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Calculating the Real Impact of Your Sales Content – Soirée, San Francisco

| 49 min read


Jen Spencer: Good morning, everybody. I’m really excited to talk about one of my personal favorite topics, sales enablement. The reason why is because I come from a world of very revenue-driven marketing. And to me, sales enablement has always been such a critical part of what my job is as a marketer. Now, it’s so wonderful that there’s actually a name to it, right? And there’s a community of people. I’m looking forward to digging into this with our panelists. But before we do, I wanted to ask a question.

When you think about your sales organization, how many people here have some kind of standard celebration that sales reps do when they close a deal? Like, GIPHYs that are sent out over Zoom or Slack, or some people I know have gongs, they hit bells, or things like that. How many of you know that your sales reps will consistently cite the amazing sales content that they used during the sales process to close the deal, the ROI calculator that changed the prospect’s mind, the vendor comparison guide that squashed out the competition? No, nobody. We tend to forget about that as sales reps when we close a deal.

So, I’m also half marketer, half salesperson, so I have some empathy for them. But the fact of the matter is that we all know that sales content does have the power to influence deals, influence revenue, and the more that we can actually start to quantify that, the more we can actually identify the analytics that are surrounding that content, and then we can actually improve it. And we can start to do really exciting things and we can look at how do we improve MQL to SQL conversion, SQL to opportunity, opportunity to close? How do we take a 90-day sales cycle and shorten it to 60? This is the power of sales content. And this is what we’re going to talk about today.

So, I have questions for the panelists. I’m going to have them introduce themselves and then we’ll leave some time at the end for some Q&A. As you have questions that are coming up during the discussion, please do jot them down so you don’t forget. Alright. So, let’s start, we’ll start right here with you and share a little bit about yourself and what your company does and why you’re here.

Tony Kavadas: Absolutely. Good morning, everyone. My name is Tony Kavadas. So, I handle global sales and alliances for a company called MediaFly. Before I get to that, I just wanted to say a little bit about my background, because I too am passionate about sales enablement and productivity, etc. I’m going to give you a different angle today because I’ve been in sales for 23 years. Technical sales, sales, sales management. I’ve even run productivity organizations, the old term for sales enablement, for very large organizations. And you know, when I ran into MediaFly, I was so enamored by the fact that now there were tools, better tools, out there to help people calculate ROI, sell better, and so forth. So, I joined the company and now I want to share that passion and help other businesses adopt technology like these. Thank you.

Oksana Walton: Hi everyone. My name is Oksana Walton. I lead — and it’s a highfalutin word, I’m a team of one — sales enablement at a small (compared to some of the panelists) company. We are mighty team of 300. I have 24 sales reps on my team, which could make things easier and harder at the same time. I’m in the, I think, fortunate position to build sales enablement from ground up and also unfortunate position because “we hired you, why do we need to give you anything else?” So, a lot of challenges of smaller organizations and a lot of rewards. Chef is a small Seattle-based company and we help companies manage complexity with application development, delivery, updates, and security through software. To give you like a little bit of the level down from that, applications.

So, some of our customers, like Alaska Airlines, they call themselves a software company with wings. What it means is their business value in applications that they deliver to their end customers. It could be an airport terminal, it could be mobile app, and there’s a very large complexity that lurks below this application life cycle. So, that’s what my company does. Long sales cycles, very complex, lots of key stakeholders in the process. A little bit about myself, I kind of fumbled upon sales enablement, like many of you. I’ve done many things in life, including sales, which I guess made me credible to teach other people how to sell.

Juliana Stancampiano: I’m Juliana Stancampiano. I have a company called Oxygen. I started it in 2008 in Seattle. And like many people, I also stumbled into the sales enablement before it was probably even called sales enablement, similar to your story. What was interesting as we looked at the different panels that were here today is that we have a lot of passion — Oxygen is a services and technology company working with a lot of Fortune 1000 companies, I would say, and a lot of different experience across many, many different types of companies, different industries. And we have a huge passion for how the salesperson is actually going to use the thing that we’re creating in order to get a meeting, get the next meeting, get the next meeting, close a deal.

Over the last few years, we’ve found that we end up working or running into more and more of the product marketers and the marketing side. And we come at it from a very different angle. I was kind of curious about this panel and what we were going to get out of it and like having that mix of marketing and sales enablement and sellers. I think we’re all chasing the same end goal, but we come at it from such different angles. I think that it’s a really rich conversation that we can have about what is it that we’re actually driving and how do we get that one thing that they will then say, “I closed this deal and thank goodness I had X to get there.” Or why. I’m excited to have the conversation today.

Charles Derupe: Hi, everyone. Thank you for coming here today into this panel. I know there’s a lot more, so thank you for your choice. Thank you for having us. My name is Charles Derupe. I am the sales content manager at Square. Many of you may have heard of Square, but I think one of the challenges that we have as a company is evolving our brand, right? A lot of people still know us as the little white reader. But we have this ecosystem and this platform. Where I can come from today and help out is how did we grow in our thinking to get to 50 sales reps all the way up to 200 international multi-cities? Then, how do you work cross-functionally to have that change in brand, to have that change in mindset for your salespeople and for the prospects that they sell to? So, I’m very excited to be here today.

JSp: Wonderful. Well, Charles, I want to keep you in the hot seat, and because I think it’s so amazing that your role is 100% dedicated to sales content, and we’re here talking about the impact that sales content has. So, how do you define that? How do you measure that to kind of show kind of progress and growth within your own department?

CD: Yeah. So, I’m going to break it down in two ways. First is going to be how it impacts your salespeople internally. I think for the most part, everyone has the same idea of how does it affect win rates? How does it affect flips? How does it bring in more business? But a lot of businesses are growing right now, a lot of sales enablement teams are starting with one person where that’s not their main priority for content. So, when you think about the complexity, wherever it is, I think impact is how do you enable your sales representatives to have more efficient and effective conversations with their prospects in terms of value and differentiation. How do you have them talk about it in a professional way to gain the confidence of the prospect that they can be consultants? So, that’s one way to look at it in a 10,000-foot-view.

On this second end, which is cross-functional, I know a lot of us here have different teams, disparate teams that may work in silos. A lot of us are working on relationships. But for them, impact is completely different from sales, right? So, if you’re working with marketing, it may be impressions. If you’re working with brands, it could be what are the values and the mission of your company. Again, taking a step back, the impact here is all about working together towards the customer journey, the customer path.

As sales, you sit in a critical place, because you are kind of that gateway into the rest of the funnel, to pass it down to an account manager, etc. So, how are you thinking about that customer journey? And I believe that’s how you get buy-in from the rest of your organization to help support you and to help support the greater organization.

JSp: Are there other panelists? Are you seeing a similar definition of sales impact? I know in a lot of organizations it’s really focused on revenue of how are we driving ROI and now even just revenue. But new business revenue tends to be this focus that we have with blinders on. I don’t know if anyone else has anything to share on that topic.

OW: Yeah. I think it kind of depends how you define content because there are a lot of things content can help you do. And one is to convert your leads, another is to create thought leadership. Third is to educate yourselves. I mean, there’s a lot of things and every one I think is measured slightly differently. I like the tying it to the customer journey, and it is ideally tied to your seller’s journey and the Salesforce stages, right? And your CRM.

From my perspective, I’m measured on, of course, lead conversion, as any marketing team is. I’m part of marketing. So, we are trying really hard right now to find ways to tie our metrics to our pipeline generation metrics and digital marketing metrics.

JSt: I’d probably add to that as well that what we’re seeing across clients is that they’re breaking it down more and more. So, to your question about there’s this very macro view, yes, we all want to drive revenue. But what does that actually mean and how do we drive revenue? And when you start breaking it down into the steps, depending on all the different sales roles that you have, it looks different across the different roles.

We recently heard about driving from marketing where somebody was saying “we’re expecting to get conversation ready leads.” So, if you think about that from marketing to sales, what does the conversation-ready lead look like? I find that that’s something that you can very much measure. Whatever it was, the push that’s going out and what people are responding to. And is it, “Hey, somebody clicked on this and so you should go and talk to them.” Or is it, “Hey, somebody clicked and they specifically were looking at these areas.” Now it’s a conversation you can start with somebody to be able to start that sales cycle. So, I think we’re seeing it being broken down in a lot more of a micro-view versus the big macro “Yes, that’s out there and we all get it”. But how do we get there and how do we help our sellers get those is becoming more important for our clients.

CD: It’s like teeing up your sales reps to be able to, again, have that effect.

JSt: Right. I mean, I’ve been on the end of like, “this person reached out.” It was like, “well, do you know why?” No. Okay. I won’t go create magic.

JSp: I love that you’re pointing out the relevance of the context of the click, not just the click itself. Tony, what are you doing? What are you seeing in your organization to track the impact of sales content?

TK: Yeah, absolutely. Great question. We absolutely use our platform, both from a content management side as well as the presentation platform, and we use our ROI tools. People in our company do actually say “that ROI tool helped me close a deal.” But what’s really important as the buying journey has changed as we hear from the analysts that I see walking around here today, we know that the sales reps are no longer the early-on educators as they were when I started selling. That talks to the micro-content and being able to have different types of content available. Not necessarily case studies anymore, and heavyweight pieces of content, but more flexible and dynamic.

What we do is we make that available to our sales reps and we actually tag it to opportunities within Salesforce, within our CRM, right? So, we know at what stage in the cycle is this piece of content being used? And then we can track that back to actual revenue and pipeline generation, so we know what content we should do more of, what we should do less of. What I’m finding is in the past, systems allowed us to track content that got downloaded, right? I went to a portal, I downloaded it, or someone went to the website and download it, but I didn’t know how many times someone viewed it or actually used it.

I feel like we’re on this verge of a new dimension of data to marketers, which is great. My wife’s a head of marketing authorization and I’m in sales. So we’ve got that same mix in the household. But it’s great because now our marketing department knows exactly what content is working and what doesn’t. We’re using machine learning and other things to kind of be a little bit smarter than we can think and figure out, what should we no longer use? What should we promote at different stages in the sales cycle, and so forth. And ultimately, what drives revenue.

JSp: Excellent. One of the things that I’m always reminded of when I come to events like the Sales Enablement Soiree is you come to sessions, you get all this great information, there are all these things. Yes, these are things that I believe in. We want to start implementing, we want to execute, but then the reality sets in of you’re only one person, one team, you can’t do everything. You need to prioritize. Oksana, being from a smaller, in comparison to the rest of the panel, organization, when do you start a content strategy? What makes the most sense?

OW: Yeah. Well, again, it depends what you define is a content strategy. This is probably my third company where I come in and the first meeting with the leadership, they’re like, “someone’s got to clean this cesspool of our content repository.” Fill in the blank. It could be Box, G-Drive, Dropbox. “Oksana, would you be able to go through the millions of documents and just delete the old ones? Can you do that for us?” I’m slowly dying inside, and how do I push back as hard as I can on my first day? How do I dodge that bullet?

The step we are at at the small company, and I’m really curious to hear how middle-size and bigger companies handle this, we are really putting it in the internal interface that is useful, accessible, and sales reps love to use. I love the combination of CRM. We’re not quite there yet, but that’s our stage right now. Whether it should have been started before me or after me, it’s hard to say, right? Because smaller companies have a lot of things on their plates and first they need to create a lot of content and then they start thinking about how they’re going to actually organize it and strategize around it. So, my answer is as early as possible. The reality, you know what it is.

JSp: Maybe we can get into some examples. I love hearing what’s working in an organization, as granular as possible. Charles, what do you see, what kind of content is resonating the most? Do you see sales reps are attracted to this or customer success teams are attracted to this? You must kind of notice some things that are a little hotter than others internally.

CD: Yeah, of course. The other day we went to our sales team meeting. I was like, “Hey, there’s this new piece of content that we created” and what makes my heart very happy is afterwards, I get the Slack of like, “where can I get this? Can I send this out today?” On one end, we’re talking a lot about external content. And so in terms of external content, what I love seeing is our case studies. But not just case studies, video case studies, and why video case studies, right? There’s research that indicates that 95% of videos are taking in and have more retention than text. Purchasers are decision-makers. There’s a 64% to 85% increase in their intent to buy after seeing a video. And it just makes it alive, right? Rather than writing in an email, you see it, you see the integration of your product. For us, we’re seeing a lot of demand for these kinds of case studies, especially if you have a wide range in products that you have. That’s one thing.

I would be very much remiss as well to not mention, but all prospects want accurate information. So I know we’re talking a lot about external content, but what are you doing to make sure that the internal content you have is also centralized, being used, and being updated in a way so that your salespeople can be more credible? So, that’s a couple of things we’re seeing there.

JSp: Great. I’d love to hear from other panelists, examples of whether it’s external or internal content that you’re seeing a lot of success with.

Yeah, go ahead. Well, I will share because it’s actually working right now, and it’s cheap to produce, meaning it’s not taking a lot of resources from you or you don’t have to hire a lot. Podcasts, internal podcasts. The idea is to mix the media, right? You are feeding sales reps PowerPoint, and they are sick of it. So, why don’t you convert the same story into snackable podcasts. Come up with a fun name that you use internally and record recent wins. Just key points. Just do a little deal anatomy and release it in that snackable format that everyone can listen to on the go. They’re a highly mobile force. Sales reps love it. It’s easy to produce, easy to start, and it also feeds the pipeline for customer references. The customer success team, they want to know what recent wins are, so they fit it into their pipeline of customer references. So it kind of works as a win-win. And you get to know the sales team and you get to know the most recent sales wins.

JSt: Yeah, I would just add into that, and this kind of goes back to the content that you were talking about earlier, is that we have a proliferation of content today, and our problem’s not, we need more content. We need more very specific content and we need to know how to use the content in order to continue having these customer conversations. We’ve been working with a lot of clients and getting very granular per role. What does somebody need? And giving them one place to go depending on what their individual sales role is. With all of the curated content, which is where the sales enablement responsibility comes in as you have to keep it up to date, curated, easy to access, understandable, and we’ve been packaging things where it’s kind of all these different modalities in order to do something with a client.

And it’s more of a package view where it’s like, “Hey, here’s some videos of how other sellers have done this before that you’re going to want to watch.” And these are like low-end videos, to your point, like record it via Zoom or whatever. We’ve had sellers in airport lounges doing their recordings. It’s very authentic from that standpoint. And a lot of times it’s, this just happened, this is how it went, and then packaged with, and here’s some of the documentation you’re going to need to go and edit this potentially for your prospect. But here’s the kind of tools or resources that you have in order to do this sale. And so not just putting it out there, but making sure it’s super relevant. It’s based on the role, because then you’re able to start measuring the content, which is kind of where we started the conversation is, how do you measure the success of the content if it’s not role-based and based on what the role is expected to do in sales? Everything that we look at, and that’s why we got into the technology side, because being able to do this in a role-based view is not necessarily easy.

JSp: Do you want to add, Tony? I was going to ask you, what are some of the ways that you measure? Then also the other thing I’m curious about is once you know what content has the most significant impact, how do you make sure your team is prioritizing that content over something else that maybe they’re just accustomed to because they’ve been sending the same generic email template out to the same group of people for two years?

TK: So first, if I could just add something on the table, because I thought all that was really great feedback. One thing that we’re doing with our direct or indirect sellers is more dynamic content. So what I mean by that is we still use presentations, but we don’t use monolithic 30 page, 60 page decks. We call them vignettes. So think of a mini-decks, snackable decks. What we might do is we might have a deck that talks about the different lines of business. Everyone’s got their wheel of value, right? From there, when you’re actually going in and along with the way the sellers changed, the seller chooses their own experience and the rep will need to be able to go, but the rep has to be able to pivot, and they have to be very flexible so that you could click on one area that says, technology or architecture, and it might pull up a really detailed slide. You might click on another one and it pulls up a video, right?

So we mix and match very dynamic content to do that, which is really neat, and allows that seller to be, I call it the moment of the bead of sweat, the moment of truth. When you’ve got to answer in front of that customer in a face to face meeting or on the phone, and it’s either you or you might miss the next call, right? You may not get invited back.

Your next question was about how do we promote good content and things like that. One of the things we do is on the one side, we do leverage CRM a lot. The reason why I talk about CRM is because CRM or a marketing automation software has great details and PR attributes about your customers and prospects. We’d be remiss not to use that in serving up the right content to our sellers. Because some of our sellers have five minute sales cycles. Some of them have long sales cycles. No matter what it is, that one interaction I’ve got, if I come with one piece of material and it’s the wrong one, I might lose the audience and I might not get the next meeting. Because it is all about getting the next meeting, moving forward, etc. For customers and for our team that doesn’t rely on CRM as heavily. We also can just promote content. That is widely used in the system. We know what good reps use and we can promote that. And we use machine learning and reporting to kind of surface that material so that our sellers are always going to be out there with what we call the next best piece of content.

JSp: You make it sound so easy. I’d like to go back over to Charles and Juliana. I’d like your opinion on this too. What are the barriers, what are the challenges? What are the things that interfere with our master plan?

CD: Can we have another hour on that? There are a lot of challenges, especially if you’re a growing sales team. When I was thinking about this, it’s like they are kind of three really big ones, which is one, cross-functional players who are going to help you out. If you’re a team of one sales enablement person, you can’t take 10 hours per week creating content. You have to be able to get their buy-in to say, “Hey, yes, this is aligned with our goals and this is aligned with our strategy. And yeah, this is going to make an impact on the customer journey.” So, that’s a really big barrier there. As enablement folks, you have to do your research of what are the goals of your marketing team, of your brand, team, of your studio team, and where do those things align? And say this is part of the customer journey.

The second thing is your tech stack. As you grow, especially if you’re small, you may not have the money for really sophisticated solutions, so you just have to start somewhere. How we did it when we were starting is take surveys, right? Like ask them do they feel prepared? Do they feel like this content is talking directly to their pain points?

Then I think the third thing is training. If you have your own trainers and you say, “Hey, I want to dedicate an hour of training in this quarter or in this month”, you’re probably going to say, “Hey, there are a lot of skills training that we’ve already got backed up, so we probably won’t be able to do that”. You have to find these small ways to integrate this. Whether that’s a sales team meeting and you’re launching a new piece of content. Tell them where it’s going to be used, how it’s going to be used, and where they can access it. Same thing with, we have an internal sales newsletter to tell them, “Hey, these are the new content that you have.” Again, reinforce that this is where you’re going to use it. This is how you’re going to use it, who you’re sending it to, and where you can access it. So, those three things, if you can figure those out, 100% please come to me and tell me. But it’s a little small progress.

JSp: I love the sales newsletter and now maybe we need to up-level it and we can do an internal podcast. You know, these are the specials of the day to share with the sales team. I think we have time for one more question here. This is kind of a quickfire question to end on: the biggest takeaway. If there’s like nothing else that everyone learns today besides this. I’m really putting the pressure on here. What’s the biggest takeaway you want to leave these sales enablement professionals with? We’ll start with Tony.

TK: Yeah. You just made a comment saying “you make it sound so easy” and I would say what’s neat, and I guess I started my monologue with this, but not on purpose, but it just kind of came to fruition. When I was back in sales enablement role, we didn’t have toolsets that are out there. And so I think the biggest takeaway for me is that there are different ways to be looking at content and analyzing it, as I mentioned. A new dimension of data of what actually is getting used with customers, I think is fantastic for marketing people to understand what more content should we do.

I will throw a quick thing in there. One of our customers is Pepsi. And they used our system for six months. They ran reports and they basically determined that 99% of the content they created for sales never got used. So, if you think about PepsiCo and how big that is, how much, I mean, millions of dollars were spent, but they ended up retooling their strategy and coming up with a better content strategy that was more effective to engage with their clients. I think for me, the big aha or the thing to take away is that there are things out there, like us, that could help you get up and running very fast and get really good results.

JSp: Oksana, a quick tip?

OW: I’m thinking back to your comment, aligning your content to the buyer’s journey. I think it’s a powerful exercise. You can quickly go through and define what the journey looks like. Ideally, your sellers are going through the same journey and just create a bill of material. You know, what does the content look like through the stages? You can do it through some qualitative surveys and this quantitative analysis, but start there and then you can maybe wind it up and identify your gaps. For a smaller organization, that’s a good way to attack this.

JSt: I would say ruthless prioritization, both of what you’re doing and what’s going out to your sellers. Know why you’re doing it, and know how it’s supposed to be used. If it’s not clear, don’t do it.

CD: For me, it’s sales enablement or sales content is a team sport. The earlier that you can create these relationships with your cross-functional partners, not only will you have more access to funding, but you’ll also have access to manpower. Then at the end of the day, you can say, “Hey, our sales team not only enables our salespeople, it’s also creating a greater impact to the rest of the organization.” Plus, they have tech that you probably don’t have access to today to gauge the metrics of how their content is being used. Really utilize them as a resource. But the first part is the buy-in and aligning on your goals.

Emcee: Excellent advice. Thank you so much everybody. Thank you all. For me, the big takeaway is, it’s not just about content, it’s about the guidance and the context around it and the ability to close-loop that with actually measuring it. Really good discussion. Let’s go to the audience and take a few questions. Right here in front.

Audience 1: Thank you so much for such amazing insight. I’m really curious to understand how you view that balance between coming from that marketing perspective and kind of that prospect and getting that pazazz out there versus training content to make sure that your sales teams, your channel partners, and even your customers have the information they need for new things, break fixes, things like that. And how you balance that life cycle and that production life cycle as well?

TK: We kind of look at readiness and how do we get someone ready to go out and have that discussion? And it could be sales, it could be channel. It could be whoever, right? That’s going to go out and talk. And then we’ve got specific content that is aimed at how do I engage with the customer and so forth. It’s a pretty clear delineation because we even include quizzes and lessons and we allow them to record what they do. Again, video is always great. Short video, so now that you did this, do it back into the camera on your computer and it goes to your manager and they look at that minute to see how you’ve done it. To me, it’s very distinguished as far as, how do we educate first, get people ready to go out?

CD: If you’re balancing as well between internal training content versus external content and saying, should I be focusing on this? Take a look at your sales strategy and find out from your managers and your leads of where in the sales funnel they’re having problems. Then that can help you to say, this piece of content should help that from a sales concept, professional perspective. Maybe it’s like we’re having troubles just sourcing people. How are you taking a look at what are those intriguing value points and impact of other merchants that have used our product.

JSp: I just want to add really fast to, to this conversation as well. I started my career as a high school teacher. I started from the perspective of, “okay, the students need to learn this and how am I going to reverse engineer the way that they’re going to understand it and receive it?” And that same situation, that’s the same thing applies whether you’re talking about external, buyer-facing content, and you’re talking about internal. If I send a sales newsletter out to my sales team, but they’re not going to read it, then this is the feudal exercise, right? So, it’s the same thing for any content you’re creating externally. I think you really have to dig into the psychology and the behaviors of how people act. You make sure that the messages are going to be accessible because the worst thing ever is for a marketing team is to produce a lot of content and then it’s actually falling flat with our audiences, both internal and external.

Audience 2: The company that I’m working at, we’re hiring 90 new sales reps every single month. So we have this constant challenge of brand new learners versus experienced learners or those that have been at the company for a year, two years, three years. It generates this interesting challenge for us, at least around change management. As we deliver new content, they may not have context of what’s being changed. Do you have any best practices that you’ve used to kind of help you in your change management that just make that much easier?

CD: Is this in terms of internal content or external content?

Audience 2: In my case, it’s internal.

OW: I was part of the company that was rapidly growing, not at your scale but pretty close. We ended up really breaking up the beginner versus advanced, especially on the onboarding content. Onboarding content was really focused on soft skills, our selling process, our selling methodology. Then we would release the new hires to the wild and bring them back for advanced where you really put a lot of product and a lot more technology, if it’s a technology company, or your solution-based content in front of them. It’s a very good question.

JSp: Your sales reps, are they being hired in cohorts or is it just like every day you don’t know who’s going to show up near today?

Audience 2: We have new hire classes once a month, but they are starting every Monday.

JSp: I would highly recommend a cohort kind of classroom-based approach. Then they have a team that they can rely on to collaborate with, just like a study group, and you set those expectations to support them. It’s a bit more of an infrastructure change. But really when you’re onboarding at that level, I think that’s the only way you stay sane.

CD: Yeah, and I think a big part of that is your LMS as well, right? You probably have onboarding that’s a classroom, but if you have different sales reps in different segments or different roles, you need to have those paths in your LMS to say, you have this skillset, here’s content specifically for you so that we can release you into the wild, but you’re still being supported in your six month, nine month ramping. So, really try to tie those in. And in terms of external content, make sure that those are in your trainings as well. If you’re doing an outbound, a skill-set training, say, this is how you use content and outbound. These are the content pieces that you should look at. Merging all of those together in your learning is really important.

TK: One other thing that I’ve done in my past is we did have the cohorts, which is a great idea, but we’ve also done a buddy system so that you take someone from the same team that’s been around a little bit longer and pair them up. That’s kind of like an uplink, if you will, to help navigate this. If you’re taking on 90 people a quarter, that’s a lot. You’ve also got attrition and other things. One of the things that’s really important that we do is we share what is the most used content and what’s most successful content. And so that way they can go in one place on a page that says, you should be looking here for content to engage with customers and sales cycles, but those are some of the things that we’ve done.

JSt: The only thing I’d add in real quick is that if there’s content context or content that’s missing, you should put it back in. If you’re worried about them not having it, I’d add it back into the onboarding. You need to know this, this is what changed, or whatever it is. I’d give them that context in order to get them ramped, if that’s important to you.

JSp: I’m going to add one more thing: don’t forget about manager training. That way their manager knows exactly what they’re supposed to be engaged with as well.

Audience 3: Great discussion. Thanks. I have a two-sided question about external content. So first of all, from the buyer’s side, do any of you do any sort of investigation about what buyers are looking for from their side? Actually, what do they want to hear? What content works from their perspective, not just a sales perspective. The other side of that is internally. Where are you guys creating external content versus all those marketing people and how does that work and how are you making nice in the playground?

CD: I want to start again and keep bringing this back to the cross-functional partnership that you have, especially in marketing. Number one, they’re a great resource for insights. They are consistently doing research on a monthly, yearly basis. I just got into a meeting with someone from our brand team and they were saying, “well, a lot of C-level decision-makers need to understand more about the values of your company versus how it’s being made.” But on the opposite end, if you’re listening to your sales reps, they’re saying, “well, no, they’re asking me how it works”. Like, give me a case study of implementation and what the impacts are. So where does that meet? Sometimes you say, let’s do both, but I want to make sure that some of your content about the values focuses on the merchants and how they started their business versus just talking about your company all the time.

Again, do your research in terms of what their quarterly and their yearly goals are, and then again, take a look at the overlap. Come to them and say, “Hey, I noticed that you wanted to do better seller stories to get our brand into a different shape. Let’s do that together because I think that we have a gap that you can help with.” Have them help you.

JSt: Yeah, similar to Charles, we’ve been getting everybody in the room together to figure it out together and have that empathy across marketing, product, marketing sellers, and sales enablement all together to see what the end-to-end looks like. And we’ve been doing more work of creating a holistic experience versus breaking it down into, here’s product marketing stuff, here’s the training aspect. If you actually look at it as an experience that somebody goes through in order to create an outcome, you can create a holistic view that everybody’s a part of and everybody knows what their roles and responsibilities are to get to that end goal.

That kind of blew my mind the first time we actually thought about it, where it was like, actually, if we create this playbook as an experience instead of as a playbook, we don’t have to create training for the playbook. We could just create an experience that somebody goes through and they get everything that they need in a way that’s easy to consume. It’s an experience. We think about all the experiences that we have as consumers day to day, and I believe that if we start thinking about the B2C experiences that we have and bringing those in house, like why do we treat our employees any differently and give them lots of death by voiceover PowerPoints? It’s a terrible experience. What we see is that those click-through rates are really fast. They spent two minutes, they just answered the questions so that they could say they did it and checked a box. So, is the outcome checking the box or is the outcome that they have to do something? And if we think about it in a different way and have some empathy with our people internally, I think you’ll get a lot more productivity out of somebody.

Audience 4: Quick question for the panel. Can you speak to the generational differences you have between your sellers and your buyers? That’s something that my company is running into now that our sellers are all in the baby boomer category. Our buyers are all millennials and the two are not talking to each other.

OW: It’s a great question. I was recently chatting with our CEO. I can do that with a 300-person company. He said the type of seller that we need for our solution is not a traditional enterprise rep. We need someone a lot more entrepreneurial because we’re finding things out as we go along. I don’t have an answer for how to bridge that gap.

JSp: I feel like with every question I’ve wanted to jump out of my seat and say, “we need to talk about buyer personas”. That’s the foundation of everything that you do. And actually, your sales team needs to really understand the psychographics of each of your buyers, why they buy. We’re not just talking about job description, age, demographic. We’re talking the psychographics. Then, they need to be able to flex their muscles to speak to someone the way that that buyer wants to be spoken to.

And I think that actually needs to be impacting our hiring profiles as well. I don’t know if anyone else on the panel has any thoughts, but there used to be this idea of what a salesperson was. Get the guy who was in the Navy Seals. Well, maybe your buyer isn’t going to want to buy from that kind of person. I’d love to know if anyone else has any thoughts on that.

CD: I feel like with that, it’s thinking about it as a consultative way. So, for those who have folks who are straight out of college who are outbound callers, we’re selling to business owners and you’re 22, 23-years-old and you’ve never started a business yourself. And so the way that we’ve tackled that is insights-driven selling. How are you going to basically tell them a little bit more about the industry, the pain points that that persona has, and say, “actually, we talk to thousands of business owners every single day, and one of the pain points they have is that they would rather spend two hours of the week rather than being on the computer, putting in their payroll hours to just get it done like that. What would you do if I bought you those two hours back?” So, really getting into what are their pain points, what are you trying to solve, and what value are you giving to them?

I’m a millennial, or consider myself a millennial. How are you taken more seriously? I’m young, I’m in a workplace full of older people. I’m talking to folks here who have a lot more years of experience than I do. But how do I do that? I can pull up a stat that says people retain 95% of the message on video. So, insights-driven selling is extremely powerful. You’ve got to get that into your practice.

OW: What we consider internally is buddying up with HR in defining the profile of a seller and strength of a seller that will fit our sales cycle and our audience. We consider a strength finding exercise that will take everybody through from the hiring process on.

JSt: There are actually a lot of similarities between boomers and millennials, and you should extract those and then give them that, because there’s actually a lot more overlap there than there is with the generation in between. I did some research and I’m happy to share that. And Howard Dover, who’s at UT Dallas was with me. He’s got some insights into that of companies that have struggled with different generations. But when we actually mapped them out, the millennials and the boomers had more in common than generation X, which is in the middle, and just totally lost.