Entry & Exit #64 The New Playbook for Scaling a Security Business With AI

Scaling a security business isn't just about hiring more people. It's about getting more out of the team you already have.In this episode of Entry & Exit, Stephen Olmon and Collin Trimble break down how they're using international employees and AI agents at Alarm Masters to automate estimating, prospecting, sales support, and daily operations.They share what's working, where human oversight still matters, and how to build systems that support growth without unnecessary overhead.

Scaling a security business isn't just about hiring more people. It's about getting more out of the team you already have.

In this episode of Entry & Exit, Stephen Olmon and Collin Trimble break down how they're using international employees and AI agents at Alarm Masters to automate estimating, prospecting, sales support, and daily operations.

They share what's working, where human oversight still matters, and how to build systems that support growth without unnecessary overhead.

In this episode:

→ Freeing up salespeople to focus on selling

→ Combining international employees with AI automation

→ Automating proposals, prospecting, and appointment setting

→ Building AI agents that communicate and work together

→ Streamlining service quotes, customer follow-ups, and operations

→ Why AI still needs human oversight

→ Building the systems and infrastructure to support growth

Connect:

Stephen Olmon — https://x.com/stephenolmon

Collin Trimble — https://x.com/TXAlarmGuy


Owned and Operated
New Episodes Every Wednesday!

Subscribe For More

Kind of zooming out.

We tried early on to hire okay people at really cheap rates. Find the best, smartest, brightest, hardest working people you can. Got into the AI world and I started seeing people say, Oh yeah, I've got a whole team of digital voices. Like, yeah, what? Do you have like five Claude threads named sales, marketing? Like, what is what are we talking about here? That's funny.

That's

funny because it's true. But I actually saw the future 10 years ago. At times we are going to want to personify and put skin on digital employees and throw them on a screen, but you can further integrate them into your business.

And it's a lot of like random things, it's not just like one structured task that you could just like AI out of it.

I think we should have our AI employees listen to our podcast and send us feedback. I agree. Welcome to Entry and Exit. My name is Steven Ullman, and I have my co-host and business partner with me, Colin Trimble. And we run this podcast to help people out, help people understand how to grow and scale their business. And one of the ways that we have done that is by building digital employees, like AI-based team members. And we're going to talk about how we engage with them and how we have our team members engage with them in our business. So let's let's talk about uh in a little more detail um how when we take things off their plate, like what are some things that we've taken off of our salespeople's plates and how?

Yeah. Or let's start with the let's start with the order of operations of which we've taken stuff off their plate. How about that? Yeah. Uh and I think it's important to delineate the things we've taken off from international versus AI. And so I think we should talk through sort of our journey to a segmented sales. We're gonna summarize a lot and we're gonna consolidate a lot because we don't want to go too deep onto this topic uh because we should stick around.

Um, but I would say the very first thing is we hired a sales guy and we said, Hey man, you need to be prospecting. He said, Man, I would love to. I am slammed with uh creating proposals. It takes forever. Uh, and so the first thing we did is we hired an international employee that uh their job exclusively was to work with the salesperson to collect the information and generate the proposals and follow an estimation playbook where they would notice trends from the ops department. So they would say, Hey, um, how did we do on hours here? And the ops team would say, You were way under hours. It's like, okay, why? And so they would start to learn the nuances of that. And then it was like, oh, you were under hours. Like, great. So we have a little bit of wiggle room on the next proposal that's similar to this. So creating some of that knowledge and documenting it in such a way that we can be more competitive. A salesperson does not have the bandwidth to do that. They do not, even if they're in a post-mortem, they're not exclusively focused on how do I create the most competitive, accurate quotes possible. They're figuring out how do I do this as fast as possible. It's 7:30. Uh, I'm on season three of Silo, and I only have two episodes left, and I want to go to bed. And that's what they're doing with their quotes. Um, and so what we started with was hiring international employee who was doing that for us, and he he crushed it. Shout out Felix. He's now a supervisor for our inside sales group. Um, and he managed that, and that took a massive load off of our salesperson's plate. So that was the first thing we did. We actually doubled down on that as our next sort of iteration because we found that Felix was getting overwhelmed as we started to scale the team. We're like, man, one guy can't support three people. And so uh we ended up building an AI agent that using natural language and looking up historical quotes will actually build the full proposal for you and then drop it into Salesforce with the markups, scope of work, exclusions, subscriptions, every everything written in there. And it just takes time for the salesperson and Felix to just review to make sure it's all kosher. Um, so that was the first big bucket, right? Is like getting estimation proposal generation off of the plate of the salesperson and into the hands of an international employee, and then it was international plus AI, and it'll always be that way. We're gonna always have Felix involved. He is the keeper of the keys for our proposal and design generation stuff. Even now, our reps, even though now our reps are doing some proposals just straight into Eddie, our estimation agent. Felix is still laying eyes on pretty much everything that's being generated. And it's gonna be like that. Uh because we're gonna be making tweaks, we're gonna be making adjustments.

We created an AI agent that goes and scrapes publicly available data to uh Stu, is his name. Um, thanks, Stu. Shout out Stu. Shout out, Stu. Um, to find uh publicly available data, to find compelling events and triggers to find prospects. So we would go, okay, so we want senior living, that's our ideal customer profile. We want to find a reason to call on them, not just show up. So we started scraping public data about uh staff changes, fire citations, OSHA citations, etc. Okay, so now we've got we've got an ideal client profile, we we've got a prospect, we know in a compelling event, but we don't have the contact information. So then we built the side agent on top of Stu, Stu B, that basically goes and enriches it, uses both Apollo, which is an API service, and it also just does a massive waterfall scraping the internet to find more leads.

Um and then it surfaces it uses some inference, doesn't it, too? Like it's got some intelligence.

Yeah, so it'll it'll uh use inference to find emails. Like so if it finds, if it knows the executive director's name is Becky Smith, and it can't find Becky Smith's email online, but it does know that Frank Albertson is the janitor and his email is out there, and it's F Albertson at whatever, it'll say, okay, well then maybe B Smith at, and then it'll actually use a little SMTP server to ping the email address to see if it's kicking back, like returning, hey, this is not a valid email address. Then what's really cool about that, so it creates the lead, and then what it actually does is it layers on a point of view. So it says, hey, here's who you're talking to, here's their role, here's the facility, here's the general size of facility. It's 450 beds, it's an independent living facility, it's just it got freshly renovated, it got recently acquired. You're talking to the executive director, and it presents that information so that the salesperson has that we call it a POV point of view, going into the customer. And so then we will actually just have them do drop-ins on that, but also simultaneously, our international SDR is making phone calls on that to set booked appointments. Um, and so that was the first fill the calendar is fill it with booked appointments and drop-ins um to be able to get in front of customers more often.

And so now you've taken off at this point the estimation appointment booking, and you're starting to make their world smaller. Yeah, right? Like you're starting to make the salesperson's role tighter and you know, gives them clarity, frankly, like brain space. Like I just think you're gonna close at a little bit higher rate when you're not as distracted, like squirrel, right, you know, all the time. Yeah. So I I so that's first first couple things. Anything else that you want to highlight or things that we're thinking about doing next?

Yeah, this is a little aside that I'm I haven't even told you this is something that I'm gonna start building when I get some more capacity. Is uh for the drop-ins, I'm gonna start having, I've already told them to start doing this, to start taking pictures of themselves in the lobby of wherever they're at, put it into the Slack channel, and then I'm gonna have the AI agent take that picture and email it to the executive director to say, Hey, sorry I missed you while I was here. I'd love to come back and make a picture of the two of us next time.

Okay, so I love that. And I thought what you were gonna go was one of two ways. I thought you were gonna superimpose the executive director with them. Like, great to see you. Yeah, that is funny. Like, wait, when did we meet? Yeah, or or like actually use a direct mail API and like send a photo of you there. Yeah, that both of those, anyways, we can play with that. Yeah, by the way, little little sidebar. Um, I think we should have our AI employees listen to our podcast and send us feedback. I agree. Um I and and then they can they have emails, yeah, so they can subscribe. And and if you aren't subscribed, that's a great point. You should be like our AI employees, you should subscribe to our newsletter, to our channel, give us a like, a comment, tell your mom, tell a friend. Yeah, and because Stu and Kevin and Chase and all of them, all of our AI friends are going to as well. Yeah.

Yeah, so we have some agents, uh, both Stu and Kevin. Stu is almost entirely trigger-based. So Stu is searching the internet, looking for changes in public data, flagging that and producing a morning digest to our team.

Yeah.

Kevin is both proactive, listening and scanning calls, finding demand and surfacing that in a morning digest, and also uh reactive, meaning he's a chat agent, and there's a chat service where he can say, Hey, uh rep, the rep says, Hey, Kevin, find me leads in this area or whatever, and he'll go do that. And so um they both kind of interact uh with the individual, but they also can interact with each other. So, like Stu can send a message to uh Kevin uh under certain circumstances as it relates to like, or actually, it's really more the other way. Kevin will send a message to Stu for route planning. So it'll be like, Hey, can you put a route together for this? And Sue's like, yeah, bam, and I'll send the meeting invites. And then Stu sometimes can reference to Kevin if they want to look at the parcels of land, but we're not doing that a ton, but it has happened where they'll be like, go look this up. And Sue's like, hey, at Kevin in Slack, like, can you do this? One really cool example, one that I did not build this agent. It's um, I don't know why he named it. It's uh Albert built Ollie. Oh, Ollie, the operations agent. And um Ollie is trigger-based on when we close when a deal, it pushes a bunch of workflows out, creates a work order, sends the deposit invoice, sends the opening of the project email to the internal team and Slack messages, creates a folder. Um, but then it also will uh do it, it's really cool because it also serves the service team. So if a technician puts notes and says, hey, we need a return trip meeting because we need a quote, it'll actually take the notes, copy and paste it into Eddie's channel. Eddie will do all of the estimation and push the parts back to Ollie, and Ollie will then put them into Salesforce and generate the service quote. So they are like having some conversations back and forth. Obviously, we can see all of that in Slack that's happening real time. And it's really just saved us a bunch of time. I mean, think about how often this happens in people's businesses where it happened in ours for years. Technician says, I need a quote for this customer, and their brain turns off, like, okay, I've told the office there needs to be a quote. And like I put my notes in there. But then the office folks are like, oh yeah, I gotta do that, and I gotta get it to the person that's gonna do the quote. And it's like only a couple of people on the scheduling team know how to do that, and then they're like coordinating, and then you gotta get a thing, and it's like just doesn't happen, or it happened takes too long. Now it's just like bam, it's done. Like within an hour.

That was really cool. Well, I think where this is gonna go is at times we are going to want to personify and put skin on digital employees and throw them on a screen and have voice to voice. Yeah, and today that's already possible, like with Hey Jen or 11 Labs. Yep. And basically, like working with Eddie through a proposal, voice to voice, uh, is actually not far away. We couldn't force it to happen today. It'll probably be six to twelve months from now before it's like really feasible. But you can further integrate them into your business if you want. And so it'll be interesting to see how far we take that.

The next one is Chase the case agent. Chase is on the case. Chase is on the case. Shout out Paw Patrol.

Paw Patrol.

Yeah, exactly. Uh, and so Chase the case agent is basically doing what Kevin is doing for sales, but for for case handling. So he's listening and reviewing all the case stuff, and I'll say, hey, this customer sent you an email uh case handler, and you haven't responded to the customer in 24 hours. You should do something about that. And by the way, what we think you should say to the customer is this, and it drafts the full email for you, and then you can edit it right there in Slack, and it literally copies it into the Slack dedicated Slack thread for every case. So all the documentation is there and it's self-learning. We don't have agents today, trying to make sure, keep myself honest here, that are autonomously communicating with customers in a dynamic way. Like it's not saying email send, customer replies, email replies back without us uh having to transition kind of right now. Yeah, it's like, hey, it'll send one email, but then if there's a reply back, then it'll suggest some stuff and then the person has to approve. There's

like some guardrails around that because we want to make sure we deliver a good experience.

Uh being built for growth. We just talked about being kind of prepared and built for growth from a team perspective. But if that team doesn't have the underlying technology and infrastructure, it's not, it's not even just for us as you know, our whole business is built on Salesforce, it's not even just that. Like there's other elements of infrastructure you have to have as a business. Um and so are you built operationally and from like a supporting technology and systems perspective to experience that growth?

I was just having this conversation the other day with a friend in the in the industry who I had recomm I recommend a lot of different folks that say, Hey, I want to do the Salesforce thing. Can you introduce me to some great people that can implement Salesforce and some great um sales folks at Salesforce that can help us, you know, get a quote or whatever? And so I've done that probably over a dozen times for folks in the industry. And I was having a conversation with somebody recently in the industry that I had recommended, and I followed up and I said, Hey man, where are you at? Like, did you end up like what'd you do? And he said, Nah, we ended up not doing it. We realized we could save money by building it ourselves in Claude Code. And I was just like, dude, that's a mistake. Don't do that. Like, uh, could you build a product in Claude Code? Probably. Are you gonna spend more time and more dev work and more time trying to piece it together? And like, do they have all the are you gonna build a single connector for all of your other apps? Like for your VoIP system, for your QuickBook? Like, are you gonna build these connectors? And then it's just it's a time value situation. It's like, yeah, you're gonna spend a tens of thousands of dollars on Salesforce, but your time and energy that you're gonna spend building that thing, not worth it. Now, I'm not saying that you shouldn't go build features, like we use cloud code to build software apps all the time. We used to have Notion, Notion's a knowledge base. We used 50% of the power of Notion, and we were spending 500 bucks a month, and I was like, I can build this. So I built my own knowledge base. It's actually better than the way Notion is set up because it fits more specific to what we need. $500 gone. I don't have to do anything, it's a very simple feature.

But if you're talking about your operating system for your business, if uh if you found this to be helpful, we would find it helpful if you would like and comment and subscribe and forward and you know, maybe uh print out a picture of us, put it on your desk, you know, just give it a little inspiration. Small ask.

We appreciate it. Thanks everybody for listening.

Have a great week.

‍

Build it. Scale it. Sell it.

Subscribe to the playbook for growing and exiting security and fire companies, led by Alarm Masters’ Stephen Olmon and Collin Trimble.

Thank you! Your submission has been received!
Oops! Something went wrong while submitting the form.