Sales Enablement Soirée: Sales Content Insights to Improve Digital Selling, Fall 2020

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Cassandra Tenorio: Welcome to our panel on Sales Content Insights to Improve Digital Selling. I am very excited to have a discussion with our panelists today about arming sellers with the right content to engage buyers at the right time and using insights to understand what is successful. So I’d love for each of you to just go around, introduce yourself and say a little bit about yourself. Arriane, let’s start with you. 

Arriane Emdad: Awesome. I’m Arriane Emdad. I’m client delivery leader at DSG.

Cassandra Tenorio: Adrian?

Adrian Vernon: Hi, I’m Adrian Vernon. I am the director of sales enablement at MobileIron. 

Cassandra Tenorio: Andrea? 

Andrea Klein: Great. My name is Andrea Klein. I’m based in Toronto and I’m a sales enablement lead for the business and sales development team at Slack.

Cassandra Tenorio: I’m very excited about the conversation today. I really wanted to start by talking about understanding content that really resonates with your buyers and your sellers. So, how do you really ensure that sales content is actually getting used? Adrian, let’s start with you. 

Adrian Vernon: Yeah. I’d say we purchased a content management system or a sales enablement platform earlier this year and so that really has given us more visibility into who is accessing what and how often it’s being accessed. So that’s made a big difference. Now I know that not everyone can afford a platform like that. So before that, we were actually using just new Google sites to post our stuff up and we were using Bitly, which is free to use and it was a highly manual effort at that time, but at least that still gave us a high level picture of what was being accessed, what was being viewed. We didn’t know who was viewing it. Now we’re able to go a couple levels down and know exactly who’s accessing what down to the individual rep level. And it’s given us all a whole lot more insight.

Cassandra Tenorio: That’s a powerful tool, data hub, and really today we’re seeing that buyers have a lot more access to content and information now more than ever before. So how do you really ensure that reps are reaching out with content that actually provides value to your buyer? Andrea, I’d love to hear from you.

Andrea Klein: Yeah, it’s a great question. Before I moved into sales enablement, I was actually a BDR on the sales team also at Slack. So we were always being asked for content from prospective buyers and we always wondered what would be the most impactful, and what will resonate the most. I think it’s really easy to do a feature dump of everything that our product can do, we want it to be really thoughtful about what content we are delivering, just to make sure that it does land with that prospective buyer. So from an enablement perspective, we really train the field and do regular skill development sessions around this initial discovery. And when being asked to send me over content we ask and always follow up with what would resonate most with you? What would be your specific use thesis to ensure we’re tailoring what we’re sending to that prospect?

And beyond that, we’ve really doubled down on our persona based messaging, I think in our marketing collateral. So ensuring that all of our content that we’re creating and developing is specific to whoever we might be prospecting. Slack is unique in that it is a solution. I think that can be a solve for multiple lines of business in multiple personas. So developing content that’s really custom to everyone who might be speaking with and not so broad.

Cassandra Tenorio: Have you really seen buyer preferences change as remote and digital work has really increased over the last year. How have you really seen these preferences continuing to evolve as you plan for the upcoming year? Arriane, did you have any thoughts on that? 

Arriane Emdad: Definitely. I think we’re all feeling like we’re doing things virtually that we would have done in person previously and sellers who sold in person for years are now being asked to sell remotely and different muscles are used. And so the general consensus, even though we’re finding ways to be surprisingly effective in a virtual environment, the general consensus is we miss being in person. And, I do think that this next year we’ll see us move towards a more hybrid model where you have some areas that are starting to do in person selling, some areas that are still remote and as an enablement team, just really preparing for how you equip sellers when you’re not all virtual and you’re not all in person is kind of the next exciting thing that as the enablement team we’ll all be working hard on. 

Cassandra Tenorio: That’s great. One of the next things that I really want to talk about is what effective communication looks like on sales teams and communicating that latest content, what are some of the things that you’re doing at your organization to really inform and communicate with your sales reps to ensure that they’re armed with the latest content? So, Adrian, I’d love to hear from you.

Adrian Vernon: For sure, Cassandra. We’re doing a number of different things and we’re not relying on just one channel. We believe that it’s important to have multiple channels. And we think about the old standard rule of seven in advertising, and now maybe you don’t have to send something seven times for the field to act on it, but you certainly need to spend it multiple times through multiple channels.

Someone might see something in email. Someone might see something on Slack. Someone might see something in our content management system where we’re able to notify them on their mobile app, on their phone as to what the latest and greatest has been posted. So we reach them through multiple channels and we never say, “Hey, we sent out this message one time.” It’s not good enough. And so we will send out the same message as long as it’s nice, crisp, clear communication. We’ll send out the same message. It could be three, four or five times, and someone is going to see it in one of those times and then perhaps act on it. So we have no problem pinging the field as long as the communication is crisp and clear. 

We do weekly webinars as well. Our webinars are very engaging, so we do one week, we do what we call a MI60, 60 minutes of news that you can use here at MobileIron. And it’s like a new show and it’s very engaging. We put background music behind it. We do polls. We do little segments that have nothing to do with the business, and that’s intended just for people when they start multitasking, especially when we’re all at home here, it’s easy to multitask. You’ve got three or four windows up. And are you really tuned in and listening to what the speaker is saying? So, we try to make it as fun and engaging as possible with little quick tidbits outside of the normal business talk. And by doing that, we bring people kind of back to center right there on the webinar. They’re more attentive. They’re going to absorb more and it helps in our follow-up communications as well. And then the last thing I’d say, in addition to all of those channels, I mentioned, we also do five things to know every Monday and that’s, “Hey, in case you missed all of it last week. Here’s five things that you need to know,” and we kind of summarize and wrap up and we send that out through multiple channels as well.

Cassandra Tenorio: Absolutely. I love those ideas. Andrea, what are you doing at Slack to kind of arm your reps with the latest and greatest content? 

Andrea Klein: Yeah. I love that. And not too much too dissimilar to what Adrian is doing. A lot of need to know. In fact, we have a branded need to know Wednesday once a month. Which is really a cross-functional training session with everyone, from marketing to product, to obviously sales with everything that the field needs to know. So this is really more the synchronous learning, but from an asynchronous perspective and self-paced, we also try and breadcrumb a lot of material within Slack, in different channels, putting it in team meetings, really engaging with managers so they can leave their own team with the same messaging to reinforce it time after time.

Because again, when something is one and done, it typically doesn’t absorb the same way it does if you continue to reinforce the same message over and over. So we also have a variety of channels and try and make it as engaging as possible whether it’s short videos or again, this need to know training, where we also try and leverage pulling as much as possible now that we have Zoom polls and also with the need to know the theme song.

Cassandra Tenorio: I love that. How do you really ensure that sales reps retain this information to use in future interactions with their buyers? So, Adrian, I’d love to hear from you again on this one.

Adrian Vernon: Yeah. I mean, it does go to the kind of engagement that Andrea was reinforcing. They’re ensuring that they’re more engaged and it helps ensure that they’re going to retain a little bit more, they’re going to be more attentive, but more than that, I mean, we are on a quarterly certification cadence. So that every quarter we’re going to focus on one key thing, and we consult with sales leadership on that. What is it that the field absolutely has to know and needs to focus on? And that could be where they’ve got to give a five minute pitch to their manager on a particular product or something that is new in this past quarter wherever the sales leadership thinks there is a gap, then we will have a quarterly certification or really hone in and focus on that, in addition to just trying to track and hope that they’re going to retain everything from all those different engaging messages that we send out.

Cassandra Tenorio: All right. And, Arriane, did you have any thoughts on this one? 

Arriane Emdad: Definitely. I love what Adrian was saying around just make sure they know what to focus on. And we found that working with lots of different clients that really prioritizes the right sales plays is a way to cut through that noise. And so I love hearing about the alignment, like sitting down with sales leadership, sitting down with marketing, talking about what is going to be most useful for your end users. The other thing, it’s just good to remember that sales reps use and remember things that are immediately practical. And so if you’re building things that help them lead compelling conversations and your training and your coaching is all focused on helping to build conversation mastery, then you’re building this confidence that the rep can use to handle any pivots that need to happen in the conversation. And you’re helping them facilitate a discussion as opposed to delivering a pitch that they’ve practiced. And, that matters more in a virtual world than ever, because it’s much easier to get distracted when you’re sitting in your own office on your own screen than it is across the table from someone in person.

So, the last thought I would share on this is a topic I’m passionate about, and that is don’t skip the coaching. So you’re going to have reps who want to practice, and if you’re giving them information and then you’re reinforcing it with manager coaching, you’re doing two things. You’re helping to build confidence, but you’re also reinforcing that it’s important what we’ve asked you to do matters, and we’re going to look to support you. And so not skipping the coaching is huge for ensuring that things stick. 

Cassandra Tenorio: Absolutely. I love that you emphasize that. Do you have any kind of coaching tips or best practices? I know it’s a topic that you’re very interested in for our audience today, really around coaching reps to use the right content at the right time.

Arriane Emdad: Definitely. A simple principle that I apply and that our teams work really hard to apply with our clients is just think about the fact that training events don’t change people and they really just prepare people for change. And so really change your mindset from training event to training process, and how can you build, similar to what Andrea and Adrian were saying, how can you build kind of sequence learning. How can you create a combination of channels and information that then are reinforced by that manager, and the manager is equipped and knows what good coaching looks like.

Cassandra Tenorio: I’d love to have a discussion around using sales content insights to maximize effectiveness. And one of the big things that I think a lot of practitioners are looking for is feedback into what sales content is working. So how do you really get feedback on your sales content and what are those key feedback insights that are most helpful for improving selling? Arriane, I’d love to hear from you on this one again. 

Arriane Emdad: Awesome. When you think about what works, you have to remember that reps are using what they’re used to. And so sometimes the first thought is I’m just going to ask sales what they need, and they’re going to tell me, and I’m going to go build it. And when you think more about it, what has worked for them is a function of what they have access to. And you just want to be mindful that you’re not casting too narrow of a net, right. When you’re thinking about that feedback. And so for us, working with clients cross-functional teams are the right way to collect feedback and make sure that sales knows what’s out there.

And then, partnering to figure out, okay, now I have product information. I have brands and positioning information. How do I take those inputs and how do I create conversation and materials? How do I quickly create enablement at the conversation level? There are so many good tools that can give you feedback content management system that can show you what’s working, what’s not, and that’s always a great place to start. Picking the past few deals, kind of what resonated with the client, what did you show and is it different from top seller to top seller? Those are some great ways to just start getting a good sense of what’s what’s working today and what’s being underused and overviews maybe potentially in the field.

Adrian Vernon: Cassandra, if I could just add onto that. So with what Arriane was saying, I agree with that and really is good to know, go, what are your top performers doing? And, you mentioned the content management systems that give you a lot of insights, but they can also almost like the content that is working, it’s like, ants swarming to a sugar cube out on the sidewalk, right? They’re gonna come to it. And you’re going to see a big spike in that viewership and that usage you’ll win, something really, really resonates with the field. And you can see who your top performers are and exactly what they’re accessing. And our platform allows other users to go in and follow top performers. They can follow their peers and see kind of what activity they’re doing, if they choose to do that.

So I just think that just allows you then to follow up and say, all right, well, so, this is being viewed quite a bit. What is it about this content, and you can dive a little deeper to really understand what it is that’s working. We post out on our own platform all the time, wind stories, and we get an interview from the account executive on video and plus a little summary of it. And as part of that summary, we say, what content did you use to really help close this deal? And, get some insight there from some of our top wins.

Cassandra Tenorio: So we love to end all of our panels with one quick takeaway for our audience. So if you would like to leave our audience with one quick takeaway today, what would that be? Andrea, let’s start with you. 

Andrea Klein: Yeah. So on the heels of a lot of what we’re talking about right now, I would say, and maybe this is also influenced by my BDR background, but basic discovery is always so important. As enablement leaders, I think our customers are AEs and BDRs and SDRs and individual contributors, and we need to provide them with what they need to sell better, to be more successful. And then being our customers, we really need to do simple discovery, ask them what they need, where are the gaps? What are their challenges? How can we help solve their problems as we wouldn’t be an external customer. So I would say don’t skip out on discovery. It’s so important between trying to rush to solve, that’s important too, but understand the foundation of what you’re trying to solve for first.

Cassandra Tenorio: Absolutely. Adrian?

Adrian Vernon: Yeah. I would say, what I was talking about before, don’t be afraid to communicate, communicate with the field. Don’t be afraid to ping them multiple times on the same topic. As long as the communication is crisp and clear, they won’t mind it. You’re not bothering them. It’s not nagging. Repetitive communication is actually effective communication. So some people will shy away and say, I don’t want to bother the field too much about this. As long as your communications are crisp, I believe that you can’t bother them enough. 

Arriane Emdad: Yeah, I like that a lot. You can’t bother them enough. I would challenge everyone to really think hard about the conversations that you’re enabling and have they changed in the current environment and think about your team in terms of a remote selling maturity model and kind of, where is the bulk of your team? If you were to do an honest assessment, are they kind of on the lower end of the maturity model where they’re just kind of building that competency or are they on the higher end?

Where now it’s time to take it to the next level and depending on where you are, and depending on where different teams are, you’re going to have to think differently about how you reach them in this virtual environment. So having a tailored approach based on where people are in the maturity model, is a helpful way to meet reps where they are and make sure that we come out of this selling season, as strong as we can.

Cassandra Tenorio: Absolutely. I love all of the insights that you have all shared today. I think this has been a great discussion. Right now we are going to open it up to our Q and A. So if you have any questions for our speakers, feel free to type those into the questions section, and we’re going to get some of those answered for you today.


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