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 the resources we have to make sure that we’re helping them avoid frustration and continuing to point out all the time it’s saving by eliminating some of the context and tool switching that takes up way too much of their day.
RR: I’d be really curious too, when you were in those conversations with your early, we’ll call them champions, but also guinea pigs, what were some of the things that were coming up that were exciting, some of the use cases that they were enthusiastic about?
RC: I would say the number one example that I was seeing was being able to use the MCP connector to combine insights they were getting from customers with the resources available. So something as simple as, “Here are the calls I’ve had with the customer so far. What resources would speak to their pain points or challenges?”
But in addition to that, we have a lot of information in Highspot, and not all of it is going to hit in every moment of the sales cycle. And so the MCP connector would give us recommendations not only on what to share, but when to share it. For example, we would have a user say, “Here are the last three calls I’ve had with the customer. What should I share with them from Highspot?” And it would respond with maybe six pieces of content, but then it would say, “I recommend sharing pieces one, two and four right now. These other resources may be helpful as follow-up.”
The other use cases that I’ve seen pretty often are more on the marketing and product side of things, where they too are looking at customer call recordings and trying to make sure that our content speaks to the actual concerns and ever-evolving needs that our customers have. And they too have been using the MCP server to make sure the content we have speaks to today’s concerns. This allows them, again, in a place like ChatGPT, where they are doing some more sophisticated synthesis of information from various resources, to not have to jump back to Highspot and look through the information we currently have published, which has been really helpful.
And then the third one that I’ll mention, I would say this is starting to come up more often. I have had some users that have said, “I really like that I can use the MCP connector in ChatGPT to generate an initial pitch link.” So if they ask through the MCP what resources would help this customer, and it says these three, they can generate that pitch link with those three pieces of content right there in that same conversation. I think that’s been really helpful.
RR: And then it kind of expedites the time from strategy all the way through to action, where you know exactly what you need to do, you have great suggestions, and then you can, boom, from the place that you’re working in, send it out the door. That’s huge. But I’m curious, you did all of this testing, all of this evaluation, did this go the way you expected, or are people using this in ways that you had never imagined?
RC: I think it’s going as expected because of the time that we took to test it first. With a lot of other tools that are being rolled out, sometimes everyone’s so eager to get people exploring and trying that they give them access and say, “Let us know what’s working and what’s not.” And that just increases the likelihood that more people are going to stub their toe, and I think that hurts adoption.
I get to benefit from being on a team where my role allows me to slow things down a little bit and test. And because of that, I was pretty confident that when we rolled this out, we would be leading with what was most likely to work, and frustration would be minimal. And that’s certainly what we’ve found.
During the soft launch when we just said, “It’s available. Here are some basic instructions,” I did look at some stats, and at least on the ChatGPT side, the Highspot MCP connector was being used a few hundred times a month. And then once we did the full rollout that had the specific examples from, you call them champions, I call them guinea pigs, when we had those more specific examples, last month it was about 1,000 uses of that connector. So we saw that increase, and what did not increase was people reaching out to me saying, “This is broken,” and, “This isn’t working.” So it went as I expected, and that’s because we had the luxury that I know not everyone has.
RR: And I think that takes me well into the next question, which is that all of this is very new, whether it’s to the teams building it or the teams that are being asked to use it. So when you’re trying to roll out a workflow that is either a new AI tool itself or a connector to an AI tool, anything that feels unfamiliar and foggy, why do you think that change management is so important, and why did you invest so heavily in that?
RC: Change management is important, first of all, because that’s the reality of the world we live in now, that we’re constantly being asked and then sometimes required to use these new technologies. And I think a big part of my responsibility on our sales success and enablement team is to make sure that any new tool speeds them up, it doesn’t slow them down.
It makes them better at their job, and it doesn’t make them worse. If they don’t know how to efficiently leverage that tool, it’ll take them longer than it should, it’ll frustrate them, and in some cases it may cause them to make mistakes. And so making sure that you approach change management with a focus on minimizing disruption and decreasing the chance of them making a mistake or running into a wall, I think is time well spent.
Because otherwise, you’re making it much more likely that their first experience with this new tool is not going to make them faster or better, therefore they’re not going to adopt it. If it doesn’t do those things, it’s not worth their time, and it’s not worth whatever money we’re spending on it. If you want to make sure that money’s well spent, you’ve got to make sure that rollout is setting them up for quick success.
RR: I like the principle you laid out there, of any new tool, what is it meant to do? Sure, we have broader goals, but at the end of the day, it doesn’t slow them down, doesn’t make them worse. Okay, so you’re a couple months into the rollout. You have more than just a handful of folks using it now. With Highspot MCP Server and these connectors between all of the AI tools that you’re using live now, what early signals are you seeing that are telling you, “This actually was a good use of our time, and not only that, it is impacting how our sellers behave, perform, execute”?
RC: I would say two things. These AI platforms are fairly limited in the stats that you can find right now, but I do at the very least know that the connector is being used way more often now than it was the month before, than it was the month before. So there are some basic numbers that I think prove that this is being successful.
The other thing, too, is more anecdotal, and that is just people reaching out or sharing with their colleagues when the Highspot MCP connector fit into their established workflows. So what we’re seeing more often is in team sessions, when they’re talking about deals, they’re referencing, “This was the point when I used the connector to do this or that.”
And in turn, what’s happening is that information is allowing our team, when training our new users for some of these platforms, to lead with that. For example, when I’m training our new hires on Highspot, generally speaking, I’m now adding a section that talks about not just finding Highspot content in Highspot, but finding it in ChatGPT, because I know that their managers are telling them to do a lot of other things there, because there are all these other agents that are being built in that place.
And then vice versa, I mentioned earlier that the most common use we’re finding is combining customer call transcripts with Highspot content. So when I’m training them on our call recording software, I’m also mentioning the Highspot MCP, because that’s starting to settle into those workflows of how do I quickly get insights on the conversation I just had?
But now they are learning that part of that process can also involve Highspot through the MCP. So the numbers are telling us it’s being used more, so I think that’s good. But then just anecdotally, people are sharing when in the real world of my day did it actually help? And that helps us in turn set everybody up for that success by pointing out those moments.
RR: Do you have a success story that a seller brought to you and said, “In this specific deal, this worked out really well and enabled me to achieve X”? Anything like that, that you were like, “Yes, this is the win I was looking for.”
RC: There have certainly been examples where someone reached out to me, and typically it was because of a clock running.
And so they would say, for example, “The call finished. As soon as it processed, I was able to immediately give ChatGPT the call transcript, ask it what I should share in Highspot, do a quick check to make sure it was legit,” and then they were able to share that content in their follow-up with the customer.
Whereas previously, that might have taken another day. And so the example was the Highspot MCP allowed me to more quickly follow up with the customer with relevant content. The other example that I would use is more on our new hires. I’ve talked a lot about how the Highspot MCP is helping us better access the content that’s designed for our customers.
The new hires are also finding it helpful learning about our products for their own sake and how to level up. For example, asking what training exists in Highspot that can help me deal with objections. The Highspot MCP has been a quicker process, so I think that them improving their own sales skills is something that this connector speaks to as well.
RR: I love that use case, the self-serve onboarding workflow almost of I’m coming into the company, I’m confused, but I know that any answer I’m looking for lives here, and I can ask it in really natural, sometimes confused language questions that will give me the right answer without needing to have the level of detail that you might otherwise.
We kind of glossed over a question I wanted to ask earlier. What is the pie-in-the-sky vision of the kind of usage that you’re looking to eventually drive as this rollout continues on?
RC: I think the ultimate goal is to make sure that when the Highspot MCP adds genuine value, it saves them time in a common moment of their day, that we’re able to reference that in all the other training that we do.
As use increases, as we continue to get feedback on when it helped them, making sure that we go back to our training and resources on that part of the sales process, and making sure we’re calling out the value of the connector in that moment. So what we want to do is make sure that in all of our training, when it would be helpful in their day-to-day workflows, that we are calling it out, that we are giving them the information they need to use it effectively, because that is going to speed up their day.
That is going to make them more successful. So it’s less about Highspot MCP-only resources, and more about sprinkling it into all of the sales skill training that we do.
RR: Because it works best when it’s quiet. It’s one of those things that your sellers don’t need to know the tools that they’re using like the back of their hand the way you do. They just need to trust that they’ll deliver for them in the way they expect. Okay, last question for you. For anyone tuning in that’s thinking about tackling a rollout, whether it is of we’re just trying to get ChatGPT or Claude or any sort of AI tool out into the world, or we’re trying to bring our tools into it, what’s one thing about your approach that you’ve laid out here that you would say, “Please do not skip this”?
RC: Don’t skip testing. I know that people higher up in the organization are maybe a little more eager to roll things out and gain value in things, but if you skip testing, you’re less likely to realize that value. So anything you can do to give yourself time to test means it will be less painful, less embarrassing, less deflating to identify issues.
A rushed rollout is going to take more time in the long run because you’re going to have to clean it up in public, and that creates a whole new host of challenges. If you have the time to test, don’t skip it. If you’re struggling to gain that time to test, all I can say is to try and advocate by pointing out that reality. That is going to, in the long run, create a quicker time to value.
RR: The challenge with some of this is that the advice is sometimes frustrating because you know you need it, you know you need time, you know you need patience. The enthusiasm needs to be dulled a little bit before you can take it out into the world, and it’s hard, I think, especially because there’s so much pressure on a lot of folks that are doing the building, and there’s just a lot of excitement on, “I’ve spent two and a half weeks, three weeks, two months, whatever the case may be, building this. I want to bring it to life.” So I appreciate the measured advice to take a breath, take a breather, slow down to go fast. And I appreciate the time broadly. It has been really wonderful to hear what you’ve been working on and all of the work it has taken to get to this point, so thank you for coming on and joining us.
RC: Appreciate it.
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.
