How to Stand Out When You're Prospecting with Ryan O'Hara

In this episode of the Sell Your SaaS Off podcast, Ryan O'Hara tears the shackles off of your prospecting, so you can finally stand out and get meetings.

Show Notes

Episode Transcript

The following transcript was auto-generated by an AI, and may contain errors.

Daniel Ryan  0:39  

Hey, everyone, and on today's episode, we have the privilege of chatting with Ryan O'Hara. And what you'll get out of this episode is Ryan talks a lot about being yourself when you prospect and not trying to change who you are. And he dives into all sorts of creative strategies that you can get into as well as creative ways to get noticed in the hiring process. So strap in and enjoy the ride. Hey everyone, this is Daniel and today I have Ryan here from lead IQ on sell your SAS off podcast. And Ryan here is the VP of Marketing over lead IQ and he is here to help with you growing your career he started off as an SDR himself over at dine din Am I pronouncing that right di D and he's worked his way up to be the VP of Marketing over lead IQ. So if anyone knows how to advance their career, this is the guy to talk to and so that is why I have him on Ryan. so thankful for you to come on today.

Ryan O'Hara  1:41  

Thanks. I wish that we could have like montage music while I talked about this a little bit. Um, so yeah, I'm excited. Yeah, like didn't didn't do to do to do that I'm running elevated music like what I was just doing people, people are hearing this. They're probably like, What is he doing in place right now if you're if you're listening and not watching, I'm literally running in place while I do the music. But yeah, so I run stuff at lead IQ. Some I'll give you some street creds, you don't think I'm like just shooting stuff out of my face, onto the microphone. When I joined dine back in 2008. They were less than 15 people, they had a product that they sold. That was $15 a year. And they were trying to launch an enterprise product that they could sell for $200 a month. And I was the first PDR that was there, which was kind of cool. I had originally interned there as a marketer and didn't get a job right away. And I was like, I was basically really depressed. It was really sad. Like I, you know, was that guy that like, would cry in the shower once in a while, right? Everybody does that. If you're listening, you're kind of like what is going on with this? It doesn't count. If there's, you know, if you if you watch the tears off your face immediately, it's fine. Anyway, I but I graduated 2008 2009 when the financial crisis was happening, I wanted to work in marketing. But all these marketing jobs got scooped up by these people that like were more experienced and had done it before, because they were suddenly on lower jobs to just keep paying the bills because of everything that was going on. And after working as an intern, I didn't work there for six months. And I came back in as the first BDR. And me another guy, Scott Smith, who's now CEO of a company called cloudapp. And Emily burns, who is an event marketing now. We're the first BDR is that we're to dine and I started a couple weeks before they did. But we are like the original pod and group that did it. And I sucked at prospecting when I first got hired. Like I as a marketing guy, I think I'm like pretty creative. And I can come up with some crazy batshit ideas and stuff. But like, when I first got into it, I was terrible. And that's one of the reasons that like, I love giving advice to people that are just starting out because I was bad for about a quarter. And then I really figured it out. And once they figured it out, I was like, My life changed. Everything was so amazing.

Daniel Ryan  3:54  

Amazing, amazing. So it sounds like you've got a whole lot of great info and a great routine of what not to dues and what to dues we're teasing. We're doing the T's right there. Yeah. I'd love to hear you know, like, how can you SaaS sales folks set themselves up for success long term.

Ryan O'Hara  4:14  

Okay, so I'm going to tell you the biggest mistake I made for the first 90 days that I worked at the company. At dine, we're going to talk about early days of dying, and then we'll flash flash forward to like today. At some point we'll do like little flashback. You know, like, people, food and stuff. Yeah, you can do that on a podcast. So the when I first got hired, the first thing I did is I looked at what the 80s were doing for sending stuff for prospecting. I call this the monkey see monkey do effect basically, oh, they're sending those emails, they must work. So I'm going to send those emails. And this is something that happens at companies all over the place. And I know you should have a standardized pitch and a standardized process. And all those things ironed out in a big company. When you get hired. Let's say you're a pre hire member and you're you're going somewhere or like Whatever you're doing afterwards, you might have stuff that standard. The thing is, I did that for 90 days. And it wasn't me. So when I was cold calling these people after writing an email that was really formal and like, like, literally, it sounded like I was in Downton Abbey, the way I was reading these emails, and I haven't even watched that show. Like I just know, like, dear Madame, let me tell you about the dynamic platform to help you with your DNS. It was the best of times, like I literally would write crap like that in an email, and I would list off all my bullets send an email, and I had almost no responses except to take me off your list, I hate you. Or, and I'd call people and the people I'd call would be like, Look, I've told you guys to stop contacting me, please stop contacting me. And, and I was just like, man, prospecting is hard. And I suck at it. And I will this went on for about a month, month or two. And then the chief Revenue Officer at the company, Kyle York at the time, he was the director of sales, but he worked his way up, having me come into his office, and Kyle basically, like, sat me down and said, Dude, it's not working, like what do we need to do to make things work? I was doing my activities. I was working hard. Like, that wasn't the issue. And I just explained to him, like, I feel like I'm setting stuff that isn't me. Like, I feel like I'm afraid to screw up. And, you know, I was just out in the workforce for six months looking for work, I feel like everything was terrible. I basically didn't have confidence on a lot of stuff. And and he basically said, I hired Ryan to be Ryan, the guy that was making wacky marketing videos as an intern for us. Like, that guy is who I want to get in here. That's how I want you to be goby, Ryan. And it was maybe the most important thing I ever got for advice. Because I started sending really creative emails I started, I acted, I basically acted like I was doing marketing, but for one person at a time and one target account at a time. And it changed everything. My response rates at peak, over the next four years I worked there went from getting less than 1%, to shooting around, this is not faking. This is real. And I'm targeting it people that like, hate it people

Daniel Ryan  7:12  

have been there, I worked. My first BDR role was selling database monitoring platforms. So for everyone who has got no idea about the tech world selling to really techie people. All they want to do is like sit in the closet and code. Like I joke,

Ryan O'Hara  7:29  

I joke, I joke that they hit light. And maybe you're some of the industry like I used to do that. Like I worked in tech. They don't want to talk to people, a lot of them are introverted. I know I'm making generalizations. But it's one of the best parts about being a developer is you can kind of be head down and avoid people. And

Daniel Ryan  7:46  

so an interruption. Yeah. And being a chatty person, like like we are, is is tough. So basically, whatever number you spit out, I'm going to my jaw is gonna drop. I just wanted to set the stage for anyone listening who doesn't know what you're about to say,

Ryan O'Hara  7:59  

Oh, yeah, yeah. So keep in mind, too cold. Emailing was a lot different back then, in 2009 2010, things have changed a lot. It's a lot harder to get a response today than it was back then. If you're doing the automated junket stuff, but I this is not fake. We tallied up there weren't even platforms that would measure your reply rate. So I started looking at it manually, because what happened was, well, we'll catch up on this in a second. But I averaged at the end of my prospecting career there, I was getting around a low 30% response rate, which is really, really high. Like, that's really impressive. Yeah, like, it's not just me being like, Oh, I'm bragging, I'm like, these were very tailored messages, they followed a format that I kind of held really close to. And I started doing these things. And what ended up happening was, all the CEOs and people that would go to conferences would come to me to be like, we need to break into this account. We saw them everywhere at this conference, go figure it out. And like people are bringing the good accounts to me to try and go break into is like the guy that he'll figure out a way to get in, he'll figure it out somehow. And what I really learned from this from other people, like, I started to notice that like, man, if I'm going through my inbox, and I'm getting cold emails, or I'm going answering a phone, and I'm getting a sales rep that's pitching to me, I'm generally going to feel miserable. Like I don't like going through my email. I hate going through my inbox today, don't you? Yeah. So I just kind of thought, like, what if I could send a message to someone, but have the content of the email be about them, show that I care about them give a little bit of value with my value proposition that winds up and most importantly, makes them feel special and makes it so it's not a drag to go through your inbox? Like there are people in the United States I don't know if it's like this internationally, but there are people that like will watch the Superbowl just to watch advertisements. And, and like I'm not one of those. I mean, I'm I'm an actor. I was an ad geek for a little while, but like, I'm not one of those people. I love football too. But like I,

Daniel Ryan  10:06  

yeah, like oh, it's it's it's the Super Bowl ads and like, What is wrong with you? People

Ryan O'Hara  10:11  

people do it though like that's the thing. It's the same experience is what I just started doing creating the inbox, I stopped looking at what other people are doing. That was a big part of this. Another thing that I thought about was when I was in high school, I had an English teacher that was to my senior year, Mr. Roderick shout out. I don't know, he's probably dead now. But because it's just been years and he was an older guy. But yeah, if you're if you're there, cool. If not, you're being remembered right now and immortalized in this podcast. But Mr. Roderick told me about, like, there's different ways to connect with people. And when you connect with someone through words, there's kind of three stages of conversation you can add. The first is common, like current events and small talk, which I don't really like small talk like I, I wouldn't like Dude, before we recorded this podcast, we were we were talking about like, I was talking talking about how stressed I've been about stuff, like, that's a much cooler, more rewarding conversation for me whether human connection. And that, like, the point is, a lot of people will hug small talk like about the weather and like stuff like that. People don't really feel comfortable with that all the time. And it kind of gets boring after a while. The second stage of conversation is common interest, can you find something that's common that you have, with the prospect that you're reaching out to? And that's like, that was the secret that was like, what really changed everything. For me, I would start Look, I started researching these people and looking at the things that they liked. Back then people didn't post on LinkedIn that much except for job stuff. But like, I'd see people post stuff about like, I'd find their Twitter account in tech, because a lot of these people were on Twitter. And I'd see that they were talking about Game of Thrones, like the books before the series was even out. And I had, like, read the first book. And I would like see that they talk about the book in a tweet, and then bring up that the book in a cold email that I write to them. Like, I would find things that I liked, that were unique to me, I wouldn't just be like, I saw you like Game of Thrones, let me make a reference cuz you don't want to be like that lame dad that's trying to like, fit in with the kids like, yo, what's going on home, he's like, you don't want to do that, like, so like I like I would find things that I generally cared about in light that I had in common with these prospects. And I just started bringing it up on cold calls and cold emails, while blending in some of the stuff that you guys teach people about prospecting, like getting value, explaining a reason for your call, having a call to action, at least a plan of what you want to do, like, those things are super important too. But I just started to apply myself and the things that I care about in my life. And I put that into the prospecting. And at the end of the day, I'm like, there was someone on our team that would go and do like 130 140 activities a day, I would do 30. But I'd hear back from about five to eight people. And I'd turn one or two of those into an opportunity every day. And that's that's like, what it comes down to. It's really about like getting little wins. So like, that was a big start of my career. And some of the mistakes that I made is like, I was too focused on being afraid of breaking the rules a little bit I was afraid of, I thought it is what it is. And I'm just going to trust the adults. What I didn't realize is that all the people I was working with were only five or six years older than me, and also didn't know what they're doing. They're figuring some stuff out to like not a negative light, like in a beautiful, wonderful way. And they were really intelligent, wonderful people that embrace me and let me be myself there. They basically it was like a let Ryan be Ryan and it worked a lot. Here's the thing. If you're listening to this, and you're who's listening to students, like people, prospective job people, members of Prehired like, Is that is that who's listening? Yeah, genuinely, if you're, if you're listening to this, like, the thing I'm kind of trying to get to here to hit you in the fields a little bit is like, if I act like a certain person when I write emails or do cold calls, and then that person comes in inbound and calls me back, what person am I going to be when I answered the phone, and if it doesn't match with the person that just wrote that email, I want to be miserable, like I'm going to be I'm going to feel uncomfortable on these calls. And if I'm not comfortable being myself in my own skin, on a call or over an email or responding or even when you're doing a handoff and discovery, you have to put on a face the whole time. You shouldn't have to do that. You're going to think you're gonna have way more difficulty overturning objections, asking for and bringing up customer stories and thinking those things if you don't act like yourself when you prospect and that's sort of like, that was like a huge eye opener for me. It took me about a quarter to really figure it out and find my voice and stuff. And some days you're gonna have bad days and like, not feel up for like, being really creative with your emails and your calls and stuff. And you're gonna just try generic messaging and stuff. That's gonna happen sometimes you're just not going to have it but like, the days that I did that like, over like, I bet if I isolated out the days where I didn't have it, I probably had like a high 40% response rate because like, I would just find things that were in common with this person. And the other cool part is you could make a good first impression with the person when you get on a call with them. You have Something to talk about at the beginning isn't just business. And then you, you can loop it back and make it so that like, Look, I'm not just trying to get the sale, I want to get it, I want you to be my friend, and I want to get in the trench with you and help you with stuff.

Daniel Ryan  15:13  

Wow, that was awesome. Was that too long? soliloquy? I just got off of my half of my questions out. No. It's really cool. How you know, like, let Ryan be Ryan? So basically, you know, yes, I mean, and when, like, realistically, if if you're joining a BDR SDR team, you're probably going to be given scripts, you're going to be given things that you have to say, but don't let that stop you from being you basically, yeah, well, here's the thing,

Ryan O'Hara  15:43  

you're going to get scripts, you're going to get templates, you're going to get stuff like that. But at the end of the day, the thing that they're really going to care about is results. And the results, if something's not working, it's don't think that there's anything wrong with how you're executing on the script or the results. Sometimes, sometimes you got to tweak stuff a little bit for you. I'll give you another example. We have reps on our team at lead IQ that are really amazing at cold calling, we have reps on our team at lead IQ that are really amazing. At cold emailing, copy. And some, some are better at what some are good at both, some are okay at both. But whatever you're comfortable with, it's really about like leaning into your strengths for stuff. And whatever your weekend when you guys do your huddles for sales training, and you're going to be on an org or like you're going to you should be doing coaching sessions with your manager and stuff. That's when you work on the things you're weak at, and, and start honing in on those skills and stuff. The hardest part for me is I got really effective at writing cold email. And I had a lot of trouble with translating that same brand. And that same voice that I use on cold email, to phone. And I, I worked really hard to do that it got very difficult to do. But I got there eventually. And that's part of this too, is like, so being yourself is the first piece of advice. Don't just do the monkey see monkey do thing where you look at what other people are doing, and try and replicate that like, talk to people learn things. I'll tell you another thing that I heard from Beth Holland, who does a wonderful thing called flip the script, I started to this talk. And I was really angry that she did this cuz I wish I made this point in a talk that I was doing. But she said, I'm not angry. I just I think she's great. But yeah, she actually said the best reps know their accounts really well. And I think that that's something that I also learned, I just never said it in a talk like this. When you're first starting out, learn your accounts, super well know things about your accounts, not just the prospects you're going after, but the accounts, like know who their competitors are, know what it's like in their space, if they have a marketing blog, or poor content thing. And you really want to stand out and get a good response, go understand their proper their their accounts, like go read their content, understand the way that they talk about stuff right now. If you do that, it'll make your your language when you actually talk the account a lot better. That's another key part. I realized I didn't finish the point I was telling you earlier. But like the stages of conversation things so people don't like small talk, you find common interest, the other thing you can do is you can get internal feeling. So like, find a way to like, start thinking about how someone's feeling and bring that stuff up and expose yourself a little bit and you can make a better connection with someone, they'll open up with you more.

Daniel Ryan  18:29  

Yeah, awesome. Now you touched on, you found it difficult to bring your brand over to the phone, I'd love to dive into, you know, self brand, I think you know, in this in 2021. Having having a brand, not just of you know, the lead IQ brand, but there's the ryan O'Hara brand as well. I'd love to hear your take on I guess, let me put this in a good question for you. What mistakes do people make when they're first trying to start out in creating this self, you know, their their personal brands?

Ryan O'Hara  19:09  

Alright. The first one is not thinking about the audience that you're making stuff with. So I'll give an example. If you work in sales, and you get a job in a company that doesn't sell the sales reps, don't post stuff on LinkedIn about selling. don't post stuff on Twitter or Facebook about selling. Maybe you can privately talk to someone about it. But if you're trying to use those soapboxes as a way of building a brand, what you want to do is talk about stuff in your space. Be that space expert, that's like a huge, that's the first tip I have. I see so many people, I see it all the time, like I saw, there's someone I follow that will post stuff, who works at billing platform, about sales, and I'm just like that billing platform has nothing to do with sales. I'm not going to go hire you as a sales coach or something if that's what you want to do. Eventually, maybe you can do that for career stuff. But like if you're using social to really build a brand and get in front of people, which you need to, I'll talk about that in a second. You're blowing it, you're missing the point. The second problem that people do is they regurgitate and just share stuff that the company is saying. And you can talk about stuff that's happening in the company and personal experiences and stuff. But people don't buy from companies they buy from people. And so you want to build your own brand online. And the easiest way to do that is to almost be an exaggerated version of yourself. So like, if you're listening me on this podcast, go look at my LinkedIn feed, I'm the same person and the videos that I put on the link identical. Yeah, I'm the same person on my post, I literally have a couple modules I've made with Prehired, that I'm the same person. And those Doc's too, on me, and I'm like, I'm not trying to be like ob, Ryan, I'm not saying that. I mean, like, be yourself in that too. Like, when you're putting stuff out on social, you can build that brand. The reason you need to be doing stuff on social is because today, your people that you're cold, emailing cold calling, or getting hit 30 or 40 times a day, and especially at these enterprise companies, the thing is, companies will go by these databases with contacts in them. And they all hit the same contacts over and over again, you have like 10,000, users all hitting the same contacts up. If that ends up creating a problem, because they're tuning you out. If someone who recalls your name and sees it a lot more, because they keep seeing you on LinkedIn, like you've seen these posts on LinkedIn, they keep seeing these videos and stuff that they're putting up. There'll be more likely to open an email from you or call you back from a voicemail, if they see your name in the voicemail and be like, oh, cool, it's that person, I know that person. He won't believe this phenomenon. This actually happens a lot with your CEO, by the way, like, he does this too. I was talking to him about this, you guys will like, literally, you'll go to a conference. And people will come up to you and say hi, and act like they know you. Because they feel like they know you from the content that you put out. And that that's like an important part of this too. So like, be you but be an exaggerated version of yourself a little bit and make that consistent. For us. For example, everything I put out, I use this technique called brand archetypes, and I'm the jester archetype. So I'm always trying to make you laugh and be entertained and engaged. I care more about entertaining you, while giving you information than just giving you information. There's different archetypes you can pick and go through. If you actually do a search on Google, you can type in read IQ brand archetypes, I wrote a blog post about it that can help you with some stuff. But that link in the show notes? Yeah, yeah, you can, you can use those things. And it'll be a guide for you. It's like a compass of like how you want to be. So that's the second thing. First is don't post stuff that your audience doesn't care about. Second is to pick a voice and stick with that voice and be consistent. have that voice also impact your prospecting tip, if you're using that brand archetype in your social posts be the same persona, when you write an email and do a call that persona should be you by the way, it's just a piece of you that you try and keep within the same swim lane of stuff. So you're not veering off and being inconsistent all the time. And then the third one, and this one is probably the hardest, hardest thing to do is if you're trying to build a brand online, don't do it alone. You don't do it alone. So like, you have access. When you're SDR BDR, or an E or whatever you're doing in sales. You have access to people, you have access to stories, you have access to your your co workers that know a lot of stuff. You have access to your customers and you have access to your product and some stuff like that. Go pull people in and do stuff with people like Daniel and I are legit doing a podcast right now. Dude, you're gonna put this on LinkedIn with my video on and tag me, what do you think I'm gonna do? You're gonna comment on it, probably share it. And I now now my, whatever 1000 plus followers I have on LinkedIn are going to anyone that we have mutual connections for will see it. Anyone that sees stuff that you for your followers of mine are gonna see it. That's like a cycle that you can create to do this. If you don't know your space, pretend. So I know most of you might be people that are like, I don't know anything about it. And like when I worked at dyne, I didn't know anything about DNS and management infrastructure stuff.

What I did instead, is I just started listening to podcast about this stuff. I started listening to controversies reading blog posts, subscribing to places that were talking about the topics that my audience cares about. And I go Wikipedia binge these things. So like, I saw someone mentioned DNS sec, which, you know, you probably know what DNS SEC is. And if you do cool, kudos, I go on Wikipedia and read about DNS sec. And I'd be like, Oh, that's kinda interesting. They're explaining DNS sec. I don't really know what this key identifier thing is, and this internal DNS stuff, I'm going to click on that. Then I'd click on that. And before before long, it's 130 in the morning, and I'm in bed, looking at my phone be like crap, I got to work tomorrow. But like, that's another aspect of this. Learn your space, like put your ear to the ground and just listen to stuff that's going on. Subscribe the podcast Jeremy levy a on our team is amazing at this like he any speed he's the reason he's been a power a powerhouse in whatever prospecting area that companies worked at. As he gets infused in that space and learns everything. He was working at NASA site before we're doing lead IQ. And they were selling infrastructure. And Jeremy would just like, he had a CXO podcast that he listened to where they'd have CIOs on and they interview them, and he just listen to what they're talking about. And it's such an easy little thing to do. If you're, if you're listening, you're like, Aw, man, I don't really have time to do this. You know, maybe you have a family and you have work and all that stuff. The best time to do it, is go buy yourself a Bluetooth shower radio, and listen to podcasts while you shower. That's what I that's what I used to do. Back then it wasn't easy to do Bluetooth either. But like, I had a little Bluetooth radio that I'd listened to. And I just like, would crank through and listen to podcast after podcast about stuff in the tech space. Infrastructure data. We probably actually you and I probably listened a lot of the same podcast back in the day about that stuff.

Daniel Ryan  26:01  

Yeah, I mean, my first, honestly, probably not Ryan, I think you think I'm older than I am.

Ryan O'Hara  26:09  

I'll give you kudos credit. I'm just saying like you came in the same space as I did, coming up on that stuff. And like, you learn a lot about that. So like, that's another part is also go follow people, follow your customers and stuff and read what they're putting on social. If you're selling into a space where people aren't as active on social, it can be harder, but go, they have a community somewhere. Everybody has a community online right now. I mean, even weird people have like some weird things going on. There's a place for everybody go find a way to infiltrate and look at that stuff. And never ever sell it. Because if you sell it, you'll get kicked out.

Daniel Ryan  26:44  

And yeah, definitely. And I think especially with with those that aren't really active on LinkedIn, a huge tip that I was given, which I think is really, really helpful is, you know, if your job is to sell to CIOs, right, and you can't find a lot of CIOs on your on your site. If you're working for a tech company, you probably have a CIO in your company. And that's Oh, yeah, that's the CIO, who's probably going to talk to you, if you literally reach out to them be like, hey, look, I know you're busy. My whole job is to reach out to you at other companies, what's important to you? What kind of language do you use? How can I get your attention if I was trying to do this? I mean, that's just like low hanging fruit, right? Yeah. Yeah. That's a great point. By the way, I love that. Yeah, you're welcome. See, I try to bring value. So speaking of I know, we were sort of digress, we were talking about brands. Now, I'd love to use you as an example of something that I saw where you guys had a target account that you were trying to reach out to and get ahold of, and you could not get it all your emails were bouncing. And you created that video, you're essentially you're like, Look, these guys have no idea we're doing this. And you use your platform to like, promote them. And I'm pretty sure through your network, I mean, I'd love to hear the story about that. And you know, hear your version of that, because I was just following on LinkedIn. I thought it was brilliant.

Ryan O'Hara  28:14  

Oh, thanks, man. Yeah, that's actually the third or fourth time we've done that. So the story was we're trying to email LogMeIn, I'd say the account name. I can't disclose what happened from that. But good things happen for that so far. I can tell you good things have happened so far. Like there's been cool conversations, but I don't want to. I think I don't, I don't want to disrespect them.

Daniel Ryan  28:33  

Yeah, yeah, definitely. Just in the comments. You had like C suite people commenting being like, Oh, yeah.

Ryan O'Hara  28:39  

So So what happened was, Katie, who's on our SDR team, she's one of our enterprise SDRs. We do like a little huddle every week to come up with cool ideas to like prospect and stuff. She was emailing them and getting an open automatically every time she write an email, but it was happening with every account. So we were thinking like, oh, man, something must be going on. They weren't coming back as hard bounces. So the data wasn't bad. What was happening was they have some sort of email filtering service that automatically has emails get stopped from reaching people until they're reviewed by someone. And we caught that and realized that it's kind of complicated how we figured it out. But we realized that our emails weren't getting delivered. And then we ended up happening was we kind of huddled and said, What can we do to break into this account instead? And we decided to make this video but we're bummed out, the emails aren't getting delivered. So I was like, you know, I'm gonna do let's put a bumper at the beginning. That's a disclaimer saying they didn't okay as to make this we're just making this to them. And let's put it online and ask people that crowdsource tagging people from LogMeIn to get on and like the video I don't know if people can see this publicly, but if you click on the views for it on the post, I could tell you we had over 300 people from LogMeIn watch it because like LinkedIn will tell you what accounts are watching it, which is great. The video had like 7000 hits, generally In general for it, but like, I could see that I did reach a couple 100 people from LogMeIn, which is incredible. And a bunch of people just came in and tagged people that they thought would be the right person to talk to. They're using network effects. And it was amazing. Like, it was really cool. Here's the thing that people don't realize is, we didn't just make that one video, I have nine videos like that ready to go. When you go and do a campaign for prospecting, like this, and you want to do some branding and stuff, don't just do one offs, because they're really time consuming for us to set up the studio. From in the video, I have my tuxedo, I have a script that I had to write, I had to think through what I was going to say. And then I had to give it to someone on my editing team to make it I couldn't make it myself easily with like iMovie or something. But like, I wanted to outsource it to have the time done faster, like get it done faster. I didn't just make one I actually just blocked off three hours in my calendar and filmed all of them back to back to back to back to back with the same exact setup. So if you're going to do a creative prospecting tactic, don't just do a one off, like, go make a bunch of them, so that you can collect enough data to know if it works. See, because if I go and email that video, we email that we've made similar videos for a couple other prospects. I think we did like nine or 10 of them that one afternoon. We've hit we've hit and gotten meetings with about 45 to 50% of them. I think we're at 45 is the last I checked, because it's not 10 we did nine I think so like it's not a perfect number. But it's something like around 40, mid 40s booked not just responded

Daniel Ryan  31:28  

to four out of the nine. I've booked meetings with you. Yep, exactly. Yeah, well spent.

Ryan O'Hara  31:34  

Yeah, it's like I took instead of like writing a bunch of cold emails and getting nowhere and doing cold calls. We took an afternoon, it was a Friday afternoon. And like, just crank these out. The fun part is like I had my camera set up, but we have a video guy and I had him on my zoom like on my laptop right here, um, you know, hit me when it takes effect. Which is really funny. Like, he's like, he's like, do it again, that could have been better. I'm like, damn it, alright, because I'm not an actor, you know, but like, so but we've we filmed a bunch of these things, and we send it to people over email. The problem is, I could write the greatest email in the world. But 30% of emails that you send will never get read by your prospects because of technical problems, almost like it's almost like 20 to 30% is what we heard from company validity said this. Another interesting part is even if you do that a good open rate on a cold emails like 30, or 40%, which is not very good. So you start adding these things up. You don't want to just go do a crazy prospecting tactic in one channel, you want to try and figure out how to leverage a couple. I could have dm some people at LogMeIn on LinkedIn and sent them the video over LinkedIn. I would have known it got delivered. I thought this idea would be cooler. He put it online and made it public but like, like, that's what I mean. Like, you can you don't just make something for one channel and do the work. And don't just do one thing do enough, nines enough of a data sample for me to know if this idea is worth scaling. And it is by the way, like, we'll probably do more of them. problem for me is I can't just post a video trying to get a prospect every week. On a dinner. I'll lose followers probably.

Daniel Ryan  33:07  

Yeah, exactly. But what was really cool about it, for those of you who have not seen it is it was probably what, four or five minutes long? three to three minutes.

Ryan O'Hara  33:18  

I think it was only about two weeks. It was a short, we, um, some some of the ones we did I one of my favorite ones. I'm so mad about this, this is a story that no one will ever see. So I can tell people that we did one where like, it was a communication platform, I won't say which one it is. Where were we got the meeting, and they before I could get the video out to them. And I was so bad. Our CRT was that good at prospecting. Because like, they like they just they're not gonna wait for me to make these videos, they want to keep going and pastoring the account. But I was so mad because it was really funny. I have one where like, I'm talking about if I had better communication with the prospect of maybe I like, my marriage would still be around like I make and then like on camera, I just act out a meltdown. So like there's like, there's a cut of me talking to the camera, and then it's smash cuts and I'm like holding a beer be like, I'm fine Carol's unfined like, like we did a whole thing like that it would have been so funny to put up with the problems of the customer turn like the prospect already got an opt, so we never got to send it to them. who probably sent like,

Daniel Ryan  34:22  

afterward? That's like a good problem to have. But yeah, it's also probably really good for like, mid funnel because you like just see, you know, like, it's like, Hey, we put effort in. But what I was gonna say was of that two minutes of video, you were talking about them for, like, more than 90 seconds. Like, I was like, probably 80% of it was all about them. And you're talking about how they help how they do this. How do they do that? And it was just, I think, maybe you know, getting back to like, how can people succeed when they first started? You kind of end I mean, I'm sure you get it too. I get it. You You're excited, you just got into tech sales, you learning all this stuff about your product, you're all amped up, you're in the you're in the cult of whatever your product is, and you just want to tell people about it. But that doesn't work. That's

Ryan O'Hara  35:12  

no, that's actually a great point. I you know, what's funny is I don't even think of that anymore, because I'm just wired to not do that. But it's completely true. When you will do prospecting, even if it's not something crazy and wacky like a LinkedIn video, it's just something else. You want to make the bulk of what you talk about about them, not yourself. And it's like, it's such an easy habit to fall into. That was one of the mistakes I made very early to i, I'll give an example. One of the first emails I ever wrote when I was at dine was like this really long Opus, where had all the bullets and all the different features and just talking about everything. Again, I didn't know what I was doing. I was looking what other reps were doing. And I noticed I noticed that I wasn't getting responses. But you know what else I noticed? If you talk about your product or service too much in an email or call, when you actually get on the call, you have no bullets to overturn objections with it's like, it's like It's high noon. I'm not like a gun guy. I don't want people to think I'm a gun guy. But it's like it's like high noon. And you say drop you shoot your gun in it clicks because no bullets left cuz you shot it all off to set up the door. Yeah.

Daniel Ryan  36:16  

I that. That's a great analogy. And yeah, 100% it's like, well, we don't need it, this and this and this and you don't even get the opportunity to, to bring it up in the way that it could help them. They've already disqualified it.

Ryan O'Hara  36:30  

Well think about it like this to no one likes when you think of your friends, right? The friend that you always like roll your eyes and avoid is the one that's like, Hey guys, I have all these problems. mee mee mee, mee mee and you're like, yeah, I'm gonna, I'm gonna go. I might I might not. Yeah,

Daniel Ryan  36:47  

you say the friend. It's like, Oh, yeah, I went on this vacation to the beach. They're like, Oh, actually. So I went to the beach. Yeah, it was a better beach. And it's like,

Ryan O'Hara  36:54  

you know what I worry about, I worry. Sometimes, that guy will just want to share and connect with people. So I get eager, but like, my point is, no one likes that person. And if you go up to do that, in sales, you're going to simulate, take that same simulation we're talking about and do the same thing in sales. Instead, what you should do as a rep is give like, talk about them, make them feel special, but give to them over and over again, I always joke about this, when I do prospect training talks and stuff like, like with customers that close in by lead IQ, we'll do training with them if they're, if they ask for it. I say there's two kinds of people in this. Yeah, like you guys, actually, we did that we did that. That's true. There's two kinds of people in the world. There's people that drive pickup trucks. And there's people that ask friends and have pickup trucks and move shit for them. And you want to be the guy that drives the pickup truck for your prospects. Like that's a good way of thinking about it, like, find ways to get things that you can give to a prospect. If you're first starting out, you have access to people at the company, you have your network, you're going to be building a network every day, you have prospecting customer stories that you're hearing. When you get on cold calls and stuff. If you have a conversation with someone, the nurses are not interested classroom to make content with you, and then collect some stories from that content, publish it, put it out there. And not only will they feel like they're obligated to know you and stuff. But the other thing is your marketing department's going to push that content to and now you're giving that person eyeballs that they might have not heard about before, that's gonna make them feel special. But you're also gonna click that story. And now you can bring that story up with other prospects that you're cold emailing, or cold calling. Like, if I called you, Daniel and was like, hey, Daniel, I was talking to a another sales development bootcamp. And they mentioned they're having a lot of trouble with getting students to watch, sorry, getting members makes you edit that out. I know, you guys use the word members, that's getting getting members to stay engaged on video. And I was selling marketing consulting, right? Maybe I'm selling stuff that makes videos more engaging. I could, I could give you a couple ideas that would make it so that you can get engagement up on those videos and make sure everyone's finishing them and not bouncing off the page. Would you want to talk about a little bit? You're probably gonna be like, hell yeah, I want to talk about that. I want to learn that that sounds cool. And I would name drop the other SDR school probably in the email or on a cold call with it. But like, that's kind of what you can do is like you're giving ideas and you're giving wisdom to people. That's really what sales is about is giving people ideas and inspiring them to want to go get like go mobilize that action into actually turning into business afterwards.

Daniel Ryan  39:26  

Yeah, yeah. Kind of like the the Gary Vee Jab, Jab, Right Hook, right. Give, give, give ask.

Ryan O'Hara  39:33  

I did um, I did a show last week with or that? Yeah, last week with Jared Robin from Rap Genius. is one of the things he talks about is bounce passes. So like in basketball, you do a bounce pass, you pass the ball bounce off the ground picks up to the other person. He talks about you can't it's almost to give a bank account with people we didn't say like this, but it's kind of what it made me think about either bank account with people An emotional bank account and you make little deposits by giving over and over and over again. And it becomes very easy for you afterward to mobilize that personal tax return. Yeah, get it make withdrawal. A perfect example for me, this is a true story. When I was at dying, and I moved into marketing, I was I was a team lead for the BDR team. And then eventually, I took over the training for stuff I worked with like Murcia. sterol, who works there, shout out to him just saying hi. But Hi, hi. We worked on training stuff together. And when I was doing that transition, I stopped doing as many activities prospecting because I had to do time on these things. And my men, they weren't ready to transition me into a full time role doing that yet, my manager was like, hey, you're at like, no Ops, and you have like a week left in the month? Do you think you could do something to get at least 10? Like, my quarter was 15, can you get at least 10 because you're, you're like, I literally did no activity for like two weeks straight. Because like, I was making slides for the training program, I was doing some stuff in marketing, I was transitioning out of my role. So like, he's like, you don't want to end on a sad note, right? And I'm like, Alright, so I actually, I had a list that I kept on my cubicle, with names written down, and companies, and it was people that I had done stuff for. And I know it sounds really evil, but like, I just kept track of people that I did stuff for, for example,

Daniel Ryan  41:24  

I had, these are ideas you could do, I'd want to prospect really good, really good thing to do. It's like, Hey, you know what? I have? You've now been a guest on my podcast. So add me to the list you owe me.

Ryan O'Hara  41:41  

Hello, I'm here to connect. No, it's not like that. It's not like that. But like, you keep a list of this stuff. And what like, I just had a list of people. And I didn't write down what I did, because you don't want to bring that stuff up. But like, that's when you can finally start asking for a meeting. What I did is I ended up going through that list, I had about 60 people on it that I had done stuff for just like what Jared talks about with bounce passes like or pickup truck moves, I guess is what I'd be my currency for it. Just people I did stuff for some stuff you can do if you're listening. A lot of people you sell to are also hiring managers. They put job postings up you What do we do nothing but connect with people that they're probably trying to hire. So you should share their job postings. That's a really easy one you could do. That's one hack. Another one you could do is if you have a nice conversation with the person, write a write a recommendation for them on LinkedIn. That's another easy one you could do us by Hey, I, I was a vendor, I talked this person, they were respectful, really kind and nice. Good. Like if they if they do that don't actually lie like pictures, someone's nice to you and does some good stuff. If you have someone on some content that you have, that's another favor you can do. Like, it sounds bad. I'm not trying to say like, be a jerk and do these things for selfish intent. Do them to help your space and denoble. But like, collect, keep a list of those people. The end of my story is that I had to get 10 ops in one week. I just all I did is I pinged him and said, Hey, Baba, I'm going to be moving out as real soon, you're going to be working with someone else sells someone else. If it's not me, do you want to take a meeting and actually look at what we do now, before I move before moving to marketing. And like, I don't even think I had to use that urgency. I could have just said, Hey, Baba, it's it. I was wondering if you want to finally look at this. I know you guys have XYZ because we had done this together. And the amount of people that said yes, I ended up getting 11 opportunities in one week doing it just like just like, like just tapping in and being the collector. But like, it wasn't selfish. Yeah, it was it wasn't selfish, either. Like it was like, the thing we're offering could help them and the other cool part is like, I probably could have got those people earlier. I just like, I was keeping it sort of for some reason, I kind of just cashed out everything that I had afterward. So think of that emotional bank account when you're first starting out. Try and find ways to do favors for people. You're that you be the cool guy that's gonna hook people up, like ever see those prison movies were like, there's that person's like, Yo, I can get you cigarettes or like be the cool guy with the cigarettes. Don't smoke. That's how people smoke but

cheeseburgers get a McDonald's cheeseburger. Yeah, like was that like the longest CRT longest? Yeah, that's always says McDonald's. go to prison. Give people McDonald's that's

Daniel Ryan  44:18  

the lessons for teaching that's how you'll be a successful salesperson. Yeah. I'd love to sort of rapid not necessarily rapid fire but just a lot of you know the nitty gritty what people when they're first getting into the industry are thinking of right like how can or either either things to avoid or things like best practices for people just starting out that their SAS sales career, you know, what would you say you know, in order for them to make more money be successful get noticed by the supervisors for potential promotions, that kind of thing. What would you say would be your your do's and don'ts?

Ryan O'Hara  44:57  

Yeah. Oh, this is really good. Um, So I'm actually a perfect example this I got in as a BDR. Most PDR is that were working with me a dime moved into account executive roles, I didn't want to close. The biggest reason I didn't want to close was because when I was in college, I did door to door sales that I felt really shitty about closing. Like, I felt bad about it. I was wrong for thinking that way, though, I probably could have done closing and I would have liked it. I bet now that I look at in hindsight, but for me, I think one of the best things you can do is do stuff that's outside your job description. Make sure you perform and do the things your manager and teams asking you to do. But find ways to be proactive and do things out of your job description, instead of complaining about something, go try and solve it yourself and then bring the solution to someone to help them. So like, I'll give you an example. Maybe you're like, Oh man, I really need to document about, let's say you sell a widget that makes it so you can load balancer data clusters, right? And you're like, people keep asking how does this work? Maybe you go grab someone at the company, sit down with them and ask them about this. Or go talk to marketing about it. Don't ask them to go do it. If they can't do it, like, go make the doc yourself and then give it to sales enablement and say, Hey, I made this first draft, Could someone take a look at it? I'll give you a perfectly good example internally at lead IQ. We're selling to the enterprise a lot more now. And we need to make these what we're calling change management. Doc's are pretty popular. It's about changing the organization's behavior and the way they think about stuff with like, it's kind of like a buyer's guide of like, how do you get evaluate lead IQ all the way to closing, basically? And what's going to happen after you buy? And is mutual action plan? kind? Yeah, actually, a lot of people will call it that there's that's part of it. That's one page of it. But there's other stuff too, like, how is this different than what you're using right now? What stakeholders should you involve in this when you're evaluating like, there's stuff everyone's listening, they're like stealing this and doing it, that's cool. But we made the stock, I didn't come up with the skeleton at all, someone that works on our solution, architect, team, Phil, came with this idea to make the stock. And like, dude, the thing he made was like, super complicated and really thought through and beautiful and, but it wasn't something we could actually present to the market. Because Phil did that it was way easier for me as a VP to be like, not only is Phil doing stuff outside of his job description, Phil just saved me a lot of time, because he gave me a guide to work off of. And now it's easier for me to enable. And what will happen is, these people from other departments that will see that you're doing these things, will start saying, huh, this person could probably do a lot more than just prospect to help the organization. And that's kind of that's kind of a way that you can move in another example is on our team. We just promoted john Maas into a content role with me. The biggest reason is because the SDR team kept asking for content for stuff. And we're so backed up with things right now, because we've been growing and dealing with all that stuff, and hiring new people. And we have webinars and putting content out every day on LinkedIn. Like, it's super hard for me to like, hide for a week and go make something just for the SDR team or something like that. It takes a lot of work. So john was actually going in making stuff by himself, and then giving it to me and saying, hey, that's what I made. And I realized that john had a knack for making pretty good content. I usually didn't have to edit a lot of his stuff. Rishi who is working on our team, who's actually in some of the Prehired modules, just left he's working at LinkedIn. Now he got a job at LinkedIn, which is really exciting.

Daniel Ryan  48:23  

Oh, I was wondering where he went, I saw like the video of you slapping him.

Ryan O'Hara  48:29  

Everyone's like, what the hell yes. Go. Go away. I was trying to do like the Harry the Hendersons thing. Like, can you see we don't need you anymore.

Daniel Ryan  48:37  

Anyway. Yeah. It's like it's a great opportunity and ends on like, we hate you, like just leave. But like,

Ryan O'Hara  48:44  

I have a ton of projects right now that I need someone to make content for. And we have our b2b tonight show that we do that people watch and like, I need someone to help me with that project and make content with me on that and stuff. And I just was like, it's time mozzie has been prospecting here for three or four years. He's made a ton of stuff to help the organization. He actually left and came back to so like, he has some outside experience at other companies to have some perspective to add insight. And like, because he did stuff that was outside of his job description. It made it a lot easier for me to tap and be like, dude, I like came up with the idea of hiring him like, in 115 minute meeting. When I went to all the other managers and said, You guys call it this. We didn't even have to interview him. It just happened. Like, in 24 hours. we flipped him over the marketing. And he's been he's onboarding, he's in month two of onboarding with us. He's doing great. So like, you're listening to this. If you want to be an AP, maybe you start listening to a calls, maybe you go to an E that's the top performing rep and say, Can I do anything to help you on deals like Can I do anything to maybe support you a little bit or in the trade a little more in the process and stuff, like do stuff that's outside your job description. last tip I'll give you post COVID when COVID is done, if you go back into an office, is go get lunch with random people outside your department. Like, that's really helpful, too. I, I tried to get lunch with everybody at Mike were dying, like at different points, it was very hard to do. But like, it ended up making it when I left there, it was very emotional, I was really sad because I love so many people that worked at that company. But like I had to, I had an unbelievable opportunity to go be an executive at a company and like, move it like lead a marketing team. And that was like, something I really want to do, that I was working toward, and a goal that I had set. But I had all these relationships. So like, think of it like that, too. Like you're here for a moment in time. As a prospector, you'd have a certain window, you're young, you're eager, you're energetic, or you're just starting you to switch careers, and maybe you're getting involved in this stuff. The time to really take things in gratify the horns and make a difference in your life is right now. That's how you want to think about what this stuff is like a new rep, getting into getting into this dark underworld of prospecting. That's not really that dark. It's actually really cool.

Daniel Ryan  50:59  

Yeah, just look at our rooms, if you're watching the video, if you're not watching the video. Cool. That's kind of cool.

Right? I think that is an amazing way to wrap up this podcast Did you have I would love if anyone is interested in Ryan's content. He gives all sorts of amazing tips. What are the best ways that they can support you and you know if they want to learn more.

Ryan O'Hara  51:24  

So two things, if you're a pre hired member, please use the lead IQ seat that we're giving you. It can help you a lot with making your prospecting more efficient, and focusing on those higher value activities. If you're a rap and you're listening, you can go to lead hit that get started button. I get judged on that. So like if you hit that get started button and you want to try us whether it's self sign up or talking to the sales team, like hanging out with us, like we just want to hear cool conversations, cool salespeople and stuff that would help me out. Third thing and final thing that I'll bring up, add me on LinkedIn. If you do, please write a message that says you heard me on this podcast. Like I love that all the Prehired members, for example, have been adding me and they mentioned that they saw me in the Prehired courses. And I love that like it makes it clear to me as a marketer. Like, where did you find me? How did you find out about my company as opposed to like, Hey, Ryan, given your role at LinkedIn or lead IQ, I don't even know what company I work for anymore. You see that? Like, I don't need the generic message. Be real be authentic. You got this.

Daniel Ryan  52:26  

Awesome. Thank you so much, Ryan, and everyone. Remember, sell your SAS off.

Unknown Speaker  52:31  

This podcast is brought to you by Prehired. If you're looking for SDR talent, we make hiring SDRs fast and simple. Or if you're looking to break into software sales, we help you start your six figure sales career in just 12 weeks. For more information, just go to

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Guest Bio

Many years ago, a young lad emerged from his mother’s basement with the dream of making B2B sales and marketing fun. Several years later, here he is.

Ryan’s had marketing and prospecting campaigns featured in Mashable, TheNextWeb, CNN Money, and Fortune.

He was the first BDR at Dyn, helped build their client lists to the thousands, while doing sales training there from 3-100+ reps. They were acquired by Oracle in 2016 for north $600m. He loves startups, and has a soft spot in his heart for them.

Today, Ryan works at LeadIQ, overseeing all aspects of growth and marketing.