for the last month and a half or so, that’s what’s been happening. Every week, I post new updates, I continue to ask for feedback. It’s amazing the motivation a ten dollar Starbucks card will get in people responding to surveys. And during all that time I’ve been able to continue to fine-tune

  4. 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

  5. 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

  6. 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

  7. 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

  8. 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

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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
    155
  • Rating
    Clean
  • Show Website
    Win Win Podcast