AI-First Selling Is the Future of Cybersecurity Sales - Patrick Dillon CRO @ Nudge Security

Andrew Monaghan (00:41.46)

All right, well, Patrick, welcome back to the podcast. I hope you're doing well.

Patrick Dillon (00:46.275)

Andrew doing great, good to see you again.

Andrew Monaghan (00:48.686)

Yeah, we said that. so we're recording this middle of May 2026. I think we met and talked on the podcast for the first time about a year ago at RSA 2025. Is that sound about right?

Patrick Dillon (01:01.915)

That sounds about right. It's been a full year since I've seen you.

Andrew Monaghan (01:05.079)

Hard to believe, Time flies in this world where AI speeds everything up, it seems.

Patrick Dillon (01:08.552)

I know.

It's non-stop. It's non-stop for sure.

Andrew Monaghan (01:14.574)

Well, when we talked last time, were just, uh, you were in a previous company, you were launching a channel program. We talked a lot about channel stuff. If there's one thing I remember about RSA 2025, it was probably for the first year, almost everything seemed to have AI slapped on it somewhere. Right. And I thought, okay, this must be peak AI. There's, you know, must be it in cyber. It's all over the place. And then fast forward to this year's RSA, which was now, gosh, almost a couple of months ago.

It feels like everyone, everything on AI at least twice or three times. It was like to a different level. And, you you recently joined nudge security as a CRO. I think it must be an interesting challenge for you, right? How do you, how do you stand out? How do you communicate in a world where everyone's kind of in every simulay is in the same sort of space. It must be an interesting process for you.

Patrick Dillon (01:45.851)

We do.

Patrick Dillon (02:04.85)

Yeah, I think it's certainly a challenge for everyone because, as you said, everyone just all of a sudden, even folks that weren't AI first or AI native slapped AI on their booth or on their marketing materials. And next thing you know, they're the next latest and greatest things. Even companies that I used to work for 20 years ago are now AI first. And I'm like, no, that's not really it. And so it's certainly hard to distinguish sometimes. But I think, you know, a lot of our the market understands

kind of what is new, what is resonating well, and what is actually effective versus what is just connecting an LLM to your existing tool stack or to your website and calling it kind of AI first. So it's certainly a challenge, but one that I think we've done a really good job at in terms of kind of separating ourselves from a lot of the other players out there.

Andrew Monaghan (02:57.762)

How important do you think it is to be AI native or AI first?

Patrick Dillon (03:03.077)

Well, think in terms of AI, I think there's a difference between AI native and AI first and AI first can really mean a couple different things. So AI native means that you were, you're a more modern tool where AI was kind of, think integrated into your tool from, from conception. it's, know, if you're a player out there that's been around for, for 20 plus years, 10, 15 years, even, where you've got a lot of customers that are sitting on, you know, kind of heavy tech debt within their environments, whether that's on

on servers or appliances or even some cloud products, just bolting on AI doesn't necessarily make you an AI first organization. So I think there's new tools out there. You see them in identity, you see them in EDR, XDR platforms, you see them in really all aspects of cyber that are really gaining traction very quickly because they're not only solving modern solutions or modern challenges rather,

But they're doing it with modern technology. So it is much quicker to market. know, organizations are able to now, you know, act on roadmap items in a much faster pace than they were before. And I think some of those legacy, you know, players out there that takes a little bit more true hard coding to get their, their products up to date or going down those roadmap items. I think that they're going to run into some challenges now being AI first, I think.

is, two different things AI with the product outward facing and then AI internally to how you are actually utilizing AI internally as a sales organization or go to market organization in order to drive automation, to drive efficiency, to reduce costs. So certainly I think more organizations are trying to go AI first internally to be able to do those things. They can create content much more quickly than they ever could before.

They can automate processes much more efficiently than they ever could before. And so I do think the AI adoption internally is going to happen at a much faster pace than necessarily across all companies within cyber and not just the ones that are more AI native in terms of what their product looks like.

Andrew Monaghan (05:20.781)

Going back to the AI native on the product side, it feels to me like we're up against people who aren't encumbered by roadmaps or technical debt or, you know, we built this for 15 years, so we've got to figure out how we adapt it. They start from scratch and say, they're AI native. To try and combat that by not being AI native seems almost a little bit limiting. Is that something that resonates with you?

Patrick Dillon (05:46.801)

Yeah, I would think so. think that, you know, if you're, if you're trying to go against this curve, I think this is a curve that, you know, there's been fads in the past where people have been like, Oh, I'm not going to go down that path as, a vendor. I think that's more hype and you know, even Gartner has the hype cycle that they do with all, you know, product innovations. I think this one though is a little bit more than just, just hype. think the, the rapid deployment.

and acceleration of AI is too tough to ignore. I think organizations that are ignoring it and don't have deep AI strategies right now, they could be zombie companies and just don't know it yet. Where they will be so far behind when they decide to make that change that it will be, it'll be tough. There were some big changes throughout technology, different inflection points. And I think this is certainly a

a major one for sure.

Andrew Monaghan (06:43.745)

Let's say we have a seller or a leader who's trying to pick their next company and they think, I really want to get into that larger category of AI security, let's call it. Draw the map for us. What are the main buckets in there that they should be thinking about?

Patrick Dillon (06:55.216)

He

Patrick Dillon (07:01.744)

Yeah, I think I think there's two different things if you're looking at as a seller, even as a as a leader, when whenever you're looking at a new opportunity or a new organization first, and foremost, what is your what is the product actually do? I think any good sellers are looking at the company and the customer first. And what what the problem that that organization is looking to solve for that customer. If you're looking at it just internally, I think that's going to be a short term.

fix that you may have. You're always going to have problems as a salesperson or as a sales leader internally. But solving customer challenges is really where I tend to see the longer term heavy hitters, those A-list players that are always making club, gravitating to true product-led growth companies. And I think with that is that certainly you've got the newer ones that are

you know, less than five to seven years old that are that AI native. And you've got to be able to do one of really two things. You either have to take an older legacy process that people don't think works very well and get it to be very, very efficient and working much better via AI. And there's certain industries around that. know, think, you know, MDR is certainly going to be one of those where

you older legacy companies that have been out there for a while, that really have struggled to kind of keep up with a lot of their hype are going to be overtaken by some of the newer AI players out there. I think identity is another one. Identity is a very challenging, you know, probably in my career, I've worked for a couple of identity companies, by far some of the hardest products to implement, deploy and see, you know, fast ROI on.

And so you've got a lot of newer players in the market that are taking that challenge and one-upping a lot of those legacy bigger name companies. And I think in the next, you know, probably two to four years, you're going to see some of those surpass some of those legacy companies. And then I think there's some of the newer things as well. You've got your CASB, SSP, and you got third-party risk management. There's a lot of other tools that are out there that, you know, we're okay.

Patrick Dillon (09:24.864)

and AI is making them much more efficient, much more user friendly. They're able to analyze data and threads. It's not just information. It's AI then taking that information, putting it in usable formats and being able to give the end users a roadmap to be able to go and act on that data.

Andrew Monaghan (09:47.52)

One of the areas where I think it can improve a way that people don't think works that well is the real hype right now at AI for Sock. You know, the triage that's, you know, better done at scale and volume with AI rather than people. Is that something that's over that you think has played out a little bit? Seems like everyone was in AI for Sock for a couple of years there.

Patrick Dillon (10:04.004)

Yeah.

Patrick Dillon (10:11.217)

I don't know if it's necessarily played out. think everything, you know, once again, there's a hype cycle with some of that. I think people will become a little bit more efficient with that. And so does a sock just rely on AI to do all of the analysis? Is there a human in the loop? I think, you know, there's a difference between AI providing information and AI making decisions. And I think that's where there's still, you know, I think the smarter people out there in the marketplace.

are still keeping humans in the loop to truly make a lot of the decisions for the company. They're not necessarily trusting AI to make 100 % of the decisions versus taking the time to actually do some of the implementation and some of the work. So think that's where you will see some separation, not only in just SOC, but really kind of across a lot of different departments within an organization.

Andrew Monaghan (11:06.733)

If you imagine that you're not talking to me, but to a bunch of CISOs listening in on this call, how would you describe where nudge fits into all this? So I completely get the problem that you're trying to solve rather than be totally confused about, did it really mean this or that?

Patrick Dillon (11:18.789)

Ha

Patrick Dillon (11:23.022)

Yeah. Yeah. I think, you know, there's, there's certainly issues out there with anyone trying to identify kind of what, what's their place in this world when it comes to AI. And I think what, what we're seeing out there is, is one of, you know, there's so many vendors that are, that are clouding the market in terms of, we can do everything via, via AI. And I think, you know, what we try to do is, is simplify that, that'll

And it starts with visibility. think that's really the thing that drew me to nudge more than anything is the way that we're able to discover not only known applications and AI tools, but really those unknown, that shadow AI, shadow IT. And that's really, we have yet to find less than the other vendors that are out there. We're always finding more applications, more tools. were on the call with a customer.

or prospects, excuse me, the other day. And they thought that they had about 2000 total applications running in their environment. And it turned out they had 5,300 applications running in their environment. And this was with the VP of compliance who had a spreadsheet open and thought that he knew where everything was. And so I think that's one thing that we do better is we, you you can't secure, you can't govern what you can't see.

And so at Nudge Security, what we do is we provide unprecedented visibility into every single SaaS app and every AI app within your organization. We tell you what it's doing. We more importantly tell you who owns it and what they're doing with it. And then we allow those organizations to make the best business decisions for them in terms of how do they want to move forward? Do they want to allow those organizations or those individuals to continue using those products? Do they want them to block?

Using that, do they want them to be alerted to say, hey, instead of using Co-Pilot, Claude is our corporate LLM, so you need to be using this. So we give organizations, once you identify something, we give organizations a clear path that they can adopt internally that makes not only AI, but SaaS in general, much easier to operate at scale than any other vendor.

Andrew Monaghan (13:41.742)

I remember 10 years ago, Patrick, when SaaS were becoming much more, I don't know, consumer-oriented, right? And the reason Casby's took off was something you could shine a light and say, oh my God, you thought you had 10. Now you've actually got 300, right? What are you seeing out there in the market right now with adoption with the prospects that you're talking to? Are they just like, are they all just all in? Are they just trying to ignore it? Where are they?

Patrick Dillon (14:07.96)

No, I mean, well, I think we typically, you know, talk to a lot of VPs and C-level executives, both within cyber, but also within IT as well. And what they have visibility into is not necessarily the whole truth. And so they understand what's connected, what they have approved in a lot of cases, but what they're not seeing is when somebody on a corporate asset is just signing up with some sort of, you know,

a couple click connection, OAuth connection via their Gmail or Microsoft email account. And voila, they have a new tool that's running on a corporate asset that they didn't realize even existed. Those are the big problems. I think cyber professionals right now, the ones, especially if they've been in it a while, they understand the trench warfare that they've been going through. And they do a really good job of making sure that they've got a good grasp on the things that they know about. Okay, they've put in layered security.

They understand compliance. They understand attack vectors, but what they don't necessarily understand is what they can't see. And so it's the sales person, it's the marketing person that say, I just need this free tool for the seven day free trial period. And then they forget that it's still connected to their systems. And next thing you know, you've got some sort of breach that has been happening over the last

you know, X amount of, of months or days or even years, that, that could have real life consequences. we were on with, with yet again, another prospect doing a demo and it turns out that a former co deputy council, had connected to some app two years ago before he left, he'd been gone for two years and there was a, there was, you know, it was in, in the supply chain breach of affected apps.

and that they had exposure for basically two and a half years. And we were on a demo able to alert their IR team to be able to go in and do some investigations on that. But that's kind of the things I think that you're seeing is that it's, I kind of correlate this. When I grew up, I used to love horror movies. And what was the common theme of all horror movies out there? The calls coming from inside your house. And so that's what it is today. The call is literally coming from inside your house.

Patrick Dillon (16:33.888)

And you don't know about it, you know, until all of a sudden, you know, you're on camera and the, the bad man, you know, pops up behind you with the mask on and stabs you in the back. That's what cyber, you know, and IT professionals are dealing with today. And, and I think our, our buying personas have, have expanded past that. now, you know, have conversations with CFOs with, with, you compliance officers with, with legal, know, chief legal, corporate counsel, because, you know, what happens if somebody sticks

a contract in a free version of Chat GPT. Okay, does that violate some sort of covenant with that customer or with that client? What happens when a financial analyst sticks company financial data into an LLM that is not approved? Does that leak sensitive information out there as well or cause a potential breach later on down the road? I think the concerns around cyber

with AI have expanded than outside of just the cyber IT realms that you traditionally see.

Andrew Monaghan (17:37.549)

Yeah, it feels like DLP from 20 years ago when I used to sell that. You need the HR and legal and people in the room because there's real issues if things are found in certain circumstances.

Patrick Dillon (17:41.583)

Ha

Patrick Dillon (17:48.179)

Yeah. Oh, 100 % 100 % company I used to work for bought a DLP company and you're absolutely right. It's where is the data? Where is it potentially leaking to? And you know what? What can we do to potentially stop that? But yeah, you have that, you know, multiple multiplied several times with AI.

Andrew Monaghan (18:09.005)

I think one of the things that's different now, both for security practitioners and for vendor side as well, is the speed of new things happening, right? I mean, you just sit there and go, well, there's a new version of something was delivered last night and there's a whole new ramifications of what it may or may not do. And no one gets heads up about it, right? No vendor is told, by the way, this is coming out even tomorrow. You just find out because it gets announced. However, are prospects dealing with that?

Rapid change.

Patrick Dillon (18:41.51)

I think they're dealing with it in two different ways, one positive, one negative. I think the negative is yes, the products and things are changing on a vastly quicker scale than ever before. Here we were, our dev team was cranking out basically, I think it was three to four new application connectors on a weekly basis. And with the help of AI, I think that jumped.

five, six fold, you know, kind of over course of a couple of weeks. You know, so, so they certainly can see things, you know, coming at them much more fast than, than in the past. But I think some of them are taking advantage of that because there's not a single security vendor out there that, that when they're talking to a prospect, hasn't been selling ahead of the curve, you know, they're like, yes. What do you want to see in the, in the long-term and short-term roadmap items?

And now customers are like, yeah, we know you can deliver this much more quickly because of AI tools. So now something that you said, we'll get on there six to 12 months from now. They're really demanding that it's on there in one to three months, or they're not going to sign a new contract, or they're going to look at, you know, replacing you as a vendor. So I think they are utilizing that to their advantage as well to say, you know,

We know that you can do this much faster than you have been able to in the past. And if you're not set up for that, are you really a vendor that we necessarily want to continue with long term?

Andrew Monaghan (20:14.509)

And then what does that mean for the seller then? Because you're sitting there, you've been enabled, you know what our product does, and then suddenly you get asked about something you never heard of before. It's, yeah, it came out last night. How do you train the team to work with situational data?

Patrick Dillon (20:26.319)

Sellers always like to say yes to everything, unfortunately, but you know, I think, I think, in, reality, you have to be much more diligent in your responses. Okay. I think technical buyers have always been somewhat skeptical. That's why the position of sales engineer exists because they want to talk to somebody with some technical expertise that will tell them the truth about a product. you know, so the sales guy is, is always taken a little bit with,

with a little checks and balances from the technical buyer. But I think the more skilled technical buyer or technical sellers out there today will continue to do what they have done best. They will, you know, they're not going to over-promise something to their buyers. They're going to make sure that they're working with product and the engineering teams to make sure that they've got realistic timeframes for when they can get things out.

I do think though that you'll be able to communicate that more efficiently up and down the chain. So you'll be able to take the information back more directly from the customer. So for instance, everybody has call recordings on their calls now. So we use Fathom, we're pulling all that information back. we're on the phone with a customer,

we know immediately if there's a product enhancement request that they would like to be able to see. And it already has flown through there versus, I've got to get it. I've got to now update my notes. I now have to put it in some other system. Now I've got to get it to the product team. Just the speed of communication from the customer to internal teams has improved rapidly with the adoption of AI. And then I think, once again, you're going to be able to use AI to be able to help.

accelerate your roadmap in a much, more efficient way. And, you know, I think that there will be benefits on both sides, both the customer side and the technical seller side.

Andrew Monaghan (22:30.615)

Let's narrow that down a little bit more. I you joined Nudge now, what, three months ago, we taught, you mentioned before AI first. What is the go-to-market Nudge look like as Patrick comes in and tries to have an AI first go-to-market team?

Patrick Dillon (22:46.958)

Yeah, I think that's a great question and one that we discuss on a regular basis. And if you think about the way that most organizations have always kind of aligned, everybody knows the old age, old adage, people process and technology. Okay. That has been tried and true. And they're like, Oh, you can solve it with one of these three things. I think an AI first, you know, go to market is really flipping that out of its head where it's technology process and people. So you're not necessarily scaling.

with vast amounts of bodies. You're scaling with vast amounts of technology. You're getting the most efficient processes that you can, and then you're hiring more diligently. And when you're hiring, you're able to get more out of the employees because they're not having to spend as much time doing administrative tasks, doing things that they used to take a long time.

you know, for example, you can do call preps and debriefs and emails in the matter of a couple clicks. It used to take you, if you had a big call coming up, going through a K1 report, looking up the key stakeholders on LinkedIn, looking through all your notes in your notebook or in your CRM system, that took a lot of time. And then putting together questions based off that, or putting together questions based on the last five calls that you had.

That is now all a couple of clicks away. You're able to really utilize a series of tools to where we can, once again, from that call recording, automatically pull that back into our HubSpot system, align it to MedPic, or if we were using a different sales methodology, we could align it to really anything. We can put in buying factors, risk factors, risk scores into the deals.

And it can automate a lot of those things. It can create a follow-up email that then, you know, our reps can then obviously tweak, review and tweak, and then send back out. And it can learn, you know, every single time, you know, how to get better and more efficient with that. So for us, you know, we, we took a thought process of let's make sure that our sales teams are the absolute most efficient. You know, there's not a sales person out there that doesn't hate

Patrick Dillon (25:09.185)

having to update, you know, their CRM. In fact, most of them have it planned on Friday afternoon or Thursday afternoon, you know, before the end of the week to just go through and update everything. Those things should be a thing of the past, you know, nowadays, getting real time information from, from reps at the end of a day, end of a week should be a couple clicks now. And I get, you know, much more detailed reports than I ever could because

you know, we've got our financial systems, our CRM systems, our call logging systems, all connected back into Claude. And I can now just prompt into there and get, you know, information that I used to not be able to. Now, when we hire, I think we hire, we have to hire folks that are more apt to utilize those tools and be more efficient. So I don't think AI is necessarily going to replace salespeople. I think AI is going to replace

salespeople that don't effectively use AI. And so now when I scale, know, cause we're still planning on scaling significantly over the next 12 months, I've got to look at different types of candidates out there that also are going to follow that same type of philosophy and understand how to utilize these tools and get the most out of

Andrew Monaghan (26:22.573)

All right. A lot to dig into right there. Let me first of all, just an aside. I saw something a couple of weeks back. Salesforce said that their goal is that it becomes for a salesperson a headless CRM and they should just be interacting with agents. You just imagine the cheer that went up around the world. That means I'd never have to use Salesforce again. That sounds awesome. So let's talk about hiring then. So you said you'll be very careful who you hire that they thrive in that environment, not someone that

Patrick Dillon (26:40.694)

Yeah.

Andrew Monaghan (26:51.265)

comes in and goes, my God, I'm scared by what this means. How do you know you have someone that would thrive?

Patrick Dillon (26:58.389)

I think the folks that are actually utilizing that not only day to day in their current jobs, they can articulate that pretty quickly, but are they utilizing that during our interview process? If they're not, then there's something wrong there as well. This is something that I think is going to be ingrained in people for quite some time. And it provides a lot of insight into doing this. I was able to download a lot of your information and

you know, from our last podcast, from other podcasts that you did in order to prepare for this conversation. So I would expect candidates would do the same thing around that. You can ask them questions around, you know, call recording to sales methodology, to discovery questions, closing questions, how you're analyzing deals in there. And the ones that do it, they'll understand how to do it very, very quickly.

The ones that don't, I think will stumble a little bit. They'll be like, oh yeah, I use ChatGPT to do all this all the time. And it's more about how you're using connectors. And if you're using Cloud or you're using Cloud coworker, using Cloud code, you're just prompting in those things. we took, my first week on the job, we had our all company meeting and we actually took a half day to break out into teams and to solve

internal challenges around AI automation. What could we do around that? And so that's the things that we have to look for and screen for when we're doing candidates. And it's not a skill thing or an age thing. It's really a want to thing because it's the people that really want to continue to provide the best service to their customers.

can do that through a lot of efficiencies and automation with AI. So don't care if you're a 25 year seller or a much greener seller with not a lot of tenure. If you're able to utilize the tools in a more efficient way than the next guy, that's the person that I want to hire. I don't want to hire somebody that says, no, I'm bringing my Rolodex and it is an old school Rolodex.

Patrick Dillon (29:16.661)

and it takes, you know, and they're going to close now one deal a year and it might be a big deal, but they're going to close one deal a year and they're going to, you know, do their old school takes forever to do that sort of stuff. That I think is the things that are, that are really going to change. Not that those top sellers can't continue to be top sellers, but now they'll continue to win much more frequently and efficiently. if they're able to utilize, you know, AI as part of their process.

Andrew Monaghan (29:45.326)

Yeah, I see that a lot. One of my clients a few weeks back, one of the sellers just over a weekend created what he called his sales brain inside Claude. And he just pumps his deal information in there, spits out his gaps and what he needs to work on and who he needs to go meet with now. you know, it completely changed this whole world. And then you got people who sit there and go, well, I put in a prompt to chat GPT and I get some information back from it. Right. It's just such a different mindset about how to deal with it all.

Patrick Dillon (29:55.789)

Sounds great.

Patrick Dillon (30:00.33)

yeah.

Patrick Dillon (30:12.749)

I thought Claude code was a new skill that was in there that I didn't know about yet. So yeah, but you're right. You're you throw that information in there. It tells you what questions to ask. We created kind of a scoring risk spreadsheet that Claude helped to create, but you know, somewhat based on MedPig, but is pulling all of that information in and it'll score a deal for us and give us a risk profile and then it'll tell you. Based on this next call and all the information that we have.

here's what you need to do. Here are the questions that you need to ask. Here are the risks associated with that. And it looked back across all the different calls that we had with that prospect in order to generate that. All of the emails and then say, here's what you need to do coming into this meeting and here's the action items that you need to make sure that you get coming out of that.

Andrew Monaghan (31:01.611)

And in your world at Nudge, I mean, you're still a small company in this scheme of things, right? Are you expecting the sellers to drive all that in their own or do you feel like you've got to be in the loop to really hold accountability still and make sure these things are happening?

Patrick Dillon (31:16.446)

Yeah, you've got to have a process because otherwise you're going to then have more AI sprawl and SAS sprawl internally. so what we want to do is we want to break out each area of the business. So from the time the initial intent signal comes in until the time that the deal is closed and transitions over to the customer success team, while they are engaged all the way through to renewal, there needs to be a consistent set of tools and processes.

that go along with the people that manage those. So we can't have everybody just doing different things. So part of the process that I'm working on with our SE and Sales Ops team are identifying those products that we currently have. What are they doing? Are they the right tools? Do we have any overlapping tools that we can maybe get rid of one and buy another one? So then that way everybody has a clear thing. So they're not just doing.

nothing but prompts in Claude that they've got, you know, a clear definition of which tools that they could use. Now, the good thing is with connectors, you can stay in one platform a lot longer without toggling back and forth, or as I do have millions of tabs open. But you've got to have a really nice structured system for everybody to utilize because...

Once again, if it's connected to your own corporate LLM, it's going to be learning from everybody and not just from the individuals.

Andrew Monaghan (32:46.367)

If only you had a tool that would tell you what everyone's using,

Patrick Dillon (32:50.748)

Exactly. Where can I find that?

Andrew Monaghan (32:54.701)

Going back to the first thing you said though, Ryan, I think you said technology process people. Are you able to track, know, two years ago you would expect the yield from a rep of this much and now it's that much higher? And what sort of figures are we talking about in terms of percentage gain?

Patrick Dillon (33:11.326)

Yeah, so that is the process that we're trying to solve right now. So we don't, you know, at least I don't have an efficiency number right now. I couldn't tell you if that's going to be, you know, is it going to be 10 %? Is it going to be 50 % more? We are starting to calculate the time that it takes to do a lot of the research and the follow-up and trying to put that into dollar. Dollars saved, I guess, from a time perspective.

We do not have an outcome yet to say, okay, if a guy's quota was a million, now he should be able to do a million three or a million four based off of that. That's what we want to get to. And that's what I've been kind of charged with. So we're tracking it very, very closely. We did some benchmarks with our team when we first started, you know, how long it took to get deals done, how many deals were they doing at a given time? Cause there's a threshold for everybody.

you know, and there's a threshold even for AI and AI agents, there's not unlimited ones without costs associated with that. So we want to make sure that we've got humans in the loop that are at capacity, but not at burnout stage to where they are making the most money possible. Cause that's what sales, good sales reps want to do. And how can we, you know, drive more of that? There's not a single sales rep that doesn't want to make more money.

So if I can provide them tools, better tools and better processes to do that, it's just like if marketing gives them more leads, they're never gonna turn that down. And if we can get more leads with AI as well, then that's what we wanna do. So I've charged our marketing and SDR teams to get just as efficient as our sales teams in driving new, know, SALs, SQLs that get the sales reps more at bats.

And then I think through the efficiencies of AI and the processes that we put in place, we hope to see that they will close more deals. talk to me in a year and we should have some good data for

Andrew Monaghan (35:10.603)

It feels like it's something you have to closely manage. Tell a seller they can sell more is great. Tell them the quota went up by 50 % at the same time. They're like, hold on a minute. And your ability to overachieve, much easier in a 750 versus a 1.5. It feels like you have to manage that process and say, look, there's things that you're getting to be more productive, but there has to be something that goes with it that allows us to invest.

Patrick Dillon (35:36.394)

Yeah, I think that's right. And there's going to be a delicate balance because what you also don't want to do is you don't want to limit salespeople on the amount of money that they can make as well because most salespeople are coin operated. So if you say, you can only make a maximum of this, they're going to go and find a better place to be able to maximize their potential. while we want to make sure that we're making them the most efficient, we also want to make sure that we're putting good money in their pocket and that they're staying long term.

I think, you know, keeping the humanity piece of all of this AI hype is going to be important. And you've got to be able to hire really good people, not only really good people with AI, but really good people. And you want them to stay. And I think that our customers and our buyers are going to want that same thing. They're not going to want to just talk to an AI bot the whole time. I think that they certainly, you know,

late at night if they want some quick information and they want to log on and get something real quick from somebody, that's fine. But I think having that human connection is going to be vitally important as you move forward. And so we want to not only hire for efficiency and willingness to work within AI tools and AI native environment, but really that are top notch people that you would want to, on any team, regardless of what you're selling.

Andrew Monaghan (37:02.889)

Is this something you've tried so far that it just didn't go well? That kind of go back and say, let's let's put that on on the back shelf for a while.

Patrick Dillon (37:12.436)

Yeah, I think I try a lot of things on a regular basis that don't always necessarily go well. I think that's one thing that I kind of like to do on a regular basis. That's a good question. Trying to think, you know, certainly there there's different content out there that doesn't resonate as well. You know, there's because you can create content so quickly. I think with AI you're much more reticent to generate a new piece. So you know.

customizing things for events or for, you know, particular individuals or particular companies. Sometimes when you try to do too much customization and it doesn't work well, I tried to customize an AI video for an internal, you know, company meeting. And I don't know if you remember if you ever saw the movie, Airplane 2. Everybody saw Airplane, but not that many people saw Airplane 2. And I created this whole thing and it was the scene from

when William Shatner is in the control tower and he's like, all these lights are blinking and flashing. And I thought this was hilarious. And I'm delivering it to the Aussie audience and they had no clue who it was because they called it flying high, not airplane. And so, you know, I thought that this was going to be, you know, and I, you know, put in, you know, our company and all sorts of just, you know, customization via AI into that.

And I thought it was hilarious and I was literally the only person laughing in the room that time. And everybody was laughing at me versus with me. Once we got done and realized that it was named a different movie and it just didn't land very well. yeah, I think the experimentation of it is kind of fun, but you can also go down. my dog almost pulled off my laptop there, sorry.

The coziness of having a golden retriever under your feet is not always the easiest thing. But yeah, so I'm always trying new things, but that was one that definitely fell very flat.

Andrew Monaghan (39:16.749)

Yeah, that's funny. Different cultures, different impressions. You one of things that people are worried about, it seems right now, is will AI replace salespeople in some sort of way? And let me put a couple of thoughts to you. When people say AI is going to replace salespeople, salespeople come in all sorts of different shapes and sizes, right? The person is closing a 5K deal on a local thing in Florida versus the person is closing a $20 million deal for a

Patrick Dillon (39:20.768)

Yeah.

Andrew Monaghan (39:44.768)

A global agreement is a very different sales environment. That's one. then secondly, think what my thought is that what it will do is make those that have the human connection and have the credibility and the gravitas to engage properly as a human being. They're going to shine much higher than those who are in the slot, basically, in the middle of slot. So definitely things are going to raise up a little bit, but those at the top end will probably do even better than they are right now.

Patrick Dillon (40:08.0)

Yeah.

Andrew Monaghan (40:14.504)

Is that ring true for you?

Patrick Dillon (40:14.996)

Yeah, yeah, I agree 100%. I think the top people will adapt very quickly. They'll adopt the new tools. They'll continue to be the top players out there. I think those bottom third that tend to jump from place to place to place might get a deal here, might get a deal there. You know, those are the ones that I think AI will replace with that new crop of, you know, younger reps coming up.

that are taking full advantage of the tools and the processes that will make them much more efficient. I don't think AI is going to necessarily replace all people. think AI will replace people that don't take advantage of the efficiencies and the productivity gains that AI can provide. And I think if you're just not going to go down that path, that's not just sales. I think that's a lot of different positions.

If you're not taking advantage of a newer technology and newer processes around that technology, those are the folks that I think will unfortunately be left behind.

Andrew Monaghan (41:21.899)

And is there any way to train people like that? Or is it really just a mindset that they have to approach and adapt to?

Patrick Dillon (41:27.615)

I think you can train. I think there's a lot of courses and, you know, programs that pop up on a regular basis to be able to do that. There certainly has to be a willingness, but there has to be a willingness to, you know, technology, you know, has always been evolving. You know, ever since I've been in sales, I mean, you know, we were, we were around some of our kids the other day we started asking them, you know, what a, what a bunch of Gen Xers would ask them, you know, what's a fax machine, what's a beeper, all these sorts of things.

And we don't have those sort of things because technology has evolved obviously, but those things were cutting edge at the time. Ooh, somebody can page me at any given time. And then I can go to my phone booth and call them because I got a number on my pager. Ooh, that's, that's kind of cool. You know, so it's once again, the, people that take advantage of the new tools that are, that are coming out there. and there's, there's courses, there's, you know, things pop up in, in social media feeds. You can go to YouTube and, and see just, and get trained on just about anything.

Or you can actually ask, you know, Claude or Chad to create a process for you. You know, train me on this, train me on AI. What is the most efficient way based on everything you know about me, everything you know about my company, put together an AI training course, you know, for me. And so there's ways to be able to do that. I think it's with a lot of things. If you have a will, there's a way. And it's the people that just kind of stick their head in the sand and be like, nope, I'm not gonna do this regardless.

Those are going to be the ones that are going to have to figure out kind of where they fit in the world longer term.

Andrew Monaghan (42:59.837)

I feel like we're in the golden age of if you want to learn anything in the world right now, it's at your fingertips. You know, it really is. Yeah.

Patrick Dillon (43:03.691)

Oh, yeah. And you can learn it however you want. You you can create your own, you know, learning system if you're a visual learner. Great. Take all of these phone calls and generate a video for me that shows me or a cartoon that shows me, you know, what's the best way that I learn? Oh, yeah. I think you can customize just about anything you want nowadays.

Andrew Monaghan (43:26.125)

I think my challenge right now is how do I not get distracted by all the things I could be trying out and keep focused on the ones that last year, we need to deliver some things here and keep moving forward. It's amazing what's there. It really is incredible. So if you look at for the rest of the year, Patrick, and what you're achieving there at Nudge and what the sales team and the good market team is doing, what's some big highlights you're really shooting for this year that would be interesting for someone to know about?

Patrick Dillon (43:36.288)

Yeah.

Patrick Dillon (43:54.603)

Yeah, so you know, certainly, you know, we just got our series a last November. So we're looking to really invest heavily in our go to market teams, both people process and technology, or in our case, technology processing people. So we're looking to really almost triple the size of our go to market team in the next six to 12 months. So we're going to be hiring, you know, really kind of across the board. So sales, you know, all different levels.

SEs, know, channel, we still have a big channel first approach. So just like we had that conversation a year ago about what the channel program that we just launched at Airlock, we're in the process of developing a world-class channel model as well, because we do fully believe in the channel go-to-market strategy. So there's a lot of other areas that we're looking at as well. How do we, you know, as we rapidly hire

How do we enable everyone? We are a hundred percent remote company. So everybody is remote. So what type of efficiency gains through technology can you do in terms of training people, in terms of bringing them together? We're actually getting together as a team next week again to kind of go through our next phase of growth. Here's what we want to do. Here's what we want to see. So we've got a lot of big things that are...

kind of coming out, but it's really goes back to that rapid scale piece. We have some big plans and big numbers that we want to hit. Over the next, let's call it 18 months, we're almost at the midway point of 2026. So we see significant growth between now and the end of 2027. And then from there, who knows, with the efficiencies that we're able to do and-

really kind of the leadership that we have in our two co-founders. The sky's the limit for us, which is really kind of nice.

Andrew Monaghan (45:51.822)

Well, it's definitely exciting times in our industry right now. You know, for many of us, it's exciting time to be in go to market and it seems like you some good things coming up for for nudge as well. So look forward to seeing those.

Patrick Dillon (46:01.771)

yeah, we're very excited and the future is very bright for sure.

Andrew Monaghan (46:06.474)

All right, well, look forward to hear all about it in the future.

Patrick Dillon (46:09.085)

All righty. Thanks, Andrew. Appreciate it.

Andrew Monaghan (46:10.766)

Thanks a lot.