Learning in the flow of work leads to a more engaged and more confident workspace. According to research from LinkedIn, those who spend time learning at work are 39% more likely to feel productive and successful. So how can you equip, train, and coach your teams without interrupting productivity?
Shawnna Sumaoang: Hi, and welcome to the Win Win Podcast. I am your host, Shawnna Sumaoang. Join us as we dive into changing trends in the workplace and how to navigate them successfully.
Here to discuss this topic is Chris Herter, the director of sales enablement at Paycor. Thank you for joining us, Chris. I’d love for you to tell us about yourself, your background, and your role.
Chris Herter: I’m happy to be here, thanks for inviting me. My background is pretty diverse, I didn’t grow up in sales enablement. The majority of my career has been in sales as a seller and a leader of small market up to enterprise, [selling] hardware, software, and managed services. After I was done with a quota-carrying role, I transitioned more into organizational support where I spent some time in leadership development and even in marketing. But for the last six and a half years I’ve been leading the sales enablement and training team here at Paycor.
SS: We’re excited that you’re here. And now that you are in enablement, why do you think that enablement From your perspective, is a strategic imperative for businesses today, and how does having a unified enablement platform really help you to maximize the impact of your strategy?
CH: I feel – and I think this is probably a popular opinion – but without enablement, there’s no dot connection between the company’s overall strategy and sales execution. You can build a best-in-class training program, which we do, and you can have a robust tech stack, which we do, but even if you provide all of those resources, you need enablement to really provide the application to the execution.
It’s not just setting those things out there on a shelf and expecting the execution to happen. We’ve got to make sure that there is that application piece of the training that ties back to the strategy. And I think one of the things that often gets overlooked that it’s worth talking about here is we have to create a better seller experience.
So we’re competing for talent, just like we’re competing against our competitors for market share. So enable and enablement, if we can help streamline processes. Refine messaging, find ways to reduce drag, and really help sellers see those more wins in revenue, we’re going to see less seller attrition. So improving that seller experience and making their lives easier and more efficient, is very important to us.
And so if we tie that back to the unified platform, we can enable in real-time. And for us, that means more pushing and less pulling. It gives us the opportunity to have more speed to action and we can do it at scale. And one of the things I think about too, is we just want to reduce that seller drag. So we’re becoming too large of an organization now to have personalized training and do a lot of in-person events or one-to-one coaching.
Our platform really makes it easier to communicate and deliver our key sales plays that align to our top initiatives. And it gives us a place to, in a space to house all of those things where the sellers can spend less time looking and finding for the sales plays and the tools and collaterals and spend more time hunting and winning.
And I think some companies just have an intranet where these things are a repository and sellers have to find and look and try to utilize [it]. But with a unified platform, we can go to one place and one source of truth for all of the things that we need to be effective.
SS: I love that. And I’ve tried the intranet things. They don’t work quite as well, especially for sellers. In the past, what challenges have you faced when trying to build an enablement strategy that engaged your reps? And how did you overcome those challenges?
CH: There were plenty, how long is the interview? We could spend a lot of time here, but if I had to boil it down to a few, I would say we were relying on a lot of inefficient ways to communicate the strategy.
What are we doing? Why are we doing it? And what are we going to achieve? From there, we didn’t have the best way to build a playbook to make those things happen. We were using emails, PowerPoint decks, “the intranet”, if you will, that company repository that I mentioned, and those things were not efficient and not effective.
So our sellers just didn’t use it. And what you got was a lot of disparity, a lot of rogues, a lot of sellers, trying through trial and error and so to get engagement, we had to do a lot of workshops and human interaction, a lot of face-to-face, and so it just becomes harder to do that when our Salesforce growth.
Is far outpacing our sales enablement growth. We couldn’t do that one to one. And so we had to take that a step further and then through the platform, we weren’t able to measure efficacy or tie our efforts to our results. We had no line of sight to what was working. What content was working, what contents were even being used, and I wouldn’t say we fully overcame those challenges, but we’ve made a ton of progress, and it’s just happening through consistency and staying the course with our strategy and not deviating it.
If we see a dip in usage, or we see a dip in content consumption, we don’t panic. We just know that our strategy is working. We might have to put our foot on the gas in different ways. But I think for us, we really tried to think about simplification, and with Highspot as our jumping-off point, we’ve really embraced that simplification of what to know, what to do, what to say, and what to show.
We started with that and we’re sticking with it. And so our sales reps get used to that and we don’t throw them any zingers. They know that this is the play. This is the initiative. This is the stack of mail that we’re going after. And when they get used to that enablement sort of output, it becomes easier for them to engage in it.
And then, more importantly, It becomes easier for them to execute on it and drive results through it. So I would say just the consistency of having one way to deliver and one source of truth for our reps to go to has been helpful for us.
SS: You guys are really driving that consistent execution across your entire sales team. It’s amazing.
CH: Thank you.
SS: Now, prior to Highspot, I believe you all leveraged a different platform and even had some siloed solutions for both equipping and training your teams. What was the impetus that drove you all to make a change to unify your approach?
CH: I would say, me taking on the role and having more line of sight to this. I can’t take all the credit, but everything was messy and we didn’t know what we didn’t know. Our sales enablement platform, as I mentioned earlier, was more of a content repository and it eventually just became a dumping ground for everything that we created internally and externally.
And while we had the best intentions, it just wasn’t being used, it wasn’t being used properly, and it wasn’t being used effectively. And from an instructional sales training and company learning standpoint, we had even more platforms. So we sell an LMS platform. So we have our homegrown system that we sell.
Through the solution that we were trying to use. And we had another bolted-on solution for new hire training. And then we had a sales enablement platform over to the side. So whenever I was taking on this role, I’m looking around wow, we’ve got three to four places that we’re sending our sellers, sending our reps.
And none of those places are talking to each other, nothing is updated simultaneously. At the end of the day, we weren’t accomplishing what our ultimate goal was, which was making our sellers better and making them more efficient. In fact, I feel like whenever we looked at this, we started to study it and take a closer look.
I feel like what we noticed that we were creating unnecessary barriers for them to have to overcome just to do their job, just by sending them to multiple places. And I think that ties in really closely with our value prop at Paycor, it’s a unified solution, one single pane of glass. And with Highspot it’s, a similar approach, a similar value prop for how we use it too.
SS: Now, I get this question a lot, especially when I’m talking to enablement practitioners in the industry, and they really want advice on gaining buy in from leadership. How did you go about getting buy-in from leadership for making this change?
CH: I wanted to look for other internal champions. I knew that I would have a tough hill to climb if I was going to go about this on my own and try to find a budget – and budget isn’t the biggest issue, most of the time it’s change management.
So I partnered with Rachel Neely, who is our manager of communications, and she was struggling from a content governance perspective. As I mentioned earlier, It was a repository. It was a dumping ground. Once I started partnering with her she was saying, I really need a tool that’s going to help me with communication, it’s going to help me with content governance.
And so it’s funny, I’m looking for something that’s going to help enable our sellers and, have a learning platform. We combined our efforts and we both knew about Highspot, but we had our own initiatives, and then, as we started to work closer together and combined our efforts, we were able to tie those efficiency gains together. We’re able to look at different business results that we could achieve by partnering together, improving seller experience, and removing multiple platforms.
That was when it was all starting to come together. But, even after that, there was still some hesitancy from a prioritization standpoint. I think everybody said, Hey, this is great, it’s nice to have, but I think what really sealed the deal for us and where I saw some eyebrows raised and I started to see some internal buy-in was whenever I saw how Highspot, your sales team, was using digital rooms to sell to us. And that was a game changer because we were able to say, “Wow, this is how Highspot is using their own platform. This is how they’re drinking their own champagne.” And we were very impressed by that. And it was really talking to your sales team and your sales leaders and connecting them with our sales leaders to find out how they were using it.
That was really how we were starting to get more people to buy in and more people to see, “Wow, this is not just a learning management system, this is not just a content repository, there’s so much that we can do from a communication perspective, enablement perspective, learning perspective, sales perspective.”
And as we got that internal buy-in. We could bring those use cases, to my boss and my boss’s boss. And when we put it in front of them, it became a no-brainer. Then it became, all right, how do we make this happen? Instead of this isn’t something that is nice to have, it became something that is really a priority for us now. We need to get this up and running. Let’s get this ready for our kickoff.
SS: That is amazing advice for our audience. This is how you make enablement must-have, fantastic.
CH: I think what really did it for me to take that a step further is our sales rep was really good at her job. And I was always being asked to provide more things, case studies, different pricing just all, technical information.
And she was able to say, Hey, we’re supposed to sign tomorrow. I know that your procurement team isn’t even looking at the contract yet. Or, this person that was supposed to be a champion hasn’t opened up the proposal. Holy cow, that insight, we don’t have that today. We need those types of things.
And that was really, whenever I started to position This is how they’re using it. Look at what they’re gaining. Look at what this could do from a forecasting standpoint and an engagement of your buyer standpoint and really see how you all utilized it and see what we could potentially replicate. That was a big deal.
SS: I appreciate it and I will have to pass those kudos along to the team. Now, we started to connect last Fall. You actually led a session at Highspot’s user conference Spark ‘23, I hope you’re coming to Spark ‘24 in October.
CH: Oh, for sure.
SS: Yay, fantastic, that is the right answer. Now you talked about the importance of taking a more programmatic approach to your sales processes versus a suggestive one. What did that shift look like and how are you leveraging Highspot to help?
CH: Yeah, when I say suggestive, a lot of times from enablement, we were putting things out and just leaving and expecting it to be consumed and executed on. And we had pockets of success, but it wasn’t working and I mentioned earlier that because of our growth, we had to build an enablement program that was scalable, which meant that we had to make it easy.
We had to make it self-service. And in some aspects where we really had to lean in was building programs that can be leader-led. So it really became, let’s enable the leaders to enable. We would not be able to do that if we didn’t have a platform to deliver those things. So part of that was to enable those leaders to enable.
The second part was metric-driven. And when we’re able to showcase best practices. That leads to an increase in measurable results. Now things are starting to cook, right? We’re making it easier for you to get to the content. We can prove that these plays and the content consumption is leading to measurable results.
Now we’re getting more buy-in. Not only that, but whenever we go from less suggestive and more programmatic, it’s great to find the wins and showcase the wins, but I think sales wants more proof that it isn’t just theoretical. So we really didn’t stop there. It wasn’t enough in some cases, and I’m sure every organization goes through this, where sellers want to go rogue.
They don’t want to follow the playbook, they don’t want to use the resources or run the play. While we had success showing the positivity of the gains, we started to take a different approach and really look at this, from the inverse and what’s happening with our low performers and strange coincidence, right?
When we look at our low performers, we’re seeing a lot of common themes. There’s a lack of engagement in Highspot, whether we’re looking at the Play Scorecards or we’re looking at the consumption of the training programs. Pitches, Digital Room engagement, you name it, it became glaringly obvious that the low performers were just opting out.
So I would say what Highspot helped us do was give us on the enablement team and the RevOps team line of sight to what was working. And then also line-of-sight to who’s not involved. And so it went from more or less of that opting out to saying, Hey, you’re someone who’s a low performer.
And you are not utilizing the plays and the tools that we’re giving you. You’re showing a lack of will. So now we put that in the leader’s hands and that empowers them. Now it’s empowering them to use the data. It has become a partnership now and running things more programmatically. It isn’t, “Hey, training and enablement is making us do this.”
It’s training enablement is empowering our leaders to build winning teams. Training enablement is giving our leaders the tools that they can become self-sufficient. In building and running programs, they’ve got line-of-sight to the metrics on the wins. But more importantly, if we’ve got low performers, it gives us a diagnostic avenue to find out why they’re low performing.
We can’t, I said this at Spark, we can’t just say go win the game. We’ve got to find out, why we’re not getting on base, why we’re not getting runners across the plate. And if a leader can look in and Obviously, we’ve got the KPIs that we measure from a performance standpoint, but it’s those other things that aren’t so obvious.
It’s looking at, okay, are they even going into the tool? Are they even coming into work and turning on the thing that gives them the tools and resources and the plays that they should be doing every day? I feel like all of those things combined, there’s no silver bullet, there’s no magic bullet, it’s a little bit of empowering the leaders and then giving them wide a sight to what’s winning and what’s not winning.
SS: That’s a fantastic approach. And since you guys have made this shift to a more programmatic, unified approach to your enablement strategy, what are some of the key business outcomes that you’ve achieved and do you have any wins you can share with us?
CH: For sure. I think I’m probably the president of the digital room fan club. I told you how it worked on me as a buyer and I take that same energy and that same passion whenever we’re pushing this with our sellers. And I think our biggest achievements are around the digital rooms. We’ve pushed this so hard and we’ve, we continue to train on it. We know in enablement and training, this isn’t a one-and-done.
We’ve built it into our processes, and one of the things that we’ve done is we are just trying to make that so easy for the reps that there’s no excuse to not use it. And so we’re doing the work on the front end to create the templates, a light, medium, and heavy version.
And what we’re seeing, is not only is the usage going up, but again, we’re partnering with the leaders. We’re training them to give them line of sight to not just the quantity of pitches and digital rooms, but we’re also helping coach them on how they can coach on the quality. So they’re seeing what’s leaving the station if you will.
And now light bulbs are going off. They’re like, Holy cow. I can see what my reps are sending. I can see that they’re missing steps. Wow. I can see that we won this deal and I can tie it back to which digital room was used. Now I can replicate that across my sales team. And so because of that, we are able to look at who are our highest digital room adopters.
We’re able to aggregate that information and say, what are the correlations to the data? And what we’re seeing, and it’s no surprise is those highest adopters of the digital rooms. We see a huge uptick in first-time appointments. Leading to discoveries and analysis and for, our audience that knows anything about digital rooms, it’s probably no surprise to them.
What an amazing buying experience you’re creating, on the front end, and the back end, post-first-time appointment, you’ve got a robust follow-up where everything is right there. And you can track the engagement. If you’ve got a diverse buying committee and you don’t have open communications with them I can see who’s engaging in what, which, what are they engaging in, and why.
Now I can go have specific follow-ups with them, and it allows for more specificity and less vagueness with the follow-up. And we’re seeing, really positive momentum in that post-first-time appointment digital room that we said, “Hey, why not do this pre-first-time appointment? What, there’s no rule that says we can’t push out a light version of a digital room before we even have that sit down face to face with them.
And what I mean by that is once we get that meeting scheduled, we’re training our reps now to push over that light version that is, Hey, here’s a little bit about paycore, maybe here’s a client testimonial and product overview demonstration. That’s in front of them before we ever meet. Now, think about that, pause there for a second and think.
I scheduled the meeting, but there was a challenge there. I’m acting on that challenge. And this prospect has agreed to meet with me. I’ve put something in front of them. That’s tangible. That allows me to see what they’re engaging in. I take all of that. And I show up at that first time meeting. I don’t have to guess anymore about where this conversation is going to go.
I just really look at what the data is telling me. I look to see what they’re looking at, what they’re clicking into, and where their interests are. And that’s where I’m going to take the conversation. So instead of sitting back and guessing. I’m going in with insights that I didn’t have before. So maybe more than what you were looking for there, but that’s again, the president of the Digital Room fan club. And that’s where we’re, we’re doubling down there.
SS: We are happy to award you that title, Chris. That is amazing how you’ve gotten the entire team rallied around Digital Rooms. Fantastic work.
CH: Thank you.
SS: You alluded to this a little bit, but you mentioned coaching. So in addition to effectively equipping and training your teams, I’d love to understand from your perspective, what is the value of coaching for reps in the current sales landscape and how are you planning to evolve your coaching strategy?
CH: Yeah. It’s an absolute imperative for all the reasons I mentioned earlier, especially, enabling at scale and enabling our leaders. And again, I’m biased, but I feel like we’ve got a best-in-class training and enablement program. We do, but we need to equip our frontline leaders to coach in the moment, but we can’t be there.
And, while we’ve got conversational intelligence and things like that, we’ve got to make sure that we’re equipping our leaders to coach. There are some things that I call low-touch, and high-impact. Some low-touch, high-impact things that we’re doing are, leveraging video submissions.
That’s easy. If I want to, role-play the value prop, I don’t have to be in front of my leader. I can submit the video submission, and let the AI give me some tips on how to do it. It points the leaders to the right place. So those are some of the easy things, but what we’re starting to dip our toes into and, credit to Highspot for giving us this idea, we built the playbooks, and we’ve got the sales kits, but what we’re trying to do now is build that coaching playbook for the plays. So we’re running one Play for the sellers while we’re running a Play for the leaders simultaneously.
So it’s building a coaching playbook to say, these are the coaching moments. These are the things to look for. This is what your seller is going after. So Ask these questions. And so if I’m logging in as a leader and a rep is logging in as a rep, they might see different things or we’re going to push something different to the leader that, that gives them line-of-sight to what their reps should be doing. And then it gives them line-of-sight to their coaching moments, and that’s been effective. We’ve again just really dipped our toes in that, but we’re already seeing the efficacy there and we’re starting, I mentioned this a second ago, but we’re starting to do more with conversational intelligence, and I see a ton of opportunity here. We’re getting that off the ground now, but for a frontline leader to really equate it to like NFL and able to go back and look at the play tape, look at the game tape, and see, “Hey, what did we do wrong here?” “Team, what can we learn from this?”
“Hey, what are our best sellers doing to convert a first-time appointment into an analysis?” We’re able to show what we’re doing right and coach to what we’re doing wrong. And then for me, from a training perspective, I get to index all of those things and I don’t have to role-play scenarios anymore. We can watch the game tape and learn from that. A lot is going on right now. We’re really, I think we’re. We’re coming into the end of our fiscal year where we’re starting to experiment and learn things, but as we ramp up into FY ‘25 in July, I think we’re going to have a lot of these experiments already carved out to where we’re going to be running, hit the ground running where we’ve experimented.
We know what works from conversational intelligence. We know what works from the leader playbook and be able to execute on that as soon as we start the fiscal year.
SS: Amazing. Another area I know a lot of companies are experimenting in right now is around artificial intelligence or AI. And I know that you’ve been driving an evolution in your enablement program, and that is by leveraging AI. I think Paycor was one of the early adopters of some of Highspot’s AI features. Can you tell us about the ways you’re leveraging AI and its impact so far?
CH: Yeah, I’ll not necessarily enablement, but back to how we got started with Highspot, that former content repository, if you will.
One of the things that we’re trying to do is empower our content owners and have them be, the stewards of their content. They’re the SMEs, they’re the stakeholders. And so we want to empower them. And so that content description writer that’s been a huge efficiency gain and there’s a wow factor to it as well.
I think our content owners that maybe aren’t as versed in enablement technology. That excited them and that got them to really, say, Oh, this isn’t so hard to upload content. And now the descriptor is happening for me. That makes that part of it easier. But a couple of other things that have been huge efficiency gains, is the email creation and the Digital Rooms reps are just so enamored with that.
We obviously want them to add the personalization and check for accuracy, but if I can build a digital room and I have multiple pieces of content in there, and then the AI is helping me make sense of that and put it in a readable way and make it great for my buyer.
Sellers are eating that up and it makes them less apprehensive to use that solution. So that’s been a big one, but I think for me it’s probably, maybe one of the less sexier ones, but for me, my favorite has been the Copilot for finding the content or for finding the answers that the reps meet, just in the search bar, instead of typing what I might be looking for, I’m typing a question and I’m getting an answer back.
And not only am I getting an answer back, I’m getting an answer that’s also pointing me to the content that I might need. And I am just I’m a huge, believer in looking for easier. And so I’m a big proponent of that, and one of the ways that we’re fostering AI adoption throughout the company is we have an internal AI corner where we’re looking for wins and we’re looking for, “Hey, what are you doing? Share it with everyone else. Let’s replicate it.”
And it’s been neat to see that Highspot has been one of our huge champions for those AI gains, not just in the Digital Rooms and the email creation, but also in adopting Meeting Intelligence. And that’s one that I want to get off the ground a little bit more.
Candidly, there’s a lot of that out there, with Zoom and, there’s Teams, I don’t want to force anything, but I am strongly encouraging our reps to utilize the Meeting Intelligence because there’s so much potential here. I didn’t get a chance to catch the the spring webcast live today, but I got a feeling that there’s probably talk of Meeting Intelligence, being able to build that into your Digital Rooms.
And so from a seller standpoint, if I’m having a meeting with you, taking those insights and allowing that to flow in the Digital Room, that’s going to be a game changer for our reps and not only our reps, and a game changer for our buyers as well. So we’re embracing AI.
Highspot has been making it easy for us with just some of the wow factors and how easy it is. And I was mentioning this on an internal AI tiger team call yesterday, where I feel like a lot of our sellers are utilizing AI in Highspot, and they don’t even know it. And it’s not necessary for us to broadcast that this is AI.
I think what we’re trying to do is beat the drum. What efficiency are you gaining? How easy has this made for you? And so while there may be fear and apprehension of AI, we’re really focusing on: let’s make your life easier, let’s make your job easier, let’s make everything more efficient for you.
SS: Chris, you guys must be doing something right. I think you guys are doing a whole lot of things as you’ve been evolving your enablement strategy, and the numbers speak for themselves. You guys are driving an impressive 95% recurring usage rate amongst your reps, which is amazing.
I think our audience would love to understand, do you have any best practices for engaging reps in your enablement programs, maybe even, as things are shifting or changing within an organization?
CH: First, thank you. That’s nice to hear. Honestly, I’d have to give a lot of credit to our sales communication team. They’ve helped us on the enablement side remain consistent with Highspot. They’ve done such an amazing job with spot management and content governance that we’ve got a, we’ve got a nice clean house.
And, having that clean house, people want to go back to the clean house. They want to go to the rooms where things are easy to find and use inside of those rooms. And so it starts with the help that we’re getting from our sales comms team. I certainly want to give them credit.
But additionally, we make it a habit to, in terms of the best practice we’re consistent. And what I mean by that is pushing our sales communications out, we use Highspot for that. And so even if we push something out from an email standpoint or a weekly newsletter, we may just give the headline and it’s, “Hey, for more details, click here.”
So we drive everybody back to Highspot. We don’t put the juicy meaty stuff out in an email, or push out any other platform. We’ll push out the headline, but people have to come back to Highspot to get the details. So we’re creating that environment of that’s our jumping off point for everything.
And I think, if I was to say one thing about it, it’s just remain consistent and if you remain consistent, you’re going to find that you’re creating a behavior without forcing the behavior people are going to say, Oh, I had to click here from the weekly newsletter. Maybe I’ll just start there.
Maybe instead of going back to the newsletter and looking for what I needed, I know it’s going to drive me to Highspot anyway, I’ll just start at Highspot. And additionally, we’ve made the homepage so user-friendly, and we keep it refreshed, and we keep it updated with the top initiatives and the top news.
You’re not going to find something from January that’s old and outdated, and you’re not going to find anything from last fiscal year. When you open up the homepage, it’s the things that we’re talking about from the company strategy level, and it’s our top initiatives. It’s right there when you log in.
So that’s made it very easy, the consistency. And again, I use the phrase clean house, but I think your audience will know what I mean by that. If I’m coming into that clean house, I’m just going to keep coming back to it because it’s easy for me to get around and find the things that I need.
SS: I can definitely relate to that. Last question for you, Chris. What goals do you have for PayCorps in the year ahead? And how do you plan to continue to partner with Highspot to help achieve these?
CH: Yeah. So we’re continuing to grow our sales force. We’re fortunate at Paycor that we’re seeing some great growth from market share and revenue and all of the things that you want to measure.
So we’re growing our sales force as well. My north star for me and my team is ensuring first-year seller success. When I wake up in the morning that’s the first thing I think about. When I go to bed at night I think about it as well. So what that means is efficient and effective onboarding and training.
We built a really great foundation that’s got measurable results, it’s been proven out. And so what that allows us to do is keep running those programs that we built with Highspot. We run it with our new hires, we run it with our first-year sellers, and what I think is really neat about first-year sellers and Highspot is there’s a unique advantage that we’re going to take advantage of, which is we don’t have to worry about change management.
They’re coming in and on day one, they’re Highspot natives, if you will. They’re using Highspot and we’re building that into the training DNA. And so if we think about ensuring first-year seller success, and we know that we’ve got proven results using Highspot’s Plays in sales kits and Digital Rooms, we’re training on that from day one.
And so our reps are coming in. We don’t have to, get out of bad habits. We don’t have to really change. “Hey, this is the way I used to always do things.” We can train them on those proven methods and the proven platform that’s been delivering results from our tenured sales folks. So we’re really trying to build the sales kits, build the Digital Rooms, build Meeting Intelligence into their DNA from their first day.
SS: Chris, thank you so much for spending your day with us. I really appreciate the time.
CH: You’re welcome. Thank you. It’s a pleasure.
SS: 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 enablement success with Highspot.
