Win Win Podcast

A study conducted by Sales Enablement Pro found that 37% of leaders consider increasing revenue while minimizing costs for their employees to be one of their greatest challenges. So how can you maximize the impact of your investments while building your sales tech stack?

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 Tiffany Jones, the vice president of sales strategy and field operations at HackerOne. Thank you for joining us, Tiffany. I would love for you to tell us a little bit about yourself, your background, and your role.

Tiffany Jones: Thank you for having me. I’m Tiffany Jones, I am at HackerOne. I lead strategy operations and the enablement team at HackerOne. But I’ve been in the space for almost 15 years now. Before HackerOne, I was at DocuSign leading operations there from a hundred million through IPO to well over a billion in revenue.

SS: I am excited to have you here today and you obviously have extensive experience as a leader in go-to-market strategy and operations. Based on that experience, can you tell us about some of the challenges facing go-to-market teams today? 

TJ: Yeah, I think one of the biggest challenges that we face from a go-to-market team perspective is how we think about growth in this new economy. Pre-COVID it was a pretty standard path that we were growing quarter over quarter, year over year. COVID had a ton of disruptions to that process. There were some big ups for some companies and some big downs for others. Really in the tech SaaS space, there was a lot of ups. And so right now, from a go-to-market perspective, we’re all just struggling to figure out, like, how do you repeat that year-over-year growth and get back to that same equilibrium.

SS: Absolutely. And tell us about the role of revenue operations in this current landscape. How can RevOps teams help organizations really overcome some of these new challenges that we’re seeing, particularly in the growth sector?

TJ: Yeah, it’s a great question. I think a lot of times the revenue operations part of the organization gets swept under the rug when it comes to thinking about the solutions for this, but, in my experience, we’re front and center, and we play a role in how we think about the teams being organized and how they’re incentivized and building out those structures so that we can get back to that growth level, as well as with the tech stack that’s necessary, and the sales process that goes along with that to amp up the productivity of the sales team so we can get well-oiled machines with the right people in seat in the right roles to achieve those results.

SS: I love that. And I think, as you stated, a key focus for a lot of operations leaders is really driving sales productivity. What are some of the key ways that RevOps can help businesses really optimize sales productivity?

TJ: Yeah, the one that always comes to mind is systems. But there are a number of things for me that really help optimize productivity. There’s the territory design that you end up deploying in your organization. There’s the sales process that you ask each of your individual sellers within your organization to go through. And then there’s the tech staff that they actually operate in for that sales process. Aligning all three of those things that you have, when you say productivity, you’re not just talking about squeezing as many dollars out of an individual person as humanly possible and treating people more like machines every day, but really like how do you optimize their experience as sellers so that you’re asking them to do what’s most beneficial for not only themselves, but the company with the right tools at the right time, like really optimizing their experience? I find it to be really, really important.

SS: Absolutely. And, obviously one of our core audiences is enablement and sales productivity is absolutely top of mind for many enablement leaders as well. In your opinion, how can revenue operations and enablement partner together to improve sales productivity?

TJ: I think it all really starts with the sales process, thinking through what you actually want your sales team to do on a day-to-day basis, like the way that you want them to interact with customers, with other people internally, and with your tools in Sprint Center, and that’s something that the operations and enablement teams need to partner on in order for that to be something that you roll out and the sales team adopts, because you need it to not only work from a theoretical perspective, but you need the backend architecture of those systems to work together to deliver that experience for them to operate in.

I have the benefit in my current role of Managing both an enablement team and operations team. And it’s been amazing this quarter as we put together our key projects for the year to see how those are intertwined from a process go-to-market systems perspective and the sales process that we want to layer on top of that and how those project plans really are on top of each other.

It’s not, A waterfall effect where someone’s working on this and the next team takes it over. They very much are partnered hand in hand to deliver an optimized solution for the sales team.

SS: And you talked a lot about the process component but there’s also a lot of kind of joint shared ownership around the tech stack. I think that’s a really critical area of partnership between enablement and revenue operations. They, I, At least in my experience, are often trying to make sure that they’re building and optimizing that for their go-to-market teams. What are some of the key components from your perspective of an effective tech stack in today’s sales landscape?

TJ: Oh, it’s a difficult question. I feel like the landscape is ever-changing right now. There’s so much consolidation going on that there’s a constant evaluation, at least in my team, from my perspective of: are we using the right tools for the right purposes? I think when we talk about evaluating the tech stack, it’s not all a consolidation game.

I don’t think the end goal is to get to one or two systems that limit the number of clicks or logins they have, but essentially using the best of every product in a way that makes sense from a systems architecture perspective. And I keep saying architecture because I think it’s such an important part of when you have a successful sales system running. So, how are you clicking through to some of your tools? Are you doing it out of a home base or are you asking people to go back into a single sign-on tool and navigate between different tabs at different points in the day? I think you get the enablement aspect, which is here are the best of these tools.

Here’s how I want you to send emails, or to record calls, or to follow up on, and send out material to your end customers. But without the operations team, those can become very siloed events. And you need that operations team in the background, thinking about how they tie all of that information and data together so that the sales team is experiencing a much more optimized way that they’re working with the tools

SS: Absolutely. And this might lead to. Lead into the next question a little bit, but I’d love to understand, what are some of your best practices for evaluating solutions to identify the right ones that also support your overarching go-to-market strategy?

TJ: Yeah, in a perfect world, I would love to do an RFP on everything that we want to do and take a broad swath look at what’s really out there in the market.

It’s rarely what happens. Sometimes we try to pull back and do a little bit of that, but from a best practice perspective, whenever we’re presented with a need for something, I ask two questions. The first one is, do I have an existing tool that solves this and at what level does it solve it? And does that solution meet my sellers where they’re at and what they’re trying to do?

And the second question is so important. It’s very easy to answer the first one. Again, there’s a lot of consolidation going on in the tech stack world for sales, and so you probably have a tool that does whatever your team is asking to go look at right now. But is it meeting the sellers where they’re at?

Is it in the space that they want to do that activity at? Does it fit into that sales process flow appropriately? And I think that key part of the evaluation really helps to build an optimal text stack for everyone to use. And so it might be that they need to do that while they’re sitting inside of their CRM.

And so because that’s where they’re always doing it, it makes sense to have something that either is embedded there or is a tool that the CRM already offers, but perhaps it doesn’t matter. They’re doing it on their phone or one-off or in Slack or Teams. And meeting them where they’re at, I think, is the, is a really important aspect of making sure that you have a toolset that your team is actually using.

SS: Oh, absolutely. And how does an enablement platform like Highspot strategically fit into your sales tech stack?

TJ: For us, it’s a central point of information, right? We’re using it to collect information, distribute information, both internally as well as externally, as well as using the learning module to test that information.

So it’s very much an information hub for us. We use it to again, leak out to other tools that we ha

According to research from Forrester, 77% of marketing leaders report that buyers expect more personalized interactions. So how can you align your marketing strategy with the ever-changing buyer’s journey?

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 Eric Andrews, the vice president of growth marketing at TriNet. Thank you for joining Eric, I’d love for you to tell us all about yourself, your background, and your role. 

Eric Andrews: Thanks for having me, it’s nice to be here. I’ve been working in marketing for about 30 years, mostly on the client side. I’ve been at Trinet now for about two and a half years and I lead growth marketing, which, for us, includes digital marketing, demand generation, marketing enablement, and customer marketing.

I’m a firm believer in the strong connection between demand and growth enablement because, we spend a lot of money trying to generate demand, and I think we’re sub-optimizing those investments if we’re not providing the content and tools to sales to help them progress and close the leads that we’re generating for them.

SS: Fantastic. We are excited to have you here with us, Eric. Again, thank you so much for joining, and you have a unique role because you oversee both customer marketing and enablement. So from your perspective, what is the value of uniting these into one department and one strategy? 

EA: It’s also a really interesting fit, and they go together well for a couple of reasons. First, we work with customers to support new sales through the creation of case studies, customer videos, referrals, as well as references. Being able to work with the customers to sign them up to be referrals or to make referrals or be references is really important.

And then second, I think enablement can support the upsell work that we do with CRMs to ensure that they have the right messaging and tools to support that motion. 

SS: Amazing, and as you mentioned, as a marketing and enablement leader, one of your key focuses is aligning with the buyer journey to improve engagement. Why is this a key focus for your team in the current landscape? 

EA: We all know that buyers are increasingly delaying engaging with sellers until they’re deeper into the buying process. That means more of the buying process, or the journey is covered by marketing. Our goal is to try to meet prospects where they are and then provide the content and tools and experiences they need to keep them moving down the buying path.

And that doesn’t stop, once they meet with sales, right? We want to continue to provide relevant information to prospects either directly or through the salesperson right through that entire process. 

SS: It is absolutely critical. And this desire to drive better engagement is one of the key factors that led you to implement Highspot. How can an enablement platform help you streamline the buyer’s journey? 

EA: It happens in a couple of ways. First, Highspot has helped us organize and curate our enablement so that sales reps can find the content they need. And they can share it quickly, right? It’s all about trying to take time out of the buying process and make it as simple as possible for our prospects.

So for us, we built a very consistent portfolio of content across our verticals and our personas, and that means that reps increasingly know exactly where to go to get the information they need and can respond to buyer questions and buyer requests really quickly. And then second Digital Sales Rooms, using Digital Sales Rooms to share all that content means that the buying team has just one place to go for everything they need.

And if you’ve ever been involved in procuring some sort of a solution, it’s really helpful when all of that content is in one place as opposed to having to open up, dozens of emails and click through links to see, to find that one asset that you were looking for. So we think the digital sales room is another way that we’re just streamlining the process and making it easier for our prospects to, come to a decision.

SS: Now, to better align with the buyer’s journey, you actually reimagined your content strategy. It recently drove an improvement in content governance. Can you tell us more about your content strategy and its impact on the buyer’s journey? 

EA: Our content strategy is built on a couple of premises. First is quality over quantity, right? Marketers, we tend to measure success by the pound, right? I must be doing a good job. Look at all the assets I created. We developed a bill of materials that includes only about a dozen assets. And that would be for each of our go-to-market motions, right?

But it’s a dozen assets. They’re mapped to the buyer’s and seller’s journey. Our goal is not It’s not to grow those assets, but rather to make sure that bond is of the highest possible quality, that it’s up to date, and that it’s 100 percent complete for every product, every vertical, and every persona.

The second premise is around consistency. Within our bills and materials, we ensure consistency of messaging, value propositions, and voice. That sounds obvious, but when you have different people and different teams creating content, it’s not a given that the messaging is going to be consistent across All of the assets that you’re providing to sales.

And we also strive for consistency across those bills of materials. So for example, every bill of material has a battle card. All our battle cards are structured in the exact same way. So if you want to know how to handle objections, it’s always on page two of the battle card. In fact, it’s always the lower right-hand corner.

I think that consistency plays an important part in both helping sellers on board faster, but also giving them the confidence that they can find the answer to a question that a prospect is asking. They can find it quickly. It’s not, “I think I can find that.” They know exactly where to go to get the answer because it’s so consistent.

And then the last thing is we try to be more data-driven than anecdotally driven. I think if you work in enablement, everybody’s, gotten the call from the seller in Columbus who says all the sellers need this one asset. I’m telling you, everybody needs it.

And you’re like, okay, great. You build it. And then you find out the only person who used it is the guy in Columbus. So, if an asset in our bomb isn’t working, we will swap it out. Our goal is to make sure with a limited set of assets, each one is successful, but we really do try to measure success based on utilization, not based on any sort of anecdotal information.

SS: You’ve mentioned that digital rooms have been a game changer for your reps, and you’ve been able to drive an increase in buyer engagement using digital rooms. What are some of your best practices for leveraging these digital rooms? 

EA: I think probably two, three, three things, we want every opportunity that is engaged with sales to have a Digital Sales Room.

It should be at the deal level and everyone involved in that deal should be invited to that room. Second, all assets that are shared should be available in that room. And by the way, that can include conversations, if you’re using Gong or other conversation recording tools for the prospect, we want that digital sales room to be the place to go for all of the content associated with that deal.

And then finally, once the deal is won ownership of that deal room should be moved to the onboarding team, and that way, they can minimize the amount of repeat discovery they have to do with the client. It’s really making sure that the deal room stays right through the life of the client.

SS: We’ve talked a lot about buyer engagement, and I know some of the other key business metrics you focus on are improving win rate and time to close. What are some of the key ways you measure your impact on those metrics, and how do you leverage Highspot to help? 

EA: We absolutely, Look at revenue or, ACV we go annual contract value is an important measure from a marketing standpoint, but with respect to enablement in the high spot we’re looking at win rate.

We’re also looking at time to close and trying to speed up we strongly believe that having really high-quality, consistent content tools that are easily accessible by reps and easily shared with prospects is going to have an impact on both win rates and time to close. Measuring that is challenging, right?

We look at a number of things. We look at the Make sure the number of reps that are on Highspot and how frequently they’re visiting. The content utilization, both internally and externally. The number of deals Digital Sales Rooms connected. And we look at all of that against win rates and time to close.

And I think going forward, there’s a real opportunity here to start to correlate specific assets at specific points in the buyer journey and how they impact outcomes, and that’s a big data, AI, machine learning kind of exercise that I think, successful companies are increasingly investing in and are going to, it’s going to make a big difference.

SS: Amazing traction on that front. What are some of the key results you’ve been able to achieve s

In a study conducted by Sales Enablement Pro, organizations where training is led by enablement teams see a six percentage point increase in customer retention. So how can you maximize the impact of your training programs?

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 Sofia Arroyo, the revenue enablement programs lead at Clari. Thank you for joining us, Sofia. I’d love for you to tell us about yourself, your background, and your role.

Sofia Arroyo: Thanks so much for having me, Shawnna, I’m excited to be here. My name is Sofia Arroyo and I have been in enablement for over six years. I started as a sales rep as an account executive and transitioned into enablement, and have never looked back. So I’m based in the San Francisco Bay area and very excited to talk today.

SS: We’re excited to have you here. I know you recently joined the Clari team, and as you mentioned in your introduction, you bring a lot of frontline sales experience with you. How does your experience as a frontline seller guide your approach to enablement?

SA: Yeah, for me the biggest thing is understanding and emphasizing the “what’s in it for me” and “why does this matter?”

So often enablement, in a good way, is very sought after. People want to learn, people want to teach others, and get in front of sales teams overall. But, really answering the question: what’s in it for me as a seller? Why does this matter? How is it going to help me sell more, and have better conversations with customers?

That has helped me in my own experience deliver great enablement overall. A second part of this is giving focused learning. So, delivering focused learning and reducing the noise that often hits sales teams. I remember as a seller myself, feeling overwhelmed because we had so many meetings all the time.

There were tons of people coming to talk to us and thinking, “Man, what would I have wanted or what do I wish I had when I was a seller?”, and taking that focus and applying it to enablement overall. So really emphasizing, again, what’s in it for me and what do we want sellers to be able to do has helped me deliver impactful enablement programs at the companies I’ve worked for.

SS: Absolutely, it sounds like you really know what it’s like to walk in their shoes, and I expect that is especially helpful on this front. Now, I noticed something on your LinkedIn profile, and it mentions that you aim to promote a learning culture. I would love to understand, how do you foster a culture of learning amongst reps, especially with your background as a seller?

SA: I would say two ways. The first is, again, making things very relevant. When I think back to being a seller, as I mentioned, I was eager to learn and I wanted to talk to other people who were seeing success, and at the top of the leaderboards. And so I knew at that time, but I really wanted to think about, okay, what do I want to see as a learner?

And who do I want to talk to? So, a lot of that is how we make enablement and training relevant to learners and sellers to really make sure they see why it’s impactful. And then that creates that learning culture overall. So really, “Hey, I’m hungry to learn because I know it will directly impact my book of business, and it’s going to directly impact how I talk to prospects and customers, and I’m going to see success from it overall.”

The second thing is peer-to-peer learning. One of the things we don’t always emphasize in enablement is the importance of actually teaching others when we learn something. It’s that defining moment of, “We’ve actually really effortlessly implemented a new learning or behavior change when we can teach other people something.” So leveraging peer-to-peer learning to create that culture of learning from, not just folks like myself and enablement, but people who want to hear from other folks like themselves, and making sure you can connect others to people who are experiencing exactly what they are on a day-to-day basis is a great way to promote that culture of learning internally. 

SS: I love that you’re driving that. And your team implemented Highspot’s training and coaching capabilities. How does having a unified enablement platform help you deliver more effective learning programs?

SA: I will have to give a shout-out to the strategic enablement framework overall that we’ve talked about at Highspot and we’ve talked about internally here at Clari and at the companies I’ve worked at.

It’s that consistent execution piece. Training and coaching is something we all know is necessary, but it’s about implementing it in the workflow of our reps and in our learners. Having one platform where people can go to not only get the resources, and content they need to be successful, but then have access to coaching opportunities in mere real-time or when they need it makes for that flywheel of the equip, train, and coach to work effectively. It’s the only way that we can make sure that we are capturing the right behaviors and promoting the right outcomes within our organization by having a single pane of glass that we can look at when it comes to implementing enablement programs overall.

SS: Now, you mentioned earlier that you focus on designing outcome-based learning. What are some of your best practices for helping reps put learning into action and how do you leverage Highspot to help? 

SA: First and foremost, it’s meeting reps where they are. I can’t tell you the number of times, and I think part of enablement is also learning from mistakes. No one’s perfect, I’ve tried, and there’s a trial and error piece of what I’ve done and my success as well. But I think one of the biggest things I’ve heard from reps is, “Oh man, I have to keep going to all these different tools or systems to access what I need to be successful. I’m not really sure how it applies to my book of business, or what I’m doing on a daily basis.”

So, the first thing is meeting reps where they are and really making sure that you are designing enablement that again meets them in their workflow but also applies what they need to be doing on a daily basis. So if we do something on prospecting, we’re talking about, “Hey, we’re going to talk about how we prospect.”

It’s not just a 30-minute webinar on how we prospect. Death by PowerPoint is never fun, but it’s actually, “Great. Let’s pull up an account list. Take your account list. We’re going to walk through those personas that we’re targeting and best practices for that.” So, make it action-oriented when we can.

That is the benefit of the remote, virtual learning and training that we can do, is utilizing break rooms in Zoom to make it, again, action-oriented, then hit those outcomes that we’ve identified at the beginning. The other thing here is making sure that we clearly define what outcomes are at the beginning and having that conversation up front, not just with sellers, but also with our cross-functional stakeholders and partners as well.

So whenever someone comes to me and says, we want to train on this, we want to enable the field. It is, “Great. What do we want our sellers to be able to do? And how do we make sure the enablement matches that to make sure that we are hitting those outcomes?” And lastly, it’s about repetition. We have to move away from the one-and-done enablement, but really push ourselves as enablement leaders and as enablement professionals, as well as our cross-functional stakeholders, to say, “Great, you want to train on this now. What do we do in two weeks from now? In a month from now, next quarter, to reinforce that learning?” So I think making sure that we’re constantly tying back to those outcomes.

We’re utilizing things like Highspot to look at what assets are being leveraged. We’re taking analytics into account to really measure the success of our programs, not just in one moment, but also over a longer period of time as well. 

SS: That is fantastic. And you’ve been so thoughtful in the way that you’ve designed this that I imagine you want to make sure that your reps are taking full advantage of these and really adopting the training.

What are your best practices for driving adoption of your learning programs amongst your reps? 

SA: I feel like a little bit of a broken record, but I will say making it relevant. I think that paired with peer-to-peer learning, as I mentioned before, it’s been really helpful for us. Really making sure that we have voices from the field.

I think one of the key learnings I had early on in my enablement career was just taking enablement and working on it in a silo and delivering it without getting input from the field, from sellers, and from leadership. One of the ways that we’ve seen the most success from driving adoption is not just taking a top-down approach from having directors or our CRO talk about the importance of enablement, but actually having peers and other sellers talk about, “Hey, this was really impactful for me. I was able to close this deal because of X, Y, Z.”

So I think one thing is again, making it relevant, utilizing voices from the field, not being afraid to get other people involved in that way, to make sure that we can really have the biggest impact possible. The other thing I think is really supporting managers. And I think that’s something that Highspot allows us to do differently, is making sure that we are training the trainer in some cases, but also just giving them the tools and i

According to a Gartner study, about 40% of businesses have implemented a formal coaching culture for their reps. So how can a unified platform help drive a coaching culture within your organization?

To watch the video of this episode, visit our YouTube channelhere.

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 Bernie Borges, the vice president of global content marketing, Blake Graves, director of sales enablement, and Chris O’Connell, the director of global sales operations from iQor.

Thank you for joining us, Bernie, Blake, and Chris. I would love for each of you to tell me a little bit about yourself, your background, and your role. Bernie, let’s start with you.

Bernie Borges: Sure. Thank you, Shawnna, thanks for having us. I’m Bernie Borges, vice president of global content marketing at iQor and I’ve been in content marketing for the better part of the last 20-plus years in B2B. I had my own agency for a while, and joined iQor about three years ago, really focused on driving the brand awareness for iQor in the marketplace.

It’s a very competitive marketplace and producing content that can really help to amplify the brand as well as provide content that the sales team can leverage in their day-to-day selling efforts. Everything from starting conversations through the whole buyer’s journey all the way down through closing. So that’s my role and a little bit about my background.

Blake Graves: Yep. Thanks again for having us too. So yes, Blake Graves, director of sales enablement at iQor, been with iQor for almost eight years now. So I’ve got to see a lot of transformation at the company.

Really cool stuff that we’re doing with sales and marketing. My area covers sales readiness, that training aspect, and what new things are we doing from a technology perspective. Just bringing that to the sales team and this is how we should pitch it and This is the information you need to empower you or better inform your selling practices.

And of course, along with that comes the tech stack like Highspot or anything else that we’re using to enable sales from a prospect’s perspective. Highspot is an exciting new tool for us and we’re ready to start closing some deals quickly.

SS: Wonderful. And Chris, last but not least, tell us a little bit about yourself.

Chris O’Connell: I am Chris O’Connell. I’m the director of global sales operations. So I’m responsible for our CRM instance and working with our sales team to help them. And I’m really excited about the Highspot opportunity. This helps us get better information about how our content is being consumed, how it’s being deployed, which things are resonating and perhaps how they’re helping us win more business.

SS: Wonderful. Well, thank you three for joining us. Now to start, tell us about some of the challenges that your teams are facing prior to Highspot. What was the impetus for deciding to invest in a unified enablement platform? Bernie, if I could start with you, that’d be great.

BB: Sure. So, the content marketing role at iQor is only about three years old at the time that we’re recording this. And so over the past three years, we’ve been able to produce a fair amount of content that we put out into the marketplace.

And along the way, we’ve made a strong attempt to have the sales team embrace the content, use the content, and then of course, enable them to help them get into more deals, more conversations, and close more deals. What’s been missing though, is a couple of things that I think the three of us will speak to in this conversation.

One is an intelligent platform that allows us to organize the content intelligently and make it easily accessible to them, and then also be able to track how the content is being used, who’s using it, and how it’s being used. What’s the contribution to pipeline and what’s the contribution to deals won as well as deals lost, that’ll help us not only measure the impact of the content, but also feed us information that we can use to drive our strategy going forward.

So we know what content to produce more of. As well as what content we should either stop or scale back producing based on the data and how it’s used.

BG: I’m going to add to that if that’s okay. The biggest challenge for me was, and this is no offense to Microsoft at all, but we have been a very SharePoint-focused type of company for, organizing content and building, what you guys call Smart Pages. So we’re we’re attempting to do that kind of effort within something that’s a little bit more static environment. And that was very challenging because one, there’s a heavy lift on my team from the design to thoughtfully trying to lay out pages. It’s like building websites, basically is how I would compare that to. And over time, content’s going to get stale. We’re not, it might not be being refreshed enough. It’s not easy to find. That’s another big piece of that is, it’s not easy or intuitive. And that was a big challenge for us.

And Highspot is changing that entire landscape for us, because it’s a little bit more intuitive and the intelligence built in.

SS: And Chris, let’s hear from you on this front.

CO: Yeah. So, I think for me I really like the notion of providing content to the salespeople – the right kind of content – at the right time where they’re not having to hunt around and find it.

And, with the integration with the CRM, Like Salesforce, depending on which stage the deal is in we’re able to surface content that would be helpful for them to deploy, and know when it’s being used and, again, what kind of results we’re getting from that. But I like the way that your product allows us to pre-package a play or a type of content delivery that we’re going to share with a prospective leader, or client.

And so we’re really excited for, as we roll this out, how we’re going to see these wins and be able to track them and tie them back to the actual opportunities they’re working on.

SS: Thank you for giving us a little bit of that grounding context. Now, as leaders in your organization, we’d love to hear your perspective on the value of an enablement platform for your areas of expertise. Bernie, if we could start with you. What does the impact of a unified enablement platform have on your role as a marketing leader?

BB: Shawnna, I really look at it holistically. I don’t look at it just from the lens of my focus in content marketing.

I look at it holistically, and what I mean by that is now I view our tech stack to be comprised three pillars, right? A three-legged stool: you’ve got CRM. Of course, you have to have CRM. We’ve got marketing automation, and now we have a sales enablement platform or revenue enabling platform, depending on what vernacular you prefer.

But I think that rounds out our tech stack. Because now we have the ability, as we’ve been discussing here, to organize the content in an intelligent way using intelligence built into the platform, as well as – we haven’t gotten to yet, and I’m sure Blake will get to this – the ability to empower salespeople to utilize that content in ways that I’ll let Blake comment on that because that’s a very exciting element.

But the point I’m driving at is that we’ve rounded out our tech stack, right? CRM, marketing automation, and now a sales enablement platform. Now we’ve got everything we need to deploy and measure the impact of content.

BG: Exactly. And it’s obviously my cue to piggyback off of that because it’s a really good point. I think that the Digital Sales Room is also going to be a big piece of this for the sales team. And I mean that because it gives the sales team an opportunity to tailor and personalize the experience for their end user, the prospect. That is something that we’ve been missing for a while, too. We personalize our messaging and emails and LinkedIn outreach is whatever that sequence looks like. But, when it comes to building an environment where I can take my prospect and say, these are the things I feel are relevant to you, whether it’s your industry, your role the challenges that you’re having, and it looks like your environment, this is your logo.

And I think that’s a really sweet touch. But, the sales team also, the three of us continue to talk about this when we’re meeting internally. And I say this out of a lot of respect, the sales team everywhere in every industry, any company are very special people. They’re wired very differently than the rest of us and we like that, we embrace that, because that’s what makes them, so successful and in selling, and we have to cater to that. We have to curate our tech stack and how we roll these things out very carefully because once the salesperson says this doesn’t work for me, you’ve almost lost them, and it’s hard to get them to come back. And with Highspot, because of that intelligence that’s built-in, and because the three of us are thoughtfully curating the internal experience, this is going to be so much more of an easier lift for the sales team to adopt. And from a sales enablement perspective that’s a huge deal.

SS: Blake, how about you as an enablement leader? How do you envision leveraging Highspot’s unified enablement platform to help bring your enablement strategy to life at iQor?

BG: I gave a preview of that answer a minute ago, because this going back to the Digital Sales Room, video is certainly

Research from Gartner found that 91% of sales leaders reported that finding relevant content and tools for reps is a struggle without a dedicated enablement platform. So how can you simplify the rep experience with a unified platform?

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 Carolyn Hoang, the senior director of sales enablement and effectiveness at Alight Solutions. Thank you for joining us, Carolyn. I would love for you to tell us more about yourself, your background, and your role.

Carolyn Hoang: I’ve been at Alight for a little over a year and I was brought on to help develop and grow our sales enablement function at the org. My role today has evolved a little bit and right now I’m focused on supporting and developing product education and enablement and ensuring we have a robust and effective product training and enablement process as we anticipate upcoming product launches and releases.

As for my background, I’ve been in healthcare, health insurance, and the PBM space for 20 years. I initially wanted to become a pharmacist like my sister but found my niche and enjoyment on the corporate side of the business around operations and product strategies. So I’ve always said my life purpose has been helping others.

So any way that I can make that impact in any role I’m always fulfilling my purpose and that’s where it landed me here in sales enablement at Alight.

SS: We’re really excited to have you with us today, Carolyn. Now, you did mention that one of your specialties is improving efficiency in business operations and processes. How do you help drive efficiency for the business as an enablement leader?

CH: There are so many ways that we can help drive efficiency in any business, but you have to start by understanding how the business operates. So the way that I look at any organization as I come into it is understanding how are they at maturity level in a current state.

For example, process analysis and optimization, always conducting a thorough analysis of existing business processes. How do we identify bottlenecks and any inefficiencies, and what are those areas for improvement? Another area would be working closely with all of the cross-functional teams, ensuring that we can streamline or redesign business processes and eliminate any unnecessary steps.

Or automate any repetitive tasks that we can. That means establishing those standardized procedures or best practices across the organization.

SS: Now curating the right tech stack can have a huge impact on efficiency. And prior to Highspot, you had several tools, including a different readiness platform. What were some of the challenges that this led to?

CH: Yeah, assessing the right tools and technology integration or tech stack is so important for any business. And I can’t stress that enough. Some of the challenges I’ve seen most frequently is just those fragmented workflows, utilizing just multiple tools that a rep or a seller needs to switch between different platforms or accessing information or content that needs to at the right needs at the right place.

A place that’s been challenging data silos. So every tool has its own data repository, but when they’re not speaking to one another or the systems are not integrated, that poses also a huge challenge. And then, yeah, that lack of integration between platforms that is used by multiple different client facing teams.

Having that all centralized in one place eliminates that. And that’s something that I found at our organization, was that the level of integration and content management needed to be consolidated and ensure that our reps – all of our customer-facing reps – have the right content and consistent content, at the right time.

SS: What was the impetus though, for making the switch to a unified enablement platform and ultimately to implement Highspot?

CH: Yeah, in my early assessment here, I immediately saw a need just for greater integrated workflows and business processes that would ultimately centralize and create that seamless integration data across all of our customer-facing teams and all of the various enablement tools and tech stacks.

So many factors went into ultimately making the switch to Highspot as our go-to platform. But it’s more about the technology that can support our organization and our organization’s, ever-evolving needs and help us enable our sellers most effectively and efficiently.

SS: Fantastic. And in your opinion, what is the strategic value of consolidating your enablement tech stack into a unified platform rather than separate disconnected tools?

CH: I would say improving efficiency and productivity across multiple business teams. So that’s, again, data integration insights are just so important, as it helps us inform and better enable our reps through those data-driven insights and decisions that we can help continuously improve our content, our training, our platform, and also the enhanced user experience. So, having that unified platform really provides a seamless and intuitive experience on the front end, and the back end as the user, as the administrator, and really improve our user adoption and satisfaction.

So having a consistent interface and navigation across all of our enablement functions and teams, our reps can easily find the right tools, resources, and things that can lead to increased engagement and effectiveness.

SS: I love that, how you guys are thinking about both an integrated data and experience perspective, that’s fantastic. How did you go about building the business case with your stakeholders for making this change? And I think a lot of our audience would love to hear some best practices for gaining stakeholder buy-in.

CH: Engaging your various stakeholders as early as possible in the scoping process when building your business case is key.

So keeping them continuously informed and engaged throughout the process. I always say partnership and collaboration; that’s key when you take time to understand the various stakeholders. How do you identify those businesses and teams that you will work with on a day-in and day-out process?

How each of those teams operate, what are their pain points, and how can we help solve those business challenges together? Aligning different use cases and identifying what those use cases are. That resonates with each of our stakeholders and ensuring that they’re aligned on what our enablement vision goals and business outcomes that we can achieve really help solidify the buy-in and understand the “what’s in it for them” and “what’s in it for us together”.

SS: That’s a fantastic approach, always put it in the perspective of your audience, even internal ones like stakeholders. Now, you recently launched Highspot actually at your company’s sales kickoff. Can you tell us about that launch and how you leverage that key moment to help build up momentum for this change?

CH: Launching Highspot at sales kickoff was just such a perfect opportunity for us to generate buzz, and excitement really leverage different gamification opportunities to drive that early adoption and early engagement with the platform. So before we developed or kicked off at our event we built what we call the sales kickoff spot in Highspot, so that’s where reps can access all the information they need to go to before they attend the event, like the agenda, travel details, any pre-work or training that we want them to prepare or review before the sessions.

We also included this fun Easter egg in our SKO page where we use gamification like that launch experience to incentivize our sellers to complete any pre-recorded raining and get folks driving excitement and buzz around, what is Highspot? What can it do?

And to go to our Highspot booth that we had in our partner expo so what we did is we had the first three folks who finished training, found the Easter egg phrase, and went to the Highspot booth and mentioned it, then they all won a prize. After SKO, we communicated with the winners and recognized their efforts to encourage others to participate in it, but also really sprinkle that pride.

Fun and strategic learning right throughout the platform. And that helps folks from a user experience perspective to learn the platform, play around with it understand the processes, and again, help drive continuous engagement and options post-launch.

SS: I love that, that sounds like it landed well with your teams. Now I know you guys are also using Highspot to help optimize your onboarding program. I know that’s a key initiative for you all this year. How do you plan to optimize your onboarding program and how will leveraging Highspot help you to do

CH: New hire onboarding is so crucial to get right at any organization. So ensuring our reps are fully enabled with the right product knowledge and know how to position and recognize the value of messaging that resonates with the various buyers and prospects they’re talking to is key. At Alight, we made a huge effort to prioritize and build a strong and effective onboarding program this year.

And that’s something that we continue to focus on building out and continuously iterating throughout the year as well.

SS: Amazing. Now, I know that you guys are just getting started with Highspot, but what are some of the key ways that you’re measuring th

According to a study conducted by Zippia, organizations with a comprehensive training program see 24% higher profit margins. So how can you improve rep readiness with a unified platform?

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 Marc Losito, the chief of staff at FoodChain ID. Thank you for joining us, Marc. I’d love for you to tell us about yourself, your background, and your role.

Marc Losito: It’s a pleasure to be here and, currently, I serve as the Chief of Staff at FoodChain ID and the Senior Director of Strategic Initiatives.

I just finished a 23-year career in the military where I finished up in strategy and operations. And so transitioning into a strategic initiatives role or an operations-based role is exciting, and fluid for me. I’ve been at FoodChain ID for over a year now, and we’ve been employing Highspot as our primary sales enablement tool for about eight months.

SS: We’re excited to have you here with us today. Now I know when you first started at FoodChain ID, one of your first tasks was to implement an enablement platform. Tell us about that journey. Why was it a strategic priority for the business to invest in an enablement solution?

ML: Yeah, that’s a great way to phrase it, it was a journey. So, about this time last year, our executive leadership team gathered together and began to evaluate our strategic growth options, and sales enablement kept rising to the top. Brandon Taylor, our Chief Revenue Officer our champion of Highspot really put it on the front of our growth initiatives and really championed our adoption of Highspot.

It wasn’t too much longer after that, and it was about, May of last year that we began to adopt Highspot and we rolled it out in August. We have been rolling ever since. One of the key differences that we’ve seen, and it’s really just the realization of this, this growth narrative that Highspot brings to sales enablement is we were able to cut down our seller ramp time from nine months to six months immediately with the training and coaching features on Highspot and, professionalizing our onboarding, putting it all into one spot and having sellers singing off the same choir sheet, as it were.

SS: That is amazing to go from nine months to six months, and I definitely want to circle back to that. I do want to get a better sense because you were the executive sponsor for the evaluation and I know that you partnered closely with other key stakeholders in the process. How did you partner with your CRO and RevOps to find the right solution for the business and ultimately gain buy-in?

ML: That’s a great question. Our CRO, Brandon Taylor, was the champion of this growth initiative, and Ryan Wing, our Director of Revenue Operations, was crucial to making sure that we were all aligned on a collective vision, making sure that our strategic goals were synchronized, and to make sure that everything from, sales enablement content to the way we wanted to orchestrate our plays and the KPIs that we had set out, the first being to decrease that ramp time. We thought that was the closest crocodile to the canoe if you will. We’re continuing to chase, some other goals, and our CRO has really put a high bar on what we want to achieve with this. With Highspot in, shortening our sales cycle times, increasing our win rates, increasing our ACVs, and increasing our opportunity creation, but ultimately getting their buy-in was the first step and making sure that we were all aligned on what the opportunity was and what the return on investment could be if we unanimously supported the adoption.

SS: Absolutely. And I know that having one unified solution for enablement at FoodChain ID was really important rather than separate tools to equip, train, and coach your teams. In your opinion, what has been the impact of that unified experience on your sellers and their productivity?

ML: The essence here is, bringing fragmented tools from across our enterprise and bringing them into one centralized location.

It’s like switching from a vehicle that has manual steering, where you’re trying to struggle to shift and pivot with market trends, market changes, and competitor dynamics. But bringing Highspot into FoodChain ID is like switching to autopilot. You’re able to cue seller behaviors so quickly.

You’re able to pivot and adapt to key changes that you’re seeing in the marketplace and it allows for a seamless inflow of information. As a result, our sellers become more agile, more informed, they execute it. Seller behaviors and plays are better, and they’re significantly more effective. And we’re starting to see the impacts of that.

SS: Now, we alluded to one of the big wins earlier, but I know since implementation, you guys have shortened your onboarding time from nine months to six months, and you’ve also reduced ramp time by 30%. Can you walk us through how you optimized sales onboarding and ultimately drove these very impressive results?

ML: I tell you, reducing onboarding time was a challenge but it’s one that Highspot is tailor-made to go after. And so we focused on three primary areas with Highspot when it comes to onboarding, which is customized learning paths. Integrating real-world scenarios into the training process and then leveraging the enormous amount of data and feedback that you get to continuously refine your onboarding approach.

And so that triad not only expedited our onboarding process, but it ensured that new team members were sales-ready in a shorter amount of time.

SS: Fantastic. I love to hear that. In addition to onboarding, your team also focused on improving sales coaching. In your opinion, what is the value of real-world coaching for sales reps?

ML: There’s nothing that can replace real-world coaching. You’re not going to be able to automate or AI your way out of real-world, human touch. And the crucible where theory meets practice. When we’re onboarding reps, it’s not only important for them to learn in a classroom, but it’s also important to have a setting to apply, iterate, and refine their approaches in real scenarios with a feedback loop.

That accelerates their learning and adaptability. And ultimately, the adage is true that practice makes perfect. And in today’s dynamic market, that’s especially critical. 

SS: You did mention AI, so I’m curious. How do you plan to utilize innovation in the enablement space like AI to help your team deliver effective coaching?

ML: I actually have a bit of a background in AI, from graduate school and from my time in the military. I just believe that AI opens up a whole new frontier that revolutionizes sales coaching, by using AI features like meeting intelligence, we can personalize learning you can personalize it at scale you can provide real-time feedback, and more importantly is that you can identify patterns that would be impossible for humans to detect.

And it’s not about replacing the human element. Like I said, nothing is going to replace the human touch in training and coaching, but augmenting it, and learning how to use AI with that human touch is going to make coaching more impactful and insights-driven. 

SS: Absolutely. And I did not know that about your background, that you have a background in AI. So I’d love to get your opinion: how can AI help the business scale sales productivity more broadly? 

ML: I’ve seen firsthand from my time in the military, how AI can have a transformative power globally and on the battlefield. And if you think of sales as a battlefield it scales productivity by automating routine tasks that otherwise take sellers away from engaging the customers, it delivers insights that would take us ages to analyze, with torrents of data, stacks upon stacks, and personalize the customer experience as well at scale. It’s a game changer, and it turns data into a strategic asset for every organization.

SS: How do you think AI will continue to drive business innovation in the near future, especially when it comes to enablement?

ML: AI is bound to expand, especially in enablement and business innovation. I think we’re going to see AI become more integrated into daily operations. Highspot is already at the forefront here with meeting intelligence, being part of every sales engagement, and providing analytics.

I think those analytics will become more accurate over time as we, train new models and reach new heights. But at the end of the day, the potential is it’s pretty vast: from automating administrative tasks to delivering those strategic insights and shaping seller behavior and future directions to make our customer experience more delightful.

SS: Mark, last question for you. As you look ahead, how do you plan to leverage Highspot to help you achieve some of the innovation that you’re aiming to drive this year? 

ML: That’s a great question. So where do we go after our tremendous start? And I think what our CRO would tell you, and our director of revenue ops would tell you is that Highspot is poised to be a cornerstone of our strategy to drive innovation.

Internally to FoodChain ID, we refer to Highspot as the sales accelerator. It is what propels our sales cyc

According to a Forrester study, 53% of sellers said that sales technology positively impacts their results. So how can you optimize your enablement tech stack to drive 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 Sarah Gross. Thanks for joining us, Sarah. I’d love for you to tell us about yourself and your background. 

Sarah Gross: Shawnna, thank you so much for having me, I’m excited to be here today. I have spent a decade in sales and a decade in enablement, and absolutely love both spaces. I started my career as a BDR, moved into sales management and got the typical dashboard and quota, and very quickly realized there was a lot more to sales and to managing salespeople.

I ended up actually researching enablement and then got into being a practitioner myself. So, as I’ve built out teams over the years what’s been interesting is to watch how enablement went from L&D to how we think about making our team more productive, but we weren’t calling it productivity quite yet. We were like, “Oh, let’s get people from 100% to 110% of attainment” to now being the real drivers within the organization of how technology helps our team be more effective and therefore productive in what they’re doing day-to-day. 

SS: I love that and thank you again so much for joining us today. Now you and I have known each other for a while and I know that you focus deeply on a couple of core components when it comes to driving a business. That’s the people, processes, and technology. How does that approach guide the way that you build your enablement strategy? 

SG: Yeah, first things first, you have to have the right people in the right roles.

So I’m a big fan of, especially in a sales organization, right? Having that BDR, SDR structure, the account executive, the SE. And what’s important from an enablement lens is being able to make sure that everybody knows their role and function. It leads to the process side of things. So if everyone knows what role they’re playing in the sales process, then it is defining what that process is, right? Less of the upside of what are our sales stages and how we forecast, but more of what are the gates through which I need to uncover information from the customer and our internal selling team to advance, and to know that I’m in the right place of moving this opportunity forward and spending more time and resources on it.

How do we make sure that process then maps to the methodology that we’re using from a customer buying lens, as well as a selling buying lens? And then how do I make sure that we have the right technology, that I’m not asking my reps to copy and paste a Salesforce field into 15,000 different places, but rather Sales Navigator that’s layered with a Zoom info of the world and allows them to push information into that centralized repository in an easy way to build on account plans, to build on opportunity plans, and to have that structure of what good selling looks like. That’s the baseline, in my opinion, for what enablement has to have as the building blocks at the bottom of the house if you will. To then just start to do things like AI and getting into call recording and understanding what words are being used, when, where, and how.

And devising an enablement plan that is by cohorts of people that need a specific topical area.

SS: I love that you established that baseline. What are some challenges that you’ve encountered as a leader when it comes to creating an effective enablement strategy, though? And how did you overcome those?

SG: The strategies have changed over the years. I’d say at the beginning of enablement, early 2010’s, right? It was a lot about what is it. Why is it different than L&D? Why would we invest in this different team and structure? Then we evolved into, okay, they, they run the LMS, right? They’re the people that give the training.

And they may have an action item coming out of it. And then we’ve gone into this world of, Okay, we have technologies that are supporting enablement now, which is fantastic. They’re designed for enablement, and they’re giving us the right level of analytics. But how do we, as practitioners, continue to stay that we’re elevating the value of our practice?

I still see where people are just trainers or they’re just go-to-market folks who get it out to the sales team. I hear that a lot. You’re the person who helps us communicate with the revenue team and speaks their language, which is a big win in and of itself, right? We’re not being called L and D anymore, but on the flip side of things, we’re not the seat at the table, driving the go-to-market strategy.

I do see that starting to change where more companies than ever are hiring VPs of enablement. They want to attach to the operational strategy and the go-to-market strategy and have a plan Where all three of those functions are working together there was this weird trend during COVID where everyone was down-leveling their enablement to save costs, and now I’m starting to see that flip again Where we’re hiring lots of folks that are at a senior level.

They want 10 plus, 15 plus years of enablement experience to guide them on “how do I drive that productivity lever?” “How do I be smarter in how we sell in the market?” Because we do have fewer salespeople and we have a bigger market that we have to attack.

SS: Now, as we talked about in that first question, people, process, and technology, on the people side, what are some of the key things you prioritize when you’re building a high-performing enablement team?

SG: I think the people side really matters in how you build out your enablement team so that you’re embedded enough to understand the business, right? For example, if you have a role that covers everything up to ISRs, right? Inside sales reps, where they’re both covering leads and running the sales process, you need a very different enabler to support that type of practice. And someone that’s maybe in an office with them, as an example, that’s where I think it makes sense when they’re all in the office. Or someone who has experience both in running a lead gen team, also a selling team, so that they can pull those together. 

As you think of the sales structure, that’s where I think enablement has to mirror. This is why enablement teams change from time to time because it’s normal that sales structures change,  and you have to make sure that we’re constantly evolving with them. When those two structures start to look different, like when I see enablement teams aligned by product, right? They’re seen as generalists and they’re less impactful to the overall business. 

SS: That makes sense. On the process side, how have you partnered with your key stakeholders to identify process gaps and solve those inefficiencies?

SG: That’s the question always. Having really strong ops partners and being part of the conversation that you have with your chief revenue officer is important.

I think that the way that works best is that ops gives you visibility to everything that they’re showing to the sales leader. If you have a different lens, the sales leader is looking at like, “Where do I have pockets of inefficiency that I could either reduce my head count or change that headcount around?”

You’re looking at it as, “How do I have cohorts people that maybe are at that 90% mark, that they would make a lot more money and we would make a lot more money if they were at 100% or 105%.” The way I look at the data that’s being provided to me is always, “How can I think of running cohorts of people?”

So for example, I’ve had in the past where I’ve got a discovery coach, someone that I can deploy if there are people in SDR land, AE land, and SC land that need that particular topic area. And by deploying them I’m keeping my business partners. So you’ve got that strategic person that they trust introducing the session with somebody that’s focused on that particular topical area to move the needle as it comes to productivity.

I’d expect that a lot of enablement teams are probably going to have someone who’s that AI specialist over time, where their entire job is to match that internal data set with what we are hearing from our enablement tools. And how can we deploy every call we’re looking at across the system?

Deploy, if we hear X word, one sheeter, a cheat sheet to the rep in the moment. It’s a talk track that gets deployed to our SDR organization, right? Maybe it’s even a technical validation asset that’s going to our enterprise reps as they run into X integration that they don’t run into all of the time.

So I’m starting to see where I almost think SEs are always a secret sauce to a lot of organizations. To me, it’s how we capture what’s in our SE’s minds and deploy it on every call that’s happening, not just the ones that an SE is attached to. 


SS: Absolutely. And then the last piece of the puzzle: technology. How does an enablement platform help you effectively bring your strategy to life? And in your opinion, what is the strategic value of a unified platform? 

SG: First and foremost that’s definitely evolved in the past, like five-ish years. Originally, I would say we were looking at just do you have SCORM packaging. It was very traditional instructional design technology that you needed.

Now, because we’re further away from what is traditional L

In a survey conducted by Zippia, 86% of leaders in the workplace cite lack of collaboration as the top reason for workplace failures. So how can you increase stakeholder buy-in to maximize adoption and collaboration?

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 Gurneet Sagger. Thank you for joining us, Gurneet. I’d love for you to tell us about yourself, your background, and your role. 

Gurneet Sagger: Yeah, thank you for having me. I’m a bit of an enablement veteran before the word enablement was invented. And in a past life, I actually led global sales teams. So about 13 years of leading sales teams, I made the jump into the enablement world. 

SS: Wonderful, we’re excited to have you here. Now, prior to partnering with Highspot, you leveraged a different enablement platform. What was the impetus for deciding to switch platforms? 

GS: Yeah, Highspot for us is really about ease of use to the team. I think many enablement people will relate to a lot of tall tasks ahead of you with a small team. And that’s what led me to Highspot. Highspot was easy to use on the initial demos and the interface. 

SS: I love hearing that. And in bringing in Highspot, you built a really strong partnership with sales and marketing leaders including your CRO to gain buy-in. What are some of your best practices for securing stakeholder buy-in and proving the impact of an enablement platform to your CRO? 

GS: Yes, I think I’ve been very privileged to have leaders that I’ve reported to who are bought into the power that an enablement team can have. I ultimately was given the opportunity of, “Hey, Gurneet, what is it you need in order for us to scale? And what is it going to take?” And one of those key things was having a sales readiness LMS tool. And that’s why Highspot was selected. But throughout the process of getting through budgets, and headcount planning, I made sure that I had buy-in across sales, account management, marketing, and our product leaders. 

SS: That’s fantastic feedback. Now, since implementing Highspot, you’ve seen incredible momentum, including 94% recurring usage and really strong adoption in nearly every area of the platform in terms of adoption. What are your best practices for driving adoption across your go-to-market teams? 

GS: One of the things we did out of the gate is once we launched, there was no exception to be able to relay information out to go-to-market teams unless it was through Highspot.

As a company, we use Confluence, which is a phenomenal tool for the broader team, but for all the other departments to move quickly, for example, product, if there’s a new product update, to make sure that they could roll out without any delays. Having each core product leader provide the enablement team with the information in a digestible way, which could be inputted into Highspot quickly was critical for us.

And we just didn’t have any exception to the rule. Information needed to go out. It had to be leveraged through Highspot and ultimately you want to be able to, as a leader, show the ROI on the enablement tool and the costs that you’re incurring onto the company.

SS: Those are fantastic best practices, I know our audience can take a lot from that. One area that I know that you guys have really championed the success is in your onboarding program, I know that you guys have achieved a 77% active learner rate. How do you use Highspot to effectively onboard and certify reps?

GS: Highspot is the most critical tool for us. We grew headcount from 20 sellers to over 200 on the sales side and then we also grew our account management teams and we use Highspot on every single lesson. We’ve gone from a two-week onboarding program, due to high growth headcount scale, and now we’ve moved into a three-week program. And over the course of time, like many companies, you’re coming out of the pandemic, moving into a hybrid environment. But, we’ve had sellers all across the country in multiple sales hub locations.

And so Highspot enabled my small team to be able to get the learnings out and to be able to track performance quickly. Every onboarding lesson sits in Highspot with all the accompanying resources to make it easy to find for our new hires. 

SS:  Now, in your opinion, what would you say is the value of having a unified platform that allows you to deliver everything from content to onboarding and training, what is the value of having that unified for your reps? 

GS:  It’s just ultimately speed. You know, my goal as an enablement leader is to prove and show that we can increase work rate, right? Not just for our sellers, but also our account management team. And so being able to search something in Highspot. We need to make sure that you can find them.

And if a rep can’t find what they’re looking for, we’ve got good feedback loops so we can keep things updated. But, ultimately, it is getting our sellers and our go-to-market teams, the information they need, as quick as they can get it. 

SS: With all of this momentum for enablement and you’ve grown your team significantly and you’ve really done a fantastic job positioning enablement as a strategic business function.

How have you leveraged Highspot to help you scale the impact of your team on the business? 

GS: We’ve used Highspot now, not only through onboarding, but increasing locations that our sellers move into, new verticals, and new product updates. And so it’s enabled us to execute a lot quicker than had we gone through the manual process or I know for many enablement folks that are still dealing with Google drives and sorting things through that.

And so it’s enabled our leaders to be able to roll out as quick as possible. We want to make sure that we’re providing the very level best for our clients, what we call our partners here. And to do that, we’ve got to certify individuals. We have some critical verticals that we sell into that need a little bit more attention to detail.

Every time we roll something out, we certify our sellers to make sure that we’re reinforcing those learnings and then enabling them to execute. 

SS: You guys are having amazing impact. What would you say some of the key business results that you’ve achieved so far with Highspot are, and how do you go about measuring enablement success?

GS: Yeah, that’s really going to be critical for us going into this year. We’ve gone through two years of headcount growth, and now we’ve really got to start doubling down on obviously overall ramping success of our sellers. But I think, ultimately, we have a phenomenal platform and product and for us to get it into the hands of our partners and our professionals, those are the hourly workers on the platform, as quick as possible, it means education.

Being able to ramp our new hires faster, being able to train a seller one day, and within 24 hours, they’re certified, and that then unlocks further revenue streams, like further account pursuits for those individuals is really critical. 

SS: Gurneet, last question for you. As you look to the future, you’ve mentioned that you plan to take advantage of a lot of the new enablement innovations, like artificial intelligence, to continue to scale enablement’s impact.

How do you plan to leverage AI and other innovations to continue to drive business impact in the year ahead? 

GS: It’s everything from developing our call scoring and making sure that’s then aligned with our rubrics and our scorecards across all of our tool stack.

I’m excited to see what Highspot will do with AI on their product roadmap and we’re already seeing kind of improvements with just descriptions and surfacing content in the right places. And for us as a business, AI is one of those key investment areas. And so as an enablement team, we do make sure that we’re following the same charge that our leaders have set.

SS: It is an exciting future ahead that we have on that front. Gurneet, thank you so much for joining us today, I really appreciate it. 

GS: Thank you so much for having me. 

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.

A study conducted by McKinsey found that 35% of value on average is lost when implementing change initiatives. So how can you ensure maximum value during organizational change?

Shawnna Sumaoang: Hi, and welcome to the Win Win Podcast. I am your host, Shawna Sumaoang. Join us as we dive into changing trends in the workplace and how to navigate them successfully.

Here to discuss this topic is Heather Green, the Director of Enablement at Jellyvision. Thanks for joining us, Heather. I would love for you to tell us about yourself, your background, and your role.

Heather Green: Hi, thank you so much for having me, and absolutely. I started my career in an individual contributor role in sales and worked my way up through sales leadership, but quickly found my passion for enablement early on.

I’ve worked for small startups to multi-billion dollar consulting firms and through it all, I consider myself to be a bridge for the sales organization. In my current role here at Jellyvision, my goal is to provide our revenue team with really everything that they need to be successful, from net new business to retention, and that’s through our direct channel and partnership business. So my team works to bridge the gap for our revenue teams. Marketing, product, and operations and support our sales team in any way we can.

SS: You mentioned you have an extensive amount of enablement experience. What are some best practices you have when aligning your enablement strategy with the strategic initiatives of the business?

HG: Yeah, it can be a challenging one sometimes. I would say hands down building internal relationships with our business stakeholders is incredibly key to bridging those two gaps. Everyone has the ultimate goal of providing revenue at the end of the day and making us profitable, but each team has their own goals that might not overlap with each other.

I found that it’s really important to have consistent transparency and ongoing communication to make sure that I’m working with these teams in tandem which causes minimum confusion at the end of the day with our revenue teams. So a strategic initiative could be launching a new product or feature, but then that could be in peril with another initiative that RevOps is perhaps launching something new with this system, so it’s too much at once. It’s really important that we get that buy-in from our leadership teams across the organization to make sure that everything from a product launch to new rep tech, to a marketing campaign, that it’s all working cohesively together.

SS: That is amazing. And you did mention though, that it’s not always easy. What are some of the major challenges that you’ve come across in your career when it comes to effectively really bringing your enablement strategy to life?

HG: It can be tough sometimes. There are definitely challenges associated with it, but where would the fun be if it was so simple all of the time?

So, especially when it comes to enablement initiatives, it’s so very important for me to make sure that our leaders understand the value of the why behind the initiative and the what’s in it for me for the individual contributors and ultimately what our goals are going to be at the end and what everyone’s going to get back.

By getting that leadership buy-in, we can get everyone on the same page. It’s oftentimes an uphill battle but I’m a big fan of throwing on my hiking boots and climbing, right? So each step when we’re rolling out a strategic initiative it’s a long-term play. It’s not a short tactical thing. Each step is learning more about what’s important to each leader and then how we can pivot and adjust to best meet their needs to make sure that we push it forward.

SS: I love that analogy, too. Now, when you first joined Jellyvision, you noticed some key challenges with the team’s previous enablement platform. What were some of those challenges and what was really the impetus behind deciding to make a change?

HG: Other than me adoring Highspot, right? I’ve been such a fan for many years and I was lucky enough to use it at other organizations. But coming to Jellyvision for me a few years ago, I was thrilled to see how extensively our team had invested in the tech stack.

A lot of times you don’t think many organizations. So as an enablement leader, it was just music to my ears, but with our previous content management system and engagement platform, the first thing I did when I came in was I looked at it and I did an audit. I’m looking at the backend analytics, but then really seeing

Who’s using it, who’s not, what the top performers were doing, what our lower performers in that middle ground were doing. The spoiler was that not a lot of people were using the platform, which, also hurts because as an organization, you’re making that investment and you need to see that return to keep it.

And so by digging in, I started doing many different conversations with our revenue team and individual contributors to determine. What was the reason behind not using it? And the key feedback that we received is that it was just difficult to use. It was hard to find content. It was even harder to edit content.

And so it was like, why would I do that when I can just go into my Google Drive and find what I need and then edit and send it that way? It was just resounding results that it was difficult and no one wanted to engage with it. But knowing the value of a platform like that, I was able to then start putting the seeds down for making a change.

I knew we were coming up on a renewal in the upcoming six months. And so I started asking additional questions on if it did this with this work and kind of planting the seeds. And then finally got to a pilot point of taking it with our key top sales reps and showing them what Highspot could do. And then from there, we were able to move the conversation forward in making the change once they saw some of the key things that Highspot was able to offer us.

SS: I think that is fantastic. And, in addition, I know that you did a lot of work to ensure that you had buy-in from leadership to prove why the change was needed. What were some of the things that you did to ensure that you were able to secure that buy-in?

HG: Buy-in is imperative, right? Especially when budgets are tight and they’re getting tighter and tighter every single day. So for me, it was gathering all of that data from our reps. So not only the analytics in the platform that we currently had and how rough it was from an adoption standpoint but then the verbatims from our reps of saying, “Yes, if we could have a Digital Sales Room, it would mean the world because then I would be able to track with our broker clients or if I were able to be able to easily find something and edit it in the platform, I would use it.”

So I pulled together a lot of the verbatims and then I put together the ROI breakdown of what we could see in the platform. We were lucky enough in the business case I put together to start Highspot three months before our previous contract ended.

That way we could load everything into Highspot, and do a full content audit, so we were starting clean. That’s so very important too, because what you put in ultimately will drive what comes out. But that allowed us time to do that audit, load, and tag everything appropriately in Highspot. And so that way we had a really, and do enablement ahead of that as well, to start again planting the seeds that change was coming. And these are the cool things that you’ll be able to see with it for us to have that smooth transition once we ended our previous agreement.

SS: And since you guys have implemented Highspot, how have you overcome some of the challenges that the teams were previously facing?

HG: Adoption can be difficult across the board, but with Highspot, luckily, our adoption has been significantly higher than what we received with our old platform.

For us, I think it was consistently highlighting what was working, what top performers were using, and what they were seeing off of it, being able to track it back to specific deal conversations, and how they were able to move those opportunities forward through the content they were sharing. We also hold bi-weekly office hours where we share our best practices.

And in those best practices, peer learning is incredibly important for us. Making sure that we’re sharing what’s working with our tools and oftentimes when you have one person see what someone else is doing and how it’s helping them, that also helps to drive it forward. We also offered consistent training from video courses to one-to-few to one-to-one sessions. Luckily we’re in a smaller organization where we can offer that level of support, but to make sure we’re overcoming any obstacles, if someone wasn’t using the platform, myself or one of my team members would reach out and say, “What’s the problem, what’s going on?”

Oftentimes, it was just that they were uncomfortable trying something new, but after we showed them or they spoke to a peer and we had that connection, we’ve been able to get a much higher adoption rate.

SS: Fantastic. And you guys do have incredible adoption. I think you guys are at about 89% recurring usage. What are some tips that you have for building trust with reps and helping them understand the value of the enablement programs that you’re delivering?

HG: It’s really due to my team. Shout out to Max Costello, she’s hands on our Highspot champion, and we call her our enablement queen. She has done an amazing job wi

According to research conducted by Sales Enablement PRO, organizations with dedicated enablement efforts report a nine percentage-point increase in average win rates compared to organizations that do not have dedicated enablement efforts. So how can you make sure that your enablement strategy is setting your organization up for repeatable success?

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 Gail Behun, the director of revenue enablement at LivePerson. Thank you for joining us, Gail. I’d love for you to tell us about yourself, your background, and your role.

Gail Behun: Thanks for having me. So I have been here at LivePerson only a couple of months, but I’ve been in revenue enablement for about ten years. I started off as a seller and became a sales leader, and then really found the impact of sales enablement to be so powerful on the entire org. And I’m incredibly passionate about empowering salespeople and associated teams to be as efficient, and as effective as possible.

SS: I love that. On that note, I think one of the things that stood out on LinkedIn, you also mentioned your passion is around building really scalable and repeatable sales success. In your opinion, what role does enablement play in driving that for the business?

GB: I think we have to be the cheerleaders for scalable and repeatable. I think our sales leaders are very good at solving individual problems, individual quota issues, and individual deals, but enablement is well suited to look big picture at the processes and tools that we have in place that make that process repeatable. Revenue enablement has the opportunity to really streamline the effectiveness of our sellers through our tools, our talk tracks, and our training. And we’re uniquely positioned to do that because we’re not involved in a deal. We’re involved in every deal on some level.

SS:  Absolutely. Now, I know you all just implemented Highspot, but prior to that, your team had multiple separate tools to deliver enablement programs. What were some of the challenges that your organization faced with that approach?

GB: I think every organization is faced with the dreaded G-drive scope creep, where there are ten versions of this, and nine versions of this, and one lives on this drive, and this rep has downloaded the deck, and now they’re making changes on their own, and there just wasn’t tight governance. And as organizations grew, especially radically during COVID, it just got out of control.

Having a unified tool became a must-have as we and a lot of other companies have taken a slowdown in hiring and an opportunity to reset our systems moving forward.

SS: Absolutely. From your perspective, how does having a unified enablement platform help you to overcome some of the challenges to your earlier point around being able to drive scalable and repeatable sales success?

GB: My goodness, the amount of time sellers spend not selling is upwards of 70%. It’s just crazy the amount of time that they spend getting deals through the process and looking for materials and where we can cut that time down and make them more efficient. Gives them that time back to be more customized in their engagements with their customers and be able to expand their business offerings and value rather than working through cumbersome systems. And so a single source of truth is critical to that. And that’s what a unified tech stack provides. It was one of the biggest reasons for us moving to Highspot, but the bigger reason is the buyer’s experience and the Digital Sales Rooms, and having those both under one company umbrella made it a win for us.

SS: I love that. Now, another key reason your team decided to implement Highspot was to reinforce the value of enablement as really a strategic tenant for the business. What are some of the strategic initiatives that enablement supports at LivePerson and how will you leverage Highspot to help?

GB: Our team is relatively new. LivePerson went through an enablement reset. Because so much of our sales motion is grounded in the expansion phase, so much of our initiatives this year are around account expansion. And, as I said, Digital Sales Rooms are a game changer when it comes to interacting with existing customers and showing ongoing value.

And so the ongoing value metric is incredibly important for us as we double down on that facet of our business. It also helps us dramatically when you’re talking about multi-threading and getting into additional stakeholders because with existing accounts it’s very easy to have one great champion but not go deeper than that, and Digital Sales Rooms and the engagements we have through Highspot will allow us to have more powerful multi-threading and more opportunities to open more doors within our client account.

SS: I love that. I think that’s a great initiative and a way for Highspot to help support that. Now, I know one of your goals in implementing Highspot was also to ensure a really strong alignment with marketing. What are some of your best practices for collaborating with marketing and how are you driving strong alignment through Highspot?

GB: Yeah, I don’t think there’s anything more important than making sure our sellers are up on those marketing messages because those marketing messages, that’s what marketing is talking to our accounts and our customers out in the space about, it’s what we’re known for being thought leaders: having great analytics and information. So, having a single point for that information within Highspot is incredibly important.

Our marketing team and our field marketing team each have their own sections: field marketing, especially because we do a ton of customer-facing events, and so for them to organize that for all of the sellers to see where they’re going to be out live and in person, “What type of events? What are the talking points?” Become critical as well. Sellers, even before pre-COVID when we were all at home, but especially now, we have to be able to tell each other’s stories. And so marketing is great at collecting those stories. They’re telling customer stories through case studies. Enablement, we’re telling customer stories through what we call win stories, which are more behind the scenes.

So we’re creating win stories that let us interview a seller, tell the good, bad, the ugly, and then we can tie those to those case studies. And so it gives the sellers the information they need to go out to market, but also to have the conversations behind the scenes.

SS: Fantastic. Now, as we mentioned early on, you have started the work of establishing a great foundation in your implementation, and I know that you’ve just launched Highspot to your teams. What were some of your best practices to ensure a successful launch? And how are you measuring success?

GB: We had an amazing CSM implementation manager on the Highspot side who gave us some great advice, and we did a lot of ramp-up activities. We had a cheerleading squad with internal leaders who were making videos that were hosted on the Highspot page, talking to our potential users, saying, “Here’s what you’re going to love about it, here are some ways you’re going to use it.”

We wrangled in our frontline managers and our leaders to speak to why we made this move, making sure that they didn’t feel like it was just another piece of software we purchased, and that this was critical to the way that they did their jobs. Our senior project manager on the project gamified a great deal of the onboarding.

And so you could get points for different activities and she would post out the winners. And we’re not done. We’re going to continue to share those videos over the next couple of weeks. We launched Highspot at the same time, right before our sales kickoff. And so our sales kickoff pre-work was actually to create a video and host it on Highspot.

I got everybody in and using the tool. And now we have these great videos people have made that we’re scoring and we’re going to give prizes out over the next couple of weeks. So we are going to continue to hype this. We’re going to do some, sharing and awards for a great Digital Sales Room or a great engagement that somebody’s utilized the site for, to show those best practices.

And then continuing education. We just have to continue to have office hours, see what kind of questions people are asking, and make sure the site is answering those so that we can make sure we continue to build it out. We’ve launched it, but honestly, I think we’re probably 30 to 40 percent done, meaning we have a lot more to do, and that next phase is going to be driven by more interactive content, more video content, and more user-driven content as they push us to add and make more valuable for the site.

SS: And one area in particular, because you’ve mentioned it early on in the conversation where I know you aim to achieve strong adoption is in the use of digital rooms. As you’ve mentioned, it’s a great way to get deeper into the accounts that your team’s going after. How do you plan on driving adoption of Digital Rooms with your revenue-facing teams?

GB: That’s a great question. Partially by cheerleading it through their front-line managers, making sure their front-line managers are asking, Hey, here’s this deal you have in play. Let’s look at your Digital Sales Room.