Leon Hassid is the Sales Enablement and Training Leader at SecurityScorecard. In this conversation with The Collaborator he  explored how to create FOMO as part of the psychology of Enablement.

1. Daily selling tips shared via Slack – promote reps/appeal to their pride and competitiveness

2. Use Gong snippets for best practice talk tracks – no more than 2-3 minutes

3. Micro learning series – 10 min presentations? Let them tell you they want more of A, B or C and execute via your enablement platform, we use LevelJump.io

4. Mini sales enablement days/weeks – not full day sessions, 2-3 sprints – go a mile wide, inch deep, and see what sparks interest – keep it simple via Zoom

Audio Transcript

Unknown Speaker
Leon hassad as did

Leon Hassid
a seed, a seed more appropriate? Probably. Yeah. Darn.

The Collaborator
I knew I was going to get it wrong the first time. Now Leon and I were just having an amazing conversation about a couple of things that I want to share before we dive into it. First off, we were talking about what a wonderful human being Pay It Forward enablement practitioner. Adriana Rivero is Adriana works in level jump, as she works with Leon. And we were both just say how wonderful she is because she she introduced us both so we could have this conversation. So shout out to Adriana First off, but the other thing we’re just talking about, which I think is amazing, is how we both grew up on MTV TV. Beyond you grew up on it in Greece, I grew up in grew up on it in the woods of Vermont in the United States, but it was still inspirational and transformational experience.

Leon Hassid
I’m sure I was looking at the same video clips as you’re even at.

The Collaborator
Your most likely boo. Yeah, most likely we both were. Hey, do me a favor. Tell everybody a little bit about who you are, where you work what you do.

Leon Hassid
Yeah, absolutely, john. So again, thank you very much for having me here. Adriana, as well. So Leanne has seed, I currently oversee sales enablement and training. As security scorecard. I wasn’t always in sales enablement and training. I obviously grew up in the b2b world. But I grew up professionally at Deloitte, so very much on the services side, and I did sales there. So I carry the bag, which is perhaps not as common for sales enablement, folks. But you know, at some point, I just realized I enjoyed being a coach more. And that’s when I guess back in 2013 2014, they the term enablement started becoming a little bit more dominant, at least that’s what I was hearing. So I’ve been doing that for a number of years, but for the last year and a half at security scorecard, and kind of oversee pre and post sales. Just Just a few seconds on what security scorecard does, yeah, I think a lot of people will, will, it will sound familiar. So john, if you were to think of your credit rating, not gonna ask you what you’re creating rating is negative 10. If a bank were to ascertain whether they should be giving you are alone or not, that’s what they look at, they look at your credit, credit rating, and if it’s negative 10, they’re probably not going to loan you money, A or B. But they’re probably gonna need to write that off, right, right there. And then because the likelihood of you being very low, so we do the exact same things, the exact same thing, but for company’s security posture. So we can tell whether a company healthy, not just for them, but their companies they deal with as well, from an A to F grade. So I can explain it to my six year old nephew, A, B, C, D, or F. And based on that, we can tell you, where you’ve got problems and issues and help you address them. That’s it.

The Collaborator
That is so cool. Is it uh, you know, before we move on to the enablement side of the conversation, do you guys publish? Or is it is the life experience where I can sign up and get my, my rating and understand how I’m doing and how I can improve? How does that all work? Great question.

Leon Hassid
So because we’re doing all of that from the outside in, we don’t have to go into companies and ask for permission or look at their information. So this is available for every company to claim for free. Not only that, if they don’t have a great score for free, they can improve it, and we’ll work with them to make sure that they can improve it. Our vision is to make the world a safer place. We don’t feel that we need to be making money off of that, at least for your own company, when you’re trying to introduce other elements such as I want to be looking at the security posture of all the companies I do business with. So Salesforce Gong HubSpot, then, you know, the business model comes into play and you got it you gotta make a profit to survive.

The Collaborator
No, it sounds it sounds really cool. And I usually try to avoid talking too much about specific companies. But it’s um, it’s really an interesting model you’re describing there to check it out and learn a little bit more,

Leon Hassid
but didn’t overdo it.

The Collaborator
No, no, not at all. I thought it was interesting. If I thought you over going over to timeout Stop, stop. It was great. Tell us a little bit about and I didn’t feel this question in the prep, so I apologize. What can you tell us about the size of your enablement team sort of our reports and and who you support today? And it’s okay if you have to do high level because some people are more private about it than others. That’s okay too.

Leon Hassid
You can think of our sales enablement effort being supported by four separate entity vigils. So the program is amplified through the efforts of those, however, day to day responsibility, who wakes up and goes to bed at night thinking sales enablement. Unfortunately, it’s only one man show right now, that’s me, looking to expand the team probably looking to hire a couple of folks in the next few months, but it’s me, but again, um, my program is amplified through the efforts of others that I just need to be able to influence somehow.

The Collaborator
And that’s so true for all for not all of us. But for many of us in the enablement space. I don’t know the exact numbers, but I’ve had 70%, of enablement. Teams are teams of one, you know, and whether they’re hiring or not, a lot of small teams out there one or two people holding down the shop. So that’s, that’s not uncommon. Now, I got super excited when you said, You started throwing out things like FOMO I topics like that around enablement. Why are these concepts, especially at the high level of FOMO? Why is it so important? In your opinion?

Leon Hassid
Yeah, john, and you know, I’ll be frank, I am using the term FOMO, a little loosely.

Unknown Speaker
That’s okay.

Leon Hassid
You know, create that that’s shocking the system. But I’ll use an example I’ve been referring to my entire career, and it’s coming from a bad experience. So I grew up smoking cigarettes for many, many years. And I remember coming to the US, maybe when I was 18, maybe yes, I was smoking at that time. So this commercial, it said, less is more. I wasn’t very smart at the time, or at least I didn’t think I was, it took me a while to figure that out. Finally, I did. So I’ve been using that concept my entire career, in the emails that I write in the way I communicate to different audiences, when I am dealing with internal people or prospects or customers. So as an enablement person, even before COVID, every single person you’re serving internally will tell you, there’s so much noise in the system, we need less. So as an enablement leader, I just need to figure out what that push and pull balance looks like. And I’ve been finding out even before COVID, I don’t want to use that as an excuse all the time. That’s serving information in smaller chunks. And asking for people to want more seems to be the way to go with enablement, obviously, you need to do some things that lasts a little longer that that happen more frequently. But when you really are trying to understand are people finding this valuable survey, not serve it up in smaller chunks, and see whether they come back for more. And that’s where the FOMO kind of concept comes into play.

The Collaborator
I think that’s smart. Because I tend to agree we need to have these baseline foundational elements, which are not small chunks necessarily. But we need to have these these smaller micro learning micro coaching opportunities, whatever that are easier to consume quick and and wets your appetite to the level that they need it. What are these look like in your in your world, in your view, when they’re successful?

Leon Hassid
When you have the sales people coming back to you asking for more content, and more education and more training, you’re doing something right. I don’t think that’s something we hear all the time. I think more often we hear guys, this doesn’t need to be an hour make it less. These videos can be 10 minutes. Great. So example, we just did our SQL. I had six of my top performing reps do 10 minute micro learning sessions on some very, very powerful topics, examples, building business value, reaching out to the economic buyer, bringing Sandler to life. We did Sandler a few months back and other topics. And I think we would agree 10 minutes is barely enough. But I worked with those presenters, we made sure we stress the absolute key points that we wanted for us to convey to the entire revenue population. And then I had people coming back to me saying why was this so short? And then when you ask them for the feedback in the survey, the question was, from the six topics that were covered, which ones would you like us to focus on again in the next month, and the feedback was almost unanimous all six, I can’t believe this. This was in more than 10 minutes. So when you’re creating that atmosphere, that that that kind of momentum for what you’re trying to share. I think it sets you up for success. Now you need to follow up on that. Right? You don’t just stop there. So it’s it’s a constant, kind of not game that you play, but you need to be running fast.

The Collaborator
Now what was the reaction of the presenters that you asked to to do this like, hey, I want you to cover Sandler attendance. They know it wasn’t quite that generic. But well, what was their reaction? And how did you did you have to convince them that this was a, a doable, that this was something they could do, and that it makes sense to do it.

Leon Hassid
I don’t think I had a tough time trying to convince them. I’ll be honest, it didn’t really have a say in the matter. But, and I and I say that jokingly, but that was the case, I was commanding the agenda. But what I think they were struggling with was, I’m not used to less is more, I’m used to have a 1520 minutes when I talk and talk and talk. So I had to work a lot with them to make sure that the company was on point, or absolutely hitting the mark the way I thought it should be hit. And we did a little bit of rehearsal, trying to make sure that those 10 minutes absolutely mattered. And not everyone knocked it out of the park. But the ones that did generate is so much FOMO. So all the reps that were coming back and saying, I want more of that, can we please double down?

The Collaborator
That’s awesome. So let me talk to you about the reinforcement, you know, the some more of it, which in some cases is reinforcement. reinforcement, in some cases is going deeper. How do you package? How do you plan the packaging of sort of those reinforcement pieces? Is it a bunch of follow on five to 10? minute, something or others? Is it a three hour session? They like crap, now I got you. How do you see that follow up? going on?

Leon Hassid
Yeah, there’s, there’s obviously a variety of things that you can do. For us what’s worked, and I’ll be on this, this was primarily to after COVID, I’m guessing a lot of people have slack is their environment, or teams or something equivalent, we have a channel called daily selling tips. And those are literally tips. And every day, we will share something very, very short, either that we grabbed from LinkedIn, and there’s a lot of gold there. Or we’ll grab little snippets from that 10 minute presentation we did a few weeks back so that people can remember. And they can now act on whatever the message was,

Unknown Speaker
or reinforcement, right, there are a little bit of that don’t end up

Leon Hassid
exactly. Or if we had a one hour training that a lot of people missed, because you know, a lot of people don’t want to attend a one hour training on new features. But then one of our top performers actually talks about that new feature and his value proposition and gets to have a pretty important logo for us by by more business. And then you share the snippet of that recording, we use Gong, we love Gong, others may be using other software solutions. Imagine the impact that that little snippet of a minute can have versus a one hour training. And you could have been at that same place at the same position that that rep found themselves because they took the time to listen to it. I just think, you know, obviously you don’t want to have people competing against each other in any bad ways. But these are reps, these are salespeople. They’re very, very competitive as as as people are when they’re part of the same team. And they always want to know who’s doing what that I can borrow, that I can also that can also make me successful. So hitting on that kind of vanity, if you will, seems to work well, when you’re wearing an enablement hat.

The Collaborator
I love that. I love that so much. Now you You gave us a couple of really good examples around Hey, I just want a big deal is a snippet of information you can go listen to how do you identify all those potential learning opportunities or snippets of snackable? So whenever we want to call them that makes sense to get out to the team? Is that something that you’re you’re meeting with a team to get their feedback on? Is it is a you just doing a lot of work to gone. But what is that part of the process look like?

Leon Hassid
Yeah, it’s all of the above john, you’re just describing why I need more people. But you can set up some automated alerts and trackers and Gong. You can make sure that you’re part of every single team meeting that is happening across revenue, you’re not leaving that meeting, you’re part of it. And you’re just listening. You can you can be multitasking, but you’re hearing for those nuggets, you can create an environment where people are coming to you with that information preemptively so that you share and they get that recognition amongst their peers amongst their bosses. And when that happens, the beautiful thing because you’re just sitting there and this gold is just coming at you. It takes a while to get there. You need to have that credibility in those relationships. But it’s not easy. And in today’s world, we can just touch base with someone for five minutes. It’s a 30 minute zoom call. So I’m not gonna lie. I’m probably spending the majority of my time trying to package all of that not just the going snippets, but thinking about Ideas for our next QPR, thinking of ideas for our next mini sales enablement week, which we do every quarter if we can, or thinking of my next daily selling tip. But what’s important is that you’ve, you’ve made them feel familiar with how they are expected to consume information. And you don’t want to test that every once in a while, see if it’s working. because not everything does. By the way, I can tell you, though, I could do and didn’t work in the past,

The Collaborator
I was going to say, as many successes as we all have, and I hope everybody is enjoying some amount of success out there. We all have failures, we all have things that it sounded like a good idea, but it did not work out. Even with these snackable, or these smaller micro opportunities of learning, or whatever we want to call them. Have you had people push back on you and say, this didn’t work for me? You know, it seems to work for everybody else, but it’s not working for me. And if you have How have you? What have you done about that?

Leon Hassid
The number, the number of people that seem to like that is much larger than the number of people that don’t, and therefore, I’m going to value their input the most However, you do tend to see a generation issue where old school reps that perhaps grew up in a different era where b2b selling were just different. Do not mind 20 minute trainings, because they’ll they’ll be diligence diligence, they’ll just sit back and listen. And that’s why they learn. That’s they they went to university when it’s it was all about lecture, you needed to raise your hand to speak.

The Collaborator
Oh, my god, that was me. I mean, I’m in that older age group where you know, it’s exactly what it was. That was it.

Leon Hassid
That was me as well, today’s generation. So most of the people that man, our BDR team, our commercial rep team, even our sales engineer, and our CSM are not like that, that’s not how they want to learn, they want to understand where the content is making it easier for me to find it. When it’s something that I cannot just do self paced, give it to me, but in chunk of both formats. And if you want to test me after that, you’re welcome to do so I’ll perform because I’m very competitive and will get an A every single time. It’s tough when you do that scale, right? When you’re like approaching a community of 100 people that I have right now, and again, remember one man show, I hope my boss is listening. But you know, as long as you’re meeting or exceeding the expectations of most, or the majority of that population. I think you mark that as a as a success and move forward.

Unknown Speaker
Ya know,

Unknown Speaker
how do you see a change?

The Collaborator
How do you see if you’ve thought this far ahead and your problem? And you’re probably already thinking about it, we get back to a world where some percentage of us are back face to face. At some point in the future, how is that going to change? In your opinion, how you approach this? Will we use still use a lot of these exact same principles? But do some of them in person? Or what’s your thoughts there? I’m curious.

Leon Hassid
First of all, fingers crossed that we get there sometime soon. I would be lying if as an enablement leader, I told you that this environment hasn’t been beneficial, I would definitely definitely be lying. I don’t think I’m gonna give up on the way I’ve created this virtual experience for onboarding and or ever boarding our reps. What I will be appreciative of is the fact that I can go back to establishing those in person connections and establishing those relationships, which is so tough to maintain and do right now, especially with new reps that you’ve met, never met in person, you’ll never get to meet in person, at least during the ramp. And I cannot stress enough how important that is. So maybe this is not a popular opinion. I think I’ll probably maintain the status quo a keep doubling down on the virtual part of this experience. I think it’s fair to say,

The Collaborator
yeah, no interesting. I think, in my purse, from my perspective, a lot of it, a lot of it’s going to stay in terms of how we approach it, too. I’m not nearly smart enough, and none of us are to really know what the future will, will hold Exactly. But I think a lot of people stay too. But I really do. You know, you have a really interesting challenge we all do when you talk about the fact that we haven’t met these different individuals, so many new people we haven’t met, but you mentioned and that’s one challenge we all have. But you also mentioned a real positive that some people have and others don’t. You mentioned the fact that you have four people I think you said that you that you partner with to help you scale it out now is that the sales manager Energy team? Or is that a group of like top sellers? Or who are those people that you have the luxury or not the luxury but the benefit of working with?

Leon Hassid
So Good question. There’s, there’s a direct team that’s helping me amplify the program. I’m part of the awesome securityscorecard. That’s where sales enablement lives.

Unknown Speaker
And that’s fine.

Leon Hassid
Yeah, it’s it’s it’s less than common, but it works very well. Because the the opportunity you have to be up close and personal when messaging is getting developed, and product marketing campaigns are being considered when new releases are actually being planned. And you’re right there in the in the weeds with that team. I cannot tell you how a pays dividends when you’re then ready to go out to the revenue community internally, and convey what they need to know about. But to answer your question, so the product marketing team will own and help each other out when we’re trying to make sure that sales knows what’s up, messaging, full tracks, etc. But john, I mean, we, when you have a team of 100 people, you have team leads that lead six different departments, those individuals are your should be your champions, should be your advocates in terms of what you’re trying to do. So if they’re not singing from the same songbook, you got a problem, or you’re just not going to be there for too long. So the individual revenue team leaders, the team leader for bdrs, CSRS field reps is engineering. If they don’t know what you’re up to early enough, if they don’t feel that they’re being consulted about what you’re trying to do and take time away from their reps meeting their number, you better have a good reason to do it. And you better ask for their input prior to doing it. So that’s what I’ve learned to try to do in every job in my career has served me well. But that’s where the amplification comes in. And

The Collaborator
you’re right product marketing is not necessarily the common place for enablement to live. Yeah, I know. I run enablement, but I also manage our solution marketing team. Yep. And I see many of the same benefits that you just alluded to there, about, you’re much closer to what’s happening in the product, how it’s impacting the market, you’re much more involved in the messaging. And there’s real interesting to have this with me, but with with the person that heads up my solution marketing team and see if they agree with that. Yeah, cuz they may not, you know, I know. But from my perspective is fantastic. This has been so valuable. I have to say that. Let me ask you this, though. Yeah. What haven’t we covered that you want to make sure we get across to people?

Leon Hassid
Um, I think we’ve covered everything. Well, actually, given the topic that we had, john, I guess I’ll leave you with this. And I’m not the person that coined the term. So you’ll probably heard this before, probably in your podcast, john. So I’m very much a fan of ever boarding. So continuous learning. And this is how what my reps will always come back and say we’re doing too much. And my response back to them is, excuse me for feeling the need to constantly update you on what’s happening. This is cybersecurity, it changes day to day. This is software, it changes all the time, more competitors are coming in, excuse me from for wanting you to be up to date. So the ever boarding comes into play where you they’ve done their own boarding, you’ve checked that box, you need a on them. And you need to do so discreetly, so that they don’t feel that they’re getting too much pressure, and they’re not spending enough time doing their job and meeting their number. So ever boarding has been something that I followed is an approach. I’ve been doing it a security scorecard and will continue doing so. So that’s just my parting thought for us. I

The Collaborator
love that. I love that. You’ll have to come back in a few months and tell us how things have evolved as we eventually get back to the office and how what are the FOMO tips and tricks you’ve come up with along the way. Last question for you though. That basketball. Yep.

Unknown Speaker
What is it?

Leon Hassid
So our chief revenue officer, Bill Hogan, got each one of us a basketball literally 100 people received the same thing. It says the rock it’s from, I think it’s a New York thing. You can see the sky here. And he has the security scorecard logo. So it was a holiday gift. I love that little geek. He knows that the we are very sports oriented culture. That’s a greedy scorecard. So yeah, that’s that’s what it is. And I always skip it. I

The Collaborator
love that. I love that wonderful talks. Wonderful. Thank you so much for coming on and sharing so many great insights with with all of us today. Leon if people have questions for you is the best way to reach out to us on LinkedIn.

Leon Hassid
Absolutely. LinkedIn. Leanne has seen a che Ws ID, I respond within less than one minute.

The Collaborator
That goes to other problems that you may have as an individual there, but I’m with you, I tend to be just as bad. So anyway, thank you so much, seriously, appreciate it. appreciate everybody listening and have a great rest of your day.

Leon Hassid
We’ll talk soon. Thanks again for having me.

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