Unlock Sales Secrets: Top Performers vs. Average with Bob DeLuca #sales #salestips #ai

Bob, good to see you. As a way of getting started, tell us a little bit more about your story and how you got here.

Sure, Dustin. Nice to see you as well. So, I probably took a little bit of an unusual route to sales. Out of college, I actually started working in finance, and I was working for a large manufacturing company, and I was doing things like putting together budgets and production manufacturing schedules and projections. And those were kind of largely based on historical data and sales forecasts. So, I worked with a lot of salespeople and it seemed like they were having a lot more fun. I was sitting behind my desk every day just working on a spreadsheet, chained to the desk. And these guys were out and about and meeting with customers and seemed like they were making more money. And I said, this seems like a better deal. So, I decided I was going to move into sales, but I didn't have any sales experience. So, I went to a job fair and there were quite a lot of companies there. And just by happenstance, I walked up and I started to interview with a company. It turned out I knew the person who was the owner of the company, and it was a small office products company. And I knew him from sports. And he gave me a shot and I started in sales selling office products. And then, from there, I moved up. Moved into some smaller software companies and then some larger companies. And today I'm at Security Scorecard.

That's great. So you never, never looked back and stayed in sales and progressed your way. Sounds like in SaaS and cybersecurity quite a bit. Yeah. Tell us a little bit more about Security Scorecard and what you do now.

Sure. So I'm the VP of Enterprise Sales here at Security Scorecard for North America. And if you're not too familiar with us, essentially what we do is help organizations protect their global supply chain and prevent breaches. And we do that by, you know, the name says it, right? A scorecard. So that's kind of how the company originated, where we came up with some proprietary technology that would be able to sort of scan all the internet-facing assets of an organization and assign a score to their security posture. A, B, C, D, F, just like grammar school. A is good, F is bad. And then we've progressed from there. So now we do a lot more in that space, provide lots of actionable intelligence for people to make real-time decisions and do continuous monitoring across their stack and go beyond just their immediate vendor supply chain. But now you start to take a look at their vendors and their vendors' vendors, really kind of out to that nth vendor. And so, you know, we continue to expand, add a lot of new AI capabilities into our solution. We do business today with most of the Fortune 100, I believe 9 out of the 10 largest banks in the world, and we've got thousands of customers around the globe.

That's awesome. And kept it pretty simple off the start with the scorecard. That's very easy to understand. And it sounds like that boded very well. Well, good stuff. Based off all the different journeys you've had and all the different stops, a lot has changed in sales in a variety of ways. What, what stood out to you, I guess, the last few years? What, what has changed compared to, you know, maybe when you first started? Sure.

So I think a couple of things have changed, uh, in the past few years. Uh, one is, you know, everybody's working from home, you know. Uh, that really kind of started with COVID right? Uh, and the other is AI, but You know, it's hard to meet your customers and your prospects face-to-face anymore. You know, even just to try and get them out to do an event is difficult, right? People are kind of comfortable working from home. But, you know, AI has changed the way not only people buy, but the way the sales folks work as well. You know, it changed how we connect with them, right? We can really kind of personalize at scale, which is not something that we were able to do before. We can do research now much more quickly. We can get competitive intelligence. We can do predictive forecasting. We can use it for win rates. You know, we've got omnichannel marketing that we can do now where people are using things like, you know, social selling for outreach, video messages, chats. So, all that's changed, right, from the old sort of spray and pray method or dialing for dollars, right, trying to go out there and just, you know, turn up opportunities the old-fashioned way.

Yeah, for sure. There's a lot even in the last couple of years. Some of that has changed dramatically. What, what have you seen out of all those things you mentioned? What, what's been the most effective? Is it, you know, the, the video emailing? Is it some of the, the research on the front end so you're not bogged down by all the admin? What, what's been most effective, do you think, with some of the new technology?

Yeah, I think a couple of things. I mean, you know, buyers have changed too, right? They've all really sort of become self-service experts. So, you know, before you even meet them, they've, they've they've sort of pre-bought or pre-rejected you. But I think the biggest thing that I've seen is the ability to do, you know, more account-based marketing and sort of that show me you know me personalized outreach, right? So being able to figure out what's important to the client, both personally and professionally, so you can come up with, you know, sort of a message that resonates with them. I always say, you know, people don't buy features or functions, they buy solutions that do something for them that solve a business challenge. And you gotta find out what that is, right? Because everybody's got a product, Who cares? Everybody has features. Who cares? What are you going to do for me? Right? What are the challenges, the positive business outcomes that you're going to help me achieve? Right? And how do you help them internally, you know, maybe advance their career or help them with their own internal objectives?

Definitely. And it's easy to forget about that stuff because of all the fancy features and benefits and all the cool products that we have. But At the end of the day, people, people's favorite topic is typically themselves and advancing their career and all the things you're talking about. And sometimes if you just take a step back and really focus on that and that personal win, it can be really effective. So great point there. I also know you've hired quite a bit of reps over the years and I think are actively hiring now or maybe finishing that up. What have you seen specifically that separates the best salespeople from maybe, maybe the middle of the pack?

So, I think it's a couple of things. So, the sales folks that are, you know, rolling up their sleeves and getting into the details, not really just superficial conversations, but those that are really doing their research, doing their homework, taking the time to learn the client's business, what their challenges are, and really coming up with creative solutions on how they might be able to help them. The ones that are customer-facing still, when you can do it, are definitely having much more success than the ones that, you know, really just don't want to get out and meet with their clients. Highly organized, right? Don't need to be managed, self-starters, and have an ability to kind of put together a deal that's appealing to a client and able to work with them, you know, throughout the sales process and sort of get multi-threaded and have relationships across the whole organization. Those are the ones that are the most successful.

Makes sense. And I definitely agree with the The mindset of those type of folks, you're talking about some of that internal driver, you know, what motivates them. It could be money, it could be their family, it could be the recognition. But how do you, how do you dive deeper into that? How do you see that, I guess, on the front end? Because it might be hard to see that before you hire them. Maybe you see it after, good or bad. But like, how do you find that intrinsic motivation or some of the things that you mentioned? Is there— is that through the interview process or is that just a journey over time to try to— get them to that level, or do you think they're— they need to have that before they even step foot?

I think, you know, you can't teach motivation, so they either have it or they don't. You know, and there's certain folks that sort of have it, right? If you think about folks that are maybe athletes or prior military, they have that sort of competitive nature, right? And I always like to see that in the background. That doesn't mean that folks that don't have that aren't successful as well, but you can kind of probe for some of those things in an interview by asking situational questions. You know, hey, what would you do here? How would you go about this? And, you know, always you want to do your due diligence and find out. It's a small world, right? You usually probably find somebody who may know the person that you're talking to. You know, everybody looks great on a sheet of paper, but until you actually talk to them, you know, sometimes you get a little different outcome. But I always like to find folks who know other folks. That's always a good source of talent for me.

For sure. Yeah, the referrals or talking to someone that's worked with them before, asking them about a recent deal they've had to navigate that maybe was challenging. I mean, there's a lot of questions you can ask there.

And yeah, that's what I always ask, you know, tell me about a recent win that you're proud of, how you started it from, you know, the ground up, what were some of the challenges that you encountered along the way, how'd you overcome them, and, you know, what was the ultimate result? And if they really can't talk through that, then you know that maybe they really aren't right for the role.

For sure. And then that also goes into wherever you're at. Do you have existing accounts that they're trying to upsell, or do you have inbound coming in, or are these people gonna have to hunt and find new business? There's, there's definitely different mindsets for, for those situations. And on that note, what, what's your philosophy on that? Do you think, I mean, SaaS is a little bit different from other industries or cybersecurity. Is it typically Like a full-cycle sales rep where they do majority of everything, or is it certain things that they focus on, like just finding new business or finding white space? Could you, could you explain that a little bit just from your perspective? Sure.

Yeah. So here at Security Scorecard, I would say they're kind of a hybrid rep in the sense that they all have named accounts in the enterprise space. Most of them are going to be greenfield accounts, but they do have some existing business. So they have an opportunity to potentially cross-sell or upsell. Hey, you're on some of our older technology, or we see that you have some challenges in this area. By the way, we could probably help you with that. Even though you're an existing customer, there's some additional capabilities we can bring to the table. So they do some of that. They get involved not necessarily in the mechanics of doing things like renewals. That's handled by our customer success team. But that doesn't mean they're not involved, right? They have the relationship. It's, it's their client at the end of the day. And I would expect them to sort of facilitate that conversation and make sure the client is getting the most they can out of the solution. They're seeing value out of it. They're fostering that relationship. But large part of the job is, yeah, let's go out and find some new clients. Right? That's how you grow. If you're not growing, you know, you've got problems.

Yep. And also, that's how you're gonna probably make the most money too. Right? Funding those new accounts and new business. So that's why people get into sales, but it's not It takes time. You gotta be patient. You gotta build it up, especially if the sales cycle is a little more complex, which is really my next question of, I believe that you're in cybersecurity for the most part is typically more complex deals that take longer periods of time. There's a lot of stakeholders involved. There's a technical and a business sale. A lot of people, because it's a very touchy subject with cybersecurity and things that can happen. So what, where do the deals typically stall? Where do things go off the rails? Is it— Because there's such a long sales cycle, or walk us through that a little bit.

So the sales cycles can be longer. Typically when, you know, the deal size is larger, that's always going to be longer. If you're dealing with a much larger entity, that takes more time. There's a different buying process and cycle. You know, you've got to deal with budgets and committees and things of that nature. So that definitely adds time to the deal. You know, I see a lot of deals kind of get stuck in the middle stages. Where, you know, maybe we did not do a good job of systematically advancing and making sure that, you know, we are checking off everything the client thinks is important to them along the way. And, you know, I always say, like, time kills all deals, right? So if you're not continually meeting with that client and making sure that, you know, you're providing value, well, somebody else probably is. It's pretty rare. that we are talking to anybody where they're not also looking at a competitor, right? So, you need to make sure that you're getting the lion's share of that face time or those conversations with that client. So, you're the one that they think of, right? And you've got to demonstrate your value to them. And I find that sometimes, you know, reps will get caught up because they've got many projects going on. They let a little too much time get in between their last conversations and someone else maybe came in and And took that deal away from you. But that's kind of where we see deals get stuck is sort of in that middle phase. You know, if we can get to a point where the client actually tries our solution, does a proof of concept, you know, we usually have a pretty good success rate. But you got to make sure you get to that point, right?

Definitely. That makes sense. It's easy to get complacent at times, or maybe you take your foot off the gas because everything sounds great during the meeting. But if you don't, Continue to be diligent with that and, and have the discipline with, with the next step on the calendar, that type of thing, then it, it can, it can add up over time. Also, a lot of what you're saying is there's a lot of competition, right? And I'm sure you guys have awesome technology and are probably best of breed, but there's some other good competitors too. So that differentiator sometimes can be the sales rep and how they—

Right.

Come to the table, how they're prepared for meetings, how they keep the momentum. They're almost like a guide or a project manager for that. deal or situation. And at some point, I think the, the clients, it's easier to go with the, the person that they can count on that's executing, that's continuing to do stuff. And, and that can give you a slight edge if it's 50/50 and the, the technology seems pretty similar. Sometimes that will help you get over the finish line is that, that rep. Do you, do you see that too? Like the, the rep being the differentiator sometimes?

100%. You know, you hear people say sometimes, well, you know, people buy from people they like, but that quote was actually a little bit different from Carnegie. It was people won't buy from people they don't like. So that was the real quote. And, you know, that's a true statement. So, you know, if you're not somebody who's in there, you know, building value, having a positive relationship with the customer, you come off maybe a different way. You know, it doesn't matter how great your technology is, they're probably gonna go somewhere else. Yep.

Definitely. Quick transition from a leadership standpoint, because a lot of people are sales leaders like yourself out there. What's the hardest part of being a leader right now? I know you're VP of Sales. You guys have aggressive goals. You got to report to a lot of different people, get reps trained up. What's like the hardest part, you think, in 2026?

Well, I think it's, you know, getting other people to accomplish your goals for you, right? So you don't necessarily have control of your own destiny in some ways, you know, as a rep. Hey, I can go out there and I'll just keep turning over stones until I find a gem, you know, here as a sales leader. you've got to rely on others to do that, right? And so, you know, that part is a little difficult. You know, when you have things that maybe aren't going so well, sometimes those are never fun conversations where you might have to make changes. That's sort of the not fun part of the job. But it's, yeah, it's getting others to accomplish the goals of the company and your goals.

Easier said than done sometimes. And do you have any Good lessons as a sales leader? Maybe, you know, maybe a mistake you made years ago and something you learned the hard way that might help other leaders out there of what not to do potentially?

Yeah, it's probably not making the change fast enough. You know, I think everybody sees pretty early on if you've got a situation where things really just aren't gonna work. And I think by human nature, right, you always wanna give people maybe a little bit more time, the benefit of the doubt. You just kind of put yourself further and further behind the 8-ball when you do that. So, I think once you recognize that, hey, this really isn't going to work out, you need to make that change right away. I think in most cases when you do that, the person on the other end sort of expects it. You know, they know if they're not performing well. It also infects the, you know, the other members of the team. So, you know, that spreads in a negative way. So you need to kind of act on that quickly. And I, I think early on I didn't do that enough.

That's a great point. It's not easier said than done for sure, because that's a very tough conversation, but it's just part of the business. And yeah, the longer you delay that tough conversation, the more it's going to impact you and affect the rest of the team, like you said, especially if it's anything toxic going on, which may or may not be the case. Okay, that's great feedback. A little bit, you know, one more transition here. Just, we talked a little bit about AI. I know you guys use a lot of AI within your, your products and then also different tools out there. There's a lot of noise with, with AI. Things are changing daily. It can be confusing. I know, I think you mentioned you went to a trade show recently and it's like every, every sign is something about AI. And that can be confusing for sure. And Also for sales teams though, let's talk specifically for sales teams. Sure. They're, they're busy. They have a lot going on. They're getting told to use this tool and that tool. So there's a lot of things that have been published that AI tools aren't really driving the ROI that people have said they're going to. And there's a variety of reasons behind this. What have you been seeing so far with, with AI related to sales? Has it been helpful? Is it overwhelming? Or what's your perspective?

Yeah, I think a little bit of both, right? To your point, there are a lot of tools out there. So how do you figure out which is the right one that's going to really help you move the needle from a sales perspective. So, you know, we've taken an approach where we're using it for account-based marketing. So we're able to do a lot of the research and personalized outreach that, you know, would take you hours. You know, hey, I want to make a connection with this C-level person at this organization. You know, how do I know what's important to them? Maybe they did a podcast, maybe they did an interview, maybe they did, you know, an article that they wrote somewhere, or they've got a quote in a 10-K or a or an annual report, trying to track all that information down can take you hours to come up with a sentence that might be something that resonates with them. So we use that a lot today. We've invested in a couple of tools that help us really kind of consolidate that down to a couple of minutes where we can get all that information. We've also kind of rolled it out into some of our internal tools to automate some of our administrative processes. So things like Forecasting, quote creation, you know, that's coming, sort of in the works now, and that's helping us quite a bit. And we also use it for coaching. So we've got some AI tools that will allow us to analyze live calls with clients sort of after the fact. It'll go back and say, hey, you know, you did this well, or maybe you missed this or that and you should have added this here. And we can use it for practice, right? So I know the reps sometimes think that's maybe just another administrative thing, but it's, you know, it's really designed to help them. It's not there to be Big Brother. But if you can practice in a place, you know, before you get in front of a client and kind of make those mistakes in the privacy of your office, it's much better, right? So they're able to use some of those tools. And to your point, right, we have a lot that's built into our solution, but that's how we're using it for sales today for the most part.

That's great. So you guys are pretty, very, very active with it across the board compared to probably most industries. You hit the nail on the head. I think if it's stuff that can save you time, you read all these stats that the average salesperson is spending 70% of their time on non-revenue generating activities. So, so not in front of the client.

Yeah.

And it's stuff that bogs you down, that tends to burn salespeople out. So if it's admin related, that prep, the follow-up, the, the research, and you can get that time back to be your A-level version of yourself in front of the customer. I think that's key. And then practice too. That's, that's a great use case. That one takes a little bit, a little bit more effort because it's almost working out, going to the gym. We all know it's going to help us, but it can be uncomfortable, but it's way better to make a mistake on an AI bot than it is to lose a deal and lose the commission. So it makes sense. So that's great. Those are awesome use cases. What the other thing that I think is a challenge is depending on the sales team, there's varying levels of AI adoption. You could have one person that uses Claude and ChatGPT daily, and they have been for a year and a half. And then you have someone else that maybe struggles to log into a Teams meeting for whatever reason, and they're always on the road and they're just old school. I think that really affects some of this. Do you see that as well, where it's like there's different AI abilities between sales teams? Has that came up at all?

For sure. Yeah. We've got some folks that are, you know, super technical, love it. They're writing their own gems. They're building their own scripts. And then we have others that just leverage the tools that we have. Right? So I think both are fine. It just depends on, you know, what your comfort level is. But I haven't seen— thankfully, I haven't seen anyone say, hey, you know, I really don't want to use that at all. Because once they see it and figure out, hey, this can actually make me more productive and help me in my daily life in sales, They, they quickly adopt it. Right? So people can figure out a way to, to your point, you know, automate some of those administrative tasks and do things faster. They're all for it.

It's great. One more question on that, and then we'll wrap this up soon. Is a lot of noise too about AI replacing salespeople and, and this and that. Going back to what you said at the beginning, those, those A players that you're looking for, the people you're trying to hire, I don't think the demand for those type of people is gonna change anytime soon. I think it's actually going to escalate because now you have all the AI stuff that does some of the day-to-day things that maybe people were getting away with doing in the sales role. So I think it's actually going to shine a light on how important it is to have those top salespeople that can close deals and get it to the finish line. What do you think? I mean, do you think it will replace certain parts of the sales job, but not the people that can, you know, get things to the finish line? Or what are you seeing?

Yeah, I think you're right. I think, you know, it will replace some things, some tasks that folks maybe perform today. But I think in complex sales, you're still gonna need people. You know, if you're selling widgets, right, that you could just buy on the shelf going to Target or Walmart. Okay. Well, maybe, yeah, I buy those off Amazon. I don't need to interact with anybody. You know, it's easy.

It is.

But if you're talking about technology that's gonna drive your business, certainly in the cybersecurity space where you've gotta deal with things like regulations, compliance, brand reputation, real monetary loss, right? Those things. And the bad guys are always ahead of the good guys. Uh, you're gonna need to deal with people to figure out what's the right course of action and what's the right solution. So I think, you know, it'll, it'll help with the administrative stuff, take some of that stuff off your plate, get to the point where it builds quotes for you, right? That's kind of the end state for us. We're looking at that where it'll actually make suggestions. Hey, based on the conversations I've had with this client, Build me a quote for this, right? And it'll pick out the appropriate solutions for the customer. I mean, obviously, you still need to go ahead and, and proofread that and check it and make sure it makes sense. You're always gonna need people to do that, but it can help you speed up and get, get out there quicker.

Definitely. And I think the best people that are good closers right now, they're gonna figure out a way to use AI to their advantage to, to do exactly what you just said, where maybe before that would take a person an hour and a half to, to build all that and do it themselves. Now they can, Maybe spend 10 minutes just proofreading it, making sure it looks good, making a few tweaks to customize it, and it saves you all that time so that you're the best version of yourself in front of the customer. Good stuff.

All right.

Couple things to close you out, Bob, is what's one piece of advice that if you could go back and give it to yourself when you first started in sales or leadership, what would that advice be that might, might help other people?

Don't be afraid of big deal numbers, right? So I think when everybody starts out in sales, you're kind of tentative to ask for a A large deal, right? You know, asking for half a million or $1 million from someone you don't really know is intimidating, right? When you first get into sales and you start to gravitate toward these small deals, well, I can get a lot of these little ones and, you know, that'll maybe lead me to big ones later. But don't be afraid of those big numbers, right? At the end of the day, if it's something that is useful for the customer, it solves a challenge for them, and it's valuable, It doesn't matter, right? A deal's a deal.

Love it. It's so true. It can be intimidating, definitely, and you have to look at it from that perspective. All right, and then, uh, what's something you're excited about, uh, the rest of this year? Could be personally, could be professionally. What's something you're really excited about for, for the rest of this year?

Yeah, well, we're growing, um, so, you know, we're growing at 20-22%, uh, we're, uh, looking to make those numbers bigger. We're adding a lot of new technology. We just did a complete rebrand. So if you go out to Security Scorecard and take a look at our website, right, everything has now been rebranded to our Titan platform. So it's more of a platform play. We've made some acquisitions in the threat intelligence and AI space that are adding a lot of capabilities. So, you know, we really have the first truly automated full-stack TPRM platform for clients. who are worried about third-party risk. So we're excited to see where that takes us and continuing to grow for the rest of the year. We've added a lot of new folks, and we're excited to see where that takes us.

Awesome. Exciting times. And if people want to get a hold of you, what's the best way to reach out? LinkedIn, email, what do you prefer?

Yeah, LinkedIn is probably the easiest. Email is fine as well. So I do get a lot of emails, so sometimes I don't always get back right away. LinkedIn, you know, typically pops up, right? So you get a message and I'll usually hit those.

Awesome. Great stuff, Bob. Well, I appreciate you joining today and we will talk soon.

All right. Thank you.