How To Do AI Outreach On LinkedIn Without Being Spammy

Jeffro (00:01.506)
Welcome back to Digital Dominance. Now, if you’re a service business owner struggling to consistently generate leads, you’re not alone. The digital landscape is more competitive than ever and traditional outreach methods just don’t work like they used to. But what if you could automate your lead generation without losing the personal touch? That’s the dream, right? Well, today I’m joined by Casey O’Toole, founder of Linkybot, which is an AI powered platform that is tackling LinkedIn lead generation. Casey has helped over a thousand businesses generate millions in sales by blending automation.

AI automation with real human engagement. So we’re going to dive into how local service businesses like you, you know, whether you’re a contractor or medical clinic, you can use AI, LinkedIn and SEO to drive more appointments and dominate your niche. So welcome to the show, Casey.

Casey OToole – LinkyBot.ai (00:46.922)
Excellent. Happy to be here, Jeffro, loving it. Thank you for having me.

Jeffro (00:51.305)
Yeah, absolutely. before we started recording, Casey told me he’s in Costa Rica. So I’m already jealous of him, but at least I’m in California. So we’re in similar time zones, I think. Not too far off.

Casey OToole – LinkyBot.ai (01:05.038)
Yeah, and I’m in the north too, so the climate here is a lot more dry, similar to California, so it’s all good.

Jeffro (01:10.677)
Okay, nice. Yeah, I love it. I’ll go back someday. But anyways, that’s not what people are here to listen to us talk about, because I could just ramble about Costa Rica. let’s talk about, know, Casey, when a lot of business owners hear AI, they might think of spammy automation or cold robotic outreach. And we’re all tired of that. But you take a different approach, you believe it can actually enhance human connections in lead generation. So I want to start there. Can you explain how AI tools like Linkybot can automate outreach without feeling like a bot? that even possible?

Casey OToole – LinkyBot.ai (01:43.726)
Yeah, absolutely. I mean, it’s similar to like my journey with just LinkedIn automation, right? And I apply what I’ve learned in that realm to AI and it works together seamlessly. with LinkedIn automation, know, everyone is of those tools that… lets you automate your outreach and then you get these spammy type of connection requests and then a minute later you get a sales pitch and it’s really kind of like very abrasive and people don’t like it. But I’ve done this for over six years now and there are certain ways and techniques to make the automation more personalized.

Think of it like ads, right? If you get an ad for something that you have no interest in at all, you get kind of turned off a little bit. with LinkedIn, if you get an outreach message that is providing value about something that is in the topic of what your business actually is looking for, then it’s not abrasive, it’s not salesy and you’re providing value, then that can be the way to really personalize and use LinkedIn for your advantage. And that’s on the automation side. So that’s one thing. And then on the AI side is a kind of different component.

But we then take the replies from the automation that comes through, and we then run it through our system. And we make each of our AI assistants customized based on each individual’s unique personality, tone, and style. And we give it a goal that’s also kind of geared towards our clients, their dream outcome, and all this stuff and then it’s interacting with these individuals, providing value, asking questions, and then eventually leading to a book call or redirecting them to YouTube or whatever you want to do. But as long as you build it correctly, it’s incredible.

Jeffro (03:59.372)
Well, that’s interesting. So you’re using it kind of as an appointment setter to dialogue with the person and get them on your calendar all just for you while you’re sleeping. It’s just an AI bot doing that work for you.

Casey OToole – LinkyBot.ai (04:12.374)
Yep, exactly. it’s taken a lot of time to build it out the way that we do. But now that we have our systems in place, it’s pretty straightforward for us.

Jeffro (04:23.189)
So when you, obviously you said you can train it to sound like you and stuff. So do you ever identify yourself like, hey, I’m an AI bot on behalf of Casey reaching out, or is it just like, no, I’m going to pretend to be Casey and you’re never going to know?

Casey OToole – LinkyBot.ai (04:41.794)
So we pretend more or less to be the person, right? I think LinkedIn is a channel that kind of requires that approach, as opposed to voice AI, SMS, you can get away with, and it’s probably more courteous to disclose that it’s an AI assistant, right? But with LinkedIn, we sync everything with the person’s profile.

Jeffro (04:48.405)
Okay.

Casey OToole – LinkyBot.ai (05:11.786)
And so it would be kind of strange to think that you’re letting an AI thing kind of control your profile. And so we took a lot of time to make it sound and be just like a replica of each person because we know that it’s a little bit eerie when they or if they find out, right? So, yeah, so we we definitely take our time with it, but. Yeah.

Jeffro (05:39.402)
Do you have any clients who are like, I don’t know if I’m comfortable with that pretending to be me. Like, what does that look like?

Casey OToole – LinkyBot.ai (05:47.628)
So, I mean, we’re full disclosure. And if there are people who are afraid of AI pretending to be them, then they’re probably not gonna be a good client. I mean, it’s just basically the next iteration beyond automation. Automation is effectively pretending to be you too, but we have clients that don’t want that either because their brand is so important to them, their reputation. And especially, I mean, even with local service providers, for six years I’ve been working almost primarily with real estate agents, which is a local service provider. And their brand in the community is really important. And so they were always concerned about contacting a previous client and offering them a credit towards closing that they didn’t offer them originally, right? Or they don’t want the client or the prospect to know that we’re automating outreach, whatever it is. And so like it’s, if you are super hesitant about your brand or you have like an ego about anything, then yeah, this is not for you. But we do it in such a way that even if you are reaching out to a friend or a past client, whoever it might be, you’re just offering value. You’re providing information or providing an asset that they would want. So you just do it correctly and no harm, no foul.

Jeffro (07:19.67)
It’s very focused parameters, so you’re not going to go talking philosophy and say some weird thing. It’s going to be like, no, got to, hey, I’ve got this thing. If you want it, we can set you up with a call. So it’s very focused and narrow in the scope of what it’s doing and talking about.

Casey OToole – LinkyBot.ai (07:34.73)
Exactly, yeah, we give it on like a suggested conversation flow And so, you know for real estate for example You know our clients mostly want to make sure that the prospect is living in the area because you know Make sure that they’re still live in that area and that they have intention on buying or selling a home So before even offering a calendar for the prospective book with our client we kind of make them pass the post and kind of pass those two qualifying questions before we say, great, let’s schedule a call. So yeah, we do our best to customize it based on what each of our clients wants. But yeah, that’s kind of how that works.

Jeffro (08:14.889)
I want to hear some examples of how you personalize this though, because I’ve seen AI personalized outreach and it scans a profile, picks a couple of keywords, and then it says something like, hey, Saul, you’re a hockey fan, go ducks. I’m offering this free checklist. It is just kind of awkward and forced and not a way a natural human would pick out some piece of information from the profile. So I want to hear examples.

Casey OToole – LinkyBot.ai (08:43.15)
Yeah, so the way we’re doing it currently is, so we spend a lot of time in the beginning doing what I call sharpening the axe. And so sharpening the axe is you want to make sure your profile is comprehensive and is built out in a way that speaks to the pain points that your ideal target audience is struggling with and then you have to make sure your profile is verified, a couple other kind of things. But then, when we’re starting to send out direct messages and connection requests and all this stuff, you need to spend a lot of time like identifying who your target audience is and what sort of pain points they may be having in order to craft the right message. So, you know, if I’m targeting real estate, I mean, just clients, for example, or prospects, then I need to know that like the person A has enough money to buy or sell a home. So we filter based on like a fluence we can then narrow it down even more and say, what school did they go to? We can find out, reach out to people that went to the same university as you. And that works pretty well. But then the real trick is to say, hey, I know interest rates are kind of high right now. Wondering if you have been hesitant to buy or sell a home because of the interest rates. It’s a pain point that is causing people hesitation and you’re trying to like speaking to that to get them to respond.

Jeffro (10:26.726)
that’s a little more universal. It’s not going to be tied to some superficial trait that was found. It’s more like if you’ve targeted them properly, then something like that’s going to be natural.

Casey OToole – LinkyBot.ai (10:38.414)
Yeah, and that’s B2C where your client effectively is really, your audience is effectively anyone, because everyone wants to buy or sell at home. Everyone does that. When it gets to B2B, it’s a little bit different because you know the pain points, the specific pain points that, for example myself, what digital marketing agencies are going through. It’s like they are using AI, but they’re not really knowing how to leverage it for sales or like they struggle with lead follow-up. They struggle with integrating it correctly. So like I know some of the struggles they currently have and if you can like speak to those struggles, that’s even better.

Jeffro (11:17.735)
Gotcha. So are you using LinkedIn Sales Navigator in order to generate your prospect lists? Or is that something you guys do outside of that?

Casey OToole – LinkyBot.ai (11:27.884)
Yeah, we primarily use LinkedIn Sales Navigator. In fact, we require all of our clients have Sales Navigator because A, they have really good targeting filters, but B, it also increases the threshold of activity that you’re allowed to have on LinkedIn.

Jeffro (11:43.707)
Yeah.

Casey OToole – LinkyBot.ai (11:44.686)
You can send out in-mails, open in-mails, group messages, in addition to connection requests and all that stuff. So yeah, we use Sales Navigator, and then we also have the ability to import a different target audience. So if someone uses a different company like Clay or Apollo to generate a lead list, we can use that data into our system as well.

Jeffro (12:07.409)
Okay. I think a lot of service businesses don’t necessarily think of LinkedIn as a platform to go prospecting. Maybe they’re just so used to doing Facebook ads or whatever else it is. I mean, is that an opportunity or when they go there, what’s your experience with that, I guess, is the question.

Casey OToole – LinkyBot.ai (12:27.436)
Yeah, so I think it’s a great opportunity because, I mean, local service companies, clearly your clients are local, right? So you can just immediately narrow your audience down to like who could potentially be a person that needs HVAC services or plumbing or solar or whatever it is to reach your target geography. But then from there, know, LinkedIn is a professional profile. It’s a professional channel. And so if you position yourself on LinkedIn as the expert or the pro in this specific field, I mean, you’re kind of gaining your reputation just by your interactions and your posts on LinkedIn. It’s kind of like your… putting your resume more or less and all your case studies and another happy client, I just installed this roof and they were able to resell their house for twice as much as they were expecting or whatever it might be. So the more you engage with the LinkedIn platform, establish yourself as a subject matter expert, you can then even use those posts and send people DMs with a link to that post.

Jeffro (13:44.912)
Mm-hmm.

Casey OToole – LinkyBot.ai (13:45.952)
and let it do the conversion. Call me if you have a post about this new roof that you just built. Call me if you have any roofing issues or roofing questions. And then include that link in a DM. And it doubles your authority more or less.

Jeffro (14:04.368)
Yeah. So you got to put in the time and effort to have a content strategy on LinkedIn to help position you as that topical authority. And then you can leverage that when you’re doing the automated outreach so that people will look at your profile, see that you’re active and you’re posting stuff and that you are someone that they could go to as a leader in that industry. You could trust you. You’re clearly here doing this. So, okay, got it. It’s not like you could sign up tomorrow for LinkedIn with a blank profile, turn on AI and suddenly get all these leads. Like there’s some…you know, legwork you got to do to get in this position where it’s going to work for you.

Casey OToole – LinkyBot.ai (14:38.382)
Absolutely, yeah. And it’s also risky for your account if you’re just doing it without doing the pre-work. It’s just a little bit risky. I’ve sold real estate for, gosh, almost 12 years now. And when I first started in real estate, the…know, common tactic to generate business was cold calling and going to like networking events and door knocking and, and which is a common practice for a lot of local service companies. And, but the best leads are the ones that are referred to you, right? From like a past client, or it’s the ones that like do their own research, like top HVAC company in Irvine or top, you know, roofing company and so with LinkedIn, you know, there’s a lot of benefit to position yourself as the expert in that field, because then when people are searching for, you know, a roofer in Santa Barbara, then they, your profile will populate to the top. So that’s one good thing for SEO, right? You do SEO. And then, additionally, like if they’re like, they are doing their own qualifying. So it’s not necessarily a direct outreach per se. If you’re reaching out to them offering your local service, they’re not gonna just go, okay, cool, yeah, I’ll work with this person. They’re gonna look at your profile. They’re gonna see is this person legit? Does this person have any case studies or testimonials? What makes me feel comfortable working with him? And so all of those things kinda add up.

Jeffro (16:23.3)
So you gotta be a little bit established.

Casey OToole – LinkyBot.ai (16:26.222)
Exactly, exactly.

Jeffro (16:28.623)
Cool, so this would then be kind of the next step is to take some of the manual work off your plate to doing the outreach, but still leveraging all that other stuff that you’ve been doing, the content and posting and all of that. So I know there’s a bunch of shady automation platforms out there too. There are other decent ones that maybe have their pros and cons. I personally haven’t used Linkybot, so I can’t compare it, but I know there’s one like Expandee and U-Link and… You know, there’s always the question of, I use this automation ethically without coming across as spammy, which we’ve talked about, or without violating the terms of service of LinkedIn, which you hinted at in terms of, you know, not hitting it too hard, too fast when you first start, you got to ramp it up. What, yeah, what have you run into when you’re doing automation on LinkedIn in terms of issues?

Casey OToole – LinkyBot.ai (17:20.142)
So yeah, so we’ve always only offered our services that get done for you because of that exact point. In fact, well, not always. Initially, we offered kind of coaching and training on how to use it, but people would inevitably use it incorrectly, use wrong merge codes, and be all spammy. And I was like, you know what? This is not the right approach.

Like I know how to do it really well. Why don’t I just do it all for my clients so that way they don’t have to worry about it. So yeah, so we manage all of our clients’ We effectively build out their campaigns. We initiate all of the automation. And if you incorporate AI, then we kind of build that out. So we do the full suite.

Jeffro (18:15.94)
Okay, awesome. So that way they don’t have to worry about it. They can just help you answer questions up front so you know what they’re looking for and then you build it out for them and they can sit back and just take those meetings.

Casey OToole – LinkyBot.ai (18:27.572)
Exactly. And we’ve had over 1500 clients now and not one has been permanently banned. Right. So it’s like, so we know all the steps to take to like, to prevent that. And we’re still getting incredible results.

Jeffro (18:42.594)
Yeah, well, and because you have this level of automation with AI, this is going to allow you to compete with bigger brands, right? So as a local business owner, you can do something like this. You can implement this with Linkybot or some other platform on whatever else you’re going to do. But this is a way to start getting bigger results faster, right?

Casey OToole – LinkyBot.ai (19:05.475)
Yep.

Yeah, it’s like rocket fuel. So once you kind of do all your pre-work, and I always suggest also that you manually try this approach prior to any sort of automation or AI. Trying to get a feel for the types of responses you get, and you get a feel for which messages are working better than others. And then once you kind of have all that figured out, then you want to then scale and put rocket fuel on your efforts and then just let it start doing it itself.

Jeffro (19:38.305)
Yeah. Well, is there some kind of feedback loop that, you know, the AI is using these responses and then learning from them? Does it kind of do a split test in terms of the approach of the, you know, the initial connection request or anything else?

Casey OToole – LinkyBot.ai (19:52.174)
So we’ve done a lot of that, right? from our side, again, it’s been for years and so, and the efficacy of different approaches has changed over the past so many years. Now that we have AI incorporated into it, it’s really helped us quite a bit, kind of separate us from the pack because the best practice prior, to AI was you need to, in your very second message, you needed to create the report, offer value, and then ask for business. But when you do that, that’s kind of spammy. It’s like, hey, we both went to UCSB, that’s great. I’m offering a credit towards closing. Let’s schedule a call. It’s too much. But you have to, because if you don’t catch them while they’re on LinkedIn, then you’re gonna miss that lead because people only log into LinkedIn maybe once a week, right? And so you may get the person’s response from the day before, but then when you reply back to them, they’re not gonna be back for another week or so. So it’s like imperative to have something in place, whether it’s a VA, a virtual assistant, or AI built in, so that when that person responds to you, someone is there to take it over and like convert them to an appointment and so yeah, so now because we do have this, it works 24 seven. Our initial outreach or our initial welcome message after the connection request is accepted is super short. It’s like, Hey, thanks for connecting. you know, just was just curious, like, are you struggling with any AI integrations currently? Like, or how is your company handling follow up or just like something poignant and directive towards their issues. So yeah, there’s different approaches now that we can deploy because if we didn’t have something integrated, then they would reply to that and then it would be crickets. So there, exactly.

Jeffro (22:02.594)
It would just sit there. Yeah. You got to reply quickly to have the best chance at capturing or winning that business.

Casey OToole – LinkyBot.ai (22:10.155)
Absolutely.

Jeffro (22:11.732)
Awesome, well AI is constantly evolving and changing and I’m sure there’s gonna be more stuff coming in the next few years that we’re not even prepared for yet. I’m sure you guys are watching closely figuring out how you can use that to improve the messages that you guys are sending and everything. thank you for joining me today, Casey. I always like hearing about different solutions that are out there along with the different approaches to marketing, whether that’s on LinkedIn or some other platform. So for those of you listening at home, Casey has a free school community that is dedicated to mastering the use of AI on LinkedIn. So we’ll put the link in the show notes. You can be sure to check that out. And of course, reach out to Casey if you want help with automating this stuff. Last question for you, Casey. If a service business owner is skeptical about AI but kind of wants to dip their toes in, what’s the first step you’d recommend that they take?

Casey OToole – LinkyBot.ai (23:00.61)
So first step is getting used to LinkedIn. So understanding the platform, reaching out, finding your audience, testing out messages. And then,

If they’re skeptical about AI, but they’re intrigued because they’re getting some actual engagement from their manual outreach, I would say the first iterative step would be to do automation. And you gotta do it correctly. either go to a service provider like us, or be very careful when you use other ones. Because don’t use Chrome extensions, don’t do spammy messages. There’s a lot of things you wanna be kind of aware of Profile, engage with LinkedIn, and then dip your feet into the water with automation.

Jeffro (23:49.471)
Awesome. Well, thanks again, Casey, for being here today. Thanks to all you guys for listening. If you found this episode helpful, please leave a review on iTunes or Spotify. Keep moving forward, try new stuff on LinkedIn especially, and we’ll see you back here next time for the next episode. Take care.