Ryan O'hara: Converting Leads to Meetings

Why do some leads convert into sales meetings while others don’t? Is it the quality of your data? Is it the script your BDR team is using? Or is it something else? Let’s ask Ryan O’Hara. A highly successful marketer whose job is now solely focused on setting up sales meetings. Let’s examine which leads stand out, and which fall short, and what makes them so different.

Who is Ryan O'Hara?

When Ryan isn’t pretentiously typing up an “About” section on his LinkedIn profile in the third person, he’s helping fix the broken relationship between buyers and sellers. He loves helping salespeople. Helping them brand themselves better, write better cold emails, prospect better, and build their brand online as a media personality. But most of all, he loves creating business messaging that isn’t boring. Ryan has scaled marketing and sales teams at numerous successful startups. From Seed Round through exit. He’s now pursuing his lifelong dream of making B2B sales and marketing fun as Founder and CEO of Request for Meeting.

Webinar Transcript

Sourabh:
How do you get a meeting from cold outreach?

Ryan:
Okay, I'm gonna start by rattling off some stats really quick, just so people understand how hard this is. This year alone, there'll be 647 billion touches that salespeople will do with an attempt to get a meeting from somebody that's cold calls, LinkedIn, social, um, email, go down the list, right? Everybody's trying to get meetings with everybody. Um, it's just like what we're doing in marketing all the time. If you are one of those people, the average person will get prospected 700 times a year. So if you figure that that's about three or four times a day, half the battle is just standing out, being one of those people that's sending one of those activities and doing one of those things, but doing it in a way where you're like, Hey, this person doesn't suck. Um, and it kind of stems back down to a basic structure of making the person you're prospecting feel special.

That's the most important part. We'll talk about that. I can dive into that a little bit more. Um, stating your purpose of why you're contacting them in the first place, no matter what channel, phone, email, text, the thing you have to remember is most people are dumb. I'm not trying to be a jerk, but like I'm dumb too. I get cold emails and I'm like, wait, is this a cold email? I don't get it. Uh, the third part is not talking about yourself too much, but telling people who you are through your email signature, maybe one sentence value prop that lines up with a pain that someone has. And then the last part is having a call to action. Just like in marketing. What's, what do you want me to do? What's the easiest way to get a meeting? You have to ask for it.

That basic framework is what I've used for my entire career with prospecting. I didn't at first. I used to suck at prospecting when I first got outta school. And about 90 days in, my chief revenue officer, I was working at a company called Dine that Oracle bought for $600 million in 2016. And I was the first business development rep there. And the C r o, uh, Kyle York sat me down and was like, dude, I hired you to be you. What are you doing? And I was like, looking, what other people did was sending emails that other reps are sending and he's like, be yourself. And I did that and like my whole world opened up. Um, that's really what it comes down to. If you strip everything down, if you're doing value props and doing pain and sending scripts to people today, you're doing it wrong. Um, and the reason is because you're leaving that to luck. The advantage that prospecting and sales has over marketing is their hand picking who they're prospecting. And the easiest way to make a connection with someone is find something you have in common with them. And that's a huge twist that like we can all do. That's something that takes muscle memory. You have to unlearn how you write email and do calls today. I'll let you talk now and follow up and

Sourabh:
Stuff and let me, let me segue right from there, okay? And we'll take each of these one at a time again, 'cause our audience are marketers. So you've had Will's experience, but it might be from a long time ago and it's gotten much, much harder, okay? Especially when you're selling technology that has all these hoops to jump through even if they wanna buy, right? Let's take the first, the first factor of the four that you mentioned, and I'm gonna combine it with what you just said, right? Which is finding that common ground, a bridge upon which you can connect while making the other person feel important or special, okay? Yep. So as a marketer, when I'm handing a lead off to my sales team,

Ryan:
What data could

Sourabh:
I give them to help them with this so they're not starting from absolutely, you know, zero.


Ryan:
Well, I think today, especially if you're someone that works in tech, which mostly I think the people watching this are, you gotta for, for starters, gotta have your sales team wired to go research the person. I don't care if it's an in lead, that's the other thing that we make the mistake of is like, oh, I have this outbound lead. Uh, alright, things you can personalize, right? There's kind of three levels of personalization. Personalization 1.0 is what I'd call, um, prospecting based on the person's company that they work for. Guess what? You can't do that anymore. You know why every rep in the world is doing that. Here's the other problem. This is something that we need to start thinking about too, especially with post 2020. About one third of the people you prospect don't like their job. And if you go and say, Hey, it's cool that you work at Google, Google's awesome, blah, blah, blah, blah, blah, guess what?

Average person's only staying at a job for 18 months. So there's a one in three chance. The person you're prospecting is looking at job postings at night and looking for another job. Let's bunch in the other, the other two thirds. One of those three is someone that's probably really drinking the Kool-Aid and loves where they work. So you can do that and it might work. The problem is you have a whole highway of sales reps driving home at rush hour right now doing the same thing, which is why you could do personalization 2.0. Personalization 2.0 is when you prospect somebody, but you personalize it based on the individual person. There's a problem with that. Guess what reps are now doing instead? They're all doing that. And before you get all upset, only 0.4% of the activities that someone does will actually result in a meeting happening.

So if you do personalization with somebody, the issue is if you're doing it based on something you notice with their profile, we're about to enter this new slog of AI writers that are gonna be doing this and making the novelty wear off. So the only way that you can differentiate between a machine writing an email that's personalized, Hey, I see your, your, uh, outside of where Nike's based, uh, I just bought this pair of Nikes last week. That's the way you make a link to somebody is you find something that you have in common because there's an army of sales reps out there, but the only thing that you have that differentiates you from the 80 other companies that do weed generation or the other 80 other companies that do hosting in cloud or CDNs or uh, database or email marketing or go down the list of all these different tech companies.

The only thing you can do to differentiate is yourself, your background, where you've been. If I'm emailing someone in Chicago, I'm gonna have a debate with them about like, Hey, what do you think's your favorite deep dish pizza in Chicago? I like Pequods. I know some people like Giorgio, some people like Lum, I can't remember what it's called, the Ciaos. Um, you go down the list though and think of, think of all these different ways to make a connection with someone. That's how you break in and get someone's attention. Now, the most important part, and this when it's become even more dire is open rates on cold prospecting and listening to voicemails and connect rates on cold calls of all plummeted over the past 10 years. You, I can write a cold email to somebody and yeah, I could get a hundred percent open rate.

I'm like, your kid's sick of the nurse's office. Please, please open this email. Like you could say something like that and, and trick someone into opening email, but that's dishonest. You actually get a meeting with that person, they're gonna be pissed off at you, right? You gotta make the thing that you're opening up with with any of your prospecting about the prospect, not yourself. And that's, that's the key part of how do I make a prospect feel Special ways you can do it. Think of ways we make friends in real life. I i, I jokingly call it the three stages of conversation. We start with small talk and then we get drive to common interest. And when you get to common interest, it's things that you might both like and you can find that stuff professionally. It's easy. Now, you know why most executives you're selling to have to be posting on LinkedIn every week? Like they all, hi. They're literally firms that now hire and say, Hey executive, you need to be posting every week. We'll help you and consult you with that. Your leadership needs to be visible out there on the internet. Um,


Sourabh:
We'll come back to this, we'll come back to people's profiles, right? Because yep, a lot of buyers, as you said, especially you know, VP and above are visible and they're often relying on somebody. And this is just a general, general quirk in how large companies buy. Budget owners tend to be extroverts, decision makers tend to be introverts and the extroverts lean on the introverts, right, to get the decision that they need, but the extrovert will be the one that actually signs the contract. This is sort of a psychological analysis of large company, you know, buying. So I'm gonna, I'm gonna come back to something you said there, right? And, and ask this in a slightly different way. You get the meeting sales has begun their process and for a lot of marketers that sit, but not for our clients because most of them are running a b m programs, they're right there with them all the way until you have the closed loss or the closed one. Okay? Yeah. So sales gets the meeting, uh, client's receptive, asks some questions, maybe even ask for pricing, right? But it's showing some interest. And then boom, they're gone. It's been a week, it's been done. We, how do you reengage in a sales process? Ryan, how do you get a meeting again?

Ryan:
Alright, couple cool things to do here. The first thing that is, uh, holy uh, holy crap like idea here. And by the way, um, I got this actually from a d p, which I think is one of the customers you guys have worked with, right? Um, a d p does something called a mutual action plan. Have you ever heard of these? They're pretty cool for people listening at home, you should, you should set this up with your sales team. You can work with them on it. Basically what you do is when you get on that first meeting with somebody, if they agree that they're interested and they're really interested, they're not just blowing smoke and telling you, yeah, hey, I wanna do this. If you build a mutual action plan, what it basically is, is you give them, it's almost like you ever played video games like in 64 back in the day.

And like you'd buy a game guide on like how to beat Mario 64 or agree at a time or something. You're basically giving a prospect that you do a meeting with them. You sit down and say, Hey, I know that on average there's 12 people in a buying committee at a large mid-size company that I need to break into and get attention from. Let's map out goals, uh, from now to the getting the project completely onboarded. Note, a mutual action plan does not end when the contracts signed. Onboarding is part of that process. Um, a D P does this really well. So they'll go and lay out and be like, well, we need to talk to CFO, we need to talk to payroll, we need talk to hr, we need to, to talk to, um, finance and figure out payroll stuff. They go through and know all the people that they already need to talk to so that when they get that champion from that first meeting, they're looping in other people. And what you do is you set dates for each thing. So it's not like, yeah, next we're gotta do this. Oh, I'll do that in three weeks when this person's available. It's like, no, let's you really wanna do this. You're excited about this, let's go through this. And it, it's not about you closing, signing a contract and assuming the sale. It's about running the deal and making sure that you can evaluate if this is the right fit or or not for your company. Uh,

Sourabh:
Right? Because ultimately it's about solving their pain point, right? It's not about closing the deal. The deal is their beginning of where they start solving the pain point. It's like, yeah, they have to onboard, they have to actually use it, they have to find success. Then you read that mutual ground where you can expand within a company.

Ryan:
So you break in with personalization, you build up a good relationship with them. The cool part is if you lead with something that you have in call the prospect, when you actually get on a call with them and you get to that stage two of conversation, you might actually get to stage three, which is very rare, but when it happens, it's magical. It's when you get someone to expose their feelings and emotions to you. And that's fear. That's things that they're worrying about. Um, like I can give you all kinds of stories. I mean, there was an example I talked to, uh, I always tell this story, I just did a lecture at the University of New Hampshire on prospecting, and I told this story. I had a prospect once that I was working with who worked at a company called Stumble Upon. And uh, remember stumble upon the nineties, there were like a popular or early two thousands, there's a popular app where like you could get like taken to a random website.

I remember I cold called this guy, um, and I, he had a startup that he started before he started stumble upon. And I cold call and we talked about his startup on the opening call. I was like, yeah, I wanna start a startup someday. Like I saw you're into startups and we talked about startups for like five or 10 minutes. Like, yeah, it's great, no boss. Um, you get to do take more risks, like all the benefits and stuff. Anyway, I was like, look, reason I'm calling is, I wanted to see if you guys wanted to use managed d n s and stumble upon we're selling this thing that makes it a lot better for, and we ended up talking, setting up a call and stuff. At the end of the call, I was like, it was around Thanksgiving. And I was like, Hey, what, so what are you doing for Thanksgiving?

He's like, uh, I, I told him, I was like, I'm getting dinner with my dad and I've had like weird, I've had like a weird funk with my dad lately. So like I'm kind of nervous about it. And he o I was vulnerable with him and he opened up and said, you won't believe this. I'm going home to my parents this weekend. I'm coming out to them. And I was just like, this is a random person I just met 20 minutes ago on the phone that I did a cold call with. Um, this guy opened up with me and I gave him a pep talk. I'm like, if your parents don't like you, screw them. Like you could do this, blah, blah, blah. Next week we get on the call and I'm handing the deal to the account executive and they, he, I opened the call.

I'm like, Hey, how'd it go? And he is like, oh my gosh, it went great. Everything's awesome, blah, blah, blah, blah. And I'm like, dude, that's so awesome. I'm so happy for you. And I get outta the call with the AE after, like, what happened with you two? But the thing is, that guy got a job eventually working at eBay and we, we charged on web traffic at the company I was working at. He brought eBay into us. He didn't go fill out a form on our website. He could reached out to me. Then he got a job at Dropbox and he brought me over to Dropbox and I got one account from stumble upon that turned into me getting five or six accounts afterward. And it's because I got that personal reveal, feelings and pain. You wanna try and get there, it's harder to do.

But the be easiest way to do that is just like, show your cards a little bit. Be human a little bit, make that connection with somebody and figure out how to expose that in your activities that you're doing as you build up after you get a response from someone. Um, getting responses after battle. But you gotta start on that right foot of common interest so that you can get to that stage three and talk about feelings and stuff. Think about how we make friends with each other. We all, uh, have summer camp hockey, uh, go down the list of the different ways you make a bond with someone. So the other part is if a person forms a relationship with you upfront, they're less likely to blow you off. Which your original question was like, Hey, what do I do if someone knows, shows a meeting, if they do know, show a meeting, you can just nurture them with things that, you know, fit the common interest that you had in that first call.

So uncover some of that common interest. And if a person's no nonsense and just wants to get right to business, which that's gonna happen for one of the three people you talk to, especially if they're introverted, um, it's fine. It's okay. The thing is, you're, in order to get someone to mobilize and involve more stakeholders in, in the company, you're probably not gonna get a mobilizer that's introverted as much. They're more of a decision maker. You actually need to penetrate with an extrovert to actually get inside the company and make something that you're doing contagious. Um, so that's, that's my approach on it. Hopefully that wasn't too long at Epic, that, um, be thoughtful. That's a key part of your

Sourabh:
Yep. No, I get it. So I'm going to, um, I'm gonna bring this back right to the, to the balance between, between sales and marketing, right? So, so you have success, right? As you, let's say you launch a new product, you're a known brand, right? So you can get, you can get opens, people will open your emails because you're a known brand, right? You've got a reputation, but you're launching a new product. So your social proof isn't, it's not, not there, it's just very light, okay? Yeah. So getting someone to commit to a meeting is much harder. I know who you are. I I don't need the spiel on who you are. Yeah, I just don't this product, which means I don't know if it's worth my time, right? You must have dealt with this friend, right? Oh yeah. Known brand, right? But not quite an exciting value proposition.

Ryan:
What's your advice there? Yeah, so, alright, this is gonna sound kind of zoomed out a little bit, but we can get tactical if you've poke me with tactical questions after I do it. One of the most important things you need to do if you're gonna have more than one product line is you're not selling products, you're selling an idea. And that's really, really important. A really good example of this, it's kind of like the Andy Raskins model. I don't know if you know Andy Raskins, but like Andy Raskins wrote a very famous blog post, most of you have probably read it. It's called The Greatest Sales Deck I've ever seen. And it's, he talks about zoa and how Zoa had a billing platform where they had all these great features they integrates with Salesforce, it helps you, all these different things. But Zora didn't go to market selling people saying, we have the best billing platform, which is what most marketing companies do today.

What they did is they basically went out in the market and said, the subscription co economy's happening. This is the, the old way was not doing subscriptions. Microsoft has to go chase people down every three to five years and get them to repurchase Microsoft Office. No, it's better if you get customers once and keep them longer with the subscription business. And they went and basically owned everything with subscriptions and now they're, you know, they're a unicorn billion dollar company. I don't think they're publicly traded yet, but they should be <laugh>. Um, but a like, a good way of thinking about this, you need to do the same thing, but if you're gonna be adding more than one product by with your marketing, um, you might have different features, you might add different things, and you might, I I know everyone's like, oh, let's go make a category.

And some of you're probably bigger companies have tried to do this, but you need to have something that folds into that new way so that the thing you're adding to your product portfolio just blends right in with doubling down on the messaging you already have. Then you can use the social proof and your case study should reflect that messaging. So like, I'll give you a good example with requests for meeting right now. Hopefully I'm not plugging myself too much, but, um, we're talking about this problem today where prospecting is less and less effective than it was 10 years ago. And most revenue companies, or most companies that need revenue, 60% of your revenue comes from outbound prospecting. Yet only 0.4% of the activities you do will actually turn to something right there. I'm framing a problem. I could come up with 30 products that fit into that problem right now and, and if, and double down and use the same case studies and same social proof that I have for my product line as long as it blends into that big picture messaging that fits in.

Um, and you might say, well, you know, I'll, I'll, I'll give you a really good example in the history of the world. I guarantee if we rounded up and got a hundred customers that you have right now and you cold emailed them and asked them in a survey, did you buy our product because of a case study? None of them would say yes. So you can keep focusing on case studies and doing that and buying yourself some time so you don't get fired and don't get caught for being bad at your job. Or you could focus on getting really honed in product marketing messaging and have all your products fold into that big me that big picture message of the old way is this, the new way is this, I'm gonna show it to you with proof and data points around the market of how things are happening. And there's all kinds of cool angles you can take to do that. I appreciate that. And now, now we've covered data, right? We've covered

Sourabh:
Storytelling. I'm gonna take a very specific problem, just a reminder to the audience. We only have time for two more questions, so if you have one, drop it in or we'll run out of time and we always run out of time so they know this, right? Um, so let's talk about the zombie state where you've got engagement as a B, D R, right? They are responding, they're answering your questions, but you're stuck in email. You're, you're at email, you're, or you're, you're, I mean, you're not on phone, but during email or maybe even messaging, right? Yep. On Slack or let's say on LinkedIn. If it's, if it's Slack, if it's in a community, right? Yeah. And you're not able to drive any urgency for a meeting. So you've done this a lot, Ryan, I I want your advice on this, not just a tactic. Yeah. Should you continue to nurture the relationship until you feel the prospect is ready to engage? Or should you try to create urgency by outlining what they're losing by not considering the product?

Ryan:
Alright, so there's two, there's two ways to deal with this. The first is, you need to reach out to more stakeholders at that company so that it creates conversation with each other. You want them to talk about what's better? Me following someone with an ad online where they keep seeing me 'cause they visited my website, or having a coworker Slack me and say, Hey, I got pinged by the guys at, uh, request for meeting again. Um, do you wanna look into this? Like, that's what you're trying to do. You're trying to create conversations with people. Um, so that's the first thing. How do you create a conversation with someone? Well, if, uh, I, one of my favorite things, I love applying this to prospect because no one thinks of it, but, um, a lot of marketers out there have read Contagious by Jonah Berger. Have you read that book?

Um, he basically dissects and talks about, like, they did research on what makes things go viral. And there's a bunch of different steps. You can do that with prospecting. I could grab, I'm using my phone right now as a webcam. I could grab my phone, throw it on a tripod, put it on cinematic mode and make a video for that whole account. Make it really silly, make it really fun, uh, make it for the whole account, throw it up online or email it to someone and they'll share it around the office. And now I've got 80 people at a company. I did this actually at Lead iq. We had, I tried to get a meeting with LogMeIn and I did a video where I tried to audition to be their, their, um, their spokesperson. So like I put on a tuxedo and I was terrible in the video.

Like the joke was that I was terrible, but like, it basically was a minute and a half video about LogMeIn, not about Meet iq, said to the person, said, Hey, I made this, I wanted to audition to be a spokesperson for you guys. I looked at the video even though I only sent it to two or three people at the company, I had 1600 views. I know someone dropped them in Slack. I know a bunch of people clicked in and watch the video and uh, watched in Slack. And then guess what my calls and emails are about, Hey, blah blah, I saw you got about, you watch my video, haven't heard back. What's up? Yeah. Then you talk about the video instead of doing a pitch and you're like, yeah, the reason I'm talking is we had a conversation a couple weeks ago about prospecting and I haven't heard anything from our, like, we haven't scheduled a mutual action plan yet. Is this a real thing or should I let you go? So like, there's a little bit of that catch and release philosophy.