According to research from Gartner, more than half of organizations have increased their investment in AI since 2023. So, how can you effectively leverage AI to improve GTM productivity and accelerate business outcomes?
Riley Rogers: Hi, and welcome to the Win Win podcast. I’m your host, Riley Rogers. Join us as we dive into changing trends in the workplace and how to navigate them successfully.
Here to discuss this topic is Chris Sargent, the director of sales enablement at BambooHR. Thank you so much for joining us, Chris. Before we get started, I’d just love for you to tell us a little bit about yourself, your background, and your role.
Chris Sargent: Absolutely. Thank you for having me, Riley. Really excited to be spending some time with you today.
So my background, I have been leading sales enablement teams for the better part of the last 10 plus years, and prior to that I was a sales leader and a sales individual contributor. So have spent a lot of time in both roles and really help companies scale. You talked about go-to-market strategies.
My background heavily is aligned sales execution, focusing on how buyers can achieve goals and how selling and. Our ability to sell with a process with value can really be one of the greatest competitive advantages that we take to market. And in my current role at Bamboo, I oversee enablement programs globally across all of our different skill sets, all of our different segments.
And really our mission here is to equip every seller and leader with the skills to tools and processes they need to win with confidence and consistency.
RR: I love it. Confidence and consistency. That’s what everybody’s looking for. Well, we’re so excited to have you here. Especially as you mentioned, you know, you’re a pretty experienced leader and you have extensive experience spanning both the sales and the sales enablement side.
And so you’ve probably seen the landscape change a little bit recently with the acceleration of AI innovation. So I’m curious, how have you seen the challenges that go-to-market teams face change as well?
CS: Yeah, I think there’s been, you know, change is the, probably the important word there. One of the biggest shifts as it relates to specifically AI is I think the timing of AI aligning with just kind of a general trend in sales, right?
That we’ve seen, I think in the early teens to the late 2019, even into 2000, 20, 21, economies were fantastic globally. Every organization had what felt like, in a lot of cases, unlimited budget to acquire tools and technology. And I think in a lot of ways that created probably some unintentional outcomes as it relates to sales.
And in some cases it was a lot more of what I would call order taking versus what would potentially be a value driven sales cycle in a lot of cases, by no one’s fault, other than that was the nature of how buyers were buying at the time. So I think you take that. Component of that and then align that with all of those changes.
Now with AI, I think one of the biggest shifts that most organizations and sales team members as individual contributors and leaders are dealing with is that AI is happening in real time. And not only is it happening in real time, it’s new for not only the individual contributors, but a lot of it’s new for managers, it’s new for enablement teams, even the buyers who are trying to figure out how do they leverage AI.
So I think that challenge that we see is how do you understand and take the pace of AI innovation and your ability to adapt to that. And that means enablement specifically isn’t just about delivering training, but how are you actually building a culture that fosters the idea of ongoing learning experimentation across the board and cross-functional alignment to keep up with the pace of change while not sacrificing.
What really the intended outcome of is that confidence and consistency in the rep’s performance because that desired outcome doesn’t change. How you may get there is what’s changing and understanding how to put that as part of your DNA as an enablement organization and handle that pace of innovation is gonna be critical.
RR: Yeah, so we’re sort of in a perfect storm, right of change management in across a number of different areas. I think these are challenges that we’re hearing from a lot of our customers and just feeling in the market. I think you’re spot on with all of that, but rather than kind of lingering in our challenges, maybe let’s talk solutions.
So in your opinion, what is Enablement’s role in helping GTM teams overcome these challenges and achieving more success amid these changes?
CS: Yeah, it’s a very fair question, and I think this is the power of a really strong enablement organization because in that format and in that model, what you’re really asking enablement to do and what enablement should be doing is becoming the bridge between the new technology itself and the practical application at the rep level.
So our role is to really translate what I would say innovation into that action. Our job is to make sure reps just aren’t aware of AI and it’s not just. Kind of a tool that they use on the side, similar to a Salesforce and outreach and a Highspot, for example. But they’re actually using it to be effective in everything that they’re doing in their day-to-day workflow.
And I think about that in three core areas. And that’s how we’re trying to think about it is what are you doing to prepare? What are you doing in real time? And what are you doing post customer interaction that allows you to be better at your job? Because of ai and some of that’s customer facing, some of that’s internal.
Really what I it means is we’re embedding AI into every existing process. We wanna build confidence through the training and reinforcement and giving managers the tools to coach around it. And I think that goes back to not losing our North Star of if the intended outcome is customers have the best buying experience and the reps are confident and have the ability to execute.
That doesn’t change, but the modality to do it, we can make them better at their jobs, we can make them more efficient. We can create competitive advantages because of that. And it’s kind of rethinking not necessarily the intended outcome as much as thinking the journey that gets us there.
RR: Yeah. I’ve heard it put as kind of like the job doesn’t change, but the way you do the work does.
CS: Exactly.
RR: We’re all still driving towards that North Star. We just have a little bit more tools in our toolkit to get there.
CS: Yeah, totally agree. And I think that’s what every. Enablement organization. Every sales organization on the planet is trying to solve it right now, which is what does that look like?
And going back to the challenge, I think the challenge in that is there’s desired state and then there’s what can actually be executed today, all while knowing what seems like every day, every week, every month there’s some new AI application that’s being launched. And how do you kind of take all of that noise and put it into a journey that aligns with not only your AEs and your reps and your managers, but really how do your customers wanna buy from you?
RR: Yeah, and to your point, I think people are like clamoring for use cases. They’re trying to figure out how do we apply this? We have a vision, but how do we bring it to life? And so I know you guys have started putting in kind of the work to answer those questions and have started using some AI capabilities in Highspot to improve rep productivity and kind of streamline some of those workflows.
So can you talk to me a little bit about how you’re using AI to elevate your enablement efforts and how that fits into your GTM productivity strategies?
CS: Yeah. You know, I think there’s a few things and the beauty in that is, you know, we are fortunate enough to have an AI team that was hired about four years ago that’s led by a fantastic gentleman by the name of Alan Whitaker.
And part of what we’re looking at is really aligning kind of the build or buy model a little bit. But some of the ways we’re leveraging this today is, you know, I think those core focus areas of how are we helping the rep be more efficient? And then how are we helping the rep. In real time, create a better buying experience and really help customers see the value of what it is that we do.
We all know that we’re using AI, but also buyers are using AI and they have more access to information recommendations than ever, ever before. So there’s a few ways that we’re kind of leveraging AI in a current state, but also kind of hoping we get to from a desired state perspective. And we kind of look at that in a very pragmatic and phased approach way while also.
Putting urgency and moving quickly. You know, I think about one of the most important things is we sell a platform and we sell, over the years have increased our ability and our product capabilities that go to market. And I think one of the things that’s really critical is in a lot of situations that’s being launched in real time on the back of other releases, and it’s really about guiding our sales team members to the right content at the right time, but also having that served up to them at the right time.
We don’t have a lot of technical resources here. It requires in a lot of situations where we have a lot of high velocity opportunities at Bamboo hr. So it, it’s not even about coming back with information even a day or two later, because that could be too late. So one of the ways we’re leveraging this is serving up information at the right time based off of the rep’s ability to have a conversation in real time.
It reduces time spent searching for content, for answers. It’s feeding that up proactively and it’s really increasing confidence in what our sellers need in the moment versus even, like I said, taking 30 minutes or an hour and coming back to that. One of the most powerful ways we’re also using AI is really how to engage.
Data to better understand what’s resonating with our buyers and using those insights to fine tune our messaging and also which messaging we use. You know, one of the ways we’re currently leveraging Highspot, and it’s been extremely powerful for us, is understanding the content that makes the most sense, right?
I think that the standard back and forth between most organizations and specifically marketing and sales is, hey, we’re creating content for you. Why aren’t you using it? And I think what. AI has allowed us to do is for reps to find information on content that’s been the most relevant at the right time.
Highspot serves that up in a way that allows us not only to look at that in real time, but it’s recommending that also based off of what Highspot seeing on the backend from an analytics perspective being tied to the most revenue producing opportunities. That’s been a huge win for us in really increasing our rep’s ability to be faster, but also more accurate.
Sometimes I think we just worry about being fast. It doesn’t help if unless we’re accurate. This has kind of allowed us to go down that model on both sides.
RR: Yeah, it is hard to strike that balance when you know 30 minutes is too late, but. How are you gonna put together something strategic in such a short period of time?
And I know one of the things that your team’s also kind of been leaning into a little bit is you mentioned on LinkedIn actually that continuous improvement is a big priority for you, and one of the ways that you’re using AI is with skill feedback to kind of support that ongoing learning loop. So how are you using that and how is that helping you, as you said, lean into continuous improvement?
CS: Yeah, great question. I think one of the key things for us that’s been really, really indicative is about a year ago we kind of looked at our call analytics and call intelligence tools and wanted to see potentially if there was an opportunity for us to get a little bit more. Proactive in the way we were leveraging that to get insights, identify opportunities, and replicate things that were going well.
And about six to seven months ago, even prior to me joining the organization, holistically looked and transitioned to what I would call an even more powerful AI enhanced call analytics to really not only capture real conversations. Allow it. The ability to provide things like real-time contextual feedback and use things like prompts to better understand why things were going well, but more importantly maybe where things weren’t going well.
And what was really powerful in that is that was such a manual process for us before. And not only was it manual. It wasn’t necessarily consistent manager to manager, right? Some managers were better at it. Some managers had more time to invest just depending on the, the size of their teams and the amount of workload that they were working on.
So instead of really waiting for a scheduled reviewer’s, shadow session, reps and managers could get real time guided insights and feedback so that when it came time for the actual coaching, it was very prescriptive. It was really, really, really powerful and it felt more individualized versus, Hey, we’re gonna have an enablement team come in and do a skill development session on, you know, executing a mutual action plan or getting access to key players.
We could actually take that now to the individual level and focus on a skill development that made coaching more specific, more intentional, more timely, and ultimately more impactful for that skill development. Now, there is one thing that we are looking at as well, and we haven’t deployed this yet, but I’m assuming I’m not alone in this.
Which is really, we have a pretty large sales organization all at different parts of their career. Also different managers at different parts of their career. And one of the things we wanted to do to, to drive more time for the managers to actually coach and spend time doing all the things they’re supposed to do, is we’re actually in the process of evaluating some AI role playing tools that use avatars.
I know. That is not unique to us in any way, shape, or form, but when we think kind of along, like what’s happening now and what’s happening over the next two to three months, we’ll be deploying those to really also help the reps have a, a safe place and a consistent place to practice those skills.
RR: Yeah. That’s so awesome to hear. I think, you know, sales coaching is one of those things that PLA teams everywhere, and so hearing that you can find these solutions that make you not only excited but certain in your programs is wonderful. And it really does sound like you’ve put together some very intentional programs to help your team succeed.
And I think the data’s kind of showing that it’s working. We’ve seen that you’ve driven really strong engagement from your GTM teams, such as a 96% recurring usage rate of Highspot. So curious, you know, we’ve talked about the strategy. How are you then driving that adoption? Do you have any best practices you could share?
CS: I think enablement teams each and every day and organizations are always trying to, you know, go through the process of how do I make the information or the programs or the projects or content that we’re taking to market actually be adopted and be used. And you know, I think one of the things that always has resonated with me, and I think about this phrase often, there’s a great enablement leader by the name of Roderick Jefferson, and many years ago, he gave a piece of feedback about the difference between training and enablement. And I’m paraphrasing this, so if anyone who knows this quote better than me, feel free to correct me.
I believe he said, you train animals, you enable humans. And I think one of the things that always resonated with me about that then is if I want to enable someone, I need to get the lens of how they’re executing. And for us, that adoption, that 96% recurred usage in Highspot really started with making Highspot not only the single source of truth, but also putting it in a place where the sellers already live and breathe today from day one.
It was critical for us that not only does every new hire here at Bamboo get trained to rely on Highspot for almost everything and have it not only live within that world, but for things like messaging, playbooks, objection handling, product updates, everything goes through there. But I also think it was more than that.
One of the values that we’ve seen in Highspot is really our ability to have that proactive information fed at the opportunity level in our CRM tool. It allows the reps to get just in time information when they need it, but also when it’s most critical. Not only do we have the ability then to kind of.
Indoctrinate them, so to speak, as a new rep. They’re also getting fed in real time, something that’s actually beneficial to them, and it’s proving its use case time and time again in real time, which has been a huge adoption ability for us. I think another thing. That has been super beneficial is going back to that adoption piece.
We also cross collaborated and cross-functionally with other organizations like product marketing and product that absolutely see the benefit of that’s how their content gets used. So at the end of the day, the proof in the pudding and starting with that why and making it that single source of truth.
We put it exactly where the reps live every single day embedded in our CRM. But when reps saw the tool and the action that it brought in saving time and helping them win that adoption started to follow naturally. And we continue. Every single week we have a reinforcement on content being placed out of there.
It was a new muscle, and like any new muscle, we had to train that muscle. The good news is, is once we train it, we go to maintenance mode. And it’s been a much, much, much, much, much smoother process than when I’ve done this at other, other organizations where we were either under-resourced or underfunded, and we were really kind of rolling things out at a project level versus a programmatic level.
RR: Gotcha. So it’s sort of that you can take a rep to enablement, but you can’t make them drink. You need to prove the value, and you need to be building for them. I think that makes a lot of sense. Thinking a little bit about doing the work, driving the adoption, how do you then measure success? What are the key metrics you track and then now moving into kind of trying to operationalize AI, how are you measuring that as well?
CS: Yeah, very fair question. And I think this is also another thing, you know, this is my experience, been in groups with some really great enablement leaders across the board, and I feel like over the last several years, especially as that kind of transition to more. That value-based selling has become always important, but it’s become critical over the last several years with the introduction of ai, the different economic conditions and things of that nature.
Every sales leader I talk to is really trying to measure the impact that their teams are having on the business and we look at it at a few ways here. I think we look at it from what we call some of our leading and lagging indicators. Specifically, we wanna see some of the early adoption and controls that we have there.
So from a leading indicator perspective. We’re looking very closely right outta the gate. Whenever we launch a new program around things like certification rates, the usage data, early stage conversions, rates, some of that content engagement score, and then what we look at is the direct connection to the outcomes that happen, like stage progression, conversion rates, quota attainment, and sales cycle velocity.
In my four months here, that’s where we’re really starting to drive and we’re starting to see a little bit more of those lagging indicators. As a business, we kind of have a core metric to maintain and also improve those conversion rates. So that was kind of the North Star, what we looked at from working our way backwards where, okay, what gets us to those things?
And that’s where we looked at specific skills programs that we are running and we’re our rep certifying, were our managers certifying? Were they using the content that we created and did we see a correlation between those things and the performance? And we absolutely have, which has been really great for us to correlate a lot of that.
To your second part of that question, as it relates to AI, I think we’re kind of looking at it from a few different ways. We are by no means the experts of AI measurement, but we, we have put some things in place that we’re looking at trying to get better constantly, which first and foremost is. Are we giving the reps more time to do more sales focused activities?
So it, it’s one thing of it to create some time savings, but it’s also another thing to say within that time, did we help you be more intentional? Did we help you be more accurate? Did you use the right content or the right information? Or were you fed that in a way that helped you create a differentiating experience or a consistent experience in that engagement with a prospect or existing customer?
When we can do that for at the rep level, we then want to drive AI driven insights on the backend to really look at how that impact coaching can take place at the conversational and the deal outcomes level. That’s the correlation. We’re kind of looking on that backend. Our ideal state would be able to also look at.
How do we either add more propensity and volume to what our existing AEs are doing? Time savings is great, but what are you doing with that time on the backend, right? Is it, Hey, more time to go, you know, play ping pong down in the break room, which is always a great thing. I’m not saying that’s a bad thing by any stretch of the imagination.
But it does allow it to be more intentional. It does allow us to be more powerful in the capacity of each of our reps. I always have heard a great quote from John Barrows, who I’m sure many people know. And one of the things I’ve heard him say specifically about ai, and I think about this as we measure AI, is really good sellers and really go to organizations that help their sellers.
AI will augment what they do. Anyone stuck kind of in the old way of selling it will replace you in what you do. And I think that’s how we look at, how are we leveraging and augmenting that AI to look at the time savings, but long-term, how do we make it so they’re more intentional, more accurate, and produce some of those more outcomes at the individual level?
And then how does that really embrace the impact coaching conversations on the backend?
RR: Yeah, I think the lucky part of being kind of mired in all of this change is that we’re building our metrics as we’re figuring out what we can reasonably do. And so when you have that philosophy that you led with of Know Your North Star, ask the questions that will help you understand what actually drives there, and fill out those leading and lagging indicators as you’re doing the work.
That’s gonna be a helpful philosophy, and that’s gonna get you through to figuring out those metrics. I’m curious too, as you’ve been looking at these indicators for AI and also just for your broader enablement programs, have you seen any particular business results with Highspot or any wins that you’d like to share? Things that you’re really proud of?
CS: Yeah, I think there’s a few things, and I kind of break these down by kind of what I’d call some of those leading and lagging and I think, you know, some of them directly correlate to, to business outcomes. I think a few things that have really driven up is how our reps and how our team members are meeting customers where they’re at.
But then I would also say on the backend, how has training and coaching improved because of that? And I think that’s a huge, huge, huge win for us. When I kind of look at over the last, you know, four to six months, some of the numbers that pop out I, I kind of. Share with you that I think are relevant? I think one of the really cool things that we have seen is we’ve seen a 91% engagement with our buyers, especially with external shares that’s gone up massively.
I think we tracked something like we’ve had nearly 30,000 views during this window and period of. External content that customers were viewing, but also what they were sharing internally with other parts of their organization. We had no clue what was going on with content when we shared it before. And why does that actually matter?
Because we started to correlate some of the in increase in in buyer engagement, the increase in some of the sales play views, which actually went up over 260% for us, up to 31%. That was so powerful, and I kind of think about that at the just in time level. One of the other things that that really resonated with us is the findability ratio, and from a content management perspective, historically prior to our engagement with Highspot and leveraging the AI, everything that was recorded with that.
One of the major complaints that Bamboo got from a lot of our reps were, oh man, it’s really hard to find things when I need them. That just in time moment sometimes passes, as I mentioned earlier, and even if it takes me 30 minutes to an hour to send a follow up, sometimes I don’t have that. And we look at that findability ratio that we have of a seven.
We saw our click-through rates go up dramatically. I think they went up 32% and the amount of items we had viewed as reps were going through the process of engaging a prospect in real time went up 14%. Why does all of that matter? Because I think as we looked at, okay, we’re giving you the right. Content and clearly it’s helping it create engagement with our prospects and customers.
Does that, what does that engagement lead to on the backend? And one of the biggest things we found across certification and consistency across that was when you kinda look at some of the certifications we launched with AI across the board, and I’m focusing just in a Q1 of this year, we had two really big certifications.
That were across the entire revenue organization, one of them being a skills related focus, and one of them being a specific platform product related focus. We certified 300 users in one, over 300 users in another one, and with the manual time that that would’ve had taken prior, we were able to save almost 220 hours from an enablement.
Side with the AI, with only these two certifications. So scalability became a really, really important thing from an operational side for our enablement team and our managers who are typically having to do this at a very, very manual level. So why does all of that matter as a business? What we’ve correlated is our reps that are leveraging this in executing this are performing at about a 25 to 30% improvement level across their peers that maybe haven’t adopted this yet.
So some really nice leading and lagging indicators of the power of AI and the power of what these tools can bring to the table. Are we perfect at it? By no stretch of the imagination, we still have some laggards that we’re trying to bring up, but we have seen some of those economies of scale grow with the reps that really have embraced this, and even some of the others that kind of, some laggards initially still have some of those, but the proof has been in the pudding there for us and, and it’s been a fantastic investment.
RR: Those are I to begin. Incredible wins, great numbers. 30,000 views is incredible. I love the way you kind of told that story of how your wins compound. You know, you start with content, you make things accessible, all of a sudden your reps can use it, and now buyer engagement improves and then it just continues to grow and you have this feedback loop of continuous improvement To your point earlier.
Many compliments. I know, as you said, you’re always moving, you’re always improving, you’re always growing. So in that spirit of continuous improvement, curious if you could talk to me a little bit about maybe what’s in the future, what is that potential long-term value of embracing AI for Bamboo, and how are you gonna continue doing so down the line?
CS: Yeah, so I, I think for us, the intentionality there is really around scalability. It comes down to that one thing, the long-term value for us is scalability. That’s a little bit general in a response, but let me kind of give some context to that as to why scalability is important, right? AI is so fantastic.
It allows our enablement team to support more reps, do it more personally without having to necessarily grow linear head count. And I think that’s a challenge. We’ve been, you know, our executive team, very forward thinking, thinks very much about those things and is very intentional about how we’re leveraging that to not only scale what we do, but do so in a very intentional and respectful and responsible way. Really when we think about what’s happening, so when I talk about scalability as well, it also is looking at it at the rep level and giving our reps access to the personalization at an individual contributor level for career development and coaching and guidance, but doing it at scale so we can consistently up level the team with really.
Without burning out our frontline managers, our enablement resources, because the two most precious commodities that we view here at BambooHR are clearly our customers, but also our people. Those two resources are so vital and so important, so when we think about our. AI strategy and, and an enablement.
It’s how do we create scalability with some of the unknowns that frankly exist today. Our organization has moved very quickly. We’ve kind of gone through a renaissance of our own, and there’s been a lot of changes, even just at the operational level here. Part of the way we look and are very intentional for scalability with AI is.
What does AI allow us? Not only do today, but what’s coming down the road that allows us to invest in changes that we don’t even know about yet? And how do we continue to do that to scale human application across the AI intentional application? And that’s kind of how we’re looking at that.
RR: I love that. I think it’s, you know, a great philosophy and I think it’s something that a lot of people are kind of gonna be embracing in the coming days.
Just one last question for you. Speaking of that, you know, philosophies that other people can lean on to close, if you could give us one, maybe two pieces of advice for other enablement leaders who are looking to improve sales productivity with AI, what would that be?
CS: Yeah, this is a, I feel like a golden ticket question that I think everyone’s trying to solve for.
I think for me is, I think everyone has an AI initiative that I speak with. I, I, I doubt there’s any organization that isn’t looking at how to do that. But what I would say is don’t treat it as necessarily a separate initiative. I, I think about how do you embed it to an earlier comment to kind of bookend the, the conversation a little bit is it’s not necessarily, and, and to your point about.
Changing the intended outcome as much as how you do it. So embedding it into your sales process, embedding it into your organizational processes. One of the things that was really helpful for us is we kind of took the visual representation of what an enablement team member does, but also if our customer, our internal resources like our sellers.
What does the journey look like for them as they start their day, they start their interactions, they prepare, they engage. And then kind of that post-call, post interaction, what does that look like? And what we said is let’s map that out. And then we started small with one or two use cases that were kind of low hanging fruit that directly supported the productivity like.
Surfacing the right content during calls or providing real call time feedback. And then what we really wanted to do is we really wanted to listen and we wanted to map out what did we think we could do now? What did we want the like ideal state to look like? And then we sat down and we asked our reps and we said.
How are you performing along this? We have data that shows us how we think you’re performing, but what’s working, but more importantly, what’s not working and how do we make those shifts so that we can make sure that we’re actually making a difference? And I think the big key for us was it, we didn’t think about it and we kind of took a step back almost as like a tool roll out.
And what we really wanted to make this about was changing behavior. It wasn’t necessarily about, oh, here’s this new AI tool. Go use it. Like we may have rolled out. CRM training. In the past it was what is the behavior change that is associated with this? And really that’s the best thing that we could do is make AI feel intuitive, make it indispensable, make it, build it into how your reps are working so that it becomes.
Just like, almost like breathing. You don’t think about it, but you definitely feel it if it’s not there. And that’s kind of one of the things I always talk about is how do you embed AI, align it with that AI journey and how they’re engaging with the customer in a day in the life. And as you embed it in there, it becomes part of what they do and then they start to feel it when it’s not there.
But that would be, that would be my biggest piece of feedback for anyone that’s looking at it, is don’t treat it as a separate initiative, embed it into everything that you do. Map it against how you expect your internal teams to work and you start to find the adoption follows.
RR: Awesome. Well, this has been so wonderful, Chris, so insightful, and I think this is kind of the insights that people are really looking for.
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 enablement success with Highspot.
