Episode 80: Building Rep Confidence in a Digital Sales World


Shawnna Sumaoang
Shawnna Sumaoang
Vice President, Marketing -Community, Highspot
Cara Holt
Cara Holt
Director, Sales Enablement, Learning A-Z
Podcast Transcript

A study conducted by Gartner found 62% of sellers who lost a virtual deal believed it would have been won if conducted in person. So how can you ensure rep confidence in today’s digital sales landscape?

Shawnna Sumaoang:
Hi, and welcome to the Win Win Podcast. I’m 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 Cara Holt, the director of sales enablement at Learning A-Z. Thank you for joining us, Cara, I’d love for you to tell us about yourself, your background, and your role. 

Cara Holt:
I have been in education for 20-plus years, which is scary to say in some form. So I started as a kindergarten teacher and then quickly started leading teams around my third year. I was a curriculum leader, then an instructional coach, and then I was eventually assistant principal before I stepped out. I came into the world of ed tech not really knowing what it was, but I knew that professional learning and training was definitely a passion of mine.

And so I went into training teachers first. And then because of where I was and the product that I was selling or representing, I realized that our sales team didn’t know how to position something. And so that’s how I say I accidentally fell into sales enablement. It really wasn’t like a thing or a term that I’d heard before.

And so that was about five years ago now. And so started working with sales teams, started building Materials for them, job aids, training materials, and then really started building certification courses. And what does that mean? And what does training look like? And so training just exploded from there.

Built my way up into the enablement space – I lead an amazing team here at Learning A to Z. We all collaborate cross-functionally. Sales enablement is a big cross-functional collaborator. And so we all have those different functions and we lead an amazing sales team here that helps educators. That’s really what our goal is, just to provide them with the materials and resources that really make their life easier.

SS: As someone with two elementary school children, I have to say, I think you’re a saint for all that you have done in your earlier career. And I love that path that you followed from your career standpoint to lead you to enablement, that is amazing. And it aligns with something that I had seen on your LinkedIn profile because you shared that your passion is sales empowerment. How does this influence your approach to your enablement strategy?

CH: Yeah, so it’s so funny because the term sales empowerer really came from when I got here to Learning A-Z. They had sales enablement before, but really it was sales ops. I had to work to really redefine who we were. One of the things that I did when I was introducing myself to my reps was I would say, “I’m really here to help empower you to do your job, whether that means tools, whether that means training, or certifications, all of those things, that’s what I’m here to do.”

One of my reps spoke up and she was like, “So really what you’re saying is you’re a sales empowerer.” Yes, that’s exactly what I am. And so we just took that and read with it, I was like, that’s amazing. That’s who I want to be. I don’t want to be sales enablement, now I want to be a sales empowerer and I really want to empower them to feel confident. Like our solution – we know that our solution is there to help students and teachers and I want them to be able to position that and be able to speak to that and feel really comfortable when they’re in front of our customers, that really buyer-centric lens.

That’s really what I say, that goes back to that cross-functionality. We work with all the different teams. We’re really here to help empower our reps. And what does that mean? And it’s tools like Highspot that help do that. 

SS: On the note around enablement platforms, before implementing Highspot, you noted that 80% of your reps really struggled to locate content when they needed it. What impact did that have on your sales team’s confidence?

CH: When I came to Learning A-Z it was really important to me to not come in like a wrecking ball. They had an enablement function but we knew we were doing things differently. And so I started performing a gap analysis, really what were the areas that were missing and how could I come in and help to solve problems for them and really empower them in all those places.

And one of the places that really stuck out to me at the beginning was that 80% of my reps didn’t have confidence in finding the material. We had a platform that was really like digital asset management – there was no real structure, there were no analytics behind it, there were no Digital Sales Rooms.

So they were really, pulling materials. One of our head of sales had pulled an iteration of a playbook that was seven iterations old, and that is not a good look. And what are they printing? What are they sharing? And I know as an administrator, or past administrator, when you hand me papers in this digital world, they’re going to get lost on my desk. I’m not going to be able to go back and look at them or find them. And then you have no idea if I really reviewed it, like what that meant for me. And so I had come from a company that had Highspot and I had some knowledge, but the thing is, I didn’t want to come in saying Highspot is the solution, right? You don’t know. You’re at a new place, you want to give them the time. I did my due diligence and I spent time, speaking to their many different platforms that have that similar function. One of our sister companies uses Highspot as well and so at the end of the day that’s who’s showing through as the right solution for us as well.

SS: I love that. So I know that that analysis you did was definitely part of the impetus for deciding to invest in an enablement platform, and I know that you helped lead the evaluation for the right platform. As you said, you wanted to make sure it was the right fit for the organization that you’re at currently. So what made you ultimately decide to partner with Highspot again? 

CH: I spoke to lots of different platforms and people – great people – and met great solutions along the way, just not maybe the right solution for us. The thing that really stood out is Highspot has amazing people, they really do. Going back to, these are people that are going to partner with you and stick with you through your implementation journey. And I had seen that support before. And so I knew I had that to count on. Also, Highspot’s a leader in their field, really it’s the top. And when I was thinking of what platform are we going to get, that was really important to me that we had an innovative platform that was going to take our feedback and really make those changes to the best benefit of their customers.

I knew it was user-friendly. That was something that was really important to me because our team was going to be building Highspot from scratch, and doing the content mitigation from our other platforms. So all of those pieces, taking all of those pieces into consideration, Highspot just kept coming up to the top for me, and that was something that I was working with our head of sales at the time, our senior vice president, now the president of our company.

He was in it with me, and we were going to all these different demos and he had one in his mind that he really wanted. And so it was through that I was even able to help him change his mind and see the benefits that Highspot could bring to our table.

SS: Since you launched last November, you have already seen some amazing results – you guys are driving 93% recurring usage. Can you tell us about some of the impact that this has had on sales confidence now?

CH: So we haven’t relaunched our survey yet, we wanted to give time for implementation.

However, the one thing that we noticed right off the bat is when we came to our all sales meetings and people were sharing content, or product marketing was sharing. My team had a back channel joke where it was like Highspot, Highspot, Highspot – every time they said it, we’d put like a cheer in our chat.

We just knew that they were loving it, all teams were loving it and they were creating different things. And it’s been fun to even see how marketing has created some plays for different campaigns and different pieces that we’ve been able to take and have big wins for.

So being able to see our sales reps are now taking the ownership of leading some of our trainings of things that they’ve learned and sharing best practices, and really seeing that grow has been a huge win for us. And just hearing, like I said, every meeting with “Highspot, Highspot, Highspot”, “Make sure you go here, you’ve done this”, we have a place where they can share their wins – and that’s been a lot of their wins is being able to share a Pitch or being able to share a Digital Sales Room. And so hearing that and knowing okay, we’ve made an impact in this space, has been really rewarding for our team. 

SS: Now, as important as it is to have a single source of truth for your reps, it’s also important that you pair that with a really robust governance strategy. How are you focusing on improving content governance and how is that also helping to drive sales confidence?

CH: It’s still something that I’m really trying to work on, it’s still one of our grow areas because when we initially mitigated from our first platform, we just took everything over. And so now we’re sitting here and that’s the one number I would like to see come up is that content governance because now we’re able to use the analytics that we’re getting from sales to feel like, what are they actually using, what things are just sitting here and not being utilized? We have made a beautiful platform where everything is really nicely organized and they can go to specific Spots for each one of our products because we have a really robust product portfolio. Everything is organized and there for them, and I think that has impacted their confidence in a positive way. But now we can use those analytics, we launched in November, we have those months behind us. So now we can actually start looking at what’s being utilized, how it’s being utilized, what’s winning.

And I report that out to senior leadership on a monthly basis. What is our top content? What are they using? And how does that affect our win rates? And being able to see that has an impact on both marketing and sales.

SS: Absolutely. Now, you’ve touched on it a little bit already. But I know a key way that you focus on empowering your teams is the use of Digital Rooms. What are some of the key ways that you’re leveraging Digital Rooms with your teams today? 

CH: Digital Rooms was one of our favorite features that we were going to get because, like I said, as an assistant, principal when you hand me papers it’s going to get lost on my desk. But now in this digital world, I can open that up, I can go back to it, I can share it. It provides all those opportunities because I know that there’s a statistic out there that says now most sales are being done online, and so it empowers our reps in that way to have the analytics and see the Digital Rooms. We actually had a rep just recently share how she’s customizing it per month and putting the top five things you should see this month, and honing in on the things that are happening in the product, the campaigns, the webinars that we may be releasing and really customizing her Digital Room in that way to share it with customers. To not just be a Pitch, but a tool that’s really partnering with them long-term, and sharing with them new things that were coming out and really being that lifelong partner, and not just trying to get that sale.

That’s really who we are as an education company. And seeing that, and seeing how they’ve been utilizing those Digital Rooms has been probably one of the most exciting things. And building more templates for them so that they have those pieces, and then sharing templates that are landing really well in the market, and then being able to share that and have those pieces has been really beneficial to them.

SS: Amazing. And how are you also then leveraging Digital Rooms to gather insights on what’s working and what’s not both for your sales team as well as your buyers?

CH: Being able to have those analytics, really we were driving blind before, we didn’t know. And so now being able to pull those analytics that’s on the coordinator on my team works with me and we really review that.

So that we know what to report out to sales, we know what to report out to marketing on what’s landing with customers. What’s resonating with them? What can we make sure that we provide more of? So having all of those pieces and really being able to use that data and be data-driven in that way, it’s something that we never had before.

So it’s really opened up a whole new avenue for us as far as the strategy goes and being able to share those analytics. 

I love that. And you guys are seeing just absolutely. Amazing impact. You guys have seen some fantastic success with over 400k in closed won revenue in the first few months, and 10 million in open opportunities associated with Highspot. How did you drive these results? 

CH: I think that having that connection to our CRM and being able to see analytics like that has been huge. I think to be able to drive those results really started with a strong implementation. We actually started with a different coordinator leading the implementation efforts. He actually went on to a new adventure, super happy for him, but that meant that there was going to be a transition in that position, but we never lost traction. That implementation of Highspot was super important to us and making sure that they had the training that they need as the enablement team, they had the pieces that they need to really feel confident in the platform. So that when they were sharing, when they were pitching, that it was having an impact. And so that’s where I think, and we also paired it with some certifications and different trainings that were happening.

And so with that came sharing new decks, sharing new scripts, and being able to see how they’re utilized and like what they’re sharing in those Digital Rooms based on the certifications of their trainings that we’ve just had has really made an impact for my team, but for sales to see what is impacting our market.

SS: Fantastic. Cara, last question for you, I really appreciate all of the insights that you’ve shared. How are you continuing to build on the momentum that you’ve achieved so far to continue to help drive a lot of this business impact? And how are you planning on leveraging Highspot to help? 

CH: Highspot has amazing webinars. They have this new thing called Learning Circles where we can learn from other enablers. I’ve reached out to other enablers that are in the ed-tech space to hear, “What are you doing? What’s working?” I think instead of seeing them as competitors, but seeing them as collaborators is an important part of that strategy when you’re implementing a new tool to see hey, how are you doing this and how can I learn from you?

Utilizing the chat features and the different things I can reach out to other people that are Highspot users, I think is really important. We want to make sure that this is something that continues to be sticky, that it continues to have a high recurring usage.

We’ve seen such an impact already. We just want to make sure that now we’re leveraging best rep strategies. We’re allowing them to share big wins, that we’re highlighting those in our all-sales meetings. That we’re bringing that to the surface, that we’re really looking at that content, driving that engagement, utilizing those plays to be that one-stop shop to help them learn different strategies or different campaigns that we’re sharing.

Really utilizing all of those pieces and driving usage and growth in the future I think is really going down to now that we’ve implemented it, now that we’re starting to see, now let’s go back and analyze the data and where can we take it to the next level. Because that’s really what I want to see. I want to see us be able to take it to that next level and really share best practices. Not just within in-house, but with other enablers as well. 

I love that. And you participating in this is absolutely a fantastic first step in sharing it with other enablers. So thank you again, Cara, so much for joining us. I really appreciate it. 

CH: Yeah, of course. It was great being here today. 

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.

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