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Quantum Leap Podcast Future of Sales in the Enterprise
Justin Michael Vendor Neutral's Sales Futurist
Justin Michael

Future of Sales in the Enterprise

Episode 12 -

Andy Kaplan

Founder, Elastic Infosec and Hackback Gaming

Everyone is wondering how sales in the enterprise is going to change in the pandemic and beyond, there’s the speed, the frenetic pace of sales, and sales technology. Our host Justin Michael and Andy Kaplan from Elastic InfoSec delve into the future of sales and enterprise sales technology. If you’re wondering where marketing and sales are headed in a world of automation, artificial intelligence, machine learning listen today.

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Future of Sales in the Enterprise

Everyone is wondering how sales is going to change in the pandemic and beyond, there’s just the speed, the frenetic pace of sales, and sales technology. Our host Justin Michael and Andy Kaplan from Elastic InfoSec delve into the future of sales and enterprise sales software. If you’re wondering where marketing and sales are headed in a world of automation, artificial intelligence, machine learning listen today.


Justin Michael Welcome back to the Neutral Zone’s Quantum Leap Podcast, I am Justin Michael, your host. I’m joined today by Andy Kaplan, who is the founder of Elastic InfoSec. Super cool name. Andy. I’d love to explain to the viewers what that means.


Andy Kaplan Yeah, yeah, certainly. So, my background is in cybersecurity sales for about 10 years. I’ve learned by working at large companies and startups. And one of the things that I found through my work is there is, there’s been a great market for smaller cybersecurity startups and service providers to have sales assistants and I decided to go out on my own and provide that contracted sales, sales, and marketing service to them. And I felt that Elastic InfoSec was a very suitable name. These companies could scale, could scale up very, very quickly, bring me on board, and have an automatic salesperson out there working for them and also helping them with events and even helping tuning products. So that’s, this has been quite a journey.


Justin Michael That’s great, it speaks to the future of work.


Andy Kaplan It does. It does, yeah.


Justin Michael Factional work. And so, what advice do you have to leaders listening about implementing these models? I know a lot of people take a position of only going internal, but there’s some advantages to finding, you know, an elastic bench, bringing in people outside. Your internal organization has various disciplines. But yeah, like how are you convincing folks to do it? Are they seeing the vision? Are you bringing it external cultures in so that they can be more cutting edge?


Andy Kaplan That’s a great question because very traditionally the sales function is one that is hired from within. It’s you’re giving someone quota. You’re giving someone responsibility. And it’s not so much of a contracted position, I’d say. But I would say that is changing over the last couple of years, looking at the business development position, which is now contracted out, and many companies are becoming more comfortable with that model. This goes a bit of a step beyond. And originally my thought was to work with some perhaps international companies that were looking to break into the US or utilize my contacts in the Pacific Northwest. I live in Portland. But what I found is, for a lot of companies, they are looking to open up a new market. Perhaps it is a new perhaps it is a new territory within the northwest, or it is a new product that they’re looking to present to the greater US. And they want to have a flexible resource to place on that product or project just to see, hey is this going to work or not or what lessons are we going to learn? And so those are absolutely some of the conversations I’m having with some of the smaller maybe the mid-sized companies. They’re not quite ready to hire on a full-time person for this position for whatever reason. And they just want to be able to test it out. And I provide that resource.


Justin Michael I love that. So, tell me about sort of the future of sales in the enterprise and a lot of folks listening are wondering how it’s going to change in the pandemic and beyond, there’s just the speed, the frenetic pace of sales and sales technology, and then there’s also the crisis. But your opinions on both would be very interesting.


Andy Kaplan Sure, sure. So I’ll tell you, as far as sales methodology and tools, for the most part, organizations I’ve worked for have been fairly far behind, at least on toolset that I think that there’s a great modernization that’s happening now as a lot of these different tools are being crafted to be able to assist salespeople, salespeople like me, to find and engage clients. I think as far as, but just kind of going back to maybe the original question, how are things changing? I’m of the belief that. I am providing a sales and marketing service. I have to be good at all these different activities from being able to find prospects, engage with them, bring them into the funnel, explain from a sales perspective why they should be looking at our product or service, and of course, closing. So, while perhaps three, three years ago or so, maybe the sales function was being parsed into a number of different people, and you had a sales department and marketing and business development, I see things maybe going in a bit of a different direction as a result of this crisis. You know, I’m, I make myself responsible for all those things and the reason being there are great differences from industry to industry, product to product, even locations. What may work in the Northwest may not work in California. And especially because we don’t have golf tournaments now, we don’t have fancy dinners, you know, all that’s gone out the window. So now we have to be very creative in finding ways to bring people in and find ways to. How do you build out your community? How do you build out your network? And that is very much your responsibility. Whereas before it was important. Now it’s critical. Now it’s critical. Who’s going to pick up the phone? Who’s going to answer that e-mail? Because we all know that there are all those sales tools that are out there that are barraging people with both and making it less, making them maybe more hesitant to pick up the phone or answer that email because they don’t know if it’s a real person or not.


Justin Michael How do you stand out in that environment? This comes from a marketing and sales perspective. There’s an event component, so virtual events all kind of seem the same. We’re in constant zoom calls. All the e-mails are like in “this uncertain times”, you get this monotony. How are you coming in as this independent consultant to bring fresh perspectives? What innovation in regard to marketing sales events can you share with folks that are looking to spice those up or be unique? Right before you could throw a golf tournament or go watch a race or something cool and do something for nonprofits. There’s all sorts of these cool ways to integrate digital and analog and now there’s somewhat of a limitation.


Andy Kaplan I think, first of all, put together a plan and stick with it for some period of, some long term period. Make it a, make it nine months, make it a year, make it a couple of years. The problem I’ve seen with a lot of organizations is they try something once and it may or may not work and they don’t do it and they don’t do it again or it’s very sporadic that’s number one. But for me, I found that I’ve always been pretty creative in putting together our own events for companies, especially, well, especially when we were able to get together. But now that we’re not we’ve developed a and on a game, hack back gaming is something that we created for, mainly for cybersecurity people, for instant response tabletops. And the really cool thing about this is we’re able to work with different vendors, put their technology into the game and have prospects and customers play the game and essentially utilize that technology and leave knowing more about the technology than when they came in. And so it’s a pretty powerful marketing tool that we use. And as in all my events, there is no selling. There’s no pitching. There’s really great camaraderie. I make sure that I have a core group of people in there that are helping to kind of drive the sense of having fun within that event. You’re right. There’s absolutely zoom burnout right now. And I, I’ve seen the different events out there of having drinks with your rep or having whiskey delivered. And I think some of those that worked out OK. But the reality is when I talk to people, the events that they really want, the really the ones that they really crave or the ones that help them build community, ones that really help that really do help them with their job and what they do and ones that can allow them to relax and be able to become more human around their counterparts. And that’s a lot of times I think that what’s missed. In addition to being a safe space, where they’re not being pitched all the time is another big differentiator.


Justin Michael It’s a really good point. So where do you think marketing and sales are going? We’re in the world of automation, artificial intelligence, machine learning, how much of that are you using? You’re coming from a cybersecurity side. So we could talk a little bit more about that. But I think most of the people listening are there somewhere in sales, operations, marketing somewhere across these disciplines and you’re out there doing this factional consulting. Are you using automation? Are you seeing that it’s going to get there? Are you more networking, getting referrals? How are you developing the funnel remotely, and then beyond the pandemic, just where do you see these technologies going? Towards singularity? It’s interesting. I’d love your view.


Andy Kaplan Thanks. Yeah. So I’d say I’m a networker. I’m a networker. I find I find ways to have our customers, even our prospects become our advocates. And that could be through our or the Hackback Gaming. It can be through the work that I’m doing with other companies or somewhere in my deep, dark past people that I know on LinkedIn, I post on LinkedIn probably about once a week or so on activities that I have. Sometimes it’s even I write a little piece on what it’s like growing a small consultancy. I write about Hackback Gaming and comment on my other friends and fellow well, other people’s posts. But as far as automation tools I’ve used, I’ve tried to use a number of them over the years and the issue that I’ve run into is really the lack of personalization. And in order, I can send out those mass emails but the open rate and the response rate has been significantly smaller versus me finding ways to sort through, say, LinkedIn Navigator, find those set of contacts that are most likely going to be my type, whatever that type might be, and be able to figure out are they linked to people I know? Or understand what their interests, what their motivations are, and then maybe target messages directly to them, mostly by email. Sometimes it’s through a LinkedIn message. But that has really formed the basis for me going out and finding my business.


Justin Michael What kind of messages that people actually respond to you? Like you talk about personalization. What does it really take? Is it because you actually really know someone in common? Or you can solve something like I think people are struggling right now to figure out what marketing message and what sales message is going to actually breakthrough for the decision-makers.


Andy Kaplan Yeah, well, I’ll tell you what not to do, and that is try to link with someone and then five seconds later, there’s a pitch or some type of canned LinkedIn message that’s going out. And I’m not sure which automated program is doing that, but that just needs to stop. It falls, it just it’s a turnoff. I get that quite a bit. I’d say whatever your venue is, whether it’s LinkedIn, whether it’s Twitter, you know, wherever you are finding your way to engage with people, concentrate on that area and, and find ways to very much personalize it. You’re with and if there might be a number of small wins there, perhaps the one win is OK, you’ve found a way to engage with someone via LinkedIn. You’ve sent them a little note. And I always, if I try to link with someone, I always personalize the note, love what you had to say in this area where we work together here or we work together with someone else, perhaps we can link to, follow them for a while, comment on what they’re doing. Don’t pitch. There will be that opportunity, but it’s not going to happen in that first couple of interactions and I and that means that those that are are kind of like following this model can be a little frustrated because it takes time. It takes patience. And also you also have to have management that are OK with this, because I’ve certainly had managers that have looked at what I’ve done and they’re like, that’s great, Andy. But it’s like, it’s kind of playtime, you know, who’s buying? Who’s buying now? But the reality is my sales cycles are six, nine, 12 months, it takes a long time, it takes a long time. So you have to build that pipeline of people, that community. You absolutely have to take that time, in my opinion, to build that up in order to create that voice, for them to think whenever they need something, they come to you. And that’s where I found the wins.


Justin Michael Yeah. Rich community. You’re making a community around this game, we’re kind of in this time of the micro-communities, people have left LinkedIn groups, not really sure why, gone into private Slack channels, networking groups, online groups, meetups. What brings executives into an infosec community or a sales community or marketing? I think people listening are going, how should I build a community? What platform should it be on? How do I then garden the thing and feed it? I don’t have the time. Like community building. How does that just natural for you? Because your this networker? How do you? Just, we need some advice like a utility.


Andy Kaplan It certainly comes natural to me and I really enjoy it. I’ve worked with people that need it. They don’t want to do it at all and I get it. So if you are one of those people that hates it you probably need to link up with the person that loves it or does it as their job and find ways to build that network together. And I’m not exactly sure how that would work, but I know that those people are out there, and especially if they’re working for some company that has a sales department or a marketing department, there absolutely needs to be that level of communication. And, you know, how will you build that network? How will you build that community of buyers? And I’d say once again the Hackback gaming has been a great way for me to bring in these people, I’ve had pre COVID we had our CSO dinners where I’d have 10 or 12 local CSO’s get together for a really nice dinner and we’d have a range of conversations for that dinner. Some nights might be a little more technical in nature. We might talk about someone, one person within the group that’s struggling with some type of incident response issue. Others might be more personal, like this time of year might the conversation might be. OK, let’s talk goal setting for 2021. What do you thinking? And it’s and the answers have been really surprising because once you are able to collect people and they trust you and they trust the group, you know we go well beyond any technology discussion. And I love that. I enjoy, I greatly enjoy that. And when we’ve created that community of trust where people can go out to others and say, hey, you want to, you want to go to this, you bet that’s ultimately what you’re looking to do. Create something that those people that are attending or inviting others to come join your circle. It takes time. It really does. There’s no shortcut. And that kind of goes back to my earlier point. You can’t just do it once and just be like, all right, we’re going to try to get in six months or farther down the road. Maybe quarterly is pretty good. Monthly can be a lot. But schedule it, put it in your schedule that this is going to happen every single quarter or whatever timeframe you think because we’re all really busy, we’re all going to move on to the next thing, but these events are the things that have people coming back to me year after year and it’s been at times a lifesaver for my career, especially in sales, as turbulent as things may be.


Justin Michael Yeah. So tell me about how do you accelerate sales cycles and velocity? Because things tend to extend, a lot people gave verbals. Then this whole thing hit, then it fell off. How do you create urgency remotely? How do you do big deals? Two questions like everyone wants speed it up and get deals done and there’s also the myth that it’s going to be really hard to do the bigger deals, six and seven figure deals because we can’t be in peron. But this digitization is the future. We should be able to do these deals with the new paradigm of remote. So yeah if you’d take me through those two concepts. I love your view.


Andy Kaplan I’ve always been a big fan of MEDDIC as a kind of a sales action plan. You know, that helps you understand some of the metrics, who’s doing the evaluating, who is signing off in this day and age, unfortunately, there’s bad news. There are more people that are signing off on these deals, especially in the age of COVID, with budgets being reallocated. It’s there are shadowy characters that are out there that are now a part of these deals. That means now more than ever, your champion on the inside in MEDDIC speak really needs to help be your guide. Like where? Because many times they don’t even know what’s going to happen once they open up the door entering into purchasing. But you do have to be very, very aware of what is, what those next steps are, who you need to meet, who you need to present to, what time frames they really have and I think the lesson I’ve learned over the last year or so has been nothing ever, ever gets done just because the problem is, there’s a problem or something is broken. You absolutely have to find that business issue. What is it about that problem that is affecting the business to do what they need to do? And that is that for me has been the key that has helped unlock a lot of these deals that are out there. Because once you understand that, that helps, you better understand which people you need to be communicating with. Who you need to bring in to that group. Once again, I guess it comes down to community, your community within that that sales that that one hundred or five hundred or million dollars sale. You know what people do you need to have understanding where you are, what you understand, what the next steps will be, who’s going to be signing off, and when? Because it is more difficult. But I maintain that the process really hasn’t changed a lot. It’s just there are just more people within that process.


Justin Michael So help, when you use MEDDIC, I don’t know if everybody knows about these qualification frameworks. There was the age of BANT; budget, authority, need, timeline. There’s this novel enterprising thing called MEDDIC, which talks about the economic buyer, which is the E without going to a huge definition. I just wanted to find out to listeners. So, yeah, that’s really helpful. How do you stay motivated talk to us about mindset, the mindset of a modern settler and we’ll kind of close with that?


Andy Kaplan Sure thing. I’m a big goal setter. I love putting together love, baby love. I put together my quarterly chart targets for the work that I’m doing to make sure that I’ve got a good piece for the amount of calls and amount of pipeline that I’m creating. You’ve got to find ways to celebrate your wins, especially as a solopreneur, whatever that might be. I’ve joked you know, as a solopreneur of the past year and a half, I’ve been employee of the month for the past year and a half. It’s pretty good, you know, but I am not drawing salary. I am absolutely paid by my clients to put on our events via Hackback Gaming. And I, I find great joy in those events. I really do that, those events are absolutely my pathway to happiness. The other work I’ve done with the Elastic infosec of being a sales contractor, being a marketing contractor, kind of like subcontractor within that sales function, I find great joy in growing these small companies and helping them be able to tune their product to whatever market that they’re, that they are serving. And in many times that success, I find is achieved by me being phased out. They’ve grown to be large enough that they’re like, OK, we like the work that you’re doing, but we’re very nervous about having the sales contractor position. We need to hire internally and make sure that we have a full time, completely engaged person. And I’m OK with that. We’ve set up the contract such that we can move on our different paths and remain friends and remain civil about it and that and in the end, I get references. I’ve been I’ll say I’ve been paid well for the work that I’ve done. And they’ve got a growing business that I can look at and be really proud of the work that I’ve accomplished.


Justin Michael I love it. Andy. Well, thank you for sharing today in The Neutral Zone on Vendor Neutral on Quantum Leap. We’d love to have you back again. Really exciting hearing about remote work and motivation, qualification, ways to create community. It’s a great episode. Where can people find you and find your awesome game?


Andy Kaplan Sure, sure. I’d say it right now we just put out a brand new website. I’m very proud of it. w w w Hackback gaming dot com is where you can find me. You can also find me on LinkedIn Andy Kaplan in Portland, Oregon. But thanks so much, Justin. I greatly appreciate the time too.


Justin Michael Thank you Andy. Have a great one.


Andy Kaplan Alright, take care.


About Our Guest, Andy Kaplan:

Andy’s current ventures at Elastic Infosec and HackBack Gaming engage his passion for creating and administering uniquely tailored sales and marketing strategies for small cybersecurity startups and service providers that create growth. He has developed a successful history of building businesses by harmonizing technical resources with customer requirements, strengthening alliances with partners, and creating right-sized products to meet market needs. His enterprise security software sales experience includes roles at staid industry giants and scrappy startups. Kaplan has a BS in Mechanical Engineering from the University of Delaware. He and his wife enjoy finding new hiking, biking, windsurfing, skiing, and restaurant spots near their home in Portland, Oregon. He can be best reached through LinkedIn and is always interested in discussing collaborative opportunities and growing his community of cybersecurity professionals.


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